RIFAXIMIN

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

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

Structure Search

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:44:56 UTC 2023` Edited by `admin` on `Fri Dec 15 15:44:56 UTC 2023`
Record UNII	L36O5T016N
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

RIFAXIMIN

Official Name

English

(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

Common Name

English

RIFAXIMIN [USAN]

Common Name

English

rifaximin [INN]

Common Name

English

NSC-758957

Code

English

RIFAXIMIN [VANDF]

Common Name

English

RIFAXIMIN [EP IMPURITY]

Common Name

English

RIFAXIMIN [ORANGE BOOK]

Common Name

English

RIFAMYCIN L 105

Common Name

English

RIFAXIDIN

Common Name

English

L-105

Common Name

English

RIFAXIMIN [EP MONOGRAPH]

Common Name

English

Rifaximin [WHO-DD]

Common Name

English

RIFAXIMIN [MART.]

Common Name

English

RIFAXIMIN [MI]

Common Name

English

XIFAXSAN

Brand Name

English

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)-

Systematic Name

English

RIFAXIMIN [JAN]

Common Name

English

4-DEOXY-4'-METHYLPYRIDO(1',2'-1,2)IMIDAZO(5,4-C)RIFAMYCIN SV

Common Name

English

Classification Tree Code System Code

WHO-ATC

D06AX11

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

NDF-RT

N0000007911

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

NDF-RT

N0000007911

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

WHO-VATC

QD06AX11

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

FDA ORPHAN DRUG

778520

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

NDF-RT

N0000007911

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

WHO-VATC

QA07AA11

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

NCI_THESAURUS

C258

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

FDA ORPHAN DRUG

109497

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

WHO-VATC

QJ51XX01

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

WHO-VATC

QG51AA06

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

NDF-RT

N0000175500

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

WHO-ATC

A07AA11

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

NDF-RT

N0000007911

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

LIVERTOX

NBK548082

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

Code System Code Type Description

SMS_ID

100000091946

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

INN

5244

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

RXCUI

35619

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

RxNorm

CAS

80621-81-4

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

LACTMED

Rifaximin

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

EVMPD

SUB10312MIG

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

FDA UNII

L36O5T016N

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

DAILYMED

L36O5T016N

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

MERCK INDEX

m9615

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

Merck Index

ChEMBL

CHEMBL1617

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

CHEBI

75246

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

USAN

EE-33

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

NCI_THESAURUS

C61926

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

NSC

758957

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

DRUG CENTRAL

2379

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

EPA CompTox

DTXSID7045998

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

DRUG BANK

DB01220

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

MESH

C042734

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

PUBCHEM

6436173

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

WIKIPEDIA

RIFAXIMIN

Created by admin on Fri Dec 15 15:44:56 UTC 2023 , Edited by admin on Fri Dec 15 15:44:56 UTC 2023

PRIMARY

Related Record Type Details


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> INDUCER


					L36O5T016N

RIFAXIMIN

EXCRETED UNCHANGED

Comments:

After oral administration of 400 mg 14C-rifaximin to healthy volunteers, approximately 97% of the dose was recovered in feces, almost entirely as unchanged drug, and 0.32% was recovered in the urine.

Qualification:

FECAL


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Related Record Type Details


					9NA6W8ZKA9

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					Z67LEM9P1W

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					X5ZC3G20EC

16-DESMETHYL-16-(HYDROXYMETHYL)RIFAXIMIN

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					394N1Z644H

2-AMINO-4-METHYLPYRIDINE

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					DU69T8ZZPA

RIFAMYCIN

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					8DDB535DJI

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					JAA5V227IW

6-O,14-DIDEHYDRORIFAXIMIN

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					PI53N820JV

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

Related Record Type Details


					L36O5T016N

RIFAXIMIN

ACTIVE MOIETY

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC				POPULATION: HEALTHY SUBJECTS

Biological Half-life	PHARMACOKINETIC				POPULATION: ISB-D PATIENTS

Tmax	PHARMACOKINETIC				POPULATION: HEALTHY SUBJECTS AND ISB-D PATIENTS