Nalbuphine

Identification

Summary

Nalbuphine is an opioid agonist-antagonist used to treat pain, for pre and postoperative analgesia, and for analgesia in labor and delivery.

Generic Name
Nalbuphine
DrugBank Accession Number
DB00844
Background

A narcotic used as a pain medication. It appears to be an agonist at kappa opioid receptors and an antagonist or partial agonist at mu opioid receptors. Nalbuphine is the only opioid analgesic that is not a controlled substance in the United States.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 357.4434
Monoisotopic: 357.194008357
Chemical Formula
C21H27NO4
Synonyms
  • N-cyclobutylmethyl-4,5α-epoxy-3,6α,14-morphinantriol
  • Nalbufina
  • Nalbuphin
  • Nalbuphine
  • Nalbuphinum
External IDs
  • EN-2234 A

Pharmacology

Indication

For the relief of moderate to severe pain.

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Nalbuphine is a synthetic opioid agonist-antagonist analgesic of the phenanthrene series. Nalbuphine's analgesic potency is essentially equivalent to that of morphine on a milligram basis. The opoioid antagonist activity of nalbuphine is about one-fourth to that of nalorphine and 10 times to that of pentazocine. Nalbuphine by itself has potent opioid antagonist activity at doses equal to or lower than its analgesic dose. When administered following or concurrent with mu agonist opioid analgesics (e.g., morphine, oxymorphone, fentanyl), nalbuphine may partially reverse or block opioid-induced respiratory depression from the mu agonist analgesic. Nalbuphine may precipitate withdrawal in patients dependent on opioid drugs. Nalbuphine should be used with caution in patients who have been receiving mu opioid analgesics on a regular basis.

Mechanism of action

The exact mechanism of action is unknown, but is believed to interact with an opiate receptor site in the CNS (probably in or associated with the limbic system). The opiate antagonistic effect may result from competitive inhibition at the opiate receptor, but may also be a result of other mechanisms. Nalbuphine is thought primarily to be a kappa agonist. It is also a partial mu antagonist analgesic, with some binding to the delta receptor and minimal agonist activity at the sigma receptor.

TargetActionsOrganism
AKappa-type opioid receptor
agonist
Humans
AMu-type opioid receptor
antagonist
Humans
ADelta-type opioid receptor
antagonist
Humans
Absorption

The mean absolute bioavailability was 81% and 83% for the 10 and 20 mg intramuscular doses, respectively, and 79% and 76% following 10 and 20 mg of subcutaneous nalbuphine. Clinical studies show that the duration of analgesic activity of the drug can range from 3 to 6 hours.

Volume of distribution

Not Available

Protein binding

Not appreciably bound.

Metabolism
Not Available
Route of elimination

Not Available

Half-life

The plasma half-life of nalbuphine is about 5 hours.

Clearance

Not Available

Adverse Effects
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Toxicity

Oral, acute LD50 is 1100 mg/kg in dog. Symptoms of overdose include primarily sleepiness and mild dysphoria.

Pathways
PathwayCategory
Nalbuphine Action PathwayDrug action
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
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Nalbuphine.
AcetophenazineThe risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Nalbuphine.
AclidiniumThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Agomelatine.
AlfentanilThe therapeutic efficacy of Nalbuphine can be decreased when used in combination with Alfentanil.
AlimemazineThe risk or severity of hypotension and CNS depression can be increased when Alimemazine is combined with Nalbuphine.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Nalbuphine.
AlmotriptanThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Almotriptan.
AlosetronThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Alosetron.
Interactions
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Food Interactions
  • Avoid alcohol. Ingesting alcohol may increase the sedative and CNS depressant effects of nalbuphine.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Nalbuphine hydrochlorideZU4275277R23277-43-2YZLZPSJXMWGIFH-BCXQGASESA-N
International/Other Brands
Mexifen (Medicus) / Nalbuphine (Mylan) / Nalpain (Orpha-Devel)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
NubainInjection, solution20 mg/1mLIntramuscular; Intravenous; SubcutaneousEndo Pharmaceuticals1979-05-152006-10-31US flag
NubainInjection, solution10 mg/1mLIntramuscular; Intravenous; SubcutaneousPhysicians Total Care, Inc.1979-05-152011-05-31US flag
NubainInjection, solution20 mg/1mLIntramuscular; Intravenous; SubcutaneousEndo Pharmaceuticals1979-05-152006-11-30US flag
NubainInjection, solution10 mg/1mLIntramuscular; Intravenous; SubcutaneousEndo Pharmaceuticals1979-05-152007-01-31US flag
NubainInjection, solution10 mg/1mLIntramuscular; Intravenous; SubcutaneousEndo Pharmaceuticals1979-05-152006-03-31US flag
NubainInjection, solution10 mg/1mLIntramuscular; Intravenous; SubcutaneousPhysicians Total Care, Inc.1979-05-152011-05-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Nalbuphine HciInjection, solution20 mg/1mLIntramuscular; Intravenous; SubcutaneousHF Acquisition Co LLC, DBA HealthFirst2019-10-29Not applicableUS flag
Nalbuphine HciInjection, solution10 mg/1mLIntramuscular; Intravenous; SubcutaneousHF Acquisition Co LLC, DBA HealthFirst2019-10-29Not applicableUS flag
Nalbuphine HydrochlorideInjection, solution20 mg/1mLIntramuscular; Intravenous; SubcutaneousBarr Laboratories1998-05-192011-02-28US flag
Nalbuphine HydrochlorideInjection, solution20 mg/1mLIntramuscular; Intravenous; SubcutaneousMcKesson Corporation dba SKY Packaging2004-12-31Not applicableUS flag
Nalbuphine HydrochlorideInjection, solution10 mg/1mLIntramuscular; Intravenous; SubcutaneousMedical Purchasing Solutions, Llc2005-07-19Not applicableUS flag
Nalbuphine HydrochlorideInjection, solution10 mg/1mLIntramuscular; Intravenous; SubcutaneousCardinal Health1989-02-032012-10-31US flag
Nalbuphine HydrochlorideInjection, solution20 mg/1mLIntramuscular; Intravenous; SubcutaneousGeneral Injectables and Vaccines,Inc.2021-04-19Not applicableUS flag
Nalbuphine HydrochlorideInjection, solution20 mg/1mLIntramuscular; Intravenous; SubcutaneousBarr Laboratories1998-05-192010-11-30US flag
Nalbuphine HydrochlorideInjection, solution20 mg/1mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2004-12-31Not applicableUS flag
Nalbuphine HydrochlorideInjection, solution10 mg/1mLIntramuscular; Intravenous; SubcutaneousBarr Laboratories1998-05-192011-03-31US flag

Categories

ATC Codes
N02AF02 — Nalbuphine
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 / Coumarans / 1-hydroxy-2-unsubstituted benzenoids / Alkyl aryl ethers / Aralkylamines / Piperidines / Tertiary alcohols / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols
show 6 more
Substituents
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Coumaran / Cyclic alcohol
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound (CHEBI:7454)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
L2T84IQI2K
CAS number
20594-83-6
InChI Key
NETZHAKZCGBWSS-CEDHKZHLSA-N
InChI
InChI=1S/C21H27NO4/c23-14-5-4-13-10-16-21(25)7-6-15(24)19-20(21,17(13)18(14)26-19)8-9-22(16)11-12-2-1-3-12/h4-5,12,15-16,19,23-25H,1-3,6-11H2/t15-,16+,19-,20-,21+/m0/s1
IUPAC Name
(1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18)-triene-10,14,17-triol
SMILES
O[C@H]1CC[C@@]2(O)[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3CC2CCC2)[C@H]1O5

References

Synthesis Reference

Michael R. Magruder, "Nalbuphine-narcotic analgesic composition and method of producing analgesia." U.S. Patent US4366159, issued August, 1981.

US4366159
General References
  1. Gear RW, Miaskowski C, Gordon NC, Paul SM, Heller PH, Levine JD: The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain. Pain. 1999 Nov;83(2):339-45. [Article]
Human Metabolome Database
HMDB0014982
KEGG Drug
D08246
KEGG Compound
C07251
PubChem Compound
5311304
PubChem Substance
46507383
ChemSpider
4470813
BindingDB
50105085
RxNav
7238
ChEBI
7454
ChEMBL
CHEMBL895
ZINC
ZINC000003812989
Therapeutic Targets Database
DAP000380
PharmGKB
PA164745372
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Nalbuphine
AHFS Codes
  • 28:08.12 — Opiate Partial Agonists
FDA label
Download (51.4 KB)
MSDS
Download (74.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionCesarean Section1
4CompletedSupportive CareNalbuphine,Fentanyl and Local Anesthetic Mixture1
4CompletedTreatmentAnaesthesia therapy1
4CompletedTreatmentInadequate or Impaired Respiratory Function / Pain1
4CompletedTreatmentPostoperative pain1
4RecruitingTreatmentPain1
4RecruitingTreatmentThe Effect of Analgesic Drugs on Respiratory Center1
4Unknown StatusTreatmentPostoperative pain2
3CompletedTreatmentPain / Sickle Cell Disease (SCD)1
3CompletedTreatmentPruritus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Barr Pharmaceuticals
  • Bristol-Myers Squibb Co.
  • Cardinal Health
  • Dispensing Solutions
  • Endo Pharmaceuticals Inc.
  • Hospira Inc.
  • Mckesson Corp.
  • Neuman Distributors Inc.
  • Physicians Total Care Inc.
  • Quality Care
Dosage Forms
FormRouteStrength
InjectionIntramuscular; Intravenous; Subcutaneous
SolutionIntravenous10 mg
Injection, solutionParenteral
Injection, solutionIntramuscular; Intravenous; Subcutaneous10 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous20 mg/1mL
SolutionIntramuscular; Intravenous; Subcutaneous
Injection, solution
SolutionIntravenous
Prices
Unit descriptionCostUnit
Nubain 20 mg/ml ampule4.9USD ml
Nubain 10 mg/ml vial3.53USD ml
Nalbuphine 20 mg/ml ampul3.2USD ml
Nalbuphine 200 mg/10 ml vial2.66USD ml
Nalbuphine 10 mg/ml ampul1.46USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)230 °C as HCl saltNot Available
water solubility35.5 mg/mL at 25 °C as HCl saltNot Available
logP1.4Not Available
pKa8.71 and 9.96 (hcl form)FDA Label
Predicted Properties
PropertyValueSource
Water Solubility2.09 mg/mLALOGPS
logP2ALOGPS
logP1.19ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.45ChemAxon
pKa (Strongest Basic)13.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.16 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97 m3·mol-1ChemAxon
Polarizability38.59 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.968
Blood Brain Barrier+0.9642
Caco-2 permeable+0.7337
P-glycoprotein substrateSubstrate0.8532
P-glycoprotein inhibitor INon-inhibitor0.8781
P-glycoprotein inhibitor IINon-inhibitor0.8923
Renal organic cation transporterInhibitor0.5431
CYP450 2C9 substrateNon-substrate0.8645
CYP450 2D6 substrateSubstrate0.5896
CYP450 3A4 substrateSubstrate0.5919
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9421
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9029
CYP450 3A4 inhibitorNon-inhibitor0.93
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9562
Ames testNon AMES toxic0.6897
CarcinogenicityNon-carcinogens0.9598
BiodegradationNot ready biodegradable0.9796
Rat acute toxicity2.6502 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.747
hERG inhibition (predictor II)Non-inhibitor0.8054
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

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
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. 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. Hoehe M, Duka T: Opiates increase plasma catecholamines in humans. Psychoneuroendocrinology. 1993;18(2):141-8. [Article]
  4. Chen SL, Huang EY, Chow LH, Tao PL: Dextromethorphan differentially affects opioid antinociception in rats. Br J Pharmacol. 2005 Feb;144(3):400-4. [Article]
  5. Tao PL, Liang KW, Sung WY, Wu YT, Huang EY: Nalbuphine is effective in decreasing the rewarding effect induced by morphine in rats. Drug Alcohol Depend. 2006 Sep 15;84(2):175-81. Epub 2006 Mar 6. [Article]
  6. Smith MA, Greene-Naples JL, Lyle MA, Iordanou JC, Felder JN: The effects of repeated opioid administration on locomotor activity: I. Opposing actions of mu and kappa receptors. J Pharmacol Exp Ther. 2009 Aug;330(2):468-75. doi: 10.1124/jpet.108.150011. Epub 2009 Apr 29. [Article]
  7. Mello NK, Mendelson JH, Sholar MB, Jaszyna-Gasior M, Goletiani N, Siegel AJ: Effects of the mixed mu/kappa opioid nalbuphine on cocaine-induced changes in subjective and cardiovascular responses in men. Neuropsychopharmacology. 2005 Mar;30(3):618-32. [Article]
  8. Gear RW, Miaskowski C, Gordon NC, Paul SM, Heller PH, Levine JD: The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain. Pain. 1999 Nov;83(2):339-45. [Article]
  9. Peng X, Knapp BI, Bidlack JM, Neumeyer JL: Pharmacological properties of bivalent ligands containing butorphan linked to nalbuphine, naltrexone, and naloxone at mu, delta, and kappa opioid receptors. J Med Chem. 2007 May 3;50(9):2254-8. Epub 2007 Apr 4. [Article]
Details
2. 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. Kishioka S, Ko MC, Woods JH: Diltiazem enhances the analgesic but not the respiratory depressant effects of morphine in rhesus monkeys. Eur J Pharmacol. 2000 May 26;397(1):85-92. [Article]
  2. Hoehe M, Duka T: Opiates increase plasma catecholamines in humans. Psychoneuroendocrinology. 1993;18(2):141-8. [Article]
  3. Zernig G, Lewis JW, Woods JH: Clocinnamox inhibits the intravenous self-administration of opioid agonists in rhesus monkeys: comparison with effects on opioid agonist-mediated antinociception. Psychopharmacology (Berl). 1997 Feb;129(3):233-42. [Article]
  4. Picker MJ: Discriminative stimulus effects of the mixed-opioid agonist/antagonist dezocine: cross-substitution by mu and delta opioid agonists. J Pharmacol Exp Ther. 1997 Dec;283(3):1009-17. [Article]
  5. McNicol ED, Boyce D, Schumann R, Carr DB: Mu-opioid antagonists for opioid-induced bowel dysfunction. Cochrane Database Syst Rev. 2008 Apr 16;(2):CD006332. doi: 10.1002/14651858.CD006332.pub2. [Article]
  6. Tao PL, Liang KW, Sung WY, Wu YT, Huang EY: Nalbuphine is effective in decreasing the rewarding effect induced by morphine in rats. Drug Alcohol Depend. 2006 Sep 15;84(2):175-81. Epub 2006 Mar 6. [Article]
  7. Smith MA, Greene-Naples JL, Lyle MA, Iordanou JC, Felder JN: The effects of repeated opioid administration on locomotor activity: I. Opposing actions of mu and kappa receptors. J Pharmacol Exp Ther. 2009 Aug;330(2):468-75. doi: 10.1124/jpet.108.150011. Epub 2009 Apr 29. [Article]
  8. Mello NK, Mendelson JH, Sholar MB, Jaszyna-Gasior M, Goletiani N, Siegel AJ: Effects of the mixed mu/kappa opioid nalbuphine on cocaine-induced changes in subjective and cardiovascular responses in men. Neuropsychopharmacology. 2005 Mar;30(3):618-32. [Article]
  9. Meerpohl JJ, Timmer A: [News from the cochrane library: mu opioid antagonists for opioid-induced bowel dysfunction]. Z Gastroenterol. 2008 Sep;46(9):917-21. doi: 10.1055/s-2008-1027720. Epub 2008 Sep 22. [Article]
  10. Peng X, Knapp BI, Bidlack JM, Neumeyer JL: Pharmacological properties of bivalent ligands containing butorphan linked to nalbuphine, naltrexone, and naloxone at mu, delta, and kappa opioid receptors. J Med Chem. 2007 May 3;50(9):2254-8. Epub 2007 Apr 4. [Article]
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. Chen JC, Smith ER, Cahill M, Cohen R, Fishman JB: The opioid receptor binding of dezocine, morphine, fentanyl, butorphanol and nalbuphine. Life Sci. 1993;52(4):389-96. [Article]
  2. De Souza EB, Schmidt WK, Kuhar MJ: Nalbuphine: an autoradiographic opioid receptor binding profile in the central nervous system of an agonist/antagonist analgesic. J Pharmacol Exp Ther. 1988 Jan;244(1):391-402. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created on June 13, 2005 13:24 / Updated on May 10, 2021 04:39