rifaximin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antibiotics, rifamycin derivatives	2379	80621-81-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: rifaximine rifaximin xifaxan refaximin	Rifaximin is a semi-synthetic derivative of rifampin and acts by binding to the beta-subunit of bacterial DNA-dependent RNA polymerase blocking one of the steps in transcription. This results in inhibition of bacterial protein synthesis and consequently inhibits the growth of bacteria. Molecular weight: 785.89 Formula: C43H51N3O11 CLOGP: 7.19 LIPINSKI: 3 HAC: 14 HDO: 5 TPSA: 198.38 ALOGS: -5.03 ROTB: 3 Status: ONP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

rifaximine
rifaximin
xifaxan
refaximin

Rifaximin is a semi-synthetic derivative of rifampin and acts by binding to the beta-subunit of bacterial DNA-dependent RNA polymerase blocking one of the steps in transcription. This results in inhibition of bacterial protein synthesis and consequently inhibits the growth of bacteria.

Molecular weight: 785.89
Formula: C43H51N3O11
CLOGP: 7.19
LIPINSKI: 3
HAC: 14
HDO: 5
TPSA: 198.38
ALOGS: -5.03
ROTB: 3

Status: ONP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.60	g	O

ADMET properties:

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Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	4	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	10.91 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	1 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	0.04 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.00 mg/mL	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
May 25, 2004	FDA	SALIX PHARMS

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Death	564.27	16.78	456	9055	373925	63105586
Inability to afford medication	360.31	16.78	81	9430	2266	63477245
Hepatic encephalopathy	360.03	16.78	112	9399	11170	63468341
Hospitalisation	253.61	16.78	158	9353	84923	63394588
Ammonia increased	248.96	16.78	69	9442	4587	63474924
Hepatic cirrhosis	151.54	16.78	74	9437	24660	63454851
Ascites	134.86	16.78	81	9430	40647	63438864
Insurance issue	123.47	16.78	43	9468	6078	63473433
Therapy interrupted	116.46	16.78	68	9443	32387	63447124
Hepatic failure	115.67	16.78	70	9441	35586	63443925

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Hepatic encephalopathy	528.58	17.29	183	9016	14502	34933230
Inability to afford medication	406.75	17.29	91	9108	1379	34946353
Death	386.98	17.29	495	8704	397554	34550178
Hospitalisation	271.61	17.29	175	9024	56727	34891005
Ammonia increased	210.83	17.29	68	9131	4301	34943431
Insurance issue	181.95	17.29	51	9148	1988	34945744
Hepatic cirrhosis	159.88	17.29	82	9117	17232	34930500
Ascites	157.57	17.29	116	9083	46455	34901277
Hepatic failure	142.19	17.29	97	9102	34434	34913298
Therapy interrupted	115.34	17.29	61	9138	13636	34934096

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Death	754.25	15.35	737	15579	565777	79162295
Hepatic encephalopathy	753.38	15.35	254	16062	23912	79704160
Inability to afford medication	682.28	15.35	149	16167	2624	79725448
Hospitalisation	375.84	15.35	236	16080	94000	79634072
Ammonia increased	368.45	15.35	112	16204	7523	79720549
Insurance issue	280.45	15.35	85	16231	5648	79722424
Ascites	263.45	15.35	174	16142	75388	79652684
Hepatic cirrhosis	223.29	15.35	119	16197	34787	79693285
Therapy interrupted	220.86	15.35	114	16202	31227	79696845
Hepatic failure	196.58	15.35	134	16182	61078	79666994

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A07AA11	ALIMENTARY TRACT AND METABOLISM ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS INTESTINAL ANTIINFECTIVES Antibiotics
ATC	D06AX11	DERMATOLOGICALS ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE ANTIBIOTICS FOR TOPICAL USE Other antibiotics for topical use
CHEBI has role	CHEBI:33281	antibiotics
CHEBI has role	CHEBI:55324	gastrointestinal drugs
CHEBI has role	CHEBI:71031	orphan drugs
FDA CS	M0019113	Rifamycins
FDA EPC	N0000175500	Rifamycin Antibacterial
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D005765	Gastrointestinal Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Hepatic encephalopathy	indication	13920009	DOID:13413
Irritable bowel syndrome with diarrhea	indication	197125005
Diarrhea due to E. Coli	indication
Traveler's diarrhea	off-label use	11840006
Hemorrhagic diarrhea	contraindication	95545007
Fever	contraindication	386661006
Pseudomembranous enterocolitis	contraindication	397683000

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	3.02	acidic
pKa2	7.28	acidic
pKa3	11.32	acidic
pKa4	12.55	acidic
pKa5	2.08	Basic

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Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
200MG	XIFAXAN	SALIX PHARMS	N021361	May 25, 2004	RX	TABLET	ORAL	10703763	Feb. 27, 2026	REDUCTION IN RISK OF OVERT HEPATIC ENCEPHALOPATHY (HE) RECURRENCE IN ADULTS
200MG	XIFAXAN	SALIX PHARMS	N021361	May 25, 2004	RX	TABLET	ORAL	10703763	Feb. 27, 2026	TREATMENT OF IRRITABLE BOWEL SYNDROME WITH DIARRHEA (IBS-D) IN ADULTS.
200MG	XIFAXAN	SALIX PHARMS	N021361	May 25, 2004	RX	TABLET	ORAL	10703763	Feb. 27, 2026	TREATMENT OF TRAVELERS DIARRHEA (TD) CAUSED BY NONINVASIVE STRAINS OF ESCHERIA COLI IN ADULT AND PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER
200MG	XIFAXAN	SALIX PHARMS	N021361	May 25, 2004	RX	TABLET	ORAL	8741904	Feb. 27, 2026	THE TREATMENT OF PATIENTS WITH TRAVELERS DIARRHEA (TD) OR THE REDUCTION IN RISK OF OVERT HEPATIC ENCEPHALOPATHY (HE) RECURRENCE
200MG	XIFAXAN	SALIX PHARMS	N021361	May 25, 2004	RX	TABLET	ORAL	7928115	July 24, 2029	METHOD OF TREATING TRAVELERS DIARRHEA
550MG	XIFAXAN	SALIX PHARMS	N021361	March 24, 2010	RX	TABLET	ORAL	7915275	Feb. 23, 2025	TREATMENT OF IRRITABLE BOWEL SYNDROME WITH DIARRHEA (IBS-D) IN ADULTS.
550MG	XIFAXAN	SALIX PHARMS	N021361	March 24, 2010	RX	TABLET	ORAL	7915275	Feb. 23, 2025	TREATMENT OF IRRITABLE BOWEL SYNDROME WITH DIARRHEA (IBS-D) IN ADULTS AND SYMPTOMS THEREOF.
550MG	XIFAXAN	SALIX PHARMS	N021361	March 24, 2010	RX	TABLET	ORAL	10703763	Feb. 27, 2026	REDUCTION IN RISK OF OVERT HEPATIC ENCEPHALOPATHY (HE) RECURRENCE IN ADULTS
550MG	XIFAXAN	SALIX PHARMS	N021361	March 24, 2010	RX	TABLET	ORAL	10703763	Feb. 27, 2026	TREATMENT OF IRRITABLE BOWEL SYNDROME WITH DIARRHEA (IBS-D) IN ADULTS.
550MG	XIFAXAN	SALIX PHARMS	N021361	March 24, 2010	RX	TABLET	ORAL	10703763	Feb. 27, 2026	TREATMENT OF TRAVELERS DIARRHEA (TD) CAUSED BY NONINVASIVE STRAINS OF ESCHERIA COLI IN ADULT AND PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Nuclear receptor subfamily 1 group I member 2	Nuclear hormone receptor	O75469	NR1I2_HUMAN		EC50	5.66		CHEMBL
Bacterial DNA-directed RNA polymerase	Enzyme		RPOA_ECOLI RPOZ_ECOLI RPOC_ECOLI RPOB_ECOLI	INHIBITOR				CHEMBL	CHEMBL

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External reference:

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ID	Source
RXM	PDB_CHEM_ID
007765	NDDF
12012	IUPHAR_LIGAND_ID
18641	MMSL
35619	RXNORM
4021474	VUID
4021474	VANDF
412553001	SNOMEDCT_US
412554007	SNOMEDCT_US
5244	INN_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
XIFAXAN	HUMAN PRESCRIPTION DRUG LABEL	1	50090-2445	TABLET	200 mg	ORAL	NDA	24 sections
XIFAXAN	HUMAN PRESCRIPTION DRUG LABEL	1	50090-2445	TABLET	200 mg	ORAL	NDA	24 sections
XIFAXAN	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5972	TABLET	200 mg	ORAL	NDA	26 sections
XIFAXAN	HUMAN PRESCRIPTION DRUG LABEL	1	54868-6154	TABLET	550 mg	ORAL	NDA	26 sections
XIFAXAN	HUMAN PRESCRIPTION DRUG LABEL	1	55154-6777	TABLET	550 mg	ORAL	NDA	24 sections
XIFAXAN	HUMAN PRESCRIPTION DRUG LABEL	1	55154-6777	TABLET	550 mg	ORAL	NDA	24 sections
XIFAXAN	HUMAN PRESCRIPTION DRUG LABEL	1	65649-301	TABLET	200 mg	ORAL	NDA	24 sections
XIFAXAN	HUMAN PRESCRIPTION DRUG LABEL	1	65649-301	TABLET	200 mg	ORAL	NDA	24 sections
XIFAXAN	HUMAN PRESCRIPTION DRUG LABEL	1	65649-303	TABLET	550 mg	ORAL	NDA	24 sections
XIFAXAN	HUMAN PRESCRIPTION DRUG LABEL	1	65649-303	TABLET	550 mg	ORAL	NDA	24 sections

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