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Details

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

SHOW SMILES / InChI
Structure of PENTAZOCINE, (-)-

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.9 nM [Ki]
75.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
227 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
1311 ng × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.3 h
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
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

Doses

DosePopulationAdverse events​
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Disc. AE: Respiratory depression, Hypotension...
AEs leading to
discontinuation/dose reduction:
Respiratory depression
Hypotension (severe)
Sources:
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Co-administed with::
benzodiazepines
Sources:
unhealthy
Disc. AE: Sedation, Coma...
AEs leading to
discontinuation/dose reduction:
Sedation
Coma
Sources:
AEs

AEs

AESignificanceDosePopulation
Respiratory depression Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Hypotension severe
Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Coma Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Co-administed with::
benzodiazepines
Sources:
unhealthy
Sedation Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Co-administed with::
benzodiazepines
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim

Drug as victim

Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Clinical effects of pentazocine in hospitalized medical patients.
1975 Feb-Mar
Mental and emotional disturbance with pentazocine (Talwin) use.
1975 Jul
Effect of drugs influencing central serotonergic mechanisms on pentazocine-induced catalepsy in mice.
1998 Dec
Pentazocine-induced fibromyositis and contracture.
1999 Jun
WHO Expert Committee on Drug Dependence. Thirty-second report.
2001
Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors.
2001 Apr
The opioid peptide analogue biphalin induces less physical dependence than morphine.
2001 Jul 20
Subjective, psychomotor, and physiological effects of cumulative doses of mixed-action opioids in healthy volunteers.
2001 Jun
Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria.
2001 Mar
Chitosan based pentazocine microspheres for intranasal systemic delivery: development and biopharmaceutical evaluation.
2001 Mar
Some of the effects of the selective sigma ligand (+)pentazocine are mediated via a naloxone-sensitive receptor.
2001 Mar 15
A multireceptorial binding reinvestigation on an extended class of sigma ligands: N-[omega-(indan-1-yl and tetralin-1-yl)alkyl] derivatives of 3,3-dimethylpiperidine reveal high affinities towards sigma1 and EBP sites.
2001 May
Sigma(2)-receptor regulation of dopamine transporter via activation of protein kinase C.
2002 Apr
[The effect of ketamine on reducing postoperative agitation after sevoflurane anesthesia in pediatric strabismus surgery].
2002 Dec
[Biopharmaceutical studies on molecular mechanisms of membrane transport].
2002 Dec
Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials.
2002 Feb
Binding of sigma receptor ligands and their effects on muscarine-induced Ca(2+) changes in SH-SY5Y cells.
2002 Feb 1
Synthesis of (+)-cis-N-(4-isothiocyanatobenzyl)-N-normetazocine, an isothiocyanate derivative of N-benzylnormetazocine as acylant agent for the sigma(1) receptor.
2002 Jun 6
[Perioperative management for nephrectomy using combined spinal-epidural anesthesia with sedation in a patient with cerebral palsy under maintenance hemodialysis].
2002 Nov
Investigation of transport mechanism of pentazocine across the blood-brain barrier using the in situ rat brain perfusion technique.
2002 Nov
Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique.
2002 Oct
Myocardial protection by anesthetic agents against ischemia-reperfusion injury: an update for anesthesiologists.
2002 Oct
Development and use of a computer program to detect potentially inappropriate prescribing in older adults residing in Canadian long-term care facilities.
2002 Oct 14
Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats.
2003 Apr
Efficacy of intrathecal morphine for analgesia following elective cesarean section: comparison with previous delivery.
2003 Aug
Gabapentin in the management of pentazocine dependence: a potent analgesic--anticraving agent.
2003 Jul
Opioid prescription for terminally ill outpatients in a district of northern Italy: a retrospective survey.
2003 Jul
Migratory hydroamination: a facile enantioselective synthesis of benzomorphans.
2003 Jul 23
Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice.
2003 Oct
Procaine hydrochloride fails to relieve pain in patients with acute pancreatitis.
2004
Effect of insulin hypoglycemic stress on nociceptive responses to mu- and kappa-opioid receptor agonists at LH-surge in female rats.
2004 Apr
Delta-opioid receptor agonist reduces severity of postresuscitation myocardial dysfunction.
2004 Aug
Involvement of P-glycoprotein in blood-brain barrier transport of pentazocine in rats using brain uptake index method.
2004 Jun
Sigma-2 receptors are specifically localized to lipid rafts in rat liver membranes.
2004 Jun 16
Experimental pain models reveal no sex differences in pentazocine analgesia in humans.
2004 May
Intrathecal morphine, but not buprenorphine or pentazocine, can induce spastic paraparesis after a noninjurious interval of spinal cord ischemia in the rat.
2004 Nov
Retroperitoneoscopic live donor nephrectomy: extended experience in a single center.
2004 Sep
Using mixed agonist-antagonists.
2005 Feb
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
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 Fri Dec 15 15:05:53 UTC 2023
Edited
by admin
on Fri Dec 15 15:05:53 UTC 2023
Record UNII
768DQ5A5AI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENTAZOCINE, (-)-
Common Name 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)-
Systematic Name English
LEVOPENTAZOCINE
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)-, CIS-(-)-
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)-, (2R,6R,11R)-
Common Name English
PENTAZOCINE, L-
Common Name English
PENTAZOCINE 2R,6R,11R-FORM
MI  
Common Name English
PENTAZOCINE 2R,6R,11R-FORM [MI]
Common Name English
CIS-(-)-PENTAZOCINE
Common Name English
(2R,6R,11R)-1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTEN-1-YL)-2,6-METHANO-3-BENZAZOCIN-8-OL
Common Name English
(-)-.ALPHA.-PENTAZOCINE
Common Name English
L-PENTAZOCINE
Common Name English
(-)-PENTAZOCINE
Common Name English
Code System Code Type Description
CAS
10279-67-1
Created by admin on Fri Dec 15 15:05:53 UTC 2023 , Edited by admin on Fri Dec 15 15:05:53 UTC 2023
SUPERSEDED
CAS
7488-49-5
Created by admin on Fri Dec 15 15:05:53 UTC 2023 , Edited by admin on Fri Dec 15 15:05:53 UTC 2023
PRIMARY
MERCK INDEX
m8503
Created by admin on Fri Dec 15 15:05:53 UTC 2023 , Edited by admin on Fri Dec 15 15:05:53 UTC 2023
PRIMARY Merck Index
FDA UNII
768DQ5A5AI
Created by admin on Fri Dec 15 15:05:53 UTC 2023 , Edited by admin on Fri Dec 15 15:05:53 UTC 2023
PRIMARY
PUBCHEM
441278
Created by admin on Fri Dec 15 15:05:53 UTC 2023 , Edited by admin on Fri Dec 15 15:05:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID40904917
Created by admin on Fri Dec 15 15:05:53 UTC 2023 , Edited by admin on Fri Dec 15 15:05:53 UTC 2023
PRIMARY
IUPHAR
1606
Created by admin on Fri Dec 15 15:05:53 UTC 2023 , Edited by admin on Fri Dec 15 15:05:53 UTC 2023
PRIMARY
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