pentazocine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 µM/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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 2.769 Moderate 0.70
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.773 Moderate 0.70
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 26.853 10^-6 cm/s Moderate 0.70
dh-clint Dog hepatocyte intrinsic clearance 45.499 uL/min/10^6 cells Moderate 0.70
dppb Dog plasma protein binding (% unbound) 22.030 % Moderate 0.70
fcs-ppb Fetal calf serum protein binding (% unbound) 36.100 % Moderate 0.70
herg hERG pIC50 5.212 pIC50 Moderate 0.70
hh-clint Human hepatocyte intrinsic clearance 25.704 uL/min/10^6 cells Moderate 0.70
hlm-clint Human liver microsomal intrinsic clearance 45.499 uL/min/mg protein Moderate 0.70
hppb Human plasma protein binding (% unbound) 22.590 % Moderate 0.70
kinase-safety-class ACVR2A,ACVR2B,AKT2,AKT3,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,IGF1R,ITK,JAK2,JAK3,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPKAPK2,MET,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 49
kinase-selectivity-class EIF2AK3,EPHB4,GRK2,MAP2K6,TEK 5
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.706 Moderate 0.70
mh-clint Mouse hepatocyte intrinsic clearance 250.611 Moderate 0.70
mppb Mouse plasma protein binding (% unbound) 31.970 Moderate 0.70
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.948 Moderate 0.70
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 42.070 % Moderate 0.70
rh-clint Rat hepatocyte intrinsic clearance 241.546 uL/min/10^6 cells Moderate 0.70
rh-fuinc Rat hepatocyte fraction unbound in incubation 70.580 % Moderate 0.70
rppb Rat plasma protein binding (% unbound) 27.640 % Moderate 0.70
solubility-dd Solubility at pH 7.4 in DMSO 549.541 uM Moderate 0.70

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 hypersensitivity 656.37 33.38 235 941 463374 90163897
Drug abuse 225.89 33.38 70 1106 82277 90544994
Lip erosion 41.73 33.38 8 1168 1230 90626041
Scleroderma 33.48 33.38 9 1167 6252 90621019

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 tract infection bacterial 81.74 27.53 16 788 1893 42618638
Respiratory tract infection viral 72.50 27.53 16 788 3390 42617141
Ileal perforation 71.20 27.53 13 791 1058 42619473
Gastric perforation 62.91 27.53 14 790 3079 42617452
Drug hypersensitivity 58.38 27.53 31 773 99358 42521173
Arteriospasm coronary 46.98 27.53 12 792 4726 42615805
Respiratory tract infection 43.73 27.53 17 787 26305 42594226
Scleroderma 35.87 27.53 8 796 1770 42618761

FDA Adverse Event Reporting System (Geriatric)

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 hypersensitivity 435.98 28.08 212 2442 453878 110132767
Respiratory tract infection bacterial 74.03 28.08 16 2638 2400 110584245
Amaurosis fugax 68.60 28.08 15 2639 2375 110584270
Ileal perforation 64.52 28.08 13 2641 1387 110585258
Scleroderma 63.38 28.08 17 2637 6324 110580321
Respiratory tract infection viral 59.89 28.08 16 2638 5862 110580783
Gastric perforation 52.99 28.08 14 2640 4915 110581730
Urinary tract disorder 41.56 28.08 12 2642 5832 110580813
Skin fibrosis 41.36 28.08 9 2645 1391 110585254
Ocular discomfort 41.20 28.08 13 2641 8520 110578125
Arteriospasm coronary 40.37 28.08 13 2641 9087 110577558
Altered state of consciousness 40.33 28.08 22 2632 57604 110529041
Haemorrhagic stroke 38.80 28.08 14 2640 13775 110572870
Generalised oedema 37.14 28.08 17 2637 30687 110555958
Lip erosion 33.54 28.08 8 2646 1858 110584787
Head discomfort 31.04 28.08 13 2641 18987 110567658
Drug abuse 31.01 28.08 29 2625 177382 110409263

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N02AD01 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Benzomorphan derivatives
ATC N02AD51 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Benzomorphan derivatives
MeSH PA D000700 Analgesics
MeSH PA D000701 Analgesics, Opioid
MeSH PA D000759 Adjuvants, Anesthesia
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D009292 Narcotic Antagonists
MeSH PA D009294 Narcotics
MeSH PA D018689 Sensory System Agents
FDA MoA N0000175685 Partial Opioid Agonists
FDA MoA N0000175686 Competitive Opioid Antagonists
FDA EPC N0000175688 Partial Opioid Agonist/Antagonist
CHEBI has role CHEBI:35476 antipsychotic agent
CHEBI has role CHEBI:35480 analgesic

Related Drugs by ATC class:

N02AD Benzomorphan derivatives 2 drugs
naloxonephenazocine

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

SpeciesUseRelation
Dogs Pain accompanying postoperative recovery, fracture, trauma, and spinal disorders Indication
Horses Pain caused by colic Indication

🐶 Veterinary products

ProductApplicantIngredients
Talwin-V Sterile Aqueous Injection Zoetis Inc. 1

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
Kappa-type opioid receptor GPCR Ki 8.66 WOMBAT-PK
Delta-type opioid receptor GPCR EC50 7.31 WOMBAT-PK
Transmembrane protein 97 Enzyme Ki 5.83 CHEMBL
Mu-type opioid receptor GPCR Ki 8.41 WOMBAT-PK
Mu-type opioid receptor GPCR Ki 8.16 CHEMBL
Kappa-type opioid receptor GPCR Ki 7.12 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.92 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane other Ki 8.27 CHEMBL
Opioid receptor GPCR IC50 7.90 CHEMBL
Sigma intracellular receptor 2 Membrane receptor Ki 5.83 CHEMBL

External reference:

IDSource
4019882 VUID
N0000147967 NUI
D00498 KEGG_DRUG
64024-15-3 SECONDARY_CAS_RN
17146-95-1 SECONDARY_CAS_RN
4018257 VANDF
4018258 VANDF
4019882 VANDF
C0030873 UMLSCUI
CHEBI:7982 CHEBI
CHEMBL100116 ChEMBL_ID
DB00652 DRUGBANK_ID
CHEMBL3989510 ChEMBL_ID
CHEMBL3989509 ChEMBL_ID
D010423 MESH_DESCRIPTOR_UI
441278 PUBCHEM_CID
1674 INN_ID
RP4A60D26L UNII
104973 RXNORM
5251 MMSL
5252 MMSL
d00334 MMSL
001583 NDDF
001584 NDDF
001585 NDDF
387213004 SNOMEDCT_US
39608003 SNOMEDCT_US
71533000 SNOMEDCT_US
91013003 SNOMEDCT_US
RP4A60D26L INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Pentazocine and naloxone HUMAN PRESCRIPTION DRUG LABEL 2 0591-0395 TABLET 50 mg ORAL ANDA 28 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 22 sections
Pentazocine Hydrochloride and Acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 43386-670 TABLET 25 mg ORAL ANDA 22 sections
PENTAZOCINE HYDROCHLORIDE AND NALOXONE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 2 43386-680 TABLET 50 mg ORAL ANDA 23 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 25 sections
Pentazocine and naloxone HUMAN PRESCRIPTION DRUG LABEL 2 68387-531 TABLET 50 mg ORAL ANDA 21 sections