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Identification
NamePentazocine
Accession NumberDB00652  (APRD01173)
TypeSmall Molecule
GroupsApproved
Description

The first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. (From AMA Drug Evaluations Annual, 1991, p97)

Structure
Thumb
Synonyms
SynonymLanguageCode
FortralNot AvailableNot Available
PentazocinGermanINN
PentazocinaSpanishINN
PentazocineFrenchINN
PentazocinumLatin INN
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Talwininjection, solution30 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2010-10-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Talwininjection, solution30 mg/mLintramuscular; intravenous; subcutaneousHospira, Inc.2010-10-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Talwininjection, solution30 mg/mLintramuscular; intravenous; subcutaneousGeneral Injectables & Vaccines, Inc2010-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
FortalSanofi-Aventis
FortralSanofi-Aventis
FortwinTerapia
PangonL.B.S.
PentaginDaiichi Sankyo
SosegonSanofi-Aventis
StopainBeximco
Talwin PXSanofi-Aventis
Brand mixtures
Brand NameIngredients
ExpergesicPentazocine and Paracetamol
ForacetPentazocine and Paracetamol
Talacenpentazocine + acetaminophen
Talwinpentazocine + naloxone
Salts
Name/CASStructureProperties
Pentazocine Hydrochloride
ThumbNot applicableDBSALT001009
Pentazocine Lactate
ThumbNot applicableDBSALT001010
Categories
CAS number359-83-1
WeightAverage: 285.4238
Monoisotopic: 285.209264491
Chemical FormulaC19H27NO
InChI KeyVOKSWYLNZZRQPF-GDIGMMSISA-N
InChI
InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m0/s1
IUPAC Name
(1R,9R,13R)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6-trien-4-ol
SMILES
C[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CC=C(C)C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 6,7-benzomorphans. These are opioid alkaloids based on the tricyclic 6,7-benzomorphan skeleton. Benzomorphans lack the C ring of morphine.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
Class6,7-benzomorphans
Sub ClassNot Available
Direct Parent6,7-benzomorphans
Alternative Parents
Substituents
  • 6,7-benzomorphan
  • Benzazocine
  • Tetralin
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the relief of moderate to severe pain.
PharmacodynamicsPentazocine is a potent analgesic which when administered orally in a 50 mg dose appears equivalent in analgesic effect to 60 mg (1 grain) of codeine. Onset of significant analgesia usually occurs between 15 and 30 minutes after oral administration, and duration of action is usually three hours or longer. Onset and duration of action and the degree of pain relief are related both to dose and the severity of pretreatment pain. Pentazocine weakly antagonizes the analgesic effects of morphine and meperidine; in addition, it produces incomplete reversal of cardiovascular, respiratory, and behavioral depression induced by morphine and meperidine. Pentazocine has about 1/50 the antagonistic activity of nalorphine. It also has sedative activity.
Mechanism of actionThe preponderance of evidence suggests that pentazocine antagonizes the opioid effects by competing for the same receptor sites, especially the opioid mu receptor.
AbsorptionWell absorbed from the gastro-intestinal tract.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half life2 to 3 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Pentazocine Action PathwayDrug actionSMP00686
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9931
Blood Brain Barrier+0.9769
Caco-2 permeable+0.7902
P-glycoprotein substrateSubstrate0.9014
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IIInhibitor0.6975
Renal organic cation transporterInhibitor0.6982
CYP450 2C9 substrateNon-substrate0.7947
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7819
CYP450 1A2 substrateInhibitor0.5886
CYP450 2C9 substrateNon-inhibitor0.8321
CYP450 2D6 substrateInhibitor0.8147
CYP450 2C19 substrateNon-inhibitor0.8585
CYP450 3A4 substrateNon-inhibitor0.8155
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.778
Ames testNon AMES toxic0.8231
CarcinogenicityNon-carcinogens0.9322
BiodegradationNot ready biodegradable0.9888
Rat acute toxicity2.4411 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6301
hERG inhibition (predictor II)Inhibitor0.5
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Hospira inc
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintramuscular; intravenous; subcutaneous30 mg/mL
Prices
Unit descriptionCostUnit
Talwin 30 mg/ml vial14.78USD ml
Talwin 30 mg/ml ampul4.86USD ml
Talwin 30 mg/ml1.64USD ml
Talwin 50 mg Tablet0.47USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point146.3 °CPhysProp
logP4.64DAYLIGHT (1999)
pKa8.88SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.122 mg/mLALOGPS
logP4.44ALOGPS
logP3.89ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.59ChemAxon
pKa (Strongest Basic)12.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.8 m3·mol-1ChemAxon
Polarizability33.86 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesN02AD01
AHFS Codes
  • 28:08.12
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (48.4 KB)
Interactions
Drug Interactions
Drug
AlvimopanIncreases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
TriprolidineThe CNS depressants, Triprolidine and Pentazocine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Food Interactions
  • Take without regard to meals. Avoid alcohol.

Targets

1. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

References:

  1. Levine JD, Gordon NC: Synergism between the analgesic actions of morphine and pentazocine. Pain. 1988 Jun;33(3):369-72. Pubmed
  2. Martin BR, Katzen JS, Woods JA, Tripathi HL, Harris LS, May EL: Stereoisomers of [3H]-N-allylnormetazocine bind to different sites in mouse brain. J Pharmacol Exp Ther. 1984 Dec;231(3):539-44. Pubmed
  3. Kamei J, Iwamoto Y, Misawa M, Nagase H, Kasuya Y: Effects of diabetes on the antinociceptive effect of (+/-)pentazocine in mice. Res Commun Chem Pathol Pharmacol. 1994 Apr;84(1):105-10. Pubmed
  4. Picker MJ, Benyas S, Horwitz JA, Thompson K, Mathewson C, Smith MA: Discriminative stimulus effects of butorphanol: influence of training dose on the substitution patterns produced by Mu, Kappa and Delta opioid agonists. J Pharmacol Exp Ther. 1996 Dec;279(3):1130-41. Pubmed
  5. Saha N, Datta H, Sharma PL: Effects of morphine, buprenorphine, pentazocine and nalorphine on acquisition and extinction of active avoidance responses in rats. Indian J Physiol Pharmacol. 1990 Jul;34(3):179-82. Pubmed

2. Kappa-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Kappa-type opioid receptor P41145 Details

References:

  1. Chien CC, Pasternak GW: (-)-Pentazocine analgesia in mice: interactions with a sigma receptor system. Eur J Pharmacol. 1995 Dec 27;294(1):303-8. Pubmed

3. Sigma non-opioid intracellular receptor 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Sigma non-opioid intracellular receptor 1 Q99720 Details

References:

  1. Chien CC, Pasternak GW: (-)-Pentazocine analgesia in mice: interactions with a sigma receptor system. Eur J Pharmacol. 1995 Dec 27;294(1):303-8. Pubmed
  2. Colabufo NA, Contino M, Inglese C, Niso M, Perrone R, Roperto S, Roperto F: In vitro and ex vivo characterization of sigma-1 and sigma-2 receptors: agonists and antagonists in biological assays. Cent Nerv Syst Agents Med Chem. 2009 Sep;9(3):161-71. Pubmed
  3. Dun Y, Thangaraju M, Prasad P, Ganapathy V, Smith SB: Prevention of excitotoxicity in primary retinal ganglion cells by (+)-pentazocine, a sigma receptor-1 specific ligand. Invest Ophthalmol Vis Sci. 2007 Oct;48(10):4785-94. Pubmed
  4. Mamolo MG, Zampieri D, Zanette C, Florio C, Collina S, Urbano M, Azzolina O, Vio L: Substituted benzylaminoalkylindoles with preference for the sigma2 binding site. Eur J Med Chem. 2008 Oct;43(10):2073-81. Epub 2007 Sep 26. Pubmed
  5. Pal A, Hajipour AR, Fontanilla D, Ramachandran S, Chu UB, Mavlyutov T, Ruoho AE: Identification of regions of the sigma-1 receptor ligand binding site using a novel photoprobe. Mol Pharmacol. 2007 Oct;72(4):921-33. Epub 2007 Jul 10. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 15, 2014 16:59