dextropropoxyphene ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
844 469-62-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dextropropoxyphene
  • propoxyphene hydrochloride
  • dextropropoxyphen
  • propoxyphene
  • d-Propoxyphene
  • propoxyphene napsylate
  • propoxyphene HCl
  • destropropoxifene
A narcotic analgesic structurally related to METHADONE. Only the dextro-isomer has an analgesic effect; the levo-isomer appears to exert an antitussive effect.
  • Molecular weight: 339.48
  • Formula: C22H29NO2
  • CLOGP: 5.21
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 0
  • TPSA: 29.54
  • ALOGS: -4.91
  • ROTB: 9
  • Status: OFM
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g O
0.30 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.02 mg/mL Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 50 %
MRTD (Maximum Recommended Therapeutic Daily Dose) 19.15 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 12 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 15 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.24 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 18 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AKT2,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,JAK3,MAP3K7,MAPK12,MAPK7,MET,NTRK2,PDK2,PDK4,PIK3CB,PIM2,PRKDC,SIK2,SIK3,TEK 34
kinase-selectivity-class AXL,EIF2AK3,EPHB4,GRK2,PDK4,TEK 6
pfas-class PFAS structural alert (1 = True, 0 = False) 0

Approvals:

DateAgencyCompanyOrphan
Aug. 16, 1957 FDA

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 498.54 79.76 248 2387 463361 90162451
Vaginal flatulence 231.50 79.76 57 2578 12581 90613231
Proctitis 220.83 79.76 57 2578 15202 90610610
Female genital tract fistula 216.64 79.76 58 2577 17810 90608002
Radiculopathy 209.93 79.76 57 2578 18448 90607364
Vaginal discharge 207.08 79.76 57 2578 19407 90606405
Chronic sinusitis 200.18 79.76 58 2577 23744 90602068
Paraesthesia oral 188.03 79.76 59 2576 31600 90594212
Macular degeneration 177.48 79.76 59 2576 37911 90587901
Oral candidiasis 173.35 79.76 57 2578 35398 90590414
Frequent bowel movements 150.54 79.76 58 2577 56877 90568935
Colitis ulcerative 143.82 79.76 57 2578 60209 90565603
Colitis 138.97 79.76 58 2577 69884 90555928
Haematochezia 138.20 79.76 58 2577 70855 90554957
Rectal haemorrhage 132.80 79.76 59 2576 82685 90543127
Procedural pain 106.32 79.76 39 2596 33321 90592491
Toxicity to various agents 89.93 79.76 71 2564 287775 90338037
Therapeutic product effect incomplete 85.72 79.76 59 2576 193837 90431975

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
Toxicity to various agents 120.70 104.89 49 270 229087 42391929

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 405.69 87.05 206 2611 453884 110132598
Vaginal flatulence 241.22 87.05 57 2760 12087 110574395
Female genital tract fistula 228.73 87.05 58 2759 16461 110570021
Proctitis 222.41 87.05 57 2760 16870 110569612
Vaginal discharge 219.22 87.05 57 2760 17851 110568631
Radiculopathy 214.88 87.05 57 2760 19279 110567203
Macular degeneration 213.14 87.05 58 2759 21601 110564881
Chronic sinusitis 204.71 87.05 58 2759 25026 110561456
Paraesthesia oral 192.09 87.05 59 2758 33612 110552870
Oral candidiasis 167.68 87.05 57 2760 44703 110541779
Toxicity to various agents 165.95 87.05 119 2698 480436 110106046
Frequent bowel movements 145.20 87.05 58 2759 71332 110515150
Colitis ulcerative 137.30 87.05 57 2760 77306 110509176
Colitis 125.10 87.05 58 2759 102265 110484217
Rectal haemorrhage 119.35 87.05 59 2758 119774 110466708
Haematochezia 118.39 87.05 58 2759 115466 110471016
Procedural pain 108.90 87.05 39 2778 35526 110550956

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N02AC04 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Diphenylpropylamine derivatives
ATC N02AC54 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Diphenylpropylamine derivatives
ATC N02AC74 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Diphenylpropylamine derivatives
MeSH PA D000700 Analgesics
MeSH PA D000701 Analgesics, Opioid
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D009294 Narcotics
MeSH PA D018689 Sensory System Agents
FDA MoA N0000175684 Full Opioid Agonists
FDA EPC N0000175690 Opioid Agonist
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35482 opioid analgesic
CHEBI has role CHEBI:51177 antitussive
CHEBI has role CHEBI:55322 ฮผ-opioid receptor agonist

Related Drugs by ATC class:

N02AC Diphenylpropylamine derivatives 4 drugs
bezitramidedextromoramidemethadonepiritramide

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Hypovolemia contraindication 28560003
Orthostatic hypotension contraindication 28651003
Hypercapnia contraindication 29596007
Depressive disorder contraindication 35489007
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Paralytic ileus contraindication 55525008 DOID:8442
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Substance abuse contraindication 66214007
Poisoning by acetaminophen contraindication 70273001
Agoraphobia contraindication 70691001 DOID:593
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Gastrointestinal hemorrhage contraindication 74474003
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Cor pulmonale contraindication 83291003 DOID:8515
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Hemophilia contraindication 90935002
Disorder of biliary tract contraindication 105997008 DOID:9741
Anemia due to enzyme deficiency contraindication 111577008
Prolonged QT interval contraindication 111975006
von Willebrand disorder contraindication 128105004 DOID:12531
Seizure disorder contraindication 128613002
Prolonged PR interval contraindication 164947007
Obsessive-compulsive disorder contraindication 191736004 DOID:10933
Insomnia contraindication 193462001
Acute pancreatitis contraindication 197456007 DOID:2913
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Exacerbation of asthma contraindication 281239006
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Panic disorder contraindication 371631005 DOID:594
Hypoxia contraindication 389086002
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Myocardial infarction in recovery phase contraindication 418044006
Central nervous system depression contraindication 418072004
Congenital long QT syndrome contraindication 442917000
Acute erosive gastritis contraindication 444926003
Acute exacerbation of asthma contraindication 708038006




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.26 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
Mu-type opioid receptor GPCR AGONIST WOMBAT-PK CHEMBL
Sodium channel protein type 5 subunit alpha Ion channel WOMBAT-PK
Glutamate receptor ionotropic, NMDA 3A Ion channel IC50 5.30 WOMBAT-PK

External reference:

IDSource
4019915 VUID
N0000148000 NUI
D00482 KEGG_DRUG
1639-60-7 SECONDARY_CAS_RN
26570-10-5 SECONDARY_CAS_RN
71517 RXNORM
4017511 VANDF
4017512 VANDF
4019915 VANDF
C0033493 UMLSCUI
CHEBI:51173 CHEBI
CHEMBL1237104 ChEMBL_ID
CHEMBL1213351 ChEMBL_ID
CHEMBL3989716 ChEMBL_ID
DB00647 DRUGBANK_ID
D011431 MESH_DESCRIPTOR_UI
10100 PUBCHEM_CID
7593 IUPHAR_LIGAND_ID
C084813 MESH_SUPPLEMENTAL_RECORD_UI
2224 MMSL
5373 MMSL
5374 MMSL
d00360 MMSL
001574 NDDF
001575 NDDF
001576 NDDF
117005003 SNOMEDCT_US
387042001 SNOMEDCT_US
56297001 SNOMEDCT_US
6837005 SNOMEDCT_US
740 INN_ID
CB2TL9PS0T UNII
CB2TL9PS0T INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
PROPOXYPHENE NAPSYLATE AND ACETAMINOPHEN HUMAN PRESCRIPTION DRUG LABEL 2 12634-537 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections
Propoxyphene HUMAN PRESCRIPTION DRUG LABEL 1 16590-198 CAPSULE 65 mg ORAL ANDA 13 sections
Darvon-N HUMAN PRESCRIPTION DRUG LABEL 1 16590-874 TABLET, FILM COATED 100 mg ORAL NDA 14 sections
Propoxyphene Napsylate and Acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 21695-280 TABLET, FILM COATED 100 mg ORAL ANDA 23 sections
Propoxyphene and Acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 63874-201 TABLET, FILM COATED 100 mg ORAL ANDA 29 sections
PROPOXYPHENE NAPSYLATE AND ACETAMINOPHEN HUMAN PRESCRIPTION DRUG LABEL 2 67296-0104 TABLET 100 mg ORAL ANDA 19 sections
PROPOXYPHENE NAPSYLATE AND ACETAMINOPHEN HUMAN PRESCRIPTION DRUG LABEL 2 67296-0105 TABLET 100 mg ORAL ANDA 19 sections
Propoxyphene Napsylate and Acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 67296-0378 TABLET, FILM COATED 100 mg ORAL ANDA 23 sections
Propoxyphene and Acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 68387-100 TABLET, FILM COATED 100 mg ORAL ANDA 29 sections