Morphine

Identification

Summary

Morphine is an opioid agonist used for the relief of moderate to severe acute and chronic pain.

Brand Names
Arymo, Avinza, Duramorph, Embeda, Infumorph, Kadian, M-ediat, M-eslon, MSIR, Mitigo, Ms Contin, Statex
Generic Name
Morphine
DrugBank Accession Number
DB00295
Background

Morphine, the main alkaloid of opium, was first obtained from poppy seeds in 1805.1 It is a potent analgesic, though its use is limited due to tolerance, withdrawal, and the risk of abuse.2 Morphine is still routinely used today, though there are a number of semi-synthetic opioids of varying strength such as codeine, fentanyl, methadone, hydrocodone, hydromorphone, meperidine, and oxycodone.

Morphine was granted FDA approval in 1941.13

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 285.3377
Monoisotopic: 285.136493479
Chemical Formula
C17H19NO3
Synonyms
  • (−)-morphine
  • (5alpha,6alpha)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol
  • (5alpha,6alpha)-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol
  • (5R,6S,9R,13S,14R)-4,5-epoxy-N-methyl-7-morphinen-3,6-diol
  • (5α,6α)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol
  • (5α,6α)-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol
  • (7R,7AS,12bs)-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline-7,9-diol
  • Anhydrous morphine
  • Morfina
  • Morphia
  • Morphin
  • Morphine
  • Morphinum
  • Morphium
External IDs
  • IDS-NM-009
  • N02AA01

Pharmacology

Indication

Morphine is used for the management of chronic, moderate to severe pain.2

Opiods, including morphine, are effective for the short term management of pain. Patients taking opioids long term may need to be monitored for the development of physical dependence, addiction disorder, and drug abuse.11

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofChronic intractable pain•••••••••••••••••••••• ••••••••
Used in combination to manageChronic painCombination Product in combination with: Naltrexone (DB00704)•••••••••••••••••••••• ••••••••••• ••••••••• •••••••
Management ofChronic pain••••••••••••
Used in combination to manageSevere painCombination Product in combination with: Naltrexone (DB00704)•••••••••••••••••••••• ••••••••••• ••••••••• •••••••
Treatment ofSevere pain••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Morphine binding to opioid receptors blocks transmission of nociceptive signals, signals pain-modulating neurons in the spinal cord, and inhibits primary afferent nociceptors to the dorsal horn sensory projection cells.1

Morphine has a time to onset of 6-30 minutes.1 Excess consumption of morphine and other opioids can lead to changes in synaptic neuroplasticity, including changes in neuron density, changes at postsynaptic sites, and changes at dendritic terminals.3

Intravenous morphine's analgesic effect is sex dependent. The EC50 in men is 76ng/mL and in women is 22ng/mL.5

Morphine-6-glucuronide is 22 times less potent than morphine in eliciting pupil constriction.5

Mechanism of action

Morphine-6-glucuronide is responsible for approximately 85% of the response observed by morphine administration.4 Morphine and its metabolites act as agonists of the mu and kappa opioid receptors.1 The mu-opioid receptor is integral to morphine's effects on the ventral tegmental area of the brain. Morphine's activation of the reward pathway is mediated by agonism of the delta-opioid receptor in the nucleus accumbens,2 while modification of the respiratory system and addiction disorder are mediated by agonism of the mu-opioid receptor.3

TargetActionsOrganism
AMu-type opioid receptor
agonist
regulator
Humans
AKappa-type opioid receptor
agonist
Humans
ADelta-type opioid receptor
agonist
Humans
ULymphocyte antigen 96
activator
Humans
Absorption

Morphine is absorbed in the alkaline environments of the upper intestine and rectal mucosa.6 The bioavailability of morphine is 80-100%.8 There is significant first-pass metabolism, therefore oral doses are 6 times larger than parenteral doses to achieve the same effect. Morphine reaches steady-state concentrations after 24-48 hours.1 Parenteral morphine has a Tmax of 15 minutes and oral morphine has a Tmax of 90 minutes, with a Cmax of 283nmol/L.7,8 The AUC of morphine is 225-290nmol*h/L.8

Volume of distribution

The volume of distribution of morphine is 5.31L/kg.6 Morphine-6-glucuronide has a volume of distribution of 3.61L/kg.6

Protein binding

Morphine is 35% protein bound, the metabolite morphine-3-glucuronide is 10% protein bound, and morphine-6-glucuronide is 15% protein bound.4

Metabolism

Morphine is 90% metabolized by glucuronidation by UGT2B7 and sulfation at positions 3 and 6.4 Morphine can also be metabolized to codeine, normorphine, and morphine ethereal sulfate.6

Hover over products below to view reaction partners

Route of elimination

70-80% of an administered dose is excreted within 48 hours.6 Morphine is predominantly eliminated in the urine with 2-10% of a dose recovered as the unchanged parent drug.4 7-10% of a dose of morphine is eliminated in the feces.13

Half-life

Morphine has a half life of 2-3 hours.5

Clearance

The apparent clearance of intravenous or subcutaneous morphine is 1600 mL/min.8

Adverse Effects
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Toxicity

The LD50 is 0.78µg/mL in males and 0.98µg/mL in females.9

Patients experiencing an overdose present with respiratory depression, somnolence, skeletal muscle flaccidity, cold and clammy skin, miosis, and mydriasis. Symptoms of overdose can progress to pulmonary edema, bradycardia, hypotension, cardiac arrest, and death.12 Treat overdose with symptomatic and supportive treatment which may include the use of oxygen, vasopressors, and naloxone.12

Pathways
PathwayCategory
Morphine Action PathwayDrug action
Codeine Action PathwayDrug action
Heroin Metabolism PathwayDrug metabolism
Heroin Action PathwayDrug action
Codeine Metabolism PathwayDrug metabolism
Morphine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Multidrug resistance protein 1---(T;T) / (C;T)T AlleleEffect Directly StudiedPatients with this genotype may have an increased analgesic response to morphine.Details
Mu-type opioid receptor---(A;A)A AlleleEffect Directly StudiedPatients with this genotype may have an increased analgesic response to morphine.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Morphine is combined with 1,2-Benzodiazepine.
AbaloparatideThe risk or severity of adverse effects can be increased when Morphine is combined with Abaloparatide.
AbametapirThe serum concentration of Morphine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Morphine can be increased when combined with Abatacept.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Morphine.
Food Interactions
  • Avoid alcohol. Concomitant use may lead to profound sedation, respiratory depression, coma, and death.
  • Take with or without food. There is no significant different in the AUC or Cmax of oral extended release tablets when taken with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Morphine acetateVEO43W5229596-15-6CLDOGJORCNORLA-VYKNHSEDSA-N
Morphine hydrochlorideJ28GE0ROVX52-26-6XCKKIKBIPZJUET-VYKNHSEDSA-N
Morphine hydrochloride trihydrateQ5F3AS69LF6055-06-7XELXKCKNPPSFNN-BJWPBXOKSA-N
Morphine mesylateQXB8THK8QY335328-17-1MHEMFNFIWLUDDJ-VYKNHSEDSA-N
Morphine nitrateDV2P23JCWV596-16-7VHBDDUMTLJSZDR-VYKNHSEDSA-N
Morphine phosphate1LQ9207LZE596-17-8KZSZGTYWWBPNKB-VYKNHSEDSA-N
Morphine sulfateDY70C97N3064-31-3USAHOPJHPJHUNS-IFCNUISUSA-N
Morphine sulfate pentahydrateX3P646A2J06211-15-0GRVOTVYEFDAHCL-RTSZDRIGSA-N
Morphine tartrateU3NSU23LHD302-31-8SVTKSKRNLMAUKF-HAIKCVHQSA-N
International/Other Brands
Kapanol (Mayne Pharma/Glaxo) / MSIR (Purdue Pharma) / Oramorph (Boeringher Ingelheim)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Arymo ERTablet, film coated, extended release15 mg/1OralZyla Life Sciences US LLC2017-02-01Not applicableUS flag
Arymo ERTablet, film coated, extended release60 mg/1OralZyla Life Sciences US LLC2017-02-01Not applicableUS flag
Arymo ERTablet, film coated, extended release30 mg/1OralZyla Life Sciences US LLC2017-02-01Not applicableUS flag
AvinzaCapsule, extended release60 mg/1Oralbryant ranch prepack2002-03-202014-03-01US flag
AvinzaCapsule, extended release30 mg/1Oralbryant ranch prepack2002-03-202010-07-15US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AstramorphInjection0.5 mg/1mLEpidural; Intrathecal; IntravenousAstrazeneca Ab1990-10-012012-11-30US flag
AstramorphInjection1 mg/1mLEpidural; Intrathecal; IntravenousAstrazeneca Ab1990-10-012012-06-30US flag
AstramorphInjection0.5 mg/1mLEpidural; Intrathecal; IntravenousAstrazeneca Ab1990-10-012012-08-31US flag
AstramorphInjection1 mg/1mLEpidural; Intrathecal; IntravenousAstrazeneca Ab1990-09-302013-03-31US flag
AstramorphInjection1 mg/1mLEpidural; Intrathecal; IntravenousAstrazeneca Ab1990-10-012013-04-30US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
EmbedaMorphine sulfate pentahydrate (100 mg/1) + Naltrexone hydrochloride (4 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUS flag
EmbedaMorphine sulfate pentahydrate (20 mg/1) + Naltrexone hydrochloride (.8 mg/1)Capsule, extended releaseOralStat Rx USA2009-08-13Not applicableUS flag
EmbedaMorphine sulfate pentahydrate (50 mg/1) + Naltrexone hydrochloride (2 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUS flag
EmbedaMorphine sulfate pentahydrate (30 mg/1) + Naltrexone hydrochloride (1.2 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUS flag
EmbedaMorphine sulfate pentahydrate (80 mg/1) + Naltrexone hydrochloride (3.2 mg/1)Capsule, extended releaseOralPfizer Laboratories Div Pfizer Inc2009-08-13Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Morphine SulfateMorphine sulfate pentahydrate (20 mg/1mL)Solution, concentrateOralPhysicians Total Care, Inc.2006-01-232013-01-15US flag
Morphine SulfateMorphine sulfate pentahydrate (15 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousBaxter Laboratories2002-12-022013-10-31US flag
Morphine SulfateMorphine sulfate pentahydrate (15 mg/1)TabletOralGlenmark Generics, Inc. USA2006-08-012009-06-26US flag
Morphine SulfateMorphine sulfate pentahydrate (40 mg/1mL)Injection, solutionIntrathecalCantrell Drug Company2012-08-242015-03-13US flag
Morphine SulfateMorphine sulfate pentahydrate (10 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousWest-Ward Pharmaceuticals Corp.1971-01-012017-04-30US flag

Categories

ATC Codes
A07DA52 — Morphine, combinationsN02AA51 — Morphine, combinationsN02AA01 — MorphineN02AG01 — Morphine and antispasmodics
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Morphinans
Sub Class
Not Available
Direct Parent
Morphinans
Alternative Parents
Phenanthrenes and derivatives / Tetralins / Coumarans / Aralkylamines / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Trialkylamines / Secondary alcohols / Oxacyclic compounds
show 3 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Coumaran / Ether
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
morphinane alkaloid, organic heteropentacyclic compound (CHEBI:17303) / Alkaloids, Isoquinoline alkaloids (C01516)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
76I7G6D29C
CAS number
57-27-2
InChI Key
BQJCRHHNABKAKU-KBQPJGBKSA-N
InChI
InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1
IUPAC Name
(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraene-10,14-diol
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O

References

Synthesis Reference
US4764615
General References
  1. Pacifici GM: Metabolism and pharmacokinetics of morphine in neonates: A review. Clinics (Sao Paulo). 2016 Aug;71(8):474-80. doi: 10.6061/clinics/2016(08)11. [Article]
  2. Kim J, Ham S, Hong H, Moon C, Im HI: Brain Reward Circuits in Morphine Addiction. Mol Cells. 2016 Sep;39(9):645-53. doi: 10.14348/molcells.2016.0137. Epub 2016 Aug 9. [Article]
  3. Beltran-Campos V, Silva-Vera M, Garcia-Campos ML, Diaz-Cintra S: Effects of morphine on brain plasticity. Neurologia. 2015 Apr;30(3):176-80. doi: 10.1016/j.nrl.2014.08.004. Epub 2014 Nov 11. [Article]
  4. Klimas R, Mikus G: Morphine-6-glucuronide is responsible for the analgesic effect after morphine administration: a quantitative review of morphine, morphine-6-glucuronide, and morphine-3-glucuronide. Br J Anaesth. 2014 Dec;113(6):935-44. doi: 10.1093/bja/aeu186. Epub 2014 Jul 1. [Article]
  5. Lotsch J: Pharmacokinetic-pharmacodynamic modeling of opioids. J Pain Symptom Manage. 2005 May;29(5 Suppl):S90-103. doi: 10.1016/j.jpainsymman.2005.01.012. [Article]
  6. Hoskin PJ, Hanks GW: Morphine: pharmacokinetics and clinical practice. Br J Cancer. 1990 Nov;62(5):705-7. [Article]
  7. Glare PA, Walsh TD: Clinical pharmacokinetics of morphine. Ther Drug Monit. 1991 Jan;13(1):1-23. [Article]
  8. Stuart-Harris R, Joel SP, McDonald P, Currow D, Slevin ML: The pharmacokinetics of morphine and morphine glucuronide metabolites after subcutaneous bolus injection and subcutaneous infusion of morphine. Br J Clin Pharmacol. 2000 Mar;49(3):207-14. [Article]
  9. Shigeev S: Severity of opiate intoxication to gender and age. Soud Lek. 2007 Jan;52(1):21-4. [Article]
  10. FDA approvals [Link]
  11. NIH [Link]
  12. FDA Approved Drug Products: Infumorph Morphine Sulfate Injection [Link]
  13. FDA Approved Drug Products: Morphine Sulfate Oral Tablets [Link]
  14. FDA Approved Drug Products: Morphine Sulfate Oral Solution [Link]
  15. FDA Approved Drug Products: MS Contin (Morphine Sulfate) Oral Extended Release Tablet [Link]
  16. FDA Approved Drug Products: Kadian (Morphine Sulfate) Oral Extended Release Capsules [Link]
  17. FDA Approved Drug Products: INFUMORPH (morphine sulfate), Preservative-free, injectable solution, for intrathecal or epidural infusion, using a continuous microinfusion device, CII [Link]
Human Metabolome Database
HMDB0014440
KEGG Drug
D08233
KEGG Compound
C01516
PubChem Compound
5288826
PubChem Substance
46505161
ChemSpider
4450907
BindingDB
50000092
RxNav
7052
ChEBI
17303
ChEMBL
CHEMBL70
ZINC
ZINC000003812983
Therapeutic Targets Database
DAP000071
PharmGKB
PA450550
PDBe Ligand
MOI
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Morphine
PDB Entries
1q0y / 7u62 / 8ef6
FDA label
Download (277 KB)
MSDS
Download (52.6 KB)

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableActive Not RecruitingOtherPost-Operative Confusion1somestatusstop reasonjust information to hide
Not AvailableActive Not RecruitingPreventionAcute Pain / Analgesia / Chronic Pain / Morphine / Neuropathic Pain / Postoperative pain / S-ketamine1somestatusstop reasonjust information to hide
Not AvailableActive Not RecruitingPreventionAnalgesia / Dexmedetomidine / Elderly / Long Term Outcomes / Surgery1somestatusstop reasonjust information to hide
Not AvailableActive Not RecruitingTreatmentPostoperative pain1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableAbdominal Injuries / Analgesia / Local Anaesthetic / Postoperative pain1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
  • King pharmaceuticals inc
  • Actavis elizabeth llc
  • Ekr therapeutics inc
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia and critical care
  • Hospira inc
  • Mallinckrodt chemical inc
  • Meridian medical technologies inc
  • Watson laboratories inc
  • Roxane laboratories inc
  • Clonmel healthcare ltd
  • Endo pharmaceuticals inc
  • Kv pharmaceutical co
  • Mallinckrodt inc
  • Purdue pharma lp
  • Xanodyne pharmaceutics inc
  • Actavis
Packagers
  • Actavis Group
  • Alpharma Pharmaceuticals LLC
  • Amphastar Pharmaceuticals
  • Apotex Inc.
  • APP Pharmaceuticals
  • AstraZeneca Inc.
  • Barr Pharmaceuticals
  • Baxter International Inc.
  • Blenheim Pharmacal
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Cerovene Inc.
  • Cody Laboratories Inc.
  • D.M. Graham Laboratories Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Edenbridge Pharmaceuticals LLC
  • EKR Therapeutics Inc.
  • Elan Pharmaceuticals Inc.
  • Endo Pharmaceuticals Inc.
  • Ethex Corp.
  • G & W Labs
  • Glenmark Generics Ltd.
  • Hi Tech Pharmacal Co. Inc.
  • Hospira Inc.
  • Ide Interstate
  • King Pharmaceuticals Inc.
  • KV Pharmaceutical Co.
  • Lake Erie Medical and Surgical Supply
  • Lannett Co. Inc.
  • Lehigh Valley Technologies Inc.
  • Ligand Pharmaceuticals Inc.
  • Mallinckrodt Inc.
  • Marathon Pharmaceuticals
  • Mckesson Corp.
  • Meridian Medical Technologies Inc.
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • P F Laboratories Inc.
  • Pacira Pharmaceuticals Inc.
  • Paddock Labs
  • Pharmakon
  • Pharmedium
  • Physicians Total Care Inc.
  • Purdue Pharma LP
  • Quality Care
  • Ranbaxy Laboratories
  • Roxane Labs
  • Stat Rx Usa
  • Tercica Inc.
  • Upsher Smith Laboratories
  • Watson Pharmaceuticals
  • Wockhardt Ltd.
  • Xanodyne Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
TabletOral10.000 mg
InjectionEpidural; Intrathecal; Intravenous0.5 mg/1mL
InjectionEpidural; Intrathecal; Intravenous1 mg/1mL
Capsule, coated, extended releaseOral60 mg/1
Capsule, extended releaseOral120 mg/1
Capsule, extended releaseOral30 mg/1
Capsule, extended releaseOral45 mg/1
Capsule, extended releaseOral60 mg/1
Capsule, extended releaseOral75 mg/1
Capsule, extended releaseOral90 mg/1
SolutionParenteral2.500 mg
Tablet, film coatedOral200 mg
Tablet, film coatedOral300 mg
InjectionIntramuscular; Subcutaneous10 mg/ml
InjectionIntramuscular; Subcutaneous15 mg/ml
Injection, lipid complexEpidural10 mg/1mL
Injection, lipid complexEpidural15 mg/1.5mL
Injection, lipid complexEpidural20 mg/2mL
SyrupOral5 mg / mL
Capsule, extended releaseOral
SolutionOral0.600 g
SolutionIntravenous250.000 mg
TabletOral30.00 mg
Injection, solutionEpidural; Intrathecal10 mg/1mL
Injection, solutionEpidural; Intrathecal25 mg/1mL
Capsule, extended releaseOral10 mg/1
Capsule, extended releaseOral100 mg/1
Capsule, extended releaseOral130 mg/1
Capsule, extended releaseOral150 mg/1
Capsule, extended releaseOral20 mg/1
Capsule, extended releaseOral200 mg/1
Capsule, extended releaseOral40 mg/1
Capsule, extended releaseOral50 mg/1
Capsule, extended releaseOral50 mg
Capsule, extended releaseOral70 mg/1
Capsule, extended releaseOral80 mg/1
Capsule, extended releaseOral
Tablet, extended releaseOral10 MG
CapsuleOral10 mg
CapsuleOral20 mg
CapsuleOral30 mg
CapsuleOral5 mg
Capsule, extended releaseOral10 mg
Capsule, extended releaseOral100 mg
Capsule, extended releaseOral15 mg
Capsule, extended releaseOral200 mg
Capsule, extended releaseOral30 mg
Capsule, extended releaseOral60 mg
Capsule, coated pellets10 mg
Capsule, coated pellets100 mg
Capsule, coated pellets30 mg
Capsule, coated pellets60 mg
SuppositoryRectal10 mg
TabletOral20 mg
TabletOral40 mg
SyrupOral50 mg / mL
TabletOral60 mg
InjectionEpidural; Intrathecal200 mg/20mL
InjectionEpidural; Intrathecal500 mg/20mL
Tablet, film coatedOral20 mg
TabletOral15 mg
TabletOral
Tablet, film coatedOral15 mg
TabletOral13.172 MG
SolutionIntramuscular; Intravenous; Subcutaneous0.01 g/ml
SolutionIntramuscular; Intravenous; Subcutaneous0.02 g/ml
Injection10 MG/ML
SolutionOral30 mg
SolutionOral3000000 mg
Injection, solutionEpidural; Intramuscular; Intravenous; Subcutaneous10 MG/ML
Injection, solutionEpidural; Intramuscular; Intravenous; Subcutaneous100 MG/5ML
Injection, solutionEpidural; Intramuscular; Intravenous; Subcutaneous100 MG/10ML
Injection, solutionEpidural; Intramuscular; Intravenous; Subcutaneous20 MG/ML
Injection, solutionEpidural; Intramuscular; Intravenous; Subcutaneous200 MG/10ML
Injection, solutionEpidural; Intramuscular; Intravenous; Subcutaneous50 MG/5ML
Injection, solutionParenteral10 MG/ML
Injection, solutionParenteral100 MG/10ML
Injection, solutionParenteral100 MG/5ML
Injection, solutionParenteral200 MG/10ML
Injection, solutionParenteral50 MG/5ML
SolutionEpidural0.01 G
SolutionEpidural0.02 G
Injection, solutionParenteral20 MG/ML
Injection, solutionIntramuscular; Intravenous; Subcutaneous
Tablet, extended releaseOral20 MG
Tablet, extended releaseOral45 MG
InjectionIntramuscular; Intravenous10 MG/ ML
SolutionIntramuscular; Intravenous; Subcutaneous25 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous0.01 gr
SolutionIntramuscular; Intravenous; Subcutaneous0.02 gr
SolutionIntramuscular; Intravenous; Subcutaneous50 mg / mL
SolutionEpidural; Intravenous; Subcutaneous0.5 mg / mL
SolutionEpidural; Intravenous; Subcutaneous1 mg / mL
InjectionIntramuscular10 mg/0.7mL
InjectionIntramuscular; Intravenous; Subcutaneous10 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous15 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous5 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous8 mg/1mL
InjectionIntravenous1 mg/1mL
InjectionIntravenous1 mg/30mL
InjectionIntravenous10 mg/1mL
InjectionIntravenous4 mg/1mL
InjectionIntravenous8 mg/1mL
InjectionParenteral1 mg/1mL
Injection, solutionEpidural; Intramuscular; Intrathecal; Intravenous1 mg/1mL
Injection, solutionEpidural; Intramuscular; Intrathecal; Intravenous2 mg/1mL
Injection, solutionEpidural; Intraspinal; Intrathecal; Intravenous; Subarachnoid0.5 mg/1mL
Injection, solutionEpidural; Intraspinal; Intrathecal; Intravenous; Subarachnoid1 mg/1mL
Injection, solutionEpidural; Intrathecal; Intravenous0.5 mg/1mL
Injection, solutionEpidural; Intrathecal; Intravenous1 mg/1mL
Injection, solutionIntramuscular; Intravenous10 mg/1mL
Injection, solutionIntramuscular; Intravenous2 mg/1mL
Injection, solutionIntramuscular; Intravenous4 mg/1mL
Injection, solutionIntramuscular; Intravenous5 mg/1mL
Injection, solutionIntramuscular; Intravenous8 mg/1mL
Injection, solutionIntrathecal40 mg/1mL
Injection, solutionIntrathecal; Intravenous0.5 mg/1mL
Injection, solutionIntravenous0.5 mg/1mL
Injection, solutionIntravenous1 mg/1mL
Injection, solutionIntravenous10 mg/1mL
Injection, solutionIntravenous15 mg/1mL
Injection, solutionIntravenous2 mg/1mL
Injection, solutionIntravenous25 mg/1mL
Injection, solutionIntravenous4 mg/1mL
Injection, solutionIntravenous5 mg/1mL
Injection, solutionIntravenous50 mg/1mL
Injection, solutionIntravenous8 mg/1mL
Injection, solutionIntravenous; Subcutaneous10 mg/10mL
Injection, solutionIntravenous; Subcutaneous30 mg/30mL
Injection, solution, concentrateIntravenous25 mg/1mL
Injection, solution, concentrateIntravenous50 mg/1mL
PowderNot applicable1 g/1g
SolutionOral10 mg/5mL
SolutionOral10 mg/0.5mL
SolutionOral20 mg/1mL
SolutionOral20 mg/5mL
Solution, concentrateOral100 mg/5mL
Solution, concentrateOral20 mg/1mL
SuppositoryRectal10 mg/1
SuppositoryRectal20 mg/1
SuppositoryRectal30 mg/1
SuppositoryRectal5 mg/1
TabletOral15 mg/1
TabletOral30 mg/1
Tablet, extended releaseOral100 mg/1
Tablet, extended releaseOral15 mg/1
Tablet, extended releaseOral200 mg/1
Tablet, extended releaseOral30 mg/1
Tablet, extended releaseOral60 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral15 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral30 mg/1
Tablet, film coatedOral60 mg/1
Tablet, film coated, extended releaseOral100 mg/1
Tablet, film coated, extended releaseOral15 mg/1
Tablet, film coated, extended releaseOral200 mg/1
Tablet, film coated, extended releaseOral30 mg/1
Tablet, film coated, extended releaseOral60 mg/1
TabletOral200 mg/1
LiquidIntramuscular; Intravenous; Subcutaneous10 mg / mL
LiquidIntramuscular; Intravenous; Subcutaneous15 mg / mL
SolutionIntravenous; Subcutaneous1 mg / mL
SolutionIntravenous; Subcutaneous2 mg / mL
SolutionIntravenous; Subcutaneous5 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous1 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous10 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous15 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous2 mg / mL
LiquidIntramuscular; Intravenous; Subcutaneous2 mg / mL
SolutionIntravenous1 mg / mL
SolutionIntravenous100 mg / 100 mL
SolutionIntravenous5 mg / mL
SolutionIntravenous50 mg / 50 mL
SolutionIntramuscular; Intravenous; Subcutaneous10 mg / 1 mL
SolutionIntramuscular; Intravenous; Subcutaneous2 mg / 1 mL
SolutionIntramuscular; Intravenous; Subcutaneous4 mg / 1 mL
SolutionIntramuscular; Intravenous; Subcutaneous5 mg / 1 mL
SolutionIntramuscular; Intravenous; Subcutaneous8 mg / 1 mL
SolutionOral100 mg/5mL
LiquidIntravenous; Subcutaneous1 mg / mL
LiquidIntramuscular; Intravenous; Subcutaneous25 mg / mL
LiquidIntramuscular; Intravenous; Subcutaneous50 mg / mL
LiquidIntravenous; Subcutaneous2 mg / mL
LiquidIntravenous25 mg / mL
LiquidIntravenous50 mg / mL
LiquidIntravenous1.1 mg / mL
InjectionIntramuscular; Intravenous10 mg/1ml
InjectionIntramuscular; Intravenous15 mg/1ml
InjectionParenteral15 mg/1ml
SolutionEpidural0.5 mg / mL
SolutionEpidural1 mg / mL
Injection, solutionEpidural; Intramuscular; Intrathecal; Intravenous; Subcutaneous10 mg
InjectionParenteral10 MG/ML
Granule, for suspensionOral100 MG
Granule, for suspensionOral20 MG
Granule, for suspensionOral200 MG
Granule, for suspensionOral30 MG
Granule, for suspensionOral60 MG
Tablet, extended releaseOral100 mg
Tablet, extended releaseOral15 mg
Tablet, extended releaseOral200 mg
Tablet, extended releaseOral30 mg
Tablet, extended releaseOral60 mg
Suppository, extended releaseRectal100 mg / sup
Suppository, extended releaseRectal200 mg / sup
Suppository, extended releaseRectal30 mg / sup
Suppository, extended releaseRectal60 mg / sup
Tablet, extended releaseOral5 mg / tab
Capsule, extended releaseOral120 mg / src
Capsule, extended releaseOral150 mg / src
Capsule, extended releaseOral200 mg / src
Capsule, extended releaseOral30 mg / src
Capsule, extended releaseOral60 mg / src
Capsule, extended releaseOral90 mg / src
SuppositoryRectal10 mg / sup
SuppositoryRectal20 mg / sup
SuppositoryRectal30 mg / sup
Tablet, multilayer, extended releaseOral10 mg
Tablet, multilayer, extended releaseOral20 mg
Tablet, multilayer, extended releaseOral30 mg
Tablet, multilayer, extended releaseOral5 mg
Granule, delayed releaseOral100 mg
Granule, delayed releaseOral20 mg
Granule, delayed releaseOral30 mg
Granule, delayed releaseOral60 mg
Tablet, film coatedOral10 mg
Tablet, film coatedOral100 mg
Tablet, film coatedOral30 mg
Tablet, film coatedOral60 mg
TabletOral30 MG
CapsuleOral120 mg
CapsuleOral200 mg
CapsuleOral60 mg
TinctureOral10 mg/1mL
TinctureOral10 mg / mL
SolutionOral1 g/100mL
SolutionOral10 g/1000mL
SolutionOral10 mg/1mL
SolutionOral20 MG/ML
SolutionOral30 MG/5ML
SolutionOral
SolutionOral2 mg/ml
Solution / dropsOral20 mg/ml
TabletOral100 mg/1
TabletOral60 mg/1
Tablet, extended releaseOral100 mg / tab
SyrupOral2 MG/ML
LiquidOral2 mg/5mL
InjectionIntramuscular; Intravenous10 MG/ML
SyrupOral10 mg / mL
SyrupOral20 mg / mL
Solution / dropsOral50 mg / mL
Solution / dropsOral20 mg / mL
SuppositoryRectal20 mg
SuppositoryRectal30 mg
SuppositoryRectal5 mg
SyrupOral1 mg/ml
SyrupOral1 mg / mL
TabletOral10 mg
TabletOral5 mg
TabletOral25 mg
TabletOral50 mg
SolutionEpidural; Intramuscular; Intrathecal; Intravenous; Subcutaneous10 mg/ml
InjectionParenteral100 mg
InjectionParenteral200 mg
SolutionOral5 mg/ml
Capsule, extended releaseOral120 mg
Capsule, extended releaseOral20 mg
Capsule, extended releaseOral40 mg
Prices
Unit descriptionCostUnit
Depodur 15 mg/1.5 ml vial618.18USD ml
Roxanol 20 mg/ml Solution 120ml Bottle95.98USD bottle
Morphine Sulfate 20 mg/5ml Solution 500ml Bottle65.05USD bottle
Apokyn 30 mg/3 ml cartridge52.48USD ml
Morphine Sulfate 10 mg/5ml Solution 500ml Bottle38.55USD bottle
Kadian er 200 mg capsule35.43USD capsule
Kadian er 100 mg capsule23.01USD capsule
Roxanol 20 mg/ml Solution 30ml Bottle22.99USD bottle
Morphine Sulfate 10 mg/5ml Solution 100ml Bottle21.99USD bottle
Oramorph sr 60 mg tablet21.76USD tablet
Ms contin 200 mg tablet21.5USD tablet
Kadian er 80 mg capsule18.66USD capsule
Roxanol 20 mg/ml Solution 240ml Bottle17.99USD bottle
Avinza 90 mg capsule17.56USD capsule
Oramorph sr 100 mg tablet17.16USD tablet
Kadian 100 mg 24 Hour Capsule16.93USD capsule
MS Contin 200 mg 12 Hour tablet16.32USD tablet
Kadian 100 mg capsule sr16.25USD capsule
Kadian er 60 mg capsule14.31USD capsule
AVINza 90 mg 24 Hour Capsule13.21USD capsule
Kadian 80 mg capsule sr12.96USD capsule
Avinza 120 mg capsule12.07USD capsule
Kadian er 50 mg capsule11.76USD capsule
Ms contin 100 mg tablet11.75USD tablet
Avinza 60 mg capsule11.58USD capsule
AVINza 120 mg 24 Hour Capsule11.33USD capsule
Avinza 75 mg capsule10.79USD capsule
Morphine sulfate powder10.61USD g
Avinza 45 mg capsule10.22USD capsule
Kadian 60 mg 24 Hour Capsule9.06USD capsule
Morphine Sulfate CR 200 mg 12 Hour tablet8.97USD tablet
MS Contin 100 mg 12 Hour tablet8.89USD tablet
Morphine sulf 30 mg suppository8.44USD suppository
AVINza 60 mg 24 Hour Capsule8.36USD capsule
Ms contin 60 mg tablet7.95USD tablet
Infumorph 10 mg/ml ampul p-f7.8USD ml
Kadian 50 mg 24 Hour Capsule7.71USD capsule
Kadian er 30 mg capsule7.13USD capsule
Oramorph sr 30 mg tablet6.83USD tablet
Morphine sulf 20 mg suppository6.71USD suppository
Kadian er 10 mg capsule6.35USD capsule
Morphine sulf 10 mg suppository6.25USD suppository
Avinza 30 mg capsule6.0USD capsule
MS Contin 60 mg 12 Hour tablet5.71USD tablet
Kadian er 20 mg capsule5.69USD capsule
Ms Contin 200 mg Sustained-Release Tablet5.62USD tablet
Kadian 30 mg 24 Hour Capsule4.8USD capsule
Kadian 20 mg 24 Hour Capsule4.76USD capsule
AVINza 30 mg 24 Hour Capsule4.47USD capsule
Morphine sulf 5 mg suppository4.45USD suppository
Morphine Sulfate CR 100 mg 12 Hour tablet4.33USD tablet
M-Eslon 200 mg Extended-Release Capsule4.3USD capsule
Oramorph sr 15 mg tablet4.12USD tablet
Ms contin cr 30 mg tablet4.09USD tablet
Kadian 10 mg capsule sr4.05USD capsule
Morphine Hp 50 50 mg/ml4.01USD ml
Kadian 10 mg 24 Hour Capsule4.0USD capsule
Ms contin 15 mg tablet3.58USD tablet
MS Contin 30 mg 12 Hour tablet3.26USD tablet
Novo-Morphine Sr 200 mg Sustained-Release Tablet3.09USD tablet
Pms-Morphine Sulfate Sr 200 mg Sustained-Release Tablet3.09USD tablet
Ms Contin 100 mg Sustained-Release Tablet3.02USD tablet
Morphine Sulfate CR 60 mg 12 Hour tablet3.0USD tablet
Morphine Hp 25 25 mg/ml2.9USD ml
Statex 30 mg Suppository2.55USD suppository
Kadian 100 mg Sustained-Release Capsule2.35USD capsule
Statex 20 mg Suppository2.32USD suppository
Morphine Lp Epidural 1 mg/ml2.24USD ml
M-Eslon 100 mg Extended-Release Capsule2.15USD capsule
MS Contin 15 mg 12 Hour tablet2.13USD tablet
Ms Contin 60 mg Sustained-Release Tablet1.98USD tablet
Statex 10 mg Suppository1.95USD suppository
Morph sulf 5 mg/0.25 ml vial1.83USD vial
Statex 5 mg Suppository1.75USD suppository
Novo-Morphine Sr 100 mg Sustained-Release Tablet1.66USD tablet
Pms-Morphine Sulfate Sr 100 mg Sustained-Release Tablet1.66USD tablet
Morphine Sulfate CR 30 mg 12 Hour tablet1.63USD tablet
Morphine 8 mg/ml ampule1.56USD ml
Kadian 50 mg Sustained-Release Capsule1.35USD capsule
Duramorph 0.5 mg/ml ampul1.31USD ml
Astramorph-pf 1 mg/ml ampul1.15USD ml
Ms Contin 30 mg Sustained-Release Tablet1.13USD tablet
Morphine Lp Epidural 0.5 mg/ml1.12USD ml
Morphine Sulfate 15 mg/ml1.03USD ml
Morphine Sulfate 10 mg/ml1.02USD ml
Novo-Morphine Sr 60 mg Sustained-Release Tablet1.01USD tablet
Pms-Morphine Sulfate Sr 60 mg Sustained-Release Tablet1.01USD tablet
Ratio-Morphine Sulfate Sr 60 mg Sustained-Release Tablet1.01USD tablet
M-Eslon 60 mg Extended-Release Capsule1.0USD capsule
Statex 50 mg/ml Drops0.99USD ml
Morphine Sulfate CR 15 mg 12 Hour tablet0.93USD tablet
Duramorph 1 mg/ml ampul0.91USD ml
M.O.S.-Sr 60 mg Sustained-Release Tablet0.89USD tablet
Morphine 50 mg/25 ml-d5w syr0.86USD ml
Morphine-ns 10 mg/ml syringe0.86USD ml
Morphine-ns 5 mg/ml syringe0.8USD ml
Ms Contin 15 mg Sustained-Release Tablet0.75USD tablet
Morphine 5 mg/ml vial0.74USD ml
Kadian 20 mg Sustained-Release Capsule0.73USD capsule
Astramorph-pf 0.5 mg/ml amp0.72USD ml
Morphine Sulfate 15 mg tablet0.65USD tablet
Morphine Sulfate 30 mg tablet0.65USD tablet
Morphine 1 mg/ml vial p-f0.6USD ml
Morphine-ns 1 mg/ml syringe0.58USD ml
Novo-Morphine Sr 30 mg Sustained-Release Tablet0.57USD tablet
Pms-Morphine Sulfate Sr 30 mg Sustained-Release Tablet0.57USD tablet
Ratio-Morphine Sulfate Sr 30 mg Sustained-Release Tablet0.57USD tablet
M-Eslon 30 mg Extended-Release Capsule0.56USD capsule
Morphine 0.5 mg/ml vial0.55USD ml
Morphine sulfate 50 mg/ml vial0.55USD ml
Morphine sulfate ir 30 mg tablet0.55USD tablet
Ratio-Morphine 20 mg/ml Syrup0.55USD syrup
Statex 20 mg/ml Drops0.52USD ml
M.O.S.-Sr 30 mg Sustained-Release Tablet0.51USD tablet
Morphine 1 mg/ml syringe0.48USD ml
Morphine 10 mg/ml vial0.48USD ml
Ms.Ir 30 mg Tablet0.48USD tablet
Morphine sulfate 25 mg/ml vial0.43USD ml
Morphine sulf 1 mg/ml vial0.4USD ml
M.O.S. Sulfate 50 mg Tablet0.39USD tablet
Statex 50 mg Tablet0.39USD tablet
Kadian 10 mg Sustained-Release Capsule0.38USD capsule
M-Eslon 15 mg Extended-Release Capsule0.38USD capsule
Ms.Ir 20 mg Tablet0.38USD tablet
Novo-Morphine Sr 15 mg Sustained-Release Tablet0.37USD tablet
Pms-Morphine Sulfate Sr 15 mg Sustained-Release Tablet0.37USD tablet
Ratio-Morphine Sulfate Sr 15 mg Sustained-Release Tablet0.37USD tablet
M-Eslon 10 mg Extended-Release Capsule0.33USD capsule
Morphine sulfate ir 15 mg tablet0.32USD tablet
Morphine 15 mg/ml vial0.3USD ml
Morphine-ns 25 mg/25 ml syr0.26USD ml
M.O.S. Sulfate 25 mg Tablet0.25USD tablet
Statex 25 mg Tablet0.25USD tablet
Ms.Ir 10 mg Tablet0.21USD tablet
Ratio-Morphine 10 mg/ml Syrup0.19USD syrup
M.O.S. Sulfate 10 mg Tablet0.19USD tablet
Statex 10 mg Tablet0.19USD tablet
Morphine-ns 5 mg/ml0.16USD ml
Morphine-ns 55 mg/55 ml syr0.14USD ml
Ms.Ir 5 mg Tablet0.14USD tablet
M.O.S. Sulfate 5 mg Tablet0.12USD tablet
Statex 5 mg Tablet0.12USD tablet
Morphine 1 mg/ml-d5w 100 ml0.1USD ml
Morphine-ns 150 mg/150 ml0.1USD ml
Statex 5 mg/ml Syrup0.08USD ml
Morphine 1 mg/ml-d5w 250 ml0.06USD ml
Ratio-Morphine 5 mg/ml Syrup0.05USD syrup
Ratio-Morphine 1 mg/ml Syrup0.02USD syrup
Statex 1 mg/ml Syrup0.02USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5378474No1995-01-032010-03-23US flag
CA2065210No2000-08-292012-04-06Canada flag
CA2128591No1999-03-232014-07-21Canada flag
US6066339No2000-05-232017-11-25US flag
US5931809No1999-08-032015-07-14US flag
US5962016No1999-10-052017-01-31US flag
US6193998No2001-02-272016-09-01US flag
US5997899No1999-12-072016-09-01US flag
US6241999No2001-06-052016-09-01US flag
US5807572No1998-09-152015-09-15US flag
US5891467No1999-04-062017-01-31US flag
US6171613No2001-01-092016-10-01US flag
US8685443No2014-04-012025-07-03US flag
US8158156No2012-04-172027-06-19US flag
US7682633No2010-03-232027-06-19US flag
US8623418No2014-01-072029-11-07US flag
US8685444No2014-04-012025-07-03US flag
US8846104No2014-09-302027-06-19US flag
US7815934No2010-10-192027-12-12US flag
US7682634No2010-03-232027-06-19US flag
US8877247No2014-11-042027-06-19US flag
US9192608No2015-11-242034-03-12US flag
US9072781No2015-07-072034-03-12US flag
US9248229No2016-02-022034-03-12US flag
US7955619No2011-06-072028-08-12US flag
US9044402No2015-06-022033-07-01US flag
US9549899No2017-01-242033-07-01US flag
US10314788No2019-06-112028-08-12US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)255 °CMSDS
boiling point (°C)190ºCLide DR. CRC Handbook of Chemistry. 2004
water solubility149 mg/L (at 20 °C)MSDS
logP0.87Agilent Technology. LC/MS/MS Analysis of Opiates.
pKa8.21 (at 25 °C)Agilent Technology. LC/MS/MS Analysis of Opiates.
Predicted Properties
PropertyValueSource
Water Solubility10.2 mg/mLALOGPS
logP0.99ALOGPS
logP0.9Chemaxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.26Chemaxon
pKa (Strongest Basic)9.12Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area52.93 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity80.12 m3·mol-1Chemaxon
Polarizability29.94 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier+0.9882
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.8787
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.956
Renal organic cation transporterInhibitor0.6221
CYP450 2C9 substrateNon-substrate0.7451
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7375
CYP450 1A2 substrateNon-inhibitor0.5191
CYP450 2C9 inhibitorNon-inhibitor0.9046
CYP450 2D6 inhibitorNon-inhibitor0.647
CYP450 2C19 inhibitorNon-inhibitor0.8155
CYP450 3A4 inhibitorNon-inhibitor0.9176
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7503
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9634
BiodegradationNot ready biodegradable0.9944
Rat acute toxicity2.8989 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8367
hERG inhibition (predictor II)Non-inhibitor0.874
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.42 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00vl-1090000000-adcd23ce75ad17f72cc5
GC-MS Spectrum - EI-BGC-MSsplash10-00li-8970000000-28acaf307ce4bc5aabf1
GC-MS Spectrum - CI-BGC-MSsplash10-014i-0090000000-b9cf42b077ae0fa5b50d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0090000000-98125212ed8e73f219e1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0090000000-e9f7be236d827a716c1b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0290000000-5066e10cd96a2c376676
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0kui-0930000000-793deeb91de6d2459cbe
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-100r-0900000000-f775c77035946f746daa
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ufr-0390000000-660ff44516f98e346016
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-22857c8ef81e65ad6bd3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-c5194c99a9e7f30ea0c8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-1980ff8ab9e654f16fe1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0690000000-efa51d970eaf96d3b982
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0pc9-0920000000-64a693f2f51c03129c94
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-100r-0900000000-49174c3db4b1c1847080
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-3cc8784093ef460d3030
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-4bc885836f18b77696f3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-4a16648c3e86669f2446
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0690000000-f41b2f804790e9ad8f1d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0pc9-0920000000-69393fc6563baf39d91f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-100r-0900000000-467f39309be5edfa4c01
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ufr-0390000000-bd9670761ff2a7dafc55
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-b9e60f42c2a678767a82
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-8c1871352169254d9b1b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-6a389cf3b927867326de
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-46262bf01e645a0dc860
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00v0-0090000000-aee46827f2033b36283e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lr-0090000000-9bda5d94f74b5d3cc982
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-169.4437406
predicted
DarkChem Lite v0.1.0
[M-H]-169.5998406
predicted
DarkChem Lite v0.1.0
[M-H]-171.65544
predicted
DeepCCS 1.0 (2019)
[M+H]+168.9187406
predicted
DarkChem Lite v0.1.0
[M+H]+169.7718406
predicted
DarkChem Lite v0.1.0
[M+H]+174.05101
predicted
DeepCCS 1.0 (2019)
[M+Na]+168.5961406
predicted
DarkChem Lite v0.1.0
[M+Na]+169.4978406
predicted
DarkChem Lite v0.1.0
[M+Na]+181.08281
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Mu-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
Regulator
General Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin (PubMed:10529478, PubMed:12589820, PubMed:7891175, PubMed:7905839, PubMed:7957926, PubMed:9689128). Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone (PubMed:10529478, PubMed:10836142, PubMed:12589820, PubMed:19300905, PubMed:7891175, PubMed:7905839, PubMed:7957926, PubMed:9689128). Also activated by enkephalin peptides, such as Met-enkephalin or Met-enkephalin-Arg-Phe, with higher affinity for Met-enkephalin-Arg-Phe (By similarity). Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent exchange of GDP for GTP in the G-protein alpha subunit leading to dissociation of the G-protein complex with the free GTP-bound G-protein alpha and the G-protein beta-gamma dimer activating downstream cellular effectors (PubMed:7905839). The agonist- and cell type-specific activity is predominantly coupled to pertussis toxin-sensitive G(i) and G(o) G alpha proteins, GNAI1, GNAI2, GNAI3 and GNAO1 isoforms Alpha-1 and Alpha-2, and to a lesser extent to pertussis toxin-insensitive G alpha proteins GNAZ and GNA15 (PubMed:12068084). They mediate an array of downstream cellular responses, including inhibition of adenylate cyclase activity and both N-type and L-type calcium channels, activation of inward rectifying potassium channels, mitogen-activated protein kinase (MAPK), phospholipase C (PLC), phosphoinositide/protein kinase (PKC), phosphoinositide 3-kinase (PI3K) and regulation of NF-kappa-B (By similarity). Also couples to adenylate cyclase stimulatory G alpha proteins (By similarity). The selective temporal coupling to G-proteins and subsequent signaling can be regulated by RGSZ proteins, such as RGS9, RGS17 and RGS4 (By similarity). Phosphorylation by members of the GPRK subfamily of Ser/Thr protein kinases and association with beta-arrestins is involved in short-term receptor desensitization (By similarity). Beta-arrestins associate with the GPRK-phosphorylated receptor and uncouple it from the G-protein thus terminating signal transduction (By similarity). The phosphorylated receptor is internalized through endocytosis via clathrin-coated pits which involves beta-arrestins (By similarity). The activation of the ERK pathway occurs either in a G-protein-dependent or a beta-arrestin-dependent manner and is regulated by agonist-specific receptor phosphorylation (By similarity). Acts as a class A G-protein coupled receptor (GPCR) which dissociates from beta-arrestin at or near the plasma membrane and undergoes rapid recycling (By similarity). Receptor down-regulation pathways are varying with the agonist and occur dependent or independent of G-protein coupling (By similarity). Endogenous ligands induce rapid desensitization, endocytosis and recycling (By similarity). Heterooligomerization with other GPCRs can modulate agonist binding, signaling and trafficking properties (By similarity)
Specific Function
beta-endorphin receptor activity
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Yamada H, Shimoyama N, Sora I, Uhl GR, Fukuda Y, Moriya H, Shimoyama M: Morphine can produce analgesia via spinal kappa opioid receptors in the absence of mu opioid receptors. Brain Res. 2006 Apr 14;1083(1):61-9. Epub 2006 Mar 10. [Article]
  2. Choi HS, Kim CS, Hwang CK, Song KY, Wang W, Qiu Y, Law PY, Wei LN, Loh HH: The opioid ligand binding of human mu-opioid receptor is modulated by novel splice variants of the receptor. Biochem Biophys Res Commun. 2006 May 19;343(4):1132-40. Epub 2006 Mar 23. [Article]
  3. Castro RR, Cunha FQ, Silva FS Jr, Rocha FA: A quantitative approach to measure joint pain in experimental osteoarthritis--evidence of a role for nitric oxide. Osteoarthritis Cartilage. 2006 Aug;14(8):769-76. Epub 2006 Mar 31. [Article]
  4. Johnson EA, Oldfield S, Braksator E, Gonzalez-Cuello A, Couch D, Hall KJ, Mundell SJ, Bailey CP, Kelly E, Henderson G: Agonist-selective mechanisms of mu-opioid receptor desensitization in human embryonic kidney 293 cells. Mol Pharmacol. 2006 Aug;70(2):676-85. Epub 2006 May 8. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  6. Raffa RB: A novel approach to the pharmacology of analgesics. Am J Med. 1996 Jul 31;101(1A):40S-46S. doi: 10.1016/s0002-9343(96)00137-4. [Article]
  7. doi:10.1021/cn9000236 [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled opioid receptor that functions as a receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as a receptor for various synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Plays a role in the perception of pain. Plays a role in mediating reduced physical activity upon treatment with synthetic opioids. Plays a role in the regulation of salivation in response to synthetic opioids. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Specific Function
dynorphin receptor activity
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Leventhal L, Silva RM, Rossi GC, Pasternak GW, Bodnar RJ: Morphine-6beta-glucuronide-induced hyperphagia: characterization of opioid action by selective antagonists and antisense mapping in rats. J Pharmacol Exp Ther. 1998 Nov;287(2):538-44. [Article]
  4. Kozak CA, Filie J, Adamson MC, Chen Y, Yu L: Murine chromosomal location of the mu and kappa opioid receptor genes. Genomics. 1994 Jun;21(3):659-61. [Article]
  5. Teodorov E, Modena CC, Sukikara MH, Felicio LF: Preliminary study of the effects of morphine treatment on opioid receptor gene expression in brain structures of the female rat. Neuroscience. 2006 Sep 1;141(3):1225-31. Epub 2006 Jun 6. [Article]
  6. doi:10.1021/cn9000236 [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled receptor that functions as a receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Plays a role in the perception of pain and in opiate-mediated analgesia. Plays a role in developing analgesic tolerance to morphine
Specific Function
G protein-coupled enkephalin receptor activity
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Yamada H, Shimoyama N, Sora I, Uhl GR, Fukuda Y, Moriya H, Shimoyama M: Morphine can produce analgesia via spinal kappa opioid receptors in the absence of mu opioid receptors. Brain Res. 2006 Apr 14;1083(1):61-9. Epub 2006 Mar 10. [Article]
  2. Dortch-Carnes J, Russell KR: Morphine-induced reduction of intraocular pressure and pupil diameter: role of nitric oxide. Pharmacology. 2006;77(1):17-24. Epub 2006 Mar 13. [Article]
  3. Koch T, Wu DF, Yang LQ, Brandenburg LO, Hollt V: Role of phospholipase D2 in the agonist-induced and constitutive endocytosis of G-protein coupled receptors. J Neurochem. 2006 Apr;97(2):365-72. Epub 2006 Mar 15. [Article]
  4. Galeotti N, Stefano GB, Guarna M, Bianchi E, Ghelardini C: Signaling pathway of morphine induced acute thermal hyperalgesia in mice. Pain. 2006 Aug;123(3):294-305. Epub 2006 May 2. [Article]
  5. Asensio VJ, Miralles A, Garcia-Sevilla JA: Stimulation of mitogen-activated protein kinase kinases (MEK1/2) by mu-, delta- and kappa-opioid receptor agonists in the rat brain: regulation by chronic morphine and opioid withdrawal. Eur J Pharmacol. 2006 Jun 6;539(1-2):49-56. Epub 2006 Apr 6. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  7. Kieffer BL, Gaveriaux-Ruff C: Exploring the opioid system by gene knockout. Prog Neurobiol. 2002 Apr;66(5):285-306. [Article]
  8. doi:10.1021/cn9000236 [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Binds bacterial lipopolysaccharide (LPS) (PubMed:17569869, PubMed:17803912). Cooperates with TLR4 in the innate immune response to bacterial lipopolysaccharide (LPS), and with TLR2 in the response to cell wall components from Gram-positive and Gram-negative bacteria (PubMed:11160242, PubMed:11593030). Enhances TLR4-dependent activation of NF-kappa-B (PubMed:10359581). Cells expressing both LY96 and TLR4, but not TLR4 alone, respond to LPS (PubMed:10359581)
Specific Function
coreceptor activity
Gene Name
LY96
Uniprot ID
Q9Y6Y9
Uniprot Name
Lymphocyte antigen 96
Molecular Weight
18545.345 Da
References
  1. Hutchinson MR, Lewis SS, Coats BD, Rezvani N, Zhang Y, Wieseler JL, Somogyi AA, Yin H, Maier SF, Rice KC, Watkins LR: Possible involvement of toll-like receptor 4/myeloid differentiation factor-2 activity of opioid inactive isomers causes spinal proinflammation and related behavioral consequences. Neuroscience. 2010 May 19;167(3):880-93. doi: 10.1016/j.neuroscience.2010.02.011. Epub 2010 Feb 21. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
Specific Function
arachidonic acid epoxygenase activity
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Projean D, Morin PE, Tu TM, Ducharme J: Identification of CYP3A4 and CYP2C8 as the major cytochrome P450 s responsible for morphine N-demethylation in human liver microsomes. Xenobiotica. 2003 Aug;33(8):841-54. doi: 10.1080/0049825031000121608 . [Article]
  2. Daily EB, Aquilante CL: Cytochrome P450 2C8 pharmacogenetics: a review of clinical studies. Pharmacogenomics. 2009 Sep;10(9):1489-510. doi: 10.2217/pgs.09.82. [Article]
Details
2. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function
1,8-cineole 2-exo-monooxygenase activity
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Projean D, Morin PE, Tu TM, Ducharme J: Identification of CYP3A4 and CYP2C8 as the major cytochrome P450 s responsible for morphine N-demethylation in human liver microsomes. Xenobiotica. 2003 Aug;33(8):841-54. doi: 10.1080/0049825031000121608 . [Article]
  2. Takeda S, Ishii Y, Mackenzie PI, Nagata K, Yamazoe Y, Oguri K, Yamada H: Modulation of UDP-glucuronosyltransferase 2B7 function by cytochrome P450s in vitro: differential effects of CYP1A2, CYP2C9 and CYP3A4. Biol Pharm Bull. 2005 Oct;28(10):2026-7. [Article]
  3. Daily EB, Aquilante CL: Cytochrome P450 2C8 pharmacogenetics: a review of clinical studies. Pharmacogenomics. 2009 Sep;10(9):1489-510. doi: 10.2217/pgs.09.82. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:10702251, PubMed:15470161, PubMed:15472229, PubMed:17442341, PubMed:18674515, PubMed:18719240, PubMed:19022937, PubMed:23288867, PubMed:23756265, PubMed:26220143). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:15470161, PubMed:18674515, PubMed:23756265). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (epitestosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:15472229, PubMed:17442341, PubMed:18719240, PubMed:19022937, PubMed:2159463, PubMed:23288867, PubMed:26220143). Also regulates the levels of retinoic acid, a major metabolite of vitamin A involved in apoptosis, cellular growth and differentiation, and embryonic development (PubMed:10702251). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, caderastan and zolarsatan, drugs which can inhibit the effect of angiotensin II (PubMed:18674515). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161)
Specific Function
glucuronosyltransferase activity
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60720.15 Da
References
  1. Coffman BL, Rios GR, King CD, Tephly TR: Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos. 1997 Jan;25(1):1-4. [Article]
  2. Takeda S, Ishii Y, Iwanaga M, Mackenzie PI, Nagata K, Yamazoe Y, Oguri K, Yamada H: Modulation of UDP-glucuronosyltransferase function by cytochrome P450: evidence for the alteration of UGT2B7-catalyzed glucuronidation of morphine by CYP3A4. Mol Pharmacol. 2005 Mar;67(3):665-72. Epub 2004 Dec 20. [Article]
  3. Yamada H, Ishii K, Ishii Y, Ieiri I, Nishio S, Morioka T, Oguri K: Formation of highly analgesic morphine-6-glucuronide following physiologic concentration of morphine in human brain. J Toxicol Sci. 2003 Dec;28(5):395-401. [Article]
  4. Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. doi: 10.1124/dmd.109.030635. Epub 2010 Jan 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15472229, PubMed:18004206, PubMed:18004212, PubMed:18719240, PubMed:19830808, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004206, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol, estrone and estriol (PubMed:15472229, PubMed:18719240, PubMed:23288867). Involved in the glucuronidation of bilirubin, a degradation product occurring in the normal catabolic pathway that breaks down heme in vertebrates (PubMed:17187418, PubMed:18004206, PubMed:19830808, PubMed:24525562). Also catalyzes the glucuronidation the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:18004212, PubMed:20610558)
Specific Function
enzyme binding
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1A1
Molecular Weight
59590.91 Da
References
  1. Ohno S, Kawana K, Nakajin S: Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties. Drug Metab Dispos. 2008 Apr;36(4):688-94. doi: 10.1124/dmd.107.019281. Epub 2008 Jan 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:15472229, PubMed:16595710, PubMed:18004212, PubMed:18052087, PubMed:18674515, PubMed:18719240, PubMed:19545173, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:15472229, PubMed:16595710, PubMed:23288867). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens and estrogens (PubMed:15472229, PubMed:16595710, PubMed:18719240, PubMed:23288867). Produces dihydrotestosterone (DHT) diglucuronide from the DHT after two subsequent glucoronidation steps (PubMed:16595710). Also catalyzes the glucuronidation of the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist caderastan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161, PubMed:18004212)
Specific Function
enzyme binding
Gene Name
UGT1A8
Uniprot ID
Q9HAW9
Uniprot Name
UDP-glucuronosyltransferase 1A8
Molecular Weight
59741.035 Da
References
  1. Ohno S, Kawana K, Nakajin S: Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties. Drug Metab Dispos. 2008 Apr;36(4):688-94. doi: 10.1124/dmd.107.019281. Epub 2008 Jan 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:16595710, PubMed:18719240, PubMed:23288867, PubMed:7835232, PubMed:9295060). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:7835232). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (testosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:16595710, PubMed:18719240, PubMed:23288867, PubMed:7835232, PubMed:9295060). Displays glucuronidation activity toward several classes of xenobiotic substrates, including phenolic compounds (eugenol, 4-nitrophenol, 4-hydroxybiphenyl) and phenylpropanoids (naringenin, coumarins) (PubMed:7835232). Catalyzes the glucuronidation of monoterpenoid alcohols such as borneol, menthol and isomenthol, a class of natural compounds used in essential oils (By similarity)
Specific Function
glucuronosyltransferase activity
Gene Name
UGT2B15
Uniprot ID
P54855
Uniprot Name
UDP-glucuronosyltransferase 2B15
Molecular Weight
61035.815 Da
References
  1. Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. doi: 10.1124/dmd.109.030635. Epub 2010 Jan 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:18719240, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:18719240, PubMed:23288867). Catalyzes the glucuronidation of the endogenous estrogen hormones such as estradiol and estriol (PubMed:18719240, PubMed:23288867)
Specific Function
glucuronosyltransferase activity
Gene Name
UGT2B4
Uniprot ID
P06133
Uniprot Name
UDP-glucuronosyltransferase 2B4
Molecular Weight
60512.035 Da
References
  1. Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. doi: 10.1124/dmd.109.030635. Epub 2010 Jan 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:15472229, PubMed:18674515, PubMed:18719240, PubMed:23288867, PubMed:23756265, PubMed:24641623). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:23756265). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229, PubMed:18719240, PubMed:23288867). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of calcidiol, which is the major circulating form of vitamin D3, essential for the regulation of calcium and phosphate homeostasis (PubMed:24641623). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonists losartan, candesartan and zolarsartan, which can inhibit the effect of angiotensin II (PubMed:18674515)
Specific Function
enzyme binding
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1A3
Molecular Weight
60337.835 Da
References
  1. Green MD, King CD, Mojarrabi B, Mackenzie PI, Tephly TR: Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos. 1998 Jun;26(6):507-12. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
Specific Function
antioxidant activity
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Albumin
Molecular Weight
69365.94 Da
References
  1. Zhou R, Perez-Aguilar JM, Meng Q, Saven JG, Liu R: Opioid binding sites in human serum albumin. Anesth Analg. 2012 Jan;114(1):122-8. doi: 10.1213/ANE.0b013e318232e922. Epub 2011 Oct 24. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
Specific Function
ABC-type xenobiotic transporter activity
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
ATP-dependent translocase ABCB1
Molecular Weight
141477.255 Da
References
  1. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [Article]
  2. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [Article]
  3. FDA Approved Drug Products: Morphine Sulfate Oral Tablets [Link]

Drug created at June 13, 2005 13:24 / Updated at October 10, 2024 16:16