4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate

• ChemBase ID: 529
• Molecular Formular: C22H29NO2
• Molecular Mass: 339.47116
• Monoisotopic Mass: 339.21982917
• SMILES: O(C(C(CN(C)C)C)(Cc1ccccc1)c1ccccc1)C(=O)CC
• Canonical SMILES: CCC(=O)OC(c1ccccc1)(C(CN(C)C)C)Cc1ccccc1
• InChI: InChI=1S/C22H29NO2/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/h6-15,18H,5,16-17H2,1-4H3
• InChIKey: XLMALTXPSGQGBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate
• IUPAC Traditional name: propoxyphene
• Brand Name: Algafan; Antalvic; Darvon; Darvon-N; Deprancol; Depromic; Dolene; Dolocap; Doloxen; Doloxene; Erantin; Femadol; Harmar; Kesso-Gesic; Propacet; Prophene 65; Propoxychel; Propoxyphene HCl 65; Proxagesic
• Synonyms: D-Propoxyphene; Dextropropoxyphene; Dextropropoxyphene-M; Dextroproxifeno; Propoxyphene HCl; Propoxyphene

Database IDs

• CAS Number: 469-62-5
• PubChem SID: 160963992
• PubChem CID: 15330

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.5163397
• LogD (pH = 7.4): 2.7993603
• Log P: 4.9021554
• Molar Refractivity: 102.8806 cm^3
• Polarizability: 40.66616 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.06
• LOG S: -4.91
• Solubility (Water): 4.19e-03 g/l

PROPERTIES

Physical Property

• Solubility: 19.6mg/L
• Hydrophobicity(logP): 4.4

DETAILS

DrugBank - DB00647

• Drug Groups: illicit; approved
• Description: A narcotic analgesic structurally related to methadone. Only the dextro-isomer has an analgesic effect; the levo-isomer appears to exert an antitussive effect. [PubChem]
• Indication: For the relief of mild to moderate pain
• Pharmacology: Propoxyphene, a synthetic opiate agonist, is structurally similar to methadone. Its general pharmacologic properties are those of the opiates as a group. The analgesic effect of propoxyphene is due to the d-isomer, dextropropoxyphene. It binds to the opiate receptors and leads to a decrease of the perception of pain stimuli. Propoxyphene possesses little to no antitussive activity and no antipyretic action.
• Toxicity: Coma, respiratory depression, circulatory collapse, and pulmonary edema. Seizures occur more frequently in patients with propoxyphene intoxication than in those with opiate intoxication. LD₅₀=230mg/kg (orally in rat, Emerson)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Half Life: 6-12 hours
• Elimination: The major route of metabolism is cytochrome CYP3A4 mediated N-demethylation to norpropoxyphene, which is excreted by the kidneys. ; In 48 hours, approximately 20% to 25% of the administered dose of propoxyphene is excreted via the urine, most of which is free or conjugated norpropoxyphene.
• Distribution: * 16 L/kg
• Clearance: * 2.6 L/min
• References: Coda BA, Rudy AC, Archer SM, Wermeling DP: Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers. Anesth Analg. 2003 Jul;97(1):117-23, table of contents. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Coda BA, Rudy AC, Archer SM, Wermeling DP: Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers. Anesth Analg. 2003 Jul;97(1):117-23, table of contents. Pubmed