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 Date1967 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
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 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 Sources: |
unhealthy Health Status: unhealthy Sources: |
Sedation | Disc. AE | 30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg 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 |
---|---|---|
Pentazocine addict nephropathy: a case report. | 1992 Mar |
|
Anti-inflammatory and analgesic activity of Indian Hypericum perforatum L. | 2001 Apr |
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Pharmacological actions of AH-9700 on micturition reflex in anesthetized rats. | 2001 Jan 26 |
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The opioid peptide analogue biphalin induces less physical dependence than morphine. | 2001 Jul 20 |
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[Analysis of prehospital analgesia administered to victims with traumatic injuries]. | 2001 Jul-Aug |
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Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria. | 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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Chitosan based pentazocine microspheres for intranasal systemic delivery: development and biopharmaceutical evaluation. | 2001 Mar |
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[UV-densitometry determination of pentazocine hydrochloride in tablets after low temperature extraction]. | 2001 May-Jun |
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Modulation of serotonergic neurotransmission by short- and long-term treatments with sigma ligands. | 2001 Oct |
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[Biopharmaceutical studies on molecular mechanisms of membrane transport]. | 2002 Dec |
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Fibromyositis after intramuscular pentazocine abuse. | 2002 Jul-Sep |
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Synthesis and evaluation of [18F]fluoroethyl SA4503 as a PET ligand for the sigma receptor. | 2002 Mar 15 |
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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 |
|
Investigation of transport mechanism of pentazocine across the blood-brain barrier using the in situ rat brain perfusion technique. | 2002 Nov |
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Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique. | 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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Subarachnoid block for lower abdominal and lower limb surgery: UITH experience. | 2002 Oct-Dec |
|
Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats. | 2003 Apr |
|
Enhanced sensitivity to the antinociceptive effects of kappa opioids in naltrexone-treated rats: dose- and time-dependent effects. | 2003 Dec |
|
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 |
|
SR31747A is a sigma receptor ligand exhibiting antitumoural activity both in vitro and in vivo. | 2003 Feb 10 |
|
Analgesic activity of Piper longum Linn. root. | 2003 Jun |
|
[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 |
|
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 |
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Procaine hydrochloride fails to relieve pain in patients with acute pancreatitis. | 2004 |
|
Antiproliferative and cytotoxic effects of some sigma2 agonists and sigma1 antagonists in tumour cell lines. | 2004 Aug |
|
[Intermittent complete left bundle branch block during general anesthesia]. | 2004 Dec |
|
Molecular modeling of sigma 1 receptor ligands: a model of binding conformational and electrostatic considerations. | 2004 Jan |
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Pentazocine-induced cutaneous sclerosis and panniculitis in an Indian male. | 2004 Jul |
|
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 |
|
Intrathecal morphine, but not buprenorphine or pentazocine, can induce spastic paraparesis after a noninjurious interval of spinal cord ischemia in the rat. | 2004 Nov |
|
Modulation of bradykinin-induced calcium changes in SH-SY5Y cells by neurosteroids and sigma receptor ligands via a shared mechanism. | 2004 Nov |
|
[Case report of pentazocine dependence from a standpoint of the cognitive therapy]. | 2004 Oct |
|
Retroperitoneoscopic live donor nephrectomy: extended experience in a single center. | 2004 Sep |
|
Vitamin B12-associated localized scleroderma and its treatment. | 2004 Sep |
|
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
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Record UNII |
RP4A60D26L
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Record Status |
Validated (UNII)
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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 |