NAV

Diprenorphine

Identification

Generic Name
Diprenorphine
DrugBank Accession Number
DB01548
Background

A narcotic antagonist similar in action to naloxone. It is used to remobilize animals after etorphine neuroleptanalgesia and is considered a specific antagonist to etorphine. [PubChem]

Type
Small Molecule
Groups
Illicit, Vet approved
Structure
3D
Similar Structures
Weight
Average: 425.569
Monoisotopic: 425.256608611
Chemical Formula
C26H35NO4
Synonyms
  • Diprenorfin
  • Diprenorphine
External IDs
  • M-5050
  • M5050

Pharmacology

Indication

Diprenorphine is indicated to reverse the effects of powerful opioids including etorphine and carfentanil, often used for tranquilizing large animals. This drug is not approved for use in humans.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Diprenorphine binds approximately equally to the three subtypes of opioid receptorsand antagonizes them.

TargetActionsOrganism
AMu-type opioid receptor
antagonist
Humans
ADelta-type opioid receptor
antagonist
Humans
UKappa-type opioid receptor
antagonist
Humans
UE3 ubiquitin-protein ligase TRIM13Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

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
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interactions in your software
AlfentanilThe therapeutic efficacy of Alfentanil can be decreased when used in combination with Diprenorphine.
BenzhydrocodoneThe therapeutic efficacy of Benzhydrocodone can be decreased when used in combination with Diprenorphine.
BuprenorphineThe therapeutic efficacy of Buprenorphine can be decreased when used in combination with Diprenorphine.
ButorphanolThe therapeutic efficacy of Butorphanol can be decreased when used in combination with Diprenorphine.
CodeineThe therapeutic efficacy of Codeine can be decreased when used in combination with Diprenorphine.
DextropropoxypheneThe therapeutic efficacy of Dextropropoxyphene can be decreased when used in combination with Diprenorphine.
DezocineThe therapeutic efficacy of Dezocine can be decreased when used in combination with Diprenorphine.
DiamorphineThe therapeutic efficacy of Diamorphine can be decreased when used in combination with Diprenorphine.
DihydrocodeineThe therapeutic efficacy of Dihydrocodeine can be decreased when used in combination with Diprenorphine.
DiphenoxylateThe therapeutic efficacy of Diphenoxylate can be decreased when used in combination with Diprenorphine.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Diprenorphine hydrochlorideWBS7IEP4SN16808-86-9UNPUINKKJUSSDZ-UVGWPQHUSA-N
International/Other Brands
M5050 / Revivon

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenanthrenes and derivatives
Sub Class
Not Available
Direct Parent
Phenanthrenes and derivatives
Alternative Parents
Tetralins / Azaspirodecane derivatives / Coumarans / Aralkylamines / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Tertiary alcohols / Trialkylamines / Oxacyclic compounds
show 4 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azaspirodecane / Coumaran / Dialkyl ether
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
morphinane alkaloid (CHEBI:4650)
Affected organisms
Not Available

Chemical Identifiers

UNII
1F0L5N25ZZ
CAS number
14357-78-9
InChI Key
OIJXLIIMXHRJJH-KNLIIKEYSA-N
InChI
InChI=1S/C26H35NO4/c1-23(2,29)18-13-24-8-9-26(18,30-3)22-25(24)10-11-27(14-15-4-5-15)19(24)12-16-6-7-17(28)21(31-22)20(16)25/h6-7,15,18-19,22,28-29H,4-5,8-14H2,1-3H3/t18-,19-,22-,24-,25+,26-/m1/s1
IUPAC Name
(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-(2-hydroxypropan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC3CC3)[C@]([H])(C4)[C@]11CC[C@@]2(OC)[C@H](C1)C(C)(C)O

References

General References
Not Available
KEGG Compound
C11794
PubChem Compound
443408
PubChem Substance
46506559
ChemSpider
391634
BindingDB
50001714
ChEBI
4650
ChEMBL
CHEMBL281786
ZINC
ZINC000004102215
Guide to Pharmacology
GtP Drug Page
Wikipedia
Diprenorphine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedDiagnosticBody Dysmorphic Disorders / Loss of Appetite1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.104 mg/mLALOGPS
logP3.52ALOGPS
logP2.28Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)10.42Chemaxon
pKa (Strongest Basic)9.63Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area62.16 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity118.37 m3·mol-1Chemaxon
Polarizability47.86 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9055
Blood Brain Barrier+0.9401
Caco-2 permeable+0.6893
P-glycoprotein substrateSubstrate0.9126
P-glycoprotein inhibitor IInhibitor0.5192
P-glycoprotein inhibitor IINon-inhibitor0.6992
Renal organic cation transporterInhibitor0.5797
CYP450 2C9 substrateNon-substrate0.8366
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.8142
CYP450 1A2 substrateNon-inhibitor0.9153
CYP450 2C9 inhibitorNon-inhibitor0.8692
CYP450 2D6 inhibitorNon-inhibitor0.6721
CYP450 2C19 inhibitorNon-inhibitor0.7801
CYP450 3A4 inhibitorNon-inhibitor0.8322
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9212
Ames testNon AMES toxic0.7448
CarcinogenicityNon-carcinogens0.9391
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.1511 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8366
hERG inhibition (predictor II)Non-inhibitor0.586
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Mu-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Leung K: [6-O-methyl-11C]Diprenorphine . [Article]
Details2. Delta-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Willoch F, Tolle TR, Wester HJ, Munz F, Petzold A, Schwaiger M, Conrad B, Bartenstein P: Central pain after pontine infarction is associated with changes in opioid receptor binding: a PET study with 11C-diprenorphine. AJNR Am J Neuroradiol. 1999 Apr;20(4):686-90. [Article]
  2. Jones AK, Kitchen ND, Watabe H, Cunningham VJ, Jones T, Luthra SK, Thomas DG: Measurement of changes in opioid receptor binding in vivo during trigeminal neuralgic pain using [11C] diprenorphine and positron emission tomography. J Cereb Blood Flow Metab. 1999 Jul;19(7):803-8. [Article]
  3. Kampa M, Hatzoglou A, Notas G, Niniraki M, Kouroumalis E, Castanas E: Opioids are non-competitive inhibitors of nitric oxide synthase in T47D human breast cancer cells. Cell Death Differ. 2001 Sep;8(9):943-52. [Article]
  4. Marie N, Lecoq I, Jauzac P, Allouche S: Differential sorting of human delta-opioid receptors after internalization by peptide and alkaloid agonists. J Biol Chem. 2003 Jun 20;278(25):22795-804. Epub 2003 Apr 2. [Article]
  5. Webster JM, Bentley MT, Wojcikiewicz RJ: N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine inhibits ligand binding to certain G protein-coupled receptors. Eur J Pharmacol. 2003 Aug 1;474(1):1-5. [Article]
  6. Leung K: [6-O-methyl-11C]Diprenorphine . [Article]
Details3. Kappa-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Leung K: [6-O-methyl-11C]Diprenorphine . [Article]
Details4. E3 ubiquitin-protein ligase TRIM13
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
E3 ubiquitin ligase involved in the retrotranslocation and turnover of membrane and secretory proteins from the ER through a set of processes named ER-associated degradation (ERAD). This process ac...
Gene Name
TRIM13
Uniprot ID
O60858
Uniprot Name
E3 ubiquitin-protein ligase TRIM13
Molecular Weight
46987.08 Da
References
  1. Law PY, Hom DS, Loh HH: Multiple affinity states of opiate receptor in neuroblastoma x glioma NG108-15 hybrid cells. Opiate agonist association rate is a function of receptor occupancy. J Biol Chem. 1985 Mar 25;260(6):3561-9. [Article]
  2. Pfeiffer A, Herz A: Discrimination of three opiate receptor binding sites with the use of a computerized curve-fitting technique. Mol Pharmacol. 1982 Mar;21(2):266-71. [Article]
  3. Chang KJ, Hazum E, Cuatrecasas P: Novel opiate binding sites selective for benzomorphan drugs. Proc Natl Acad Sci U S A. 1981 Jul;78(7):4141-5. [Article]
  4. Pfeiffer A, Herz A: Enhancement of delta- but not mu-opiate agonist binding by calcium. Naunyn Schmiedebergs Arch Pharmacol. 1982 May;319(2):147-53. [Article]
  5. Cvejic S, Trapaidze N, Cyr C, Devi LA: Thr353, located within the COOH-terminal tail of the delta opiate receptor, is involved in receptor down-regulation. J Biol Chem. 1996 Feb 23;271(8):4073-6. [Article]

Drug created at July 31, 2007 13:10 / Updated at February 21, 2021 18:51