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 |
---|---|---|
Pentazocine-induced fibrous myopathy. | 1975 Jan 20 |
|
Iatrogenic muscle fibrosis. Arm levitation as an initial sign. | 1975 Nov 10 |
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WHO Expert Committee on Drug Dependence. Thirty-second report. | 2001 |
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Effects of AH-9700, (+)-pentazocine, DTG and oxybutynin on micturition in anesthetized rats with acetone-induced cystitis. | 2001 Aug 24 |
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Multiple pathways of sigma(1) receptor ligand uptakes into primary cultured neuronal cells. | 2001 Aug 3 |
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[Opioid tolerance and dependence--pharmacological aspects]. | 2001 Jul-Sep |
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Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria. | 2001 Mar |
|
[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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Oxygen saturation in healthy newborn infants immediately after birth measured by pulse oximetry. | 2002 Apr |
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Evidence for sigma-1-like receptors in isolated rat liver mitochondrial membranes. | 2002 Apr |
|
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 |
|
[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 |
|
[Sedation analgesia in interventional radiology]. | 2002 Feb |
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Substance abuse monitoring by the Correctional Service of Canada. | 2002 Feb |
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Renal amyloidosis in a pentazocine addict. | 2002 Jul |
|
Sigma receptors inhibit high-voltage-activated calcium channels in rat sympathetic and parasympathetic neurons. | 2002 Jun |
|
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 |
|
Effects of adding midazolam on the postoperative epidural analgesia with two different doses of bupivacaine. | 2002 Mar |
|
Sigma1 receptor modulation of opioid analgesia in the mouse. | 2002 Mar |
|
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 |
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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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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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Subarachnoid block for lower abdominal and lower limb surgery: UITH experience. | 2002 Oct-Dec |
|
Demographics, assessment and management of pain in the elderly. | 2003 |
|
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 |
|
Intracellular dynamics of sigma-1 receptors (sigma(1) binding sites) in NG108-15 cells. | 2003 Aug |
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Postoperative pain management following caesarean section in University of Ilorin Teaching Hospital (UITH), Ilorin, Nigeria. | 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 |
|
Effects of ethanol or rimcazole on dizocilpine maleate-induced behaviors in male and female rats. | 2003 Feb |
|
Age-related changes of the binding of [3h]SA4503 to sigma1 receptors in the rat brain. | 2003 Feb |
|
Sigma1 receptor agonist-mediated regulation of N-methyl-D-aspartate-stimulated [3H]dopamine release is dependent upon protein kinase C. | 2003 Jan |
|
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 |
|
The analgesic effect of oral morphine or pentazocine for extracorporeal shock wave lithotripsy. | 2003 Mar |
|
[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 |
|
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section]. | 2003 Oct |
|
The sigma receptor ligand (+)-pentazocine prevents apoptotic retinal ganglion cell death induced in vitro by homocysteine and glutamate. | 2004 Apr 7 |
|
[Intermittent complete left bundle branch block during general anesthesia]. | 2004 Dec |
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Molecular modeling of sigma 1 receptor ligands: a model of binding conformational and electrostatic considerations. | 2004 Jan |
|
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 |
|
Retroperitoneoscopic live donor nephrectomy: extended experience in a single center. | 2004 Sep |
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
Fri Dec 16 16:20:16 UTC 2022
by
admin
on
Fri Dec 16 16:20:16 UTC 2022
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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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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 |