Dextropropoxyphene napsylateProduct ingredient for Dextropropoxyphene

Name
Dextropropoxyphene napsylate
Drug Entry
Dextropropoxyphene

Dextropropoxyphene is an analgesic in the opioid category, patented (1955) and manufactured by Eli Lilly and Company. It is intended to treat mild pain and also has antitussive and local anaesthetic effects. The drug has been taken off the market in Europe and the US due to concerns of fatal overdoses and heart arrhythmias. An estimated 10 million patients have used these products.

The drug is often referred to as the general form, "propoxyphene", however only the dextro-isomer (dextropropoxyphene) has any analgesic effect. The levo-isomer appears to exhibit a very limited antitussive effect.

Accession Number
DBSALT001000  (DB09396)
Structure
Thumb
Synonyms
d-Propoxyphene napsylate hydrate / Dextropropoxyphene napsilate / Propoxyphene napsilate / Propoxyphene napsylate
External IDs
S-9700
UNII
38M219L1OJ
CAS Number
26570-10-5
Weight
Average: 565.73
Monoisotopic: 565.249809154
Chemical Formula
C32H39NO6S
InChI Key
GBKONKCASNNUQD-VGHSCWAPSA-N
InChI
InChI=1S/C22H29NO2.C10H8O3S.H2O/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19;11-14(12,13)10-6-5-8-3-1-2-4-9(8)7-10;/h6-15,18H,5,16-17H2,1-4H3;1-7H,(H,11,12,13);1H2/t18-,22+;;/m1../s1
IUPAC Name
(2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate naphthalene-2-sulfonic acid hydrate
SMILES
O.OS(=O)(=O)C1=CC2=CC=CC=C2C=C1.CCC(=O)O[C@@](CC1=CC=CC=C1)([C@H](C)CN(C)C)C1=CC=CC=C1
External Links
PubChem Compound
33544
PubChem Substance
347827841
ChemSpider
30946
ChEBI
51179
ChEMBL
CHEMBL3989716
Wikipedia
Dextropropoxyphene
Predicted Properties
PropertyValueSource
Water Solubility0.00419 mg/mLALOGPS
logP4.06ALOGPS
logP4.9ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity102.88 m3·mol-1ChemAxon
Polarizability38.71 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon