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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
PentazocinGermanINN
PentazocinaSpanishINN
PentazocineFrenchINN
PentazocinumLatin INN
Salts
Name/CAS Structure Properties
Pentazocine Hydrochloride
Thumb Not applicable DBSALT001009
Pentazocine Lactate
Thumb Not applicable DBSALT001010
Brand names
NameCompany
FortalSanofi-Aventis
FortralSanofi-Aventis
FortwinTerapia
PangonL.B.S.
PentaginDaiichi Sankyo
SosegonSanofi-Aventis
StopainBeximco
TalwinSanofi-Aventis
Talwin PXSanofi-Aventis
Brand mixtures
Brand NameIngredients
ExpergesicPentazocine and Paracetamol
ForacetPentazocine and Paracetamol
Talacenpentazocine + acetaminophen
Talwinpentazocine + naloxone
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[7.3.1.0^{2,7}]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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassTetralins
SubclassNot Available
Direct parentTetralins
Alternative parentsPhenols and Derivatives; Piperidines; Tertiary Amines; Polyamines; Enols
Substituentsphenol derivative; benzene; piperidine; tertiary amine; enol; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.
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
Property Value Probability
Human Intestinal Absorption + 0.9931
Blood Brain Barrier + 0.9769
Caco-2 permeable + 0.7902
P-glycoprotein substrate Substrate 0.9014
P-glycoprotein inhibitor I Inhibitor 0.8563
P-glycoprotein inhibitor II Inhibitor 0.6975
Renal organic cation transporter Inhibitor 0.6982
CYP450 2C9 substrate Non-substrate 0.7947
CYP450 2D6 substrate Substrate 0.8919
CYP450 3A4 substrate Substrate 0.7819
CYP450 1A2 substrate Inhibitor 0.5886
CYP450 2C9 substrate Non-inhibitor 0.8321
CYP450 2D6 substrate Inhibitor 0.8147
CYP450 2C19 substrate Non-inhibitor 0.8585
CYP450 3A4 substrate Non-inhibitor 0.8155
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.778
Ames test Non AMES toxic 0.8231
Carcinogenicity Non-carcinogens 0.9322
Biodegradation Not ready biodegradable 0.9888
Rat acute toxicity 2.4411 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Strong inhibitor 0.6301
hERG inhibition (predictor II) Inhibitor 0.5
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Hospira inc
Packagers
Dosage forms
FormRouteStrength
SolutionIntravenous
TabletOral
Prices
Unit descriptionCostUnit
Talwin 30 mg/ml vial14.78USDml
Talwin 30 mg/ml ampul4.86USDml
Talwin 30 mg/ml1.64USDml
Talwin 50 mg Tablet0.47USDtablet
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 solubility1.22e-01 g/lALOGPS
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 area23.47ChemAxon
rotatable bond count2ChemAxon
refractivity89.8ChemAxon
polarizability33.86ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00498
KEGG CompoundC07421
PubChem Compound441278
PubChem Substance46506363
ChemSpider390041
BindingDB50001028
Therapeutic Targets DatabaseDAP000356
PharmGKBPA164744326
IUPHAR1606
Guide to Pharmacology1606
Drug Product Database2241976
RxListhttp://www.rxlist.com/cgi/generic/pentazocine.htm
Drugs.comhttp://www.drugs.com/cdi/pentazocine.html
WikipediaPentazocine
ATC CodesN02AD01
AHFS Codes
  • 28:08.12
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(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