Rifaximin

Summary

Rifaximin (CHEMBL1617) is an approved small-molecule gastrointestinal drug (ATC D06AX11); indicated across 30 conditions including diarrheal disease and hepatic encephalopathy.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: D06AX11 (+1 more)
• Indications: 30 conditions
• Clinical trials: 154
• Chemistry: 785.9 Da · C43H51N3O11

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1617
Name	Rifaximin
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	6436173
ChEBI	CHEBI:75246
ATC	D06AX11, A07AA11
Molecular formula	C43H51N3O11
Molecular weight	785.9
InChIKey	NZCRJKRKKOLAOJ-XRCRFVBUSA-N

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

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

ChEBI definition: A semisynthetic member of the class of rifamycins and non-systemic gastrointestinal site-specific broad spectrum antibiotic. Used in the treatment of traveller’s diarrhoea, hepatic encephalopathy and irritable bowel syndrome.

Pharmacological roles (ChEBI): gastrointestinal drug, orphan drug, antimicrobial agent.

Also known as: L-105, Normix, NSC-758957, Rifamycin l 105, Rifaxidin, Rifaximin, Rifaximina, Rifaximine, Rifacol, Targaxan, Xifaxan, Xifaxanta

Patent coverage: 3,650 distinct patent families (13,380 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 13,245 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 34 (assay-derived). Sample: ATP-binding cassette sub-family C member 4, Vasopressin V2 receptor, Neuronal acetylcholine receptor subunit alpha-4, Vasopressin V1a receptor, Cholecystokinin receptor type A, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Equilibrative nucleoside transporter 1, Thromboxane A2 receptor, Beta-2 adrenergic receptor.

Bioactivity

ChEMBL activities: 8 potent at pChembl ≥ 5 of 39 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
NR1I2	5.66	EC50	2200	nM	CHEMBL_ACT_6278087
DRD3	5.48	AC50	3300	nM	CHEMBL_ACT_25194138
NR1I2	5.4	EC50	4000	nM	CHEMBL_ACT_13929416
PTGS2	5.36	AC50	4400	nM	CHEMBL_ACT_25166780
ADRA2B	5.32	AC50	4800	nM	CHEMBL_ACT_25144307
SLC29A1	5.17	AC50	6800	nM	CHEMBL_ACT_25142094
OPRD1	5.08	AC50	8400	nM	CHEMBL_ACT_25154679
ADORA1	5.05	AC50	8995	nM	CHEMBL_ACT_25133596

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

30 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
diarrheal disease	4	MONDO:0001673	HP:0002014
hepatic encephalopathy	4	MONDO:0001711	HP:0001399
irritable bowel syndrome	3	MONDO:0005052	EFO:0000555
cirrhosis of liver	3	MONDO:0005155	EFO:0001422
Crohn disease	3	MONDO:0005011	EFO:0000384
rectal cancer	3	MONDO:0006519	EFO:1000657
alcoholic hepatitis	3	MONDO:0001505	EFO:1001345
infectious peritonitis	3	MONDO:0004522	EFO:0008588
collagenous colitis	3	MONDO:0000703	EFO:1001293
Helicobacter pylori infectious disease	3	MONDO:0006781	EFO:1000961
brain disorder	3	MONDO:0005560	HP:0001298
Clostridium infectious disease	3	MONDO:0024388	EFO:1000874
Parkinson disease	3	MONDO:0005180	MONDO:0005180
HIV infectious disease	2	MONDO:0005109	EFO:0000180
hepatitis C virus infection	2	MONDO:0005231	EFO:0003047
rosacea	2	MONDO:0006604	EFO:1000760
bacterial vaginosis	2	MONDO:0005316	EFO:0003932
systolic heart failure	2	MONDO:0006993	EFO:1001207
dyspepsia	2	MONDO:0002268	EFO:0008533
intestinal pseudo-obstruction	2	MONDO:0002803	EFO:1000988
Alzheimer disease	2	MONDO:0004975	MONDO:0004975
sickle cell disease	2	MONDO:0011382	MONDO:0011382
HER2 positive breast carcinoma	2	MONDO:0006244	EFO:1000294
diverticulitis	2	MONDO:0004235	MONDO:0004235
sclerosing cholangitis	1	MONDO:0018646	EFO:0004268
persian gulf syndrome	1	MONDO:0005907	EFO:0007430
neoplasm	1	MONDO:0005070	MONDO:0004992
chronic kidney disease	0	MONDO:0005300	EFO:0003884

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 154.

Phase distribution

Phase	Trials
Not specified	38
PHASE4	33
PHASE3	29
PHASE2	26
PHASE2/PHASE3	9
PHASE1/PHASE2	9
PHASE1	5
EARLY_PHASE1	5

Top trials by phase / activity

NCT	Phase	Status	Title
NCT04073290	PHASE4	RECRUITING	Prevention of Post-TIPS Hepatic Encephalopathy by Administration of Rifaximin and Lactulose
NCT05677282	PHASE4	RECRUITING	Single Dose Antibiotic Treatment of Acute Watery Diarrhea, Rifaximin Versus Azithromycin, With Loperamide Adjunct
NCT06538077	PHASE4	RECRUITING	BCAA vs. Rifaximin in Patients With Cirrhosis for Secondary Prophylaxis of HE
NCT07180615	PHASE4	NOT_YET_RECRUITING	Gut Decolonisation With Neomycin/Metronidazole or Rifaximin Before Colon Surgery
NCT07203846	PHASE4	NOT_YET_RECRUITING	Modulation of Gut MicroFLORA With Rifaximin to Reduce High Platelet Reactivity in Post-ACS Patients on Ticagrelor
NCT07426705	PHASE4	NOT_YET_RECRUITING	Effect of Multispecies Probiotic Supplementation on the Efficacy of Rifaximin α Therapy in Patients With Small Intestinal Bacterial Overgrowth (SIBO): a Randomized Placebo-controlled Trial
NCT00292344	PHASE4	COMPLETED	Rifaximin, Loperamide and the Combination to Treat Travelers’ Diarrhea
NCT00748904	PHASE4	WITHDRAWN	Rifaximin Versus Lactulose in Renal Failure
NCT00875875	PHASE4	WITHDRAWN	Single Daily Dose Rifaximin for the Treatment of Travelers’ Diarrhea
NCT01355575	PHASE4	TERMINATED	Rifaximin in Fatty Liver Disease
NCT01654939	PHASE4	WITHDRAWN	Impact of an Antibiotic (Rifaximin) on Liver Scarring in HIV-Infected Patients With Liver Disease
NCT01670149	PHASE4	COMPLETED	Rifaximin for Preventing Relapse of Clostridium Associated Diarrhoea
NCT01769040	PHASE4	COMPLETED	Intestinal Decontamination With Rifaximin. The Inflammatory and Circulatory State in Patients With Cirrhosis
NCT01842113	PHASE4	TERMINATED	Quality of Life and Nutritional Improvements in Cirrhotic Patients
NCT01842581	PHASE4	COMPLETED	The Safety/Efficacy of Rifaximin With/Without Lactulose in Participants With A History of Recurrent Hepatic Encephalopathy
NCT01846663	PHASE4	TERMINATED	Efficacy, Safety, And Pharmacokinetics Of Rifaximin In Subjects With Severe Hepatic Impairment And Hepatic Encephalopathy
NCT01946906	PHASE4	COMPLETED	The Rifaximin Study in CVID
NCT02068482	PHASE4	COMPLETED	Immunohistology in USDD and Correlation Between Bacterial Flora and Phlogosis
NCT02074280	PHASE4	UNKNOWN	Rifaximin Predicts the Complications of Decompensated Cirrhosis
NCT02158182	PHASE4	COMPLETED	Lactulose, L-ornithine L-aspartate, or Rifaximin Versus Placebo for Preventing Hepatic Encephalopathy in Variceal Bleeding
NCT02190357	PHASE4	UNKNOWN	Rifaximin Reduces the Complications of Decompensated Cirrhosis: a Randomized Controlled Trial
NCT02342639	PHASE4	COMPLETED	Rifaximin Therapy in Chronic Kidney Disease
NCT03077217	PHASE4	COMPLETED	Low-dose Rifaximin in the Treatment of Covert Hepatic Encephalopathy
NCT03219528	PHASE4	COMPLETED	A Longitudinal Study to Identify IBS Phenotypes Using Fecal Microbiota and Hydrogen Breath Testing
NCT03557788	PHASE4	COMPLETED	Changes in Microbiota and Metabolomic Profile Between Rifaximin Responders and Non-responders In Diarrhoea-Predominant Irritable Bowel Syndrome
NCT03729271	PHASE4	COMPLETED	Hydrogen Breath Test an Instrument to Predict Rifaximin-Response in Irritable Bowel Syndrome Predominant Diarrhea
NCT03818672	PHASE4	TERMINATED	Steady-State Pharmacokinetics of Rifaximin 550 mg Tablets in Healthy and Hepatically Impaired Subjects
NCT04074421	PHASE4	UNKNOWN	Effects of Continuous Treatment With Rifaximin and Probiotics on the Gut Microbiota of Patients With IBS-D
NCT04674176	PHASE4	UNKNOWN	Weight Loss Benefits of Rifaximin in an Intermittent Fasting Diet
NCT04736836	PHASE4	COMPLETED	Microbial Resistance of Rifaximin in Hepatic Encephalopathy
NCT04841980	PHASE4	UNKNOWN	Rifaximin Therapy vs Low FODMAP Diet In IBS
NCT05867550	PHASE4	COMPLETED	To Compare the Efficacy of Drugs in Combination for Treating Irritable Bowel Syndrome Associated With Diarrhea
NCT06630572	PHASE4	TERMINATED	Rifaximin in Cirrhosis: Effects on Endotoxin and Haemostatic Indexes
NCT04161053	PHASE3	RECRUITING	Efficacy and Safety of Nitazoxanide in Preventing Recurrence of Hepatic Encephalopathy
NCT05587036	PHASE2/PHASE3	RECRUITING	Effects of Rifaximin on Gut Microbiota and Emotion
NCT07522255	PHASE3	NOT_YET_RECRUITING	Rifaximin Treatment in Bloating Predominant Functional Bowel Disorders
NCT00269399	PHASE3	COMPLETED	A Trial to Compare Xifaxan to Vancomycin for the Treatment of Clostridium Difficile-Associated Diarrhea (CDAD)
NCT00298038	PHASE3	COMPLETED	A 6-month Efficacy, Safety, and Tolerability Study of Rifaximin In Preventing Hepatic Encephalopathy
NCT00328380	PHASE3	COMPLETED	Prevention of Travelers’ Diarrhea in Subjects Traveling Outside the U.S.
NCT00364689	PHASE3	TERMINATED	RICE Trial: Rifaximin In Chronic Hepatic Encephalopathy - A Randomized, Controlled Trial

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).