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
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 |
---|---|---|
Letter: Pentazocine-induced fibrous myopathy. | 1975 Jun 16 |
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Anti-inflammatory and analgesic activity of Indian Hypericum perforatum L. | 2001 Apr |
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Molecular cloning and pharmacological characterization of the rat sigma1 receptor. | 2001 Aug 1 |
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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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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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Modulation of serotonergic neurotransmission by short- and long-term treatments with sigma ligands. | 2001 Oct |
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Application of gas chromatography-surface ionization organic mass spectrometry to forensic toxicology. | 2002 Aug 25 |
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[Biopharmaceutical studies on molecular mechanisms of membrane transport]. | 2002 Dec |
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[Sedation analgesia in interventional radiology]. | 2002 Feb |
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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 |
|
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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Subarachnoid block for lower abdominal and lower limb surgery: UITH experience. | 2002 Oct-Dec |
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Cardiovascular effects of intravenous pentazocine and cyclazocine in conscious, curarized-conscious, and anesthetized dogs. | 2003 |
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Demographics, assessment and management of pain in the elderly. | 2003 |
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Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats. | 2003 Apr |
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Efficacy of intrathecal morphine for analgesia following elective cesarean section: comparison with previous delivery. | 2003 Aug |
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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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Analgesic activity of Piper longum Linn. root. | 2003 Jun |
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Role of kappa-opioid receptor activation in pharmacological preconditioning of swine. | 2003 Jun |
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Antiproliferative and cytotoxic effects of some sigma2 agonists and sigma1 antagonists in tumour cell lines. | 2004 Aug |
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[Intermittent complete left bundle branch block during general anesthesia]. | 2004 Dec |
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Pentazocine-induced cutaneous sclerosis and panniculitis in an Indian male. | 2004 Jul |
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[Case report of pentazocine dependence from a standpoint of the cognitive therapy]. | 2004 Oct |
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Vitamin B12-associated localized scleroderma and its treatment. | 2004 Sep |
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Sex-related psychological predictors of baseline pain perception and analgesic responses to pentazocine. | 2005 Apr |
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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.
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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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100000082491
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D010423
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m8503
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PENTAZOCINE
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DB00652
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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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ACTIVE MOIETY
SALT/SOLVATE (PARENT)