dextropropoxyphene Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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
MRTD (Maximum Recommended Therapeutic Daily Dose) 19.15 µM/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

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 1064.70 16.54 541 5339 243284 46436898
Completed suicide 195.48 16.54 155 5725 145765 46534417
Toxicity to various agents 145.86 16.54 155 5725 211611 46468571
Injury 79.26 16.54 56 5824 43971 46636211
Cardio-respiratory arrest 76.42 16.54 62 5818 59807 46620375
Respiratory arrest 75.13 16.54 49 5831 33767 46646415
Cardiac arrest 52.99 16.54 61 5819 90338 46589844
Poisoning 48.50 16.54 27 5853 13967 46666215
Overdose 45.52 16.54 60 5820 101919 46578263
Emotional distress 31.35 16.54 28 5852 30679 46649503
Frontotemporal dementia 25.28 16.54 6 5874 255 46679927
Spleen congestion 22.62 16.54 5 5875 154 46680028
Aortic valve calcification 22.35 16.54 6 5874 421 46679761
Thyroid adenoma 22.03 16.54 5 5875 174 46680008
Uterine perforation 19.81 16.54 12 5868 7255 46672927
Sudden death 19.22 16.54 13 5867 9491 46670691
Poisoning deliberate 18.85 16.54 12 5868 7914 46672268
Cardiomegaly 17.95 16.54 16 5864 17466 46662716
Accidental overdose 17.95 16.54 17 5863 20049 46660133
Drug abuse 17.73 16.54 30 5850 63378 46616804
Drug screen positive 17.69 16.54 9 5871 3882 46676300
Dependence 16.77 16.54 7 5873 1924 46678258

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
Drug hypersensitivity 121.80 24.63 73 2346 68446 29881613
Completed suicide 73.33 24.63 62 2357 99430 29850629
Respiratory arrest 67.40 24.63 37 2382 29221 29920838
Toxicity to various agents 64.32 24.63 75 2344 177108 29772951
Poisoning 58.62 24.63 25 2394 11357 29938702
Drug abuse 58.06 24.63 50 2369 82022 29868037
Overdose 49.00 24.63 46 2373 84291 29865768
Cardiac arrest 48.95 24.63 48 2371 92802 29857257
Accidental overdose 47.33 24.63 25 2394 18250 29931809
Agoraphobia 34.25 24.63 7 2412 233 29949826
Cardio-respiratory arrest 32.73 24.63 31 2388 57275 29892784
Neurosis 30.68 24.63 6 2413 159 29949900
Somnambulism 26.79 24.63 10 2409 3204 29946855

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
FDA MoA N0000175684 Full Opioid Agonists
FDA EPC N0000175690 Opioid Agonist
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 D009294 Narcotics
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:35482 narcotic analgesics
CHEBI has role CHEBI:55322 mu opioid agonist

Drug Use (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

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
Glutamate receptor ionotropic, NMDA 3A Ion channel IC50 5.30 WOMBAT-PK
Sodium channel protein type 5 subunit alpha Ion channel WOMBAT-PK

External reference:

IDSource
4019915 VUID
N0000148000 NUI
D00482 KEGG_DRUG
1639-60-7 SECONDARY_CAS_RN
4017511 VANDF
4017512 VANDF
4019915 VANDF
C0033493 UMLSCUI
CHEBI:51173 CHEBI
CHEMBL1213351 ChEMBL_ID
CHEMBL1237104 ChEMBL_ID
CHEMBL3989716 ChEMBL_ID
DB00647 DRUGBANK_ID
D011431 MESH_DESCRIPTOR_UI
10100 PUBCHEM_CID
7593 IUPHAR_LIGAND_ID
C084813 MESH_SUPPLEMENTAL_RECORD_UI
740 INN_ID
S2F83W92TK UNII
71517 RXNORM
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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
PROPOXYPHENE NULLPSYLATE 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 NULLPSYLATE AND ACETAMINOPHEN HUMAN PRESCRIPTION DRUG LABEL 2 67296-0104 TABLET 100 mg ORAL ANDA 19 sections
PROPOXYPHENE NULLPSYLATE 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