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Identification
NameRifaximin
Accession NumberDB01220  (APRD01218)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionRifaximin is a semisynthetic, rifamycin-based non-systemic antibiotic, meaning that the drug will not pass the gastrointestinal wall into the circulation as is common for other types of orally administered antibiotics. It has multiple indications and is used in treatment of traveller's diarrhea caused by E. coli; reduction in risk of overt hepatic encephalopathy recurrence; as well as diarrhea-predominant irritable bowel syndrome (IBS-D) in adult women and men. It is marketed under the brand name Xifaxan by Salix Pharmaceuticals.
Structure
Thumb
Synonyms
Rifamycin L 105
Rifamycin L 105SV
Rifaxidin
Rifaximin
Rifaximina
Rifaximine
Rifaximinum
Rifaximinun
Xifaxsan
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Xifaxantablet200 mg/1oralPhysicians Total Care, Inc.2008-12-14Not applicableUs
Xifaxantablet200 mg/1oralCarilion Materials Management2004-07-25Not applicableUs
Xifaxantablet550 mg/1oralPhysicians Total Care, Inc.2010-08-19Not applicableUs
Xifaxantablet200 mg/1oralDispensing Solutions, Inc.2004-07-25Not applicableUs
Xifaxantablet200 mg/1oralSalix Pharmaceuticals, Inc.2004-07-25Not applicableUs
Xifaxantablet550 mg/1oralSalix Pharmaceuticals, Inc.2010-05-01Not applicableUs
Zaxinetablet550 mgoralSalix Pharmaceuticals Inc2013-11-07Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
NormixNot Available
RifacolNot Available
XifaxsanNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIL36O5T016N
CAS number80621-81-4
WeightAverage: 785.8785
Monoisotopic: 785.352359489
Chemical FormulaC43H51N3O11
InChI KeyInChIKey=NZCRJKRKKOLAOJ-XRCRFVBUSA-N
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
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-1,3,5(35),9,19,21,25(36),26(34),28,30,32-undecaen-13-yl acetate
SMILES
CO[[email protected]]1\C=C\O[C@@]2(C)OC3=C(C)C(O)=C4C(O)=C(NC(=O)\C(C)=C/C=C/[[email protected]](C)[[email protected]](O)[C@@H](C)[C@@H](O)[C@@H](C)[[email protected]](OC(C)=O)[C@@H]1C)C1=C(N=C5C=C(C)C=CN15)C4=C3C2=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Naphthofuran
  • Macrolactam
  • 1-naphthol
  • Naphthalene
  • Benzofuran
  • Benzimidazole
  • Aryl alkyl ketone
  • Aryl ketone
  • Methylpyridine
  • Benzenoid
  • Pyridine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Acetate salt
  • Imidazole
  • Azole
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Lactam
  • Ketone
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationRifaximin has multiple indications by the FDA: for the treatment of patients (≥12 years of age) with traveller's diarrhea caused by noninvasive strains of Escherichia coli; for the reduction of overt hepatic encephalopathy recurrence in patients ≥18 years of age; and in May 2015 it was approved for irritable bowel syndrome with diarrhea (IBS-D) treatment in adult men and women.
PharmacodynamicsRifaximin is a structural analog of rifampin and a non-systemic, gastrointestinal site-specific antibiotic. This non-systemic property of the drug is due to the addition of a pyridoimidazole ring, which renders it non-absorbable. Rifaximin acts by inhibiting bacterial ribonucleic acid (RNA) synthesis and contributes to restore intestinal microflora imbalance. Other studies have also shown rifaximin to be an pregnane X receptor (PXR) activator. As PXR is responsible for inhibiting the proinflammatory transcription factor NF-kappa B (NF-κB) and is inhibited in inflammatory bowel disease (IBD), rifaximin was proven to be effective for the treatment of IBS-D.
Mechanism of actionRifaximin acts by inhibiting RNA synthesis in susceptible bacteria by binding to the beta-subunit of bacterial deoxyribonucleic acid (DNA)-dependent ribonucleic acid (RNA) polymerase enzyme. This results in the blockage of the translocation step that normally follows the formation of the first phosphodiester bond, which occurs in the transcription process.
Related Articles
AbsorptionLow absorption in both the fasting state and when administered within 30 minutes of a high-fat breakfast.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

In vitro drug interactions studies have shown that rifaximin, at concentrations ranging from 2 to 200 ng/mL, did not inhibit human hepatic cytochrome P450 isoenzymes: 1A2, 2A6, 2B6, 2C9, 2C19, 2D6, 2E1, and 3A4. In an in vitro hepa-tocyte induction model, rifaximin was shown to induce cytochrome P450 3A4 (CYP3A4), an isoenzyme which rifampin is known to induce.

Route of eliminationIn a mass balance study, after administration of 400 mg 14C-rifaximin orally to healthy volunteers, of the 96.94% total recovery, 96.62% of the administered radioactivity was recovered in feces almost exclusively as the unchanged drug and 0.32% was recovered in urine mostly as metabolites with 0.03% as the unchanged drug.Rifaximin accounted for 18% of radioactivity in plasma. This suggests that the absorbed rifaximin undergoes metabolism with minimal renal excretion of the unchanged drug
Half lifeApproximately 6 hours.
ClearanceNot Available
ToxicityLD50 > 2 g/kg (orally, in rats)
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.646
Blood Brain Barrier-0.973
Caco-2 permeable-0.6301
P-glycoprotein substrateSubstrate0.6681
P-glycoprotein inhibitor INon-inhibitor0.6985
P-glycoprotein inhibitor IINon-inhibitor0.7134
Renal organic cation transporterNon-inhibitor0.9533
CYP450 2C9 substrateNon-substrate0.8256
CYP450 2D6 substrateNon-substrate0.8783
CYP450 3A4 substrateSubstrate0.5651
CYP450 1A2 substrateNon-inhibitor0.7129
CYP450 2C9 inhibitorNon-inhibitor0.7393
CYP450 2D6 inhibitorNon-inhibitor0.875
CYP450 2C19 inhibitorNon-inhibitor0.7684
CYP450 3A4 inhibitorNon-inhibitor0.8904
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7729
Ames testNon AMES toxic0.6276
CarcinogenicityNon-carcinogens0.9055
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6259 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.994
hERG inhibition (predictor II)Non-inhibitor0.721
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral200 mg/1
Tabletoral550 mg/1
Tabletoral550 mg
Prices
Unit descriptionCostUnit
Xifaxan 550 mg tablet22.4USD tablet
Xifaxan 200 mg tablet8.97USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6861053 No1999-08-112019-08-11Us
US7045620 No2004-06-192024-06-19Us
US7452857 No1999-08-112019-08-11Us
US7605240 No1999-08-112019-08-11Us
US7612199 No2004-06-192024-06-19Us
US7718608 No1999-08-112019-08-11Us
US7902206 No2004-06-192024-06-19Us
US7906542 No2005-06-012025-06-01Us
US7915275 No2005-02-232025-02-23Us
US7928115 No2009-07-242029-07-24Us
US7935799 No1999-08-112019-08-11Us
US8158644 No2004-06-192024-06-19Us
US8158781 No2004-06-192024-06-19Us
US8193196 No2007-09-022027-09-02Us
US8309569 No2009-07-182029-07-18Us
US8518949 No2006-02-272026-02-27Us
US8642573 No2009-10-022029-10-02Us
US8741904 No2006-02-272026-02-27Us
US8829017 No2009-07-242029-07-24Us
US8835452 No2004-06-192024-06-19Us
US8853231 No2004-06-192024-06-19Us
US8946252 No2009-07-242029-07-24Us
US8969398 No2009-10-022029-10-02Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00738 mg/mLALOGPS
logP4.94ALOGPS
logP4.37ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)3.66ChemAxon
pKa (Strongest Basic)11.87ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area198.38 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity216.69 m3·mol-1ChemAxon
Polarizability82.26 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Giuseppe Viscomi, Manuela Campana, Dario Braga, Donatella Confortini, Vincenzo Cannata, Paolo Righi, Goffredo Rosini, “Polymorphic forms of rifaximin, processes for their production and uses thereof.” U.S. Patent US20050272754, issued December 08, 2005.

US20050272754
General References
  1. Cottreau J, Baker SF, DuPont HL, Garey KW: Rifaximin: a nonsystemic rifamycin antibiotic for gastrointestinal infections. Expert Rev Anti Infect Ther. 2010 Jul;8(7):747-60. doi: 10.1586/eri.10.58. [PubMed:20586560 ]
  2. Williams R, Bass N: Rifaximin, a nonabsorbed oral antibiotic, in the treatment of hepatic encephalopathy: antimicrobial activity, efficacy, and safety. Rev Gastroenterol Disord. 2005;5 Suppl 1:S10-8. [PubMed:15976747 ]
  3. Koo HL, DuPont HL: Rifaximin: a unique gastrointestinal-selective antibiotic for enteric diseases. Curr Opin Gastroenterol. 2010 Jan;26(1):17-25. doi: 10.1097/MOG.0b013e328333dc8d. [PubMed:19881343 ]
  4. Pakyz AL: Rifaximin: a new treatment for travelers' diarrhea. Ann Pharmacother. 2005 Feb;39(2):284-9. Epub 2004 Dec 14. [PubMed:15598963 ]
  5. Jalan R: Rifaximin in hepatic encephalopathy: more than just a non-absorbable antibiotic? J Hepatol. 2010 Sep;53(3):580-2. doi: 10.1016/j.jhep.2010.05.002. Epub 2010 May 31. [PubMed:20561708 ]
  6. Lawrence KR, Klee JA: Rifaximin for the treatment of hepatic encephalopathy. Pharmacotherapy. 2008 Aug;28(8):1019-32. doi: 10.1592/phco.28.8.1019. [PubMed:18657018 ]
  7. Layer P, Andresen V: Review article: rifaximin, a minimally absorbed oral antibacterial, for the treatment of travellers' diarrhoea. Aliment Pharmacol Ther. 2010 Jun;31(11):1155-64. doi: 10.1111/j.1365-2036.2010.04296.x. Epub 2010 Mar 11. [PubMed:20331580 ]
  8. Ojetti V, Lauritano EC, Barbaro F, Migneco A, Ainora ME, Fontana L, Gabrielli M, Gasbarrini A: Rifaximin pharmacology and clinical implications. Expert Opin Drug Metab Toxicol. 2009 Jun;5(6):675-82. doi: 10.1517/17425250902973695. [PubMed:19442033 ]
  9. Scarpignato C, Pelosini I: Rifaximin, a poorly absorbed antibiotic: pharmacology and clinical potential. Chemotherapy. 2005;51 Suppl 1:36-66. [PubMed:15855748 ]
  10. Gillis JC, Brogden RN: Rifaximin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic potential in conditions mediated by gastrointestinal bacteria. Drugs. 1995 Mar;49(3):467-84. [PubMed:7774516 ]
  11. Koo HL, Dupont HL, Huang DB: The role of rifaximin in the treatment and chemoprophylaxis of travelers' diarrhea. Ther Clin Risk Manag. 2009;5:841-8. Epub 2009 Nov 2. [PubMed:19898648 ]
  12. DuPont HL: Systematic review: prevention of travellers' diarrhoea. Aliment Pharmacol Ther. 2008 May;27(9):741-51. doi: 10.1111/j.1365-2036.2008.03647.x. Epub 2008 Feb 14. [PubMed:18284650 ]
  13. Romero-Gomez M: Pharmacotherapy of hepatic encephalopathy in cirrhosis. Expert Opin Pharmacother. 2010 Jun;11(8):1317-27. doi: 10.1517/14656561003724721. [PubMed:20384539 ]
  14. Scarpignato C, Pelosini I: Experimental and clinical pharmacology of rifaximin, a gastrointestinal selective antibiotic. Digestion. 2006;73 Suppl 1:13-27. Epub 2006 Feb 8. [PubMed:16498249 ]
  15. Pimentel M: Review of rifaximin as treatment for SIBO and IBS. Expert Opin Investig Drugs. 2009 Mar;18(3):349-58. doi: 10.1517/13543780902780175 . [PubMed:19243285 ]
External Links
ATC CodesA07AA11D06AX11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (478 KB)
MSDSDownload (58.4 KB)
Interactions
Drug Interactions
Drug
AcetaminophenThe serum concentration of Rifaximin can be increased when it is combined with Acetaminophen.
AfatinibThe serum concentration of Rifaximin can be increased when it is combined with Afatinib.
AlbendazoleThe serum concentration of Rifaximin can be increased when it is combined with Albendazole.
AlectinibThe serum concentration of Rifaximin can be increased when it is combined with Alectinib.
AlfentanilThe serum concentration of Rifaximin can be increased when it is combined with Alfentanil.
AmantadineThe serum concentration of Rifaximin can be increased when it is combined with Amantadine.
Aminohippuric acidThe serum concentration of Rifaximin can be increased when it is combined with Aminohippuric acid.
AmiodaroneThe serum concentration of Rifaximin can be increased when it is combined with Amiodarone.
AmitriptylineThe serum concentration of Rifaximin can be increased when it is combined with Amitriptyline.
AmlodipineThe serum concentration of Rifaximin can be increased when it is combined with Amlodipine.
AmprenavirThe serum concentration of Rifaximin can be increased when it is combined with Amprenavir.
AmsacrineThe serum concentration of Rifaximin can be increased when it is combined with Amsacrine.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Rifaximin.
AstemizoleThe serum concentration of Rifaximin can be increased when it is combined with Astemizole.
AtazanavirThe serum concentration of Rifaximin can be increased when it is combined with Atazanavir.
AtenololThe serum concentration of Rifaximin can be increased when it is combined with Atenolol.
AtorvastatinThe serum concentration of Rifaximin can be increased when it is combined with Atorvastatin.
AzelastineThe serum concentration of Rifaximin can be increased when it is combined with Azelastine.
AzithromycinThe serum concentration of Rifaximin can be increased when it is combined with Azithromycin.
BenzocaineThe serum concentration of Rifaximin can be increased when it is combined with Benzocaine.
BepridilThe serum concentration of Rifaximin can be increased when it is combined with Bepridil.
BiperidenThe serum concentration of Rifaximin can be increased when it is combined with Biperiden.
BosutinibThe serum concentration of Rifaximin can be increased when it is combined with Bosutinib.
BromocriptineThe serum concentration of Rifaximin can be increased when it is combined with Bromocriptine.
BuprenorphineThe serum concentration of Rifaximin can be increased when it is combined with Buprenorphine.
BuspironeThe serum concentration of Rifaximin can be increased when it is combined with Buspirone.
CabazitaxelThe serum concentration of Rifaximin can be increased when it is combined with Cabazitaxel.
CaffeineThe serum concentration of Rifaximin can be increased when it is combined with Caffeine.
CanagliflozinThe serum concentration of Rifaximin can be increased when it is combined with Canagliflozin.
CandesartanThe serum concentration of Rifaximin can be increased when it is combined with Candesartan.
CaptoprilThe serum concentration of Rifaximin can be increased when it is combined with Captopril.
CarbamazepineThe serum concentration of Rifaximin can be increased when it is combined with Carbamazepine.
CarvedilolThe serum concentration of Rifaximin can be increased when it is combined with Carvedilol.
CaspofunginThe serum concentration of Rifaximin can be increased when it is combined with Caspofungin.
ChloroquineThe serum concentration of Rifaximin can be increased when it is combined with Chloroquine.
ChlorpromazineThe serum concentration of Rifaximin can be increased when it is combined with Chlorpromazine.
ChlorpropamideThe serum concentration of Rifaximin can be increased when it is combined with Chlorpropamide.
ChlorprothixeneThe serum concentration of Rifaximin can be increased when it is combined with Chlorprothixene.
CholesterolThe serum concentration of Rifaximin can be increased when it is combined with Cholesterol.
CilazaprilThe serum concentration of Rifaximin can be increased when it is combined with Cilazapril.
CimetidineThe serum concentration of Rifaximin can be increased when it is combined with Cimetidine.
CiprofloxacinThe serum concentration of Rifaximin can be increased when it is combined with Ciprofloxacin.
CitalopramThe serum concentration of Rifaximin can be increased when it is combined with Citalopram.
ClarithromycinThe serum concentration of Rifaximin can be increased when it is combined with Clarithromycin.
ClofazimineThe serum concentration of Rifaximin can be increased when it is combined with Clofazimine.
ClomipramineThe serum concentration of Rifaximin can be increased when it is combined with Clomipramine.
ClotrimazoleThe serum concentration of Rifaximin can be increased when it is combined with Clotrimazole.
CobicistatThe serum concentration of Rifaximin can be increased when it is combined with Cobicistat.
ColchicineThe serum concentration of Rifaximin can be increased when it is combined with Colchicine.
ColforsinThe serum concentration of Rifaximin can be increased when it is combined with Colforsin.
CrizotinibThe serum concentration of Rifaximin can be increased when it is combined with Crizotinib.
CyclophosphamideThe serum concentration of Rifaximin can be increased when it is combined with Cyclophosphamide.
CyclosporineThe serum concentration of Rifaximin can be increased when it is combined with Cyclosporine.
DaclatasvirThe serum concentration of Rifaximin can be increased when it is combined with Daclatasvir.
DactinomycinThe serum concentration of Rifaximin can be increased when it is combined with Dactinomycin.
DasatinibThe serum concentration of Rifaximin can be increased when it is combined with Dasatinib.
DaunorubicinThe serum concentration of Rifaximin can be increased when it is combined with Daunorubicin.
DesipramineThe serum concentration of Rifaximin can be increased when it is combined with Desipramine.
DesloratadineThe serum concentration of Rifaximin can be increased when it is combined with Desloratadine.
DexamethasoneThe serum concentration of Rifaximin can be increased when it is combined with Dexamethasone.
DextromethorphanThe serum concentration of Rifaximin can be increased when it is combined with Dextromethorphan.
DiclofenacThe serum concentration of Rifaximin can be increased when it is combined with Diclofenac.
DigoxinThe serum concentration of Rifaximin can be increased when it is combined with Digoxin.
DihydroergotamineThe serum concentration of Rifaximin can be increased when it is combined with Dihydroergotamine.
DiltiazemThe serum concentration of Rifaximin can be increased when it is combined with Diltiazem.
DipyridamoleThe serum concentration of Rifaximin can be increased when it is combined with Dipyridamole.
DoxazosinThe serum concentration of Rifaximin can be increased when it is combined with Doxazosin.
DoxepinThe serum concentration of Rifaximin can be increased when it is combined with Doxepin.
DoxorubicinThe serum concentration of Rifaximin can be increased when it is combined with Doxorubicin.
DronabinolThe serum concentration of Rifaximin can be increased when it is combined with Dronabinol.
DronedaroneThe serum concentration of Rifaximin can be increased when it is combined with Dronedarone.
ElbasvirThe serum concentration of Rifaximin can be increased when it is combined with Elbasvir.
EnalaprilThe serum concentration of Rifaximin can be increased when it is combined with Enalapril.
EnzalutamideThe serum concentration of Rifaximin can be increased when it is combined with Enzalutamide.
ErgonovineThe serum concentration of Rifaximin can be increased when it is combined with Ergonovine.
ErgotamineThe serum concentration of Rifaximin can be increased when it is combined with Ergotamine.
ErythromycinThe serum concentration of Rifaximin can be increased when it is combined with Erythromycin.
EstramustineThe serum concentration of Rifaximin can be increased when it is combined with Estramustine.
EtoposideThe serum concentration of Rifaximin can be increased when it is combined with Etoposide.
EtravirineThe serum concentration of Rifaximin can be increased when it is combined with Etravirine.
FelodipineThe serum concentration of Rifaximin can be increased when it is combined with Felodipine.
FentanylThe serum concentration of Rifaximin can be increased when it is combined with Fentanyl.
FexofenadineThe serum concentration of Rifaximin can be increased when it is combined with Fexofenadine.
FidaxomicinThe serum concentration of Rifaximin can be increased when it is combined with Fidaxomicin.
FluconazoleThe serum concentration of Rifaximin can be increased when it is combined with Fluconazole.
FluoxetineThe serum concentration of Rifaximin can be increased when it is combined with Fluoxetine.
FlupentixolThe serum concentration of Rifaximin can be increased when it is combined with Flupentixol.
FluphenazineThe serum concentration of Rifaximin can be increased when it is combined with Fluphenazine.
FlurazepamThe serum concentration of Rifaximin can be increased when it is combined with Flurazepam.
FluvoxamineThe serum concentration of Rifaximin can be increased when it is combined with Fluvoxamine.
GefitinibThe serum concentration of Rifaximin can be increased when it is combined with Gefitinib.
GenisteinThe serum concentration of Rifaximin can be increased when it is combined with Genistein.
GlyburideThe serum concentration of Rifaximin can be increased when it is combined with Glyburide.
GlycerolThe serum concentration of Rifaximin can be increased when it is combined with Glycerol.
Gramicidin DThe serum concentration of Rifaximin can be increased when it is combined with Gramicidin D.
GrepafloxacinThe serum concentration of Rifaximin can be increased when it is combined with Grepafloxacin.
HaloperidolThe serum concentration of Rifaximin can be increased when it is combined with Haloperidol.
HydrocortisoneThe serum concentration of Rifaximin can be increased when it is combined with Hydrocortisone.
IdelalisibThe serum concentration of Rifaximin can be increased when it is combined with Idelalisib.
ImatinibThe serum concentration of Rifaximin can be increased when it is combined with Imatinib.
ImipramineThe serum concentration of Rifaximin can be increased when it is combined with Imipramine.
IndinavirThe serum concentration of Rifaximin can be increased when it is combined with Indinavir.
IndomethacinThe serum concentration of Rifaximin can be increased when it is combined with Indomethacin.
IsavuconazoniumThe serum concentration of Rifaximin can be increased when it is combined with Isavuconazonium.
ItraconazoleThe serum concentration of Rifaximin can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Rifaximin can be increased when it is combined with Ivacaftor.
IvermectinThe serum concentration of Rifaximin can be increased when it is combined with Ivermectin.
KetamineThe serum concentration of Rifaximin can be increased when it is combined with Ketamine.
KetoconazoleThe serum concentration of Rifaximin can be increased when it is combined with Ketoconazole.
LansoprazoleThe serum concentration of Rifaximin can be increased when it is combined with Lansoprazole.
LapatinibThe serum concentration of Rifaximin can be increased when it is combined with Lapatinib.
LevofloxacinThe serum concentration of Rifaximin can be increased when it is combined with Levofloxacin.
LidocaineThe serum concentration of Rifaximin can be increased when it is combined with Lidocaine.
LisinoprilThe serum concentration of Rifaximin can be increased when it is combined with Lisinopril.
LomitapideThe serum concentration of Rifaximin can be increased when it is combined with Lomitapide.
LoperamideThe serum concentration of Rifaximin can be increased when it is combined with Loperamide.
LopinavirThe serum concentration of Rifaximin can be increased when it is combined with Lopinavir.
LoratadineThe serum concentration of Rifaximin can be increased when it is combined with Loratadine.
LosartanThe serum concentration of Rifaximin can be increased when it is combined with Losartan.
LovastatinThe serum concentration of Rifaximin can be increased when it is combined with Lovastatin.
MaprotilineThe serum concentration of Rifaximin can be increased when it is combined with Maprotiline.
MebendazoleThe serum concentration of Rifaximin can be increased when it is combined with Mebendazole.
MefloquineThe serum concentration of Rifaximin can be increased when it is combined with Mefloquine.
Megestrol acetateThe serum concentration of Rifaximin can be increased when it is combined with Megestrol acetate.
MeprobamateThe serum concentration of Rifaximin can be increased when it is combined with Meprobamate.
MethadoneThe serum concentration of Rifaximin can be increased when it is combined with Methadone.
MetoprololThe serum concentration of Rifaximin can be increased when it is combined with Metoprolol.
MibefradilThe serum concentration of Rifaximin can be increased when it is combined with Mibefradil.
MiconazoleThe serum concentration of Rifaximin can be increased when it is combined with Miconazole.
MidazolamThe serum concentration of Rifaximin can be increased when it is combined with Midazolam.
MifepristoneThe serum concentration of Rifaximin can be increased when it is combined with Mifepristone.
MitomycinThe serum concentration of Rifaximin can be increased when it is combined with Mitomycin.
MitoxantroneThe serum concentration of Rifaximin can be increased when it is combined with Mitoxantrone.
MorphineThe serum concentration of Rifaximin can be increased when it is combined with Morphine.
NaltrexoneThe serum concentration of Rifaximin can be increased when it is combined with Naltrexone.
NaringeninThe serum concentration of Rifaximin can be increased when it is combined with Naringenin.
NelfinavirThe serum concentration of Rifaximin can be increased when it is combined with Nelfinavir.
NeostigmineThe serum concentration of Rifaximin can be increased when it is combined with Neostigmine.
NicardipineThe serum concentration of Rifaximin can be increased when it is combined with Nicardipine.
NifedipineThe serum concentration of Rifaximin can be increased when it is combined with Nifedipine.
NilotinibThe serum concentration of Rifaximin can be increased when it is combined with Nilotinib.
NintedanibThe serum concentration of Nintedanib can be decreased when it is combined with Rifaximin.
NisoldipineThe serum concentration of Rifaximin can be increased when it is combined with Nisoldipine.
NitrazepamThe serum concentration of Rifaximin can be increased when it is combined with Nitrazepam.
NitrendipineThe serum concentration of Rifaximin can be increased when it is combined with Nitrendipine.
OmeprazoleThe serum concentration of Rifaximin can be increased when it is combined with Omeprazole.
P-NitrophenolThe serum concentration of Rifaximin can be increased when it is combined with P-Nitrophenol.
PaclitaxelThe serum concentration of Rifaximin can be increased when it is combined with Paclitaxel.
Palmitic AcidThe serum concentration of Rifaximin can be increased when it is combined with Palmitic Acid.
PantoprazoleThe serum concentration of Rifaximin can be increased when it is combined with Pantoprazole.
ParoxetineThe serum concentration of Rifaximin can be increased when it is combined with Paroxetine.
PerindoprilThe serum concentration of Rifaximin can be increased when it is combined with Perindopril.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Rifaximin.
PimozideThe serum concentration of Rifaximin can be increased when it is combined with Pimozide.
PonatinibThe serum concentration of Rifaximin can be increased when it is combined with Ponatinib.
PosaconazoleThe serum concentration of Rifaximin can be increased when it is combined with Posaconazole.
PravastatinThe serum concentration of Rifaximin can be increased when it is combined with Pravastatin.
PrazosinThe serum concentration of Rifaximin can be increased when it is combined with Prazosin.
PrednisoneThe serum concentration of Rifaximin can be increased when it is combined with Prednisone.
ProbenecidThe serum concentration of Rifaximin can be increased when it is combined with Probenecid.
ProgesteroneThe serum concentration of Rifaximin can be increased when it is combined with Progesterone.
PromethazineThe serum concentration of Rifaximin can be increased when it is combined with Promethazine.
PropafenoneThe serum concentration of Rifaximin can be increased when it is combined with Propafenone.
PropranololThe serum concentration of Rifaximin can be increased when it is combined with Propranolol.
ProtriptylineThe serum concentration of Rifaximin can be increased when it is combined with Protriptyline.
QuercetinThe serum concentration of Rifaximin can be increased when it is combined with Quercetin.
QuinacrineThe serum concentration of Rifaximin can be increased when it is combined with Quinacrine.
QuinidineThe serum concentration of Rifaximin can be increased when it is combined with Quinidine.
QuinineThe serum concentration of Rifaximin can be increased when it is combined with Quinine.
RanitidineThe serum concentration of Rifaximin can be increased when it is combined with Ranitidine.
ReboxetineThe serum concentration of Rifaximin can be increased when it is combined with Reboxetine.
RegorafenibThe serum concentration of Rifaximin can be increased when it is combined with Regorafenib.
ReserpineThe serum concentration of Rifaximin can be increased when it is combined with Reserpine.
RifampicinThe serum concentration of Rifaximin can be increased when it is combined with Rifampicin.
RilpivirineThe serum concentration of Rifaximin can be increased when it is combined with Rilpivirine.
RitonavirThe serum concentration of Rifaximin can be increased when it is combined with Ritonavir.
RolapitantThe serum concentration of Rifaximin can be increased when it is combined with Rolapitant.
SaquinavirThe serum concentration of Rifaximin can be increased when it is combined with Saquinavir.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Rifaximin.
ScopolamineThe serum concentration of Rifaximin can be increased when it is combined with Scopolamine.
SelegilineThe serum concentration of Rifaximin can be increased when it is combined with Selegiline.
SertralineThe serum concentration of Rifaximin can be increased when it is combined with Sertraline.
SimeprevirThe serum concentration of Rifaximin can be increased when it is combined with Simeprevir.
SimvastatinThe serum concentration of Rifaximin can be increased when it is combined with Simvastatin.
SirolimusThe serum concentration of Rifaximin can be increased when it is combined with Sirolimus.
SorafenibThe serum concentration of Rifaximin can be increased when it is combined with Sorafenib.
SpironolactoneThe serum concentration of Rifaximin can be increased when it is combined with Spironolactone.
StaurosporineThe serum concentration of Rifaximin can be increased when it is combined with Staurosporine.
SulfinpyrazoneThe serum concentration of Rifaximin can be increased when it is combined with Sulfinpyrazone.
SumatriptanThe serum concentration of Rifaximin can be increased when it is combined with Sumatriptan.
SunitinibThe serum concentration of Rifaximin can be increased when it is combined with Sunitinib.
TacrineThe serum concentration of Rifaximin can be increased when it is combined with Tacrine.
TacrolimusThe serum concentration of Rifaximin can be increased when it is combined with Tacrolimus.
TamoxifenThe serum concentration of Rifaximin can be increased when it is combined with Tamoxifen.
Taurocholic AcidThe serum concentration of Rifaximin can be increased when it is combined with Taurocholic Acid.
TelmisartanThe serum concentration of Rifaximin can be increased when it is combined with Telmisartan.
TemsirolimusThe serum concentration of Rifaximin can be increased when it is combined with Temsirolimus.
TerazosinThe serum concentration of Rifaximin can be increased when it is combined with Terazosin.
TerfenadineThe serum concentration of Rifaximin can be increased when it is combined with Terfenadine.
TestosteroneThe serum concentration of Rifaximin can be increased when it is combined with Testosterone.
TicagrelorThe serum concentration of Rifaximin can be increased when it is combined with Ticagrelor.
TolvaptanThe serum concentration of Rifaximin can be increased when it is combined with Tolvaptan.
TrifluoperazineThe serum concentration of Rifaximin can be increased when it is combined with Trifluoperazine.
TriflupromazineThe serum concentration of Rifaximin can be increased when it is combined with Triflupromazine.
TrimethoprimThe serum concentration of Rifaximin can be increased when it is combined with Trimethoprim.
TrimipramineThe serum concentration of Rifaximin can be increased when it is combined with Trimipramine.
TroleandomycinThe serum concentration of Rifaximin can be increased when it is combined with Troleandomycin.
VenlafaxineThe serum concentration of Rifaximin can be increased when it is combined with Venlafaxine.
VerapamilThe serum concentration of Rifaximin can be increased when it is combined with Verapamil.
VinblastineThe serum concentration of Rifaximin can be increased when it is combined with Vinblastine.
VincristineThe serum concentration of Rifaximin can be increased when it is combined with Vincristine.
VinorelbineThe serum concentration of Rifaximin can be increased when it is combined with Vinorelbine.
ZimelidineThe serum concentration of Rifaximin can be increased when it is combined with Zimelidine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Ribonucleoside binding
Specific Function:
DNA-dependent RNA polymerase catalyzes the transcription of DNA into RNA using the four ribonucleoside triphosphates as substrates.
Gene Name:
rpoB
Uniprot ID:
P0A8V2
Molecular Weight:
150631.165 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Vitali B, Turroni S, Dal Piaz F, Candela M, Wasinger V, Brigidi P: Genetic and proteomic characterization of rifaximin resistance in Bifidobacterium infantis BI07. Res Microbiol. 2007 May;158(4):355-62. Epub 2007 Feb 22. [PubMed:17408927 ]
  4. Ojetti V, Lauritano EC, Barbaro F, Migneco A, Ainora ME, Fontana L, Gabrielli M, Gasbarrini A: Rifaximin pharmacology and clinical implications. Expert Opin Drug Metab Toxicol. 2009 Jun;5(6):675-82. doi: 10.1517/17425250902973695. [PubMed:19442033 ]
  5. Koo HL, Dupont HL, Huang DB: The role of rifaximin in the treatment and chemoprophylaxis of travelers' diarrhea. Ther Clin Risk Manag. 2009;5:841-8. Epub 2009 Nov 2. [PubMed:19898648 ]
  6. Scarpignato C, Pelosini I: Experimental and clinical pharmacology of rifaximin, a gastrointestinal selective antibiotic. Digestion. 2006;73 Suppl 1:13-27. Epub 2006 Feb 8. [PubMed:16498249 ]
  7. Pimentel M: Review of rifaximin as treatment for SIBO and IBS. Expert Opin Investig Drugs. 2009 Mar;18(3):349-58. doi: 10.1517/13543780902780175 . [PubMed:19243285 ]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and is...
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
References
  1. Cheng J, Shah YM, Ma X, Pang X, Tanaka T, Kodama T, Krausz KW, Gonzalez FJ: Therapeutic role of rifaximin in inflammatory bowel disease: clinical implication of human pregnane X receptor activation. J Pharmacol Exp Ther. 2010 Oct;335(1):32-41. doi: 10.1124/jpet.110.170225. Epub 2010 Jul 13. [PubMed:20627999 ]
  2. Ma X, Shah YM, Guo GL, Wang T, Krausz KW, Idle JR, Gonzalez FJ: Rifaximin is a gut-specific human pregnane X receptor activator. J Pharmacol Exp Ther. 2007 Jul;322(1):391-8. Epub 2007 Apr 18. [PubMed:17442842 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on September 26, 2016 02:14