Details
Stereochemistry | RACEMIC |
Molecular Formula | C19H27NO.ClH |
Molecular Weight | 321.885 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.C[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CC=C(C)C
InChI
InChIKey=OQGYMIIFOSJQSF-DTOXXUQYSA-N
InChI=1S/C19H27NO.ClH/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;1H/t14-,18+,19+;/m0./s1
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 |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugs.com/cdi/pentazocine.html | https://www.ncbi.nlm.nih.gov/pubmed/23370666Curator'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
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363 |
6.9 nM [Ki] | ||
Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363 |
75.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TALWIN Approved UsePentazocine 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
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 |
T1/2
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Respiratory depression, Hypotension... AEs leading to discontinuation/dose reduction: Respiratory depression Sources: Hypotension (severe) |
30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Co-administed with:: benzodiazepines Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Sedation, Coma... AEs leading to discontinuation/dose reduction: Sedation Sources: Coma |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Respiratory depression | Disc. AE | 30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Hypotension | severe Disc. AE |
30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Coma | Disc. AE | 30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Co-administed with:: benzodiazepines Sources: |
unhealthy Health Status: unhealthy Sources: |
Sedation | Disc. AE | 30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Co-administed with:: benzodiazepines Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0 |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0 |
likely | |||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/19279232/ Page: 3.0 |
||||
PubMed
Title | Date | PubMed |
---|---|---|
Clinical effects of pentazocine in hospitalized medical patients. | 1975 Feb-Mar |
|
Pentazocine-induced fibrous myopathy. | 1975 Jan 20 |
|
Letter: Pentazocine-induced fibrous myopathy. | 1975 Jun 16 |
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WHO Expert Committee on Drug Dependence. Thirty-second report. | 2001 |
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Anti-inflammatory and analgesic activity of Indian Hypericum perforatum L. | 2001 Apr |
|
Effects of AH-9700, (+)-pentazocine, DTG and oxybutynin on micturition in anesthetized rats with acetone-induced cystitis. | 2001 Aug 24 |
|
Subjective, psychomotor, and physiological effects of cumulative doses of mixed-action opioids in healthy volunteers. | 2001 Jun |
|
TRK-820, a selective kappa-opioid agonist, produces potent antinociception in cynomolgus monkeys. | 2001 Mar |
|
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 |
|
Experience with urine drug testing by the Correctional Service of Canada. | 2001 Sep 15 |
|
[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 |
|
Substance abuse monitoring by the Correctional Service of Canada. | 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 |
|
Sigma1 receptor modulation of opioid analgesia in the mouse. | 2002 Mar |
|
Synthesis and evaluation of [18F]fluoroethyl SA4503 as a PET ligand for the sigma receptor. | 2002 Mar 15 |
|
Synthesis and evaluation of 3-(4-chlorobenzyl)-8-[11C]methoxy-1,2,3,4-tetrahydrochromeno[3,4-c]pyridin-5-one: a PET tracer for imaging sigma(1) receptors. | 2002 May |
|
[Perioperative management for nephrectomy using combined spinal-epidural anesthesia with sedation in a patient with cerebral palsy under maintenance hemodialysis]. | 2002 Nov |
|
Differential effects of agonists on adenylyl cyclase superactivation mediated by the kappa opioid receptors: adenylyl cyclase superactivation is independent of agonist-induced phosphorylation, desensitization, internalization, and down-regulation. | 2003 Dec |
|
Age-related changes of the binding of [3h]SA4503 to sigma1 receptors in the rat brain. | 2003 Feb |
|
Gabapentin in the management of pentazocine dependence: a potent analgesic--anticraving agent. | 2003 Jul |
|
[Neurochemical analysis and pharmacological regulation of the corticofugal control of the nociceptive signals in the afferent pathways]. | 2003 Mar-Apr |
|
Opioid agonists have different efficacy profiles for G protein activation, rapid desensitization, and endocytosis of mu-opioid receptors. | 2003 May 23 |
|
Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans. | 2003 Nov 6 |
|
Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice. | 2003 Oct |
|
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section]. | 2003 Oct |
|
Effect of insulin hypoglycemic stress on nociceptive responses to mu- and kappa-opioid receptor agonists at LH-surge in female rats. | 2004 Apr |
|
The sigma receptor ligand (+)-pentazocine prevents apoptotic retinal ganglion cell death induced in vitro by homocysteine and glutamate. | 2004 Apr 7 |
|
Molecular modeling of sigma 1 receptor ligands: a model of binding conformational and electrostatic considerations. | 2004 Jan |
|
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 |
|
Sternoclavicular septic arthritis: review of 180 cases. | 2004 May |
|
Experimental pain models reveal no sex differences in pentazocine analgesia in humans. | 2004 May |
|
Sex-related psychological predictors of baseline pain perception and analgesic responses to pentazocine. | 2005 Apr |
|
Using mixed agonist-antagonists. | 2005 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/cdi/pentazocine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23370666
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
Edited
Wed Jul 05 23:28:16 UTC 2023
by
admin
on
Wed Jul 05 23:28:16 UTC 2023
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Record UNII |
A36BXO4PPX
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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DEA NO. |
9709
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NCI_THESAURUS |
C67413
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SUB03685MIG
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104973
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2276-52-0
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NON-SPECIFIC STEREOCHEMISTRY | |||
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218-896-9
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441277
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100000085525
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A36BXO4PPX
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M8503
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C47661
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A36BXO4PPX
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DTXSID00915701
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64024-15-3
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DBSALT001009
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264-612-1
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CHEMBL560
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