pentazocine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
narcotic antagonists/agonists related to 6,7-benzomorphan 3424 359-83-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • pentazocine
  • pentazocin
  • dl-Pentazocine
  • cis-(+/-)-Pentazocine
  • pentazocine hydrochloride
  • pentazocine lactate
  • pentazocine HCl
The first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. (From AMA Drug Evaluations Annual, 1991, p97)
  • Molecular weight: 285.43
  • Formula: C19H27NO
  • CLOGP: 4.67
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 23.47
  • ALOGS: -3.37
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g O
0.20 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.04 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 15 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.75 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 18 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 3.40 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 23 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.39 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 24, 1967 FDA HOSPIRA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug abuse 242.05 107.18 47 120 11979 2345939
Drug hypersensitivity 130.50 107.18 37 130 46606 2311312

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Respiratory depression 140.61 137.18 23 75 2224 1744459

Pharmacologic Action:

SourceCodeDescription
ATC N02AD01 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Benzomorphan derivatives
MeSH PA D000759 Adjuvants, Anesthesia
FDA MoA N0000175686 Competitive Opioid Antagonists
FDA EPC N0000175688 Partial Opioid Agonist/Antagonist
FDA MoA N0000175685 Partial Opioid Agonists
MeSH PA D000700 Analgesics
MeSH PA D000701 Analgesics, Opioid
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D009292 Narcotic Antagonists
MeSH PA D009294 Narcotics
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
General anesthesia indication 50697003
Labor pain indication 247412007
Local anesthesia indication 386761002
Suicidal thoughts contraindication 6471006
Dependent drug abuse contraindication 6525002
Alcoholism contraindication 7200002
Alcohol withdrawal delirium contraindication 8635005
Peptic ulcer contraindication 13200003 DOID:750
Asthenia contraindication 13791008
Constipation contraindication 14760008 DOID:2089
Mood swings contraindication 18963009
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Hypercapnia contraindication 29596007
Dehydration contraindication 34095006
Disorder of gallbladder contraindication 39621005 DOID:0060262
Gastrointestinal ulcer contraindication 40845000
Hypothyroidism contraindication 40930008 DOID:1459
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Bradycardia contraindication 48867003
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Ulcerative colitis contraindication 64766004 DOID:8577
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Poisoning by acetaminophen contraindication 70273001
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Gastrointestinal hemorrhage contraindication 74474003
Opioid dependence contraindication 75544000 DOID:2559
Urethral stricture contraindication 76618002
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Cor pulmonale contraindication 83291003 DOID:8515
Opioid withdrawal contraindication 87132004
Pulmonary emphysema contraindication 87433001
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Hemophilia contraindication 90935002
Anemia due to enzyme deficiency contraindication 111577008
Acute abdominal pain contraindication 116290004
Neoplasm of brain contraindication 126952004 DOID:1319
von Willebrand disorder contraindication 128105004 DOID:12531
Seizure disorder contraindication 128613002
Drug-induced psychosis contraindication 191483003 DOID:1742
Disease of liver contraindication 235856003 DOID:409
Morbid obesity contraindication 238136002 DOID:11981
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Exacerbation of asthma contraindication 281239006
Pregnancy, function contraindication 289908002
Lesion of brain contraindication 301766008
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Coma contraindication 371632003
Primary adrenocortical insufficiency contraindication 373662000
Operation on gastrointestinal tract contraindication 386621005
Hypoxia contraindication 389086002
Breastfeeding (mother) contraindication 413712001
Central nervous system depression contraindication 418072004
Dysfunction of sphincter of Oddi contraindication 430887001
Acute erosive gastritis contraindication 444926003

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.26 acidic
pKa2 9.09 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sigma non-opioid intracellular receptor 1 Membrane receptor MODULATOR EC50 8.76 WOMBAT-PK CHEMBL
Delta-type opioid receptor GPCR EC50 7.31 WOMBAT-PK
Kappa-type opioid receptor GPCR Ki 8.66 WOMBAT-PK
Mu-type opioid receptor GPCR Ki 8.41 WOMBAT-PK
Kappa-type opioid receptor GPCR Ki 7.12 CHEMBL
Mu-type opioid receptor GPCR Ki 8.16 CHEMBL
Opioid receptor GPCR IC50 7.90 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.92 CHEMBL

External reference:

IDSource
4019882 VUID
N0000147967 NUI
C0030873 UMLSCUI
D00498 KEGG_DRUG
1P2XIB510O UNII
17146-95-1 SECONDARY_CAS_RN
39608003 SNOMEDCT_US
4019882 VANDF
8001 RXNORM
387213004 SNOMEDCT_US
d00334 MMSL
001583 NDDF
CHEBI:7982 CHEBI
CHEMBL560 ChEMBL_ID
CHEMBL100116 ChEMBL_ID
DB00652 DRUGBANK_ID
CHEMBL1200327 ChEMBL_ID
1674 INN_ID
441278 PUBCHEM_CID
D010423 MESH_DESCRIPTOR_UI
CHEMBL3989509 ChEMBL_ID
CHEMBL3989510 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Pentazocine and naloxone HUMAN PRESCRIPTION DRUG LABEL 2 0591-0395 TABLET 50 mg ORAL ANDA 15 sections
PENTAZOCINE HCL AND NALOXONE HCL HUMAN PRESCRIPTION DRUG LABEL 2 16590-556 TABLET 50 mg ORAL ANDA 13 sections
Pentazocine HCl and Acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 21695-634 TABLET 25 mg ORAL ANDA 12 sections
Pentazocine Hydrochloride and Acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 43386-670 TABLET 25 mg ORAL ANDA 12 sections
PENTAZOCINE HYDROCHLORIDE AND NALOXONE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 2 43386-680 TABLET 50 mg ORAL ANDA 15 sections
PENTAZOCINE HYDROCHLORIDE AND NALOXONE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 2 61919-556 TABLET 50 mg ORAL ANDA 12 sections
pentazocine and naloxone HUMAN PRESCRIPTION DRUG LABEL 2 63304-506 TABLET 50 mg ORAL ANDA 14 sections
Pentazocine and naloxone HUMAN PRESCRIPTION DRUG LABEL 2 68387-531 TABLET 50 mg ORAL ANDA 13 sections