Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00564)
Name
Propoxyphene
Synonyms    Click to Show/Hide the Synonyms of This API
Dextropropoxyphene; propoxyphene; d-Propoxyphene; Dextropropoxyphen; Dextroproxifeno; Destropropossifene; Proxagesic; Algafan; Antalvic; Femadol; 469-62-5; Dextropropoxifeno; Dextropropoxyphenum; Darvon; Propoxyphene, (+)-; 4-Dimethylamino-3-methyl-1,2-diphenyl-2-propoxybutane; UNII-S2F83W92TK; (+)-1,2-Diphenyl-2-propionoxy-3-methyl-4-dimethylaminobutane; (+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-propionyloxybutane; alpha-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol propionate ester; (S)-alpha-(2-(Dimethylamino)-1-methylethyl)-alpha-phenylbenzeneethanol propanoate; alpha-D-4-Dimethylamino-3-methyl-1,2-diphenyl-2-butanol-propionat; S2F83W92TK; CHEBI:51173; (1S,2R)-1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propanoate; [(2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate; 2-Butanol, 4-(dimethylamino)-3-methyl-1,2-diphenyl-, propionate (ester), (2S,3R)-; 2-Butanol, 4-(dimethylamino)-3-methyl-1,2-diphenyl-, propionate, (+)-; Dextroproxifeno [Spanish]; Propoxypene; Destropropossifene [DCIT]; alpha-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol propionate; Depromic; Proxyvon; Dextropropoxifeno [INN-Spanish]; Dextropropoxyphenum [INN-Latin]; (D)-PROPOXYPHENE; Dextropropoxyphene [INN:BAN]; Dextropropoxyphene (INN); HSDB 3175; EINECS 207-420-5; USAF EL-84; Bulk dextropropoxyphene (non-dosage forms); Propoxyphene-d; DEA No. 9273; alpha-D-4-Dimethylamino-3-methyl-1,2-diphenyl-2-butanol propionate; alpha-D-4-Dimethylamino-3-methyl-1,2-diphenyl-2-butanol-propionat [German]; Darvon (Salt/Mix); Dolene (Salt/Mix); Abalgin (Salt/Mix); Doloxen (Salt/Mix); Erantin (Salt/Mix); Romidon (Salt/Mix); Benzeneethanol, alpha-(2-(dimethylamino)-1-methylethyl)-alpha-phenyl-, propanoate (ester), (S-(R*,S*))-; Doloxene (Salt/Mix); C07406; D07809; .alpha.-d-Propoxyphene; (+)-alpha-propoxyphene; alpha-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-propionoxybutane; SCHEMBL25405; GTPL7593; CHEMBL1213351; DTXSID1023524; BDBM82269; Benzeneethanol, .alpha.-[2-(dimethylamino)-1-methylethyl]-.alpha.-phenyl-, propanoate (ester), [S-(R*,S*)]-; ZINC1530769; DB00647; 2621-61-6; Benzeneethanol, alpha-((1R)-2-(dimethylamino)-1-methylethyl)-alpha-phenyl-, propanoate (ester), (alphaS)-; CAS_469-62-5; Methanol, compd. with (+-)-alpha-(2-dimethylamino)-1-methylethyl-alpha- phenylphenethyl propionate (1:1); Dextropropoxyphene 0.1 mg/ml in Acetonitrile; Dextropropoxyphene 1.0 mg/ml in Acetonitrile; Q2268608; UNII-II2G62OV6F component XLMALTXPSGQGBX-GCJKJVERSA-N; (+)-4-(Dimethylamino)-3-methyl-1,2-diphenyl-2-butanol propionate; [(2S,3R)-4-dimethylamino-3-methyl-1,2-di(phenyl)butan-2-yl] propanoate; (2S,3R)-(+)-4-(Dimethylamino)-3-methyl-1,2-diphenyl-2-butanol propionate(ester); .alpha.-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol propionate ester; 1-Benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propionate, [S-(R*,S*)]- #; (+)-Propoxyphene solution, 1.0 mg/mL in acetonitrile, ampule of 1 mL, certified reference material; Benzeneethanol, .alpha.-[2-(dimethylamino)-1-methylethyl]-.alpha.-phenyl-, propanoate, [S-(R*,S*)]-
Clinical Status
Approved
Disease Indication Lung cancer ICD-11: 2C25 [1]
PubChem CID
10100
Formula
C22H29NO2
Canonical SMILES
CCC(=O)O[C@](CC1=CC=CC=C1)(C2=CC=CC=C2)[C@H](C)CN(C)C
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/t18-,22+/m1/s1
InChIKey
XLMALTXPSGQGBX-GCJKJVERSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=10100"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 339.5 Topological Polar Surface Area 29.5
XlogP 4.2 Complexity 397
Heavy Atom Count 25 Rotatable Bond Count 9
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Propoxyphene 65 mg capsule Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Anhydrous lactose; Sodium lauryl sulfate; Magnesium stearate; Potassium chloride; Ammonia; Ferric oxide red; Ferrosoferric oxide; Potassium hydroxide; Propylene glycol; Titanium dioxide; Hypromellose; Carnauba wax; Carrageenan; Cellulose, microcrystalline; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Potassium chloride DIG Info Carbonic anhydrase IV (Ki = 90000 nM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; D&c red no. 33; Fd&c yellow no. 6; Magnesium stearate; Titanium dioxide; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company Bryant Ranch Prepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 33 DIG Info Solute carrier SLCO2B1 (Ki = 58.1 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
References
1 FDA label for approved propoxyphene from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 Characterization and anions inhibition studies of an -carbonic anhydrase from the teleost fish Dicentrarchus labrax. Bioorg Med Chem. 2011 Jan 15; 19(2):744-8.
4 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
5 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
6 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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