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Identification
Name Pentazocine
Accession Number DB00652 (APRD01173)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
L-pentazocine
Pentazocaine
Pentazocin
Salts Not Available
Brand names
Name Company
Fortalgesic
Fortalin
Fortral
Liticon
Pentagin
Soseton
Sosigon
Talwan
Brand mixtures
Brand Name Ingredients
Talacen pentazocine + acetaminophen
Talwin pentazocine + naloxone
Categories
  • Narcotics
  • Adjuvants, Anesthesia
  • Analgesics, Opioid
  • Narcotic Antagonists
CAS number 359-83-1
Weight Average: 285.4238
Monoisotopic: 285.209264491
Chemical Formula C19H27NO
InChI Key InChIKey=VOKSWYLNZZRQPF-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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Morphinans
Substructures
  • Morphinans
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Naphthalenes
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Phenylpiperidines
  • Aliphatic and Aryl Amines
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Phenylpropylamines
  • Cyclohexenes and Derivatives
  • Phenyl Esters
  • Amphetamines
  • Piperidines
Pharmacology
Indication For the relief of moderate to severe pain.
Pharmacodynamics Pentazocine 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 action The preponderance of evidence suggests that pentazocine antagonizes the opioid effects by competing for the same receptor sites, especially the opioid mu receptor.
Absorption Well absorbed from the gastro-intestinal tract.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Hepatic
Route of elimination Not Available
Half life 2 to 3 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Hospira inc
Packagers
Dosage forms
Form Route Strength
Solution Intravenous
Tablet Oral
Prices
Unit description Cost Unit
Talwin 30 mg/ml vial 14.78 USD ml
Talwin 30 mg/ml ampul 4.86 USD ml
Talwin 30 mg/ml 1.64 USD ml
Talwin 50 mg Tablet 0.47 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 146.3 °C PhysProp
logP 4.64 DAYLIGHT (1999)
pKa 8.88 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 1.22e-01 g/l ALOGPS
logP 4.44 ALOGPS
logP 3.89 ChemAxon
logS -3.4 ALOGPS
pKa (strongest acidic) 7.59 ChemAxon
pKa (strongest basic) 12.4 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 23.47 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 89.8 ChemAxon
polarizability 33.86 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00498 Link_out
KEGG Compound C07421 Link_out
PubChem Compound 441278 Link_out
PubChem Substance 46506363 Link_out
ChemSpider 390041 Link_out
BindingDB 50001028 Link_out
Therapeutic Targets Database DAP000356 Link_out
PharmGKB PA164744326 Link_out
IUPHAR 1606 Link_out
Guide to Pharmacology 1606 Link_out
Drug Product Database 2241976 Link_out
RxList http://www.rxlist.com/cgi/generic/pentazocine.htm Link_out
Drugs.com http://www.drugs.com/cdi/pentazocine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Pentazocine Link_out
ATC Codes
  • N02AD01
AHFS Codes
  • 28:08.12
PDB Entries Not Available
FDA label Not Available
MSDS show (48.4 KB)
Interactions
Drug Interactions
Drug Interaction
Alvimopan Increases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
Triprolidine The 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

Pharmacological action: yes
Actions: antagonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin

Organism class: human
UniProt ID: P35372 Link_out
Gene: OPRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions

Organism class: human
UniProt ID: P41145 Link_out
Gene: OPRK1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 1-type opioid receptor

Pharmacological action: yes
Actions: agonist
Organism class: human
UniProt ID: Q99720 Link_out
Gene: OPRS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19