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
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
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 |
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 |
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Letter: Pentazocine-induced fibrous myopathy. | 1975 Jun 16 |
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Effect of drugs influencing central serotonergic mechanisms on pentazocine-induced catalepsy in mice. | 1998 Dec |
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Pentazocine-induced fibromyositis and contracture. | 1999 Jun |
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WHO Expert Committee on Drug Dependence. Thirty-second report. | 2001 |
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Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors. | 2001 Apr |
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Pharmacological actions of AH-9700 on micturition reflex in anesthetized rats. | 2001 Jan 26 |
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[Opioid tolerance and dependence--pharmacological aspects]. | 2001 Jul-Sep |
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TRK-820, a selective kappa-opioid agonist, produces potent antinociception in cynomolgus monkeys. | 2001 Mar |
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[Influence of intubation maneuver with or without premedication for intracranial hemorrhage with unconsciousness]. | 2001 Mar |
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Some of the effects of the selective sigma ligand (+)pentazocine are mediated via a naloxone-sensitive receptor. | 2001 Mar 15 |
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Potentiation of opioid analgesia in dopamine2 receptor knock-out mice: evidence for a tonically active anti-opioid system. | 2001 Oct 1 |
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Evidence for sigma-1-like receptors in isolated rat liver mitochondrial membranes. | 2002 Apr |
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Sigma(2)-receptor regulation of dopamine transporter via activation of protein kinase C. | 2002 Apr |
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Application of gas chromatography-surface ionization organic mass spectrometry to forensic toxicology. | 2002 Aug 25 |
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Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials. | 2002 Feb |
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Substance abuse monitoring by the Correctional Service of Canada. | 2002 Feb |
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Binding of sigma receptor ligands and their effects on muscarine-induced Ca(2+) changes in SH-SY5Y cells. | 2002 Feb 1 |
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Renal amyloidosis in a pentazocine addict. | 2002 Jul |
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Fibromyositis after intramuscular pentazocine abuse. | 2002 Jul-Sep |
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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 |
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[Perioperative management for nephrectomy using combined spinal-epidural anesthesia with sedation in a patient with cerebral palsy under maintenance hemodialysis]. | 2002 Nov |
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Myocardial protection by anesthetic agents against ischemia-reperfusion injury: an update for anesthesiologists. | 2002 Oct |
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Antidiarrhoeal properties of a novel sigma ligand (JO 2871) on toxigenic diarrhoea in mice: mechanisms of action. | 2002 Oct |
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Effects of histamine and opioid systems on memory retention of passive avoidance learning in rats. | 2002 Oct 4 |
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Cardiovascular effects of intravenous pentazocine and cyclazocine in conscious, curarized-conscious, and anesthetized dogs. | 2003 |
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Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats. | 2003 Apr |
|
Permanently oriented antibody immobilization for digoxin determination with a flow-through fluoroimmunosensor. | 2003 Apr |
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Enhanced sensitivity to the antinociceptive effects of kappa opioids in naltrexone-treated rats: dose- and time-dependent effects. | 2003 Dec |
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Effects of ethanol or rimcazole on dizocilpine maleate-induced behaviors in male and female rats. | 2003 Feb |
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Sigma1 receptor agonist-mediated regulation of N-methyl-D-aspartate-stimulated [3H]dopamine release is dependent upon protein kinase C. | 2003 Jan |
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Opioid prescription for terminally ill outpatients in a district of northern Italy: a retrospective survey. | 2003 Jul |
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Role of kappa-opioid receptor activation in pharmacological preconditioning of swine. | 2003 Jun |
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The analgesic effect of oral morphine or pentazocine for extracorporeal shock wave lithotripsy. | 2003 Mar |
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Modulation of Fas receptor proteins and dynamin during opiate addiction and induction of opiate withdrawal in rat brain. | 2003 Nov |
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Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans. | 2003 Nov 6 |
|
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section]. | 2003 Oct |
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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 |
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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 |
|
Sternoclavicular septic arthritis: review of 180 cases. | 2004 May |
|
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 22:41:02 UTC 2023
by
admin
on
Wed Jul 05 22:41:02 UTC 2023
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Record UNII |
RP4A60D26L
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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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NCI_THESAURUS |
C67413
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WHO-VATC |
QN02AD01
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LIVERTOX |
NBK548498
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NDF-RT |
N0000175686
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WHO-ATC |
N02AD01
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DEA NO. |
9709
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NDF-RT |
N0000175685
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NCI_THESAURUS |
C1506
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NDF-RT |
N0000175688
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3424
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100000082491
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D010423
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3150
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M8503
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PRIMARY | Merck Index | ||
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PENTAZOCINE
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DB00652
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RP4A60D26L
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SUB09688MIG
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CHEMBL560
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1505007
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359-83-1
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RP4A60D26L
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Pentazocine
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1674
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C61884
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8001
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107430
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206-634-6
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DTXSID7023433
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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TARGET -> AGONIST |
(+)-pentazocine is active
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ENANTIOMER -> RACEMATE |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |