DT-Web

DB00652 - Pentazocine


Identification
Name Pentazocine
Accession Number DB00652 (APRD01173)
Type small molecule
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
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 285.4238
Groups approved
Monoisotopic Weight 285.209264491
Pharmacology
Indication For the relief of moderate to severe pain.
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.
Protein binding Not Available
Biotransformation Hepatic
Route of elimination Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions
Drug Mechanism of 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


Mu-type opioid receptor
Name Mu-type opioid receptor
Gene Name OPRM1
Pharmacological action yes
Actions antagonist
References
  • Levine JD, Gordon NC: Synergism between the analgesic actions of morphine and pentazocine. Pain. 1988 Jun;33(3):369-72. - Pubmed
  • 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
  • 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
  • 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
  • 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
DTHybrid score 0.7399
Kappa-type opioid receptor
Name Kappa-type opioid receptor
Gene Name OPRK1
Pharmacological action yes
Actions agonist
References
  • 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
DTHybrid score 0.5989
Sigma 1-type opioid receptor
Name Sigma 1-type opioid receptor
Gene Name SIGMAR1
Pharmacological action yes
Actions agonist
References
  • 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
  • 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
  • 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
  • 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
  • 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
DTHybrid score 0.4267

Predictions


Id Partner name Gene Name Score
467 Delta-type opioid receptor OPRD1 0.4461
4119 Cytochrome P450 2D6 CYP2D6 0.0941
706 Glutamate [NMDA] receptor subunit 3A GRIN3A 0.0795
4512 Cytochrome P450 3A4 CYP3A4 0.0757
1716 Tripartite motif-containing protein 13 TRIM13 0.0737
502 5-hydroxytryptamine 2A receptor HTR2A 0.0724
1256 5-hydroxytryptamine 6 receptor HTR6 0.0692
6030 Cytochrome P450 2B6 CYP2B6 0.0648
1262 Corticotropin-lipotropin POMC 0.0533
6107 Cytochrome P450 3A7 CYP3A7 0.0493
319 Opioid receptor, sigma 1 OPRS1 0.0462
4118 Cytochrome P450 3A5 CYP3A5 0.0379
1588 Multidrug resistance protein 1 ABCB1 0.0374
4924 Cytochrome P450 2C8 CYP2C8 0.0321
4757 Cytochrome P450 2C9 CYP2C9 0.0291
432 D(4) dopamine receptor DRD4 0.0283
638 D(3) dopamine receptor DRD3 0.0276
4137 Nociceptin receptor OPRL1 0.025
831 D(2) dopamine receptor DRD2 0.0228
824 Sodium-dependent serotonin transporter SLC6A4 0.0219
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.0187
6180 UDP-glucuronosyltransferase 2B4 UGT2B4 0.0184
6178 UDP-glucuronosyltransferase 2B7 UGT2B7 0.0179
6016 Cytochrome P450 2C19 CYP2C19 0.0179
5838 Transient receptor potential cation channel subfamily V member 3 TRPV3 0.0176
2162 Transient receptor potential cation channel subfamily M member 8 TRPM8 0.0176
1944 Transient receptor potential cation channel subfamily A member 1 TRPA1 0.0176
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0159
341 5-hydroxytryptamine 3 receptor HTR3A 0.0128
540 Sodium-dependent noradrenaline transporter SLC6A2 0.0116
813 Neuronal acetylcholine receptor subunit alpha-2 CHRNA2 0.0111
1291 cAMP response element-binding protein CREB1 0.0107
6013 Cytochrome P450 2E1 CYP2E1 0.0106
587 Serum albumin ALB 0.0105
4210 Toll-like receptor 4 TLR4 0.0096
392 Voltage-dependent P/Q-type calcium channel subunit alpha-1A CACNA1A 0.0087
590 5-hydroxytryptamine 2C receptor HTR2C 0.0084
4200 Cytochrome P450 1A2 CYP1A2 0.0084
5878 Alpha-7 nicotinic cholinergic receptor subunit CHRFAM7A 0.0082
1181 Alpha-1-acid glycoprotein 1 ORM1 0.0078
6181 UDP-glucuronosyltransferase 1-8 UGT1A8 0.0076
6078 Neuronal acetylcholine receptor subunit beta-4 CHRNB4 0.0065
20 Prostaglandin G/H synthase 1 PTGS1 0.0064
465 Calmodulin CALM1 0.0063
6106 Cytochrome P450 2C18 CYP2C18 0.006
4120 NADPH--cytochrome P450 reductase POR 0.006
3811 Cytochrome P450 19A1 CYP19A1 0.0058
6176 UDP-glucuronosyltransferase 1-3 UGT1A3 0.0058
51 Muscarinic acetylcholine receptor M3 CHRM3 0.0058
6079 Neuronal acetylcholine receptor subunit alpha-3 CHRNA3 0.0058
6145 Solute carrier family 22 member 1 SLC22A1 0.0054
136 Estrogen receptor ESR1 0.0053
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0051
439 Glutamate [NMDA] receptor subunit epsilon-4 GRIN2D 0.0045
505 Glutamate [NMDA] receptor subunit epsilon-3 GRIN2C 0.0044
464 Glutamate [NMDA] receptor subunit epsilon-2 GRIN2B 0.0041
401 Glutamate [NMDA] receptor subunit zeta-1 GRIN1 0.0039
837 Glutamate [NMDA] receptor subunit epsilon-1 GRIN2A 0.0039
318 Alpha-2A adrenergic receptor ADRA2A 0.0038
492 Histamine H1 receptor HRH1 0.0035
94 5-hydroxytryptamine 4 receptor HTR4 0.0035
5718 Cytochrome P450 2A6 CYP2A6 0.0034
320 5-hydroxytryptamine 1A receptor HTR1A 0.0033
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0033
885 5-hydroxytryptamine 1B receptor HTR1B 0.0025
458 Neuronal acetylcholine receptor subunit alpha-10 CHRNA10 0.0025
6100 BDNF/NT-3 growth factors receptor NTRK2 0.0022
1618 High affinity nerve growth factor receptor NTRK1 0.0017
6098 Potassium voltage-gated channel subfamily D member 2 KCND2 0.0016
6099 Potassium voltage-gated channel subfamily D member 3 KCND3 0.0016
1086 Potassium voltage-gated channel subfamily KQT member 2 KCNQ2 0.0016
858 Potassium voltage-gated channel subfamily A member 1 KCNA1 0.0013
789 Alpha-1D adrenergic receptor ADRA1D 0.0011
274 Muscarinic acetylcholine receptor M5 CHRM5 0.0011
450 Muscarinic acetylcholine receptor M4 CHRM4 0.0011
617 Muscarinic acetylcholine receptor M2 CHRM2 0.0009
103 Muscarinic acetylcholine receptor M1 CHRM1 0.0009
556 Alpha-1A adrenergic receptor ADRA1A 0.0009
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