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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H51N3O11
Molecular Weight 785.8785
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIFAXIMIN

SMILES

CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C4=C(C(O)=C3C)C(O)=C(NC(=O)C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C5=C4N=C6C=C(C)C=CN56

InChI

InChIKey=NZCRJKRKKOLAOJ-XRCRFVBUSA-N
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

HIDE SMILES / InChI

Molecular Formula C43H51N3O11
Molecular Weight 785.8785
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Rifaximin is a structural analog of rifampin and a non-systemic, gastrointestinal site-specific antibiotic. Rifaximin acts by inhibiting bacterial ribonucleic acid (RNA) synthesis and contributes to restore intestinal microflora imbalance. It is FDA approved for the treatment of travelers’ diarrhea, reduction in risk of overt hepatic encephalopathy (HE) recurrence and treatment of irritable bowel syndrome with diarrhea. More common side effects are: black, tarry stools; dizziness or lightheadedness; muscle spasm; rapid breathing; shortness of breath; trouble sleeping. Co-administration of cyclosporine, with XIFAXAN resulted in 83-fold and 124-fold increases in rifaximin mean Cmax in healthy subjects.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
25.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
XIFAXAN
Preventing
XIFAXAN
Primary
XIFAXAN

Cmax

ValueDoseCo-administeredAnalytePopulation
4.1 ng/mL
550 mg single, oral
RIFAXIMIN plasma
Homo sapiens
3.4 ng/mL
550 mg 2 times / day steady-state, oral
RIFAXIMIN plasma
Homo sapiens
4.8 ng/mL
550 mg single, oral
RIFAXIMIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
11.1 ng × h/mL
550 mg single, oral
RIFAXIMIN plasma
Homo sapiens
12.3 ng × h/mL
550 mg 2 times / day steady-state, oral
RIFAXIMIN plasma
Homo sapiens
22.5 ng × h/mL
550 mg single, oral
RIFAXIMIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.8 h
550 mg single, oral
RIFAXIMIN plasma
Homo sapiens
4.8 h
550 mg single, oral
RIFAXIMIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
32.5%
550 mg single, oral
RIFAXIMIN plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Travelers’ Diarrhea: The recommended dose is one 200 mg tablet taken orally three times a day for 3 days. Hepatic Encephalopathy: The recommended dose is one 550 mg tablet taken orally two times a day. Irritable Bowel Syndrome with Diarrhea: The recommended dose is one 550 mg tablet taken orally three times a day for 14 days. It can be taken with or without food.
Route of Administration: Oral
In Vitro Use Guide
The activities of rifaximin against enteropathogens were found to be as follows: a MIC50 of 4 to 8 μg/ml and a MIC90 of >8 μg/ml.
Substance Class Chemical
Record UNII
L36O5T016N
Record Status Validated (UNII)
Record Version