Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00274)
Name
Fidaxomicin
Synonyms    Click to Show/Hide the Synonyms of This API
Fidaxomicin; Tiacumicin B; Dificid; Dificlir; Lipiarmycin; OPT-80; Lipiarmicin; Difimicin; PAR-101; 873857-62-6; UNII-Z5N076G8YQ; Z5N076G8YQ; Lipiarmycin A3; Clostomicin B1; R-Tiacumicin B; Lipiarmycin A 3; Fidaxomicin [USAN:INN]; Lipiarrmycin; PAR 01; Clostomycin B1; fidaxomicin/Dificid; Fidaxomicin (Dificid); BRN 5228707; CHEMBL1255800; SCHEMBL10000818; Fidaxomicin, >=98% (HPLC); GTPL10909; DTXSID901016415; DB08874; OPT-80;PAR-101;Clostomicin B1;Tiacumicin B; S-7827; Q5446672; (2R,3S,4S,5S,6R)-6-{[(3E,5E,8S,9E,11S,12R,13E,15E,18S)-12-{[(2R,3S,4R,5S)-3,4-dihydroxy-6,6-dimethyl-5-[(2-methylpropanoyl)oxy]oxan-2-yl]oxy}-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15-trimethyl-2-oxo-1-oxacyclooctadeca-3,5,9,13,15-pentaen-3-yl]methoxy}-4-hydroxy-5-methoxy-2-methyloxan-3-yl 3,5-dichloro-2-ethyl-4,6-dihydroxybenzoate
Clinical Status
Approved
Disease Indication Clostridium difficile infection ICD-11: 1A04 [1]
PubChem CID
10034073
Formula
C52H74Cl2O18
Canonical SMILES
CC[C@H]1/C=C(/[C@H](C/C=C/C=C(/C(=O)O[C@@H](C/C=C(/C=C(/[C@@H]1O[C@H]2[C@H]([C@H]([C@@H](C(O2)(C)C)OC(=O)C(C)C)O)O)\\C)\\C)[C@@H](C)O)\\CO[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)OC(=O)C4=C(C(=C(C(=C4O)Cl)O)Cl)CC)O)OC)O)\\C
InChI
1S/C52H74Cl2O18/c1-13-30-22-26(6)33(56)18-16-15-17-31(23-66-51-45(65-12)42(61)44(29(9)67-51)69-49(64)35-32(14-2)36(53)39(58)37(54)38(35)57)48(63)68-34(28(8)55)20-19-25(5)21-27(7)43(30)70-50-41(60)40(59)46(52(10,11)72-50)71-47(62)24(3)4/h15-17,19,21-22,24,28-30,33-34,40-46,50-51,55-61H,13-14,18,20,23H2,1-12H3/b16-15+,25-19+,26-22+,27-21+,31-17+/t28-,29-,30+,33+,34+,40-,41+,42+,43+,44-,45+,46+,50-,51-/m1/s1
InChIKey
ZVGNESXIJDCBKN-UUEYKCAUSA-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=10034073"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 1058 Topological Polar Surface Area 267
XlogP 6.4 Complexity 1970
Heavy Atom Count 72 Rotatable Bond Count 15
Hydrogen Bond Donor Count 7 Hydrogen Bond Acceptor Count 18
Full List of Drug Formulations (DFMs) Containing This API
          Fidaxomicin 200 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 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
Butylated hydroxytoluene; Magnesium stearate; Talc; Titanium dioxide; Lecithin, soybean; Polyvinyl alcohol; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h); Polyethylene glycols; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Avera McKennan Hospital; Merck Sharp & Dohme
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [5]
References
1 FDA label for approved fidaxomicin from the official website of the U.S. Food and Drug Administration.
2 Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem. 2009 Apr 15; 17(8):3207-11.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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