Rifaximin

Rifaximin
Clinical data
Trade names	Xifaxan, others
AHFS/Drugs.com	Monograph
MedlinePlus	a604027
License data	US DailyMed: Rifaximin;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth
ATC code	A07AA11 (WHO) D06AX11 (WHO), QG51AA06 (WHO), QJ51XX01 (WHO);
Legal status
Legal status	CA: ℞-only; US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	< 0.4%
Metabolism	Liver
Elimination half-life	6 hours
Excretion	Fecal (97%)
Identifiers
	IUPAC name (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]-benzimida-zole-1,15(2H)-dione,25-acetate;
CAS Number	80621-81-4 ;
PubChem CID	6436173;
DrugBank	DB01220 ;
ChemSpider	10482302 ;
UNII	L36O5T016N;
KEGG	D02554 ;
ChEBI	CHEBI:75246 ;
ChEMBL	ChEMBL1617 ;
CompTox Dashboard (EPA)	DTXSID7045998 ;
ECHA InfoCard	100.111.624
Chemical and physical data
Formula	C43H51N3O11
Molar mass	785.891 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	200 to 205 °C (392 to 401 °F) (dec.)
	SMILES CC(=O)O[C@H]3[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(\C)C(=O)Nc6c2c(nc1cc(C)ccn12)c5c4C(=O)[C@@](C)(O/C=C/[C@H](OC)[C@H]3C)Oc4c(C)c(O)c5c6O;
	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 ; Key:NZCRJKRKKOLAOJ-XRCRFVBUSA-N ;
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Rifaximin is a non-absorbable, broad-spectrum antibiotic mainly used to treat travelers' diarrhea. It is based on the rifamycin antibiotics family. Since its approval in Italy in 1987, it has been licensed in more than 30 countries for the treatment of a variety of non-infectious gastrointestinal diseases like irritable bowel syndrome and hepatic encephalopathy. It acts by inhibiting RNA synthesis in susceptible bacteria by binding to the RNA polymerase enzyme. This binding blocks translocation, which stops transcription.^[4] It was developed by Salix Pharmaceuticals.^[3]^[5]^[6]

^ "Rifaximin international". Drugs.com. 2 November 2020. Retrieved 11 November 2020.
^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
^ ^a ^b "Xifaxan- rifaximin tablet". DailyMed. 1 October 2019. Retrieved 11 November 2020.
^ Koo HL, DuPont HL (January 2010). "Rifaximin: a unique gastrointestinal-selective antibiotic for enteric diseases". Current Opinion in Gastroenterology. 26 (1): 17–25. doi:10.1097/MOG.0b013e328333dc8d. PMC 4737517. PMID 19881343.
^ "Drug Approval Package: Xifaxan (Nfaximin) NDA #021361". U.S. Food and Drug Administration (FDA). Archived from the original on 19 March 2015. Retrieved 28 December 2024.
^ "Drug Approval Package: Xifaxan (rifaximin) NDA #022554". U.S. Food and Drug Administration (FDA). 26 July 2011. Retrieved 28 December 2024.

[1] "Rifaximin international". Drugs.com. 2 November 2020. Retrieved 11 November 2020.

[2] "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.

[Xifaxan_FDA_label-3] "Xifaxan- rifaximin tablet". DailyMed. 1 October 2019. Retrieved 11 November 2020.

[4] Koo HL, DuPont HL (January 2010). "Rifaximin: a unique gastrointestinal-selective antibiotic for enteric diseases". Current Opinion in Gastroenterology. 26 (1): 17–25. doi:10.1097/MOG.0b013e328333dc8d. PMC 4737517. PMID 19881343.

[5] "Drug Approval Package: Xifaxan (Nfaximin) NDA #021361". U.S. Food and Drug Administration (FDA). Archived from the original on 19 March 2015. Retrieved 28 December 2024.

[6] "Drug Approval Package: Xifaxan (rifaximin) NDA #022554". U.S. Food and Drug Administration (FDA). 26 July 2011. Retrieved 28 December 2024.

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