PENTAZOCINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H27NO
Molecular Weight	285.4238
Optical Activity	( + / - )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CC=C(C)C

InChI

InChIKey=VOKSWYLNZZRQPF-GDIGMMSISA-N

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

HIDE SMILES / InChI

Molecular Formula	C19H27NO
Molecular Weight	285.4238
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/cdi/pentazocine.html | https://www.ncbi.nlm.nih.gov/pubmed/23370666
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12379919 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016194s079s080lbl.pdf | https://www.drugbank.ca/drugs/DB00652

Pentazocine is a synthetically prepared prototypical mixed agonist-antagonist narcotic (opioid analgesic) drug of the benzomorphan class of opioids used to treat moderate to moderately severe pain. Pentazocine is sold under several brand names, such as Fortral, Sosegon, Talwin NX. Pentazocine acts as an agonist of κ-opioid receptors and as an antagonist of μ-opioid receptors. This compound may exist as one of two enantiomers, named (+)-pentazocine and (−)-pentazocine. Side effects are similar to those of morphine, but pentazocine, due to its action at the kappa opioid receptor is more likely to invoke psychotomimetic effects. High dose may cause high blood pressure or high heart rate.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363	Antagonist 2760		6.9 nM [Ki]
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363	Agonist 2662		75.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 608 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016194s079s080lbl.pdf	Primary		Approved 8360	TALWIN Approved Use Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for the relief of moderate to severe pain. Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for oral use only. Launch Date -7.7068796E10

C_max

Value	Dose	Co-administered	Analyte	Population
227 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	80 mg single, intramuscular dose: 80 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		PENTAZOCINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
102 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	40 mg single, intramuscular dose: 40 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		PENTAZOCINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1311 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	80 mg single, intramuscular dose: 80 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		PENTAZOCINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
536 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	40 mg single, intramuscular dose: 40 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		PENTAZOCINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	80 mg single, intramuscular dose: 80 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		PENTAZOCINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	40 mg single, intramuscular dose: 40 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		PENTAZOCINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	Disc. AE: Respiratory depression, Hypotension... AEs leading to discontinuation/dose reduction: Respiratory depression Hypotension (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf
30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Co-administed with:: benzodiazepines Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	Disc. AE: Sedation, Coma... AEs leading to discontinuation/dose reduction: Sedation Coma Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf

AEs

AE	Significance	Dose	Population
Respiratory depression	Disc. AE	30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf
Hypotension	severe Disc. AE	30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf
Coma	Disc. AE	30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Co-administed with:: benzodiazepines Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf
Sedation	Disc. AE	30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Co-administed with:: benzodiazepines Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1709			inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 95	CYP1A2 1032 P-gp 1527

Drug as victim

Target	Modality	Activity
CYP1A2 1032	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0	likely
CYP3A4 1709	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0	likely
P-gp 1527	substrate 3326 Sources: https://europepmc.org/article/med/24915880#R34	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 98	inhibitor 1613 Sources: https://pubmed.ncbi.nlm.nih.gov/19279232/ Page: 3.0
hERG 1632	inhibitor 1613 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151040/

Sourcing

Vendor/Aggregator	ID	URL
Chemieliva Pharmaceutical Co., Ltd	PBCM1405771
Compound Cloud	441277
Compound Cloud	441278
Compound Cloud	656697
Finetech	FT-0673607	http://www.finetechnology-ind.com/product/All%20product%20List/7488-49-5.html
MuseChem	I011222	https://www.musechem.com/product/I011222.html
NovoSeek	441278
Smolecule	S538980	http://www.smolecule.com/products/s538980
Smolecule	S538981	http://www.smolecule.com/products/s538981
THE BioTek	bt-278515	https://www.thebiotek.com/product/inhibitors/bt-278515
THE BioTek	bt-278516	https://www.thebiotek.com/product/inhibitors/bt-278516
Tetrahedron	TS54857
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0691A
ZINC	ZINC000000000596	http://zinc15.docking.org/substances/ZINC000000000596

PubMed

Title	Date	PubMed
Letter: Pentazocine-induced fibrous myopathy.	1975 Jun 16	1173609
Effect of drugs influencing central serotonergic mechanisms on pentazocine-induced catalepsy in mice.	1998 Dec	10093512
Pentazocine-induced fibromyositis and contracture.	1999 Jun	10435175
WHO Expert Committee on Drug Dependence. Thirty-second report.	2001	11851193
Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors.	2001 Apr	11182540
Pharmacological actions of AH-9700 on micturition reflex in anesthetized rats.	2001 Jan 26	11165228
[Opioid tolerance and dependence--pharmacological aspects].	2001 Jul-Sep	12092171
TRK-820, a selective kappa-opioid agonist, produces potent antinociception in cynomolgus monkeys.	2001 Mar	11325021
[Influence of intubation maneuver with or without premedication for intracranial hemorrhage with unconsciousness].	2001 Mar	11296398
Some of the effects of the selective sigma ligand (+)pentazocine are mediated via a naloxone-sensitive receptor.	2001 Mar 15	11169783
Potentiation of opioid analgesia in dopamine2 receptor knock-out mice: evidence for a tonically active anti-opioid system.	2001 Oct 1	11567069
Evidence for sigma-1-like receptors in isolated rat liver mitochondrial membranes.	2002 Apr	11934800
Sigma(2)-receptor regulation of dopamine transporter via activation of protein kinase C.	2002 Apr	11907188
Application of gas chromatography-surface ionization organic mass spectrometry to forensic toxicology.	2002 Aug 25	12127320
Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials.	2002 Feb	11812718
Substance abuse monitoring by the Correctional Service of Canada.	2002 Feb	11805743
Binding of sigma receptor ligands and their effects on muscarine-induced Ca(2+) changes in SH-SY5Y cells.	2002 Feb 1	11834244
Renal amyloidosis in a pentazocine addict.	2002 Jul	12126358
Fibromyositis after intramuscular pentazocine abuse.	2002 Jul-Sep	12432208
Sigma1 receptor modulation of opioid analgesia in the mouse.	2002 Mar	11861817
Synthesis and evaluation of [18F]fluoroethyl SA4503 as a PET ligand for the sigma receptor.	2002 Mar 15	11835521
[Perioperative management for nephrectomy using combined spinal-epidural anesthesia with sedation in a patient with cerebral palsy under maintenance hemodialysis].	2002 Nov	12481458
Myocardial protection by anesthetic agents against ischemia-reperfusion injury: an update for anesthesiologists.	2002 Oct	12374705
Antidiarrhoeal properties of a novel sigma ligand (JO 2871) on toxigenic diarrhoea in mice: mechanisms of action.	2002 Oct	12235074
Effects of histamine and opioid systems on memory retention of passive avoidance learning in rats.	2002 Oct 4	12354569
Cardiovascular effects of intravenous pentazocine and cyclazocine in conscious, curarized-conscious, and anesthetized dogs.	2003	14964736
Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats.	2003 Apr	12759132
Permanently oriented antibody immobilization for digoxin determination with a flow-through fluoroimmunosensor.	2003 Apr	12733013
Enhanced sensitivity to the antinociceptive effects of kappa opioids in naltrexone-treated rats: dose- and time-dependent effects.	2003 Dec	14665981
Effects of ethanol or rimcazole on dizocilpine maleate-induced behaviors in male and female rats.	2003 Feb	12782248
Sigma1 receptor agonist-mediated regulation of N-methyl-D-aspartate-stimulated [3H]dopamine release is dependent upon protein kinase C.	2003 Jan	12490613
Opioid prescription for terminally ill outpatients in a district of northern Italy: a retrospective survey.	2003 Jul	12770518
Role of kappa-opioid receptor activation in pharmacological preconditioning of swine.	2003 Jun	12543635
The analgesic effect of oral morphine or pentazocine for extracorporeal shock wave lithotripsy.	2003 Mar	12747344
Modulation of Fas receptor proteins and dynamin during opiate addiction and induction of opiate withdrawal in rat brain.	2003 Nov	14530904
Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans.	2003 Nov 6	14550900
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section].	2003 Oct	14598667
Effect of insulin hypoglycemic stress on nociceptive responses to mu- and kappa-opioid receptor agonists at LH-surge in female rats.	2004 Apr	15148524
The sigma receptor ligand (+)-pentazocine prevents apoptotic retinal ganglion cell death induced in vitro by homocysteine and glutamate.	2004 Apr 7	15046867
Molecular modeling of sigma 1 receptor ligands: a model of binding conformational and electrostatic considerations.	2004 Jan	14629980
Involvement of P-glycoprotein in blood-brain barrier transport of pentazocine in rats using brain uptake index method.	2004 Jun	15187451
Sternoclavicular septic arthritis: review of 180 cases.	2004 May	15118542
Using mixed agonist-antagonists.	2005 Feb	15706252

Patents

Sample Use Guides

In Vivo Use Guide

Initial dose: 30 mg by intramuscular, subcutaneous, or intravenous route. This may be repeated every 3 to 4 hours. Doses in excess of 30 mg intravenously or 60 mg intramuscularly or subcutaneously are not recommended. Maximum daily dose: 360 mg

Route of Administration: Other

In Vitro Use Guide

Cultured bovine adrenal medullary cells (1 × 10^6 / well) or SK-N-SH cells (0.3 × 10^6 / well) were preincubated with or without PTZ (Pentazocine) for the indicated times and further incubated at 37°C for another 12 min in KRH buffer containing 100 μM pargyline, 1 mM ascorbic acid, and [3H]NE (500 or 100 nM, respectively, 0.1 μCi) in the presence or absence of desipramine and PTZ. KRH buffer was composed of 154 mM NaCl, 5.6 mM KCl, 1.1 mM MgSO4, 2.2 mM CaCl2, 10 mM HEPES-Tris, and 10 mM glucose, adjusted to pH 7.4. After incubation, the cells were rapidly washed three times with 250 μl of ice-cold KRH buffer and solubilized in 500 μl of 10% Triton X-100. The radioactivity in the solubilized cells was counted with a liquid scintillation counter.

Substance Class	Chemical Created by `admin` on `Wed Jul 05 22:41:02 UTC 2023` Edited by `admin` on `Wed Jul 05 22:41:02 UTC 2023`
Record UNII	RP4A60D26L
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PENTAZOCINE

Official Name

English

(±)-PENTAZOCINE

Common Name

English

TALWIN

Brand Name

English

PENTAZOCINE [JAN]

Common Name

English

PENTAZOCINE [EP IMPURITY]

Common Name

English

PENTAZOCINE [HSDB]

Common Name

English

PENTAZOCINE [MART.]

Common Name

English

CIS-(±)-PENTAZOCINE

Common Name

English

NSC-107430

Code

English

WIN 20,228

Code

English

DL-PENTAZOCINE

Common Name

English

NIH-7958

Code

English

2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTEN-1-YL)-, (2R,6R,11R)-REL-

Common Name

English

PENTAZOCINE [VANDF]

Common Name

English

pentazocine [INN]

Common Name

English

PENTAZOCINE CIV

Common Name

English

2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTENYL)-, (2.ALPHA.,6.ALPHA.,11R*)-

Common Name

English

WIN-20228

Code

English

PENTAZOCINE CIV [USP-RS]

Common Name

English

Pentazocine [WHO-DD]

Common Name

English

(2R*,6R*,11R*)-1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTENYL)-2,6-METHANO-3-BENZAZOCIN-8-OL

Common Name

English

PENTAZOCINE [EP MONOGRAPH]

Common Name

English

PENTAZOCINE [USAN]

Common Name

English

PENTAZOCINE [MI]

Common Name

English

PENTAZOCINE [USP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413