Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00593)
Name
Rifaximin
Synonyms    Click to Show/Hide the Synonyms of This API
Rifaximin; Rifaxidin; Rifacol; Xifaxan; 80621-81-4; Rifaximine; Rifamycin L 105; Rifamycin L 105SV; Fatroximin; Normix; Rifaximina; C43H51N3O11; Rifamixin; Rifaximine [French]; Rifaximinum [Latin]; Rifaximina [Spanish]; UNII-L36O5T016N; Ritacol; CHEBI:75246; L36O5T016N; MFCD00864973; Rifaximin (Xifaxan); Rifaximin, 98%; Rifaximinum; 4-Deoxy-4'-methylpyrido(1',2'-1,2)imidazo(5,4-c)rifamycin SV; BRN 3584528; (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-1,15-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)furo[2'',3'':7',8']naphtho[1',2':4,5]imidazo[1,2-a]pyridin-25-yl acetate; 88747-56-2; Rifaxin; RedActiv; (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-25-(Acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1,15(2H)-dione; (2S,18E,28E)-25S-(acetyloxy)-5,6,21S,23R-tetrahydroxy-27S-methoxy-2,4,11,16Z,20S,22R,24R,26R-octamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1,15(2H)-dione; L 105SV; L 105 (Ansamacrolide antibiotic); rifaximinun; Flonorm; Lumenax; Spiraxin; Xifaxsan; Lormyx; Rifaximin [USAN:INN:BAN]; 4-Deoxy-4'-methylpyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV; 5-yl acetate; NCGC00095842-01; Xifaxan (TN); alpha-0817185; CHEMBL1617; DSSTox_CID_25998; DSSTox_RID_81280; DSSTox_GSID_45998; (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26S,27S,28E)-5,6,21,23,25 Pentahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca(1,11,13)trienimino)benzofuro(4,5-e)pyrido(1,2-a)benzimidazole-1,15(2H)-dione, 25-acetate; Rifaximin (JAN/USAN/INN); SCHEMBL124066; DTXSID7045998; HMS3715B19; Tox21_111529; BDBM50347620; AKOS015963053; ZINC169621200; CCG-221129; DB01220; ido[1,2-a]benzimidazol-25-yl acetate; 2,7-(Epoxypentadeca(1,11,13)trienimino)benzofuro(4,5-e)pyrido(1,2-a)benzimidazole-1,15(2H)-dione, 25-(acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-, (2S-(2R*,16Z,18E,20R*,21R*,22S*,23S*,24S*,25R*,26S*,27R*,28E))-; AC-19112; CAS-80621-81-4; D02554; J10371; AB01209738-01; AB01209738-03; AB01209738_04; Rifaximin, Antibiotic for Culture Media Use Only; 621R814; Q416073; Q-201671; (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-1,1; (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)5,6,21,23-Tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-1,15-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)[1]benzofuro[4,5-e]pyr; (7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.1^{4,7}.0^{5,35}.0^{26,34}.0^{27,32}]heptatriaconta-1,3,5(35),9,19,21,25(36),26(34),28,30,32-undecaen-13-yl acetate; 5-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)furo[2'',3'':7',8']naphtho[1',2':4,5]imidazo[1,2-a]pyridin-2
Clinical Status
Approved
Disease Indication Hepatic encephalopathy ICD-11: DB99 [1]
PubChem CID
6436173
Formula
C43H51N3O11
Canonical SMILES
C[C@H]1/C=C/C=C(\\C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)O[C@@](C4=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C5=C2N6C=CC(=CC6=N5)C)O)/C
InChI
1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1
InChIKey
NZCRJKRKKOLAOJ-XRCRFVBUSA-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=6436173"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 785.9 Topological Polar Surface Area 198
XlogP 6.9 Complexity 1590
Heavy Atom Count 57 Rotatable Bond Count 3
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 12
Full List of Drug Formulations (DFMs) Containing This API
          Rifaximin 550 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 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
Glyceryl palmitostearate; Edetate disodium; Ferric oxide red; Propylene glycol; Talc; Titanium dioxide; Polyvinyl alcohol; Silicon dioxide; Cellulose, microcrystalline; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Glyceryl palmitostearate; Edetate disodium; Ferric oxide red; Propylene glycol; Talc; Titanium dioxide; Silicon dioxide; Microcrystalline cellulose; Polyvinyl alcohol, unspecified; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Cardinal Health
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             Drug Formulation 3 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
Glyceryl palmitostearate; Ferric oxide red; Propylene glycol; Talc; Titanium dioxide; Silicon dioxide; Microcrystalline cellulose; Polyvinyl alcohol, unspecified; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Salix Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Rifaximin 200 mg tablet 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
Glyceryl palmitostearate; Edetate disodium; Ferric oxide red; Propylene glycol; Talc; Titanium dioxide; Silicon dioxide; Hypromellose, unspecified; Microcrystalline cellulose; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Salix Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Glyceryl palmitostearate; Edetate disodium; Ferric oxide red; Propylene glycol; Talc; Titanium dioxide; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Avera McKennan Hospital; Carilion Materials Management; Dispensing Solution; Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
References
1 FDA label for approved rifaximin from the official website of the U.S. Food and Drug Administration.
2 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
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.

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