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Technical details about Rifaximin, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. Also known as: Rifaxidin, Rifacol, 80621-81-4, Rifamycin l 105, Xifaxan, Rifamycin l 105sv
Molecular Formula
C43H51N3O11
Molecular Weight
785.9  g/mol
InChI Key
NZCRJKRKKOLAOJ-XRCRFVBUSA-N
FDA UNII
L36O5T016N

A synthetic rifamycin derivative and anti-bacterial agent that is used for the treatment of GASTROENTERITIS caused by ESCHERICHIA COLI INFECTIONS. It may also be used in the treatment of HEPATIC ENCEPHALOPATHY.
Rifaximin is a Rifamycin Antibacterial.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-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[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate
2.1.2 InChI
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
2.1.3 InChI Key
NZCRJKRKKOLAOJ-XRCRFVBUSA-N
2.1.4 Canonical SMILES
CC1C=CC=C(C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)OC(C4=O)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C5=C2N6C=CC(=CC6=N5)C)O)C
2.1.5 Isomeric 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
2.2 Other Identifiers
2.2.1 UNII
L36O5T016N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-deoxy-4'-methylpyrido(1',2'-1,2)imidazo(5,4c)rifamycin

2. L 105

3. L-105

4. L105

5. Redactiv

6. Xifaxan

2.3.2 Depositor-Supplied Synonyms

1. Rifaxidin

2. Rifacol

3. 80621-81-4

4. Rifamycin L 105

5. Xifaxan

6. Rifamycin L 105sv

7. Fatroximin

8. Rifaximine

9. Normix

10. Rifaximina

11. Xifaxsan

12. L-105

13. Rifamixin

14. Rifaximine [french]

15. Rifaximinum [latin]

16. Rifaximina [spanish]

17. Ritacol

18. Chebi:75246

19. 4-deoxy-4'-methylpyrido(1',2'-1,2)imidazo(5,4-c)rifamycin Sv

20. L36o5t016n

21. Rifaximin (xifaxan)

22. Nsc-758957

23. Rifaximinum

24. Brn 3584528

25. (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

26. C43h51n3o11

27. Rifaxin

28. Redactiv

29. Ido[1,2-a]benzimidazol-25-yl Acetate

30. (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

31. L 105sv

32. L 105 (ansamacrolide Antibiotic)

33. L 105

34. Rifaximinun

35. Flonorm

36. Lumenax

37. Spiraxin

38. Lormyx

39. Rifaximin [usan:inn:ban]

40. Unii-l36o5t016n

41. 5-yl Acetate

42. Ncgc00095842-01

43. (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

44. (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

45. Xifaxan (tn)

46. Mfcd00864973

47. Rifaximin [inn]

48. Rifaximin [jan]

49. Rifaximin [mi]

50. Rifaximin [usan]

51. Rifaximin [vandf]

52. Rifaximin [mart.]

53. Alpha-0817185

54. Rifaximin [who-dd]

55. Chembl1617

56. Dsstox_cid_25998

57. Dsstox_rid_81280

58. Dsstox_gsid_45998

59. (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

60. Rifaximin (jan/usan/inn)

61. Schembl124066

62. Rifaximin [ep Impurity]

63. Rifaximin [orange Book]

64. Dtxsid7045998

65. Rifaximin [ep Monograph]

66. Gtpl12012

67. Hms3715b19

68. 88747-56-2

69. Tox21_111529

70. Bdbm50347620

71. S1790

72. Akos015963053

73. Zinc169621200

74. Ccg-221129

75. Db01220

76. Nsc 758957

77. Rifaximin 100 Microg/ml In Acetonitrile

78. 2,7-(epoxy(1,11,13)pentadecatrienoimino)furo(2'',3'':7',8')naphth(1',2':4,5)imidazo(1,2-a)pyridine-1,15(2h)-dione, 25-(acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-, ( 2s,16z,18e,20s,21s,22r,23r,24r,25s,26r,27s,28e)-

79. 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))-

80. Ac-19112

81. Cas-80621-81-4

82. L/105

83. D02554

84. Ab01209738-01

85. Ab01209738-03

86. Ab01209738_04

87. Rifaximin, Antibiotic For Culture Media Use Only

88. 621r814

89. Q416073

90. Q-201671

91. (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

92. (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

93. [(7s,9e,11s,12r,13s,14r,15r,16r,17s,18s,19e,21z)-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[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] Acetate

94. 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,16z,18e,20s,21s,22r,23r,24r,25s,26r,27s,28e)-

95. 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

2.4 Create Date
2006-04-28
3 Chemical and Physical Properties
Molecular Weight 785.9 g/mol
Molecular Formula C43H51N3O11
XLogP36.9
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count3
Exact Mass785.35235945 g/mol
Monoisotopic Mass785.35235945 g/mol
Topological Polar Surface Area198 Ų
Heavy Atom Count57
Formal Charge0
Complexity1590
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameXifaxan
PubMed HealthRifaximin (By mouth)
Drug ClassesAntibiotic
Drug LabelXIFAXAN tablets contain rifaximin, a non-aminoglycoside semi-synthetic, nonsystemic antibiotic derived from rifamycin SV. Rifaximin is a structural analog of rifampin. The chemical name for rifaximin is (2 ,16 ,18 ,20 ,21 ,22 ,23 ,24 ,25 ,26 ,27...
Active IngredientRifaximin
Dosage FormTablet
RouteOral
Strength200mg; 550mg
Market StatusPrescription
CompanySalix Pharms

2 of 2  
Drug NameXifaxan
PubMed HealthRifaximin (By mouth)
Drug ClassesAntibiotic
Drug LabelXIFAXAN tablets contain rifaximin, a non-aminoglycoside semi-synthetic, nonsystemic antibiotic derived from rifamycin SV. Rifaximin is a structural analog of rifampin. The chemical name for rifaximin is (2 ,16 ,18 ,20 ,21 ,22 ,23 ,24 ,25 ,26 ,27...
Active IngredientRifaximin
Dosage FormTablet
RouteOral
Strength200mg; 550mg
Market StatusPrescription
CompanySalix Pharms

4.2 Drug Indication

Rifaximin has multiple indications by the FDA: for the treatment of patients (12 years of age) with traveller's diarrhea caused by noninvasive strains of Escherichia coli; for the reduction of overt hepatic encephalopathy recurrence in patients 18 years of age; and in May 2015 it was approved for irritable bowel syndrome with diarrhea (IBS-D) treatment in adult men and women.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Rifaximin is a structural analog of rifampin and a non-systemic, gastrointestinal site-specific antibiotic. This non-systemic property of the drug is due to the addition of a pyridoimidazole ring, which renders it non-absorbable. Rifaximin acts by inhibiting bacterial ribonucleic acid (RNA) synthesis and contributes to restore intestinal microflora imbalance. Other studies have also shown rifaximin to be an pregnane X receptor (PXR) activator. As PXR is responsible for inhibiting the proinflammatory transcription factor NF-kappa B (NF-B) and is inhibited in inflammatory bowel disease (IBD), rifaximin was proven to be effective for the treatment of IBS-D.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


Gastrointestinal Agents

Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
RIFAXIMIN
5.3.2 FDA UNII
L36O5T016N
5.3.3 Pharmacological Classes
Rifamycins [CS]; Rifamycin Antibacterial [EPC]
5.4 ATC Code

A07AA11

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


A - Alimentary tract and metabolism

A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

A07A - Intestinal antiinfectives

A07AA - Antibiotics

A07AA11 - Rifaximin


D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06A - Antibiotics for topical use

D06AX - Other antibiotics for topical use

D06AX11 - Rifaximin


5.5 Absorption, Distribution and Excretion

Absorption

Low absorption in both the fasting state and when administered within 30 minutes of a high-fat breakfast.


Route of Elimination

In a mass balance study, after administration of 400 mg 14C-rifaximin orally to healthy volunteers, of the 96.94% total recovery, 96.62% of the administered radioactivity was recovered in feces almost exclusively as the unchanged drug and 0.32% was recovered in urine mostly as metabolites with 0.03% as the unchanged drug.Rifaximin accounted for 18% of radioactivity in plasma. This suggests that the absorbed rifaximin undergoes metabolism with minimal renal excretion of the unchanged drug


5.6 Metabolism/Metabolites

In vitro drug interactions studies have shown that rifaximin, at concentrations ranging from 2 to 200 ng/mL, did not inhibit human hepatic cytochrome P450 isoenzymes: 1A2, 2A6, 2B6, 2C9, 2C19, 2D6, 2E1, and 3A4. In an in vitro hepa-tocyte induction model, rifaximin was shown to induce cytochrome P450 3A4 (CYP3A4), an isoenzyme which rifampin is known to induce.


5.7 Biological Half-Life

Approximately 6 hours.


5.8 Mechanism of Action

Rifaximin acts by inhibiting RNA synthesis in susceptible bacteria by binding to the beta-subunit of bacterial deoxyribonucleic acid (DNA)-dependent ribonucleic acid (RNA) polymerase enzyme. This binding blocks translocation, which stops transcription.


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