You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
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/1OralSalix Pharmaceuticals, Inc.2004-07-25Not applicableUs
XifaxanTablet550 mg/1OralPhysicians Total Care, Inc.2010-08-19Not applicableUs
XifaxanTablet550 mg/1OralSalix Pharmaceuticals, Inc.2010-05-01Not applicableUs
XifaxanTablet200 mg/1OralDispensing Solutions, Inc.2004-07-25Not applicableUs
XifaxanTablet200 mg/1OralCarilion Materials Management2004-07-25Not 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 KeyNZCRJKRKKOLAOJ-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
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.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
DNA-directed RNA polymerase subunit betaProteinyes
inhibitor
Escherichia coli (strain K12)P0A8V2 details
Nuclear receptor subfamily 1 group I member 2Proteinno
agonist
HumanO75469 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
AcetaminophenThe serum concentration of Rifaximin can be increased when it is combined with Acetaminophen.Approved
AfatinibThe serum concentration of Rifaximin can be increased when it is combined with Afatinib.Approved
AlbendazoleThe serum concentration of Rifaximin can be increased when it is combined with Albendazole.Approved, Vet Approved
AlectinibThe serum concentration of Rifaximin can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Rifaximin can be increased when it is combined with Alfentanil.Approved, Illicit
AmantadineThe serum concentration of Rifaximin can be increased when it is combined with Amantadine.Approved
Aminohippuric acidThe serum concentration of Rifaximin can be increased when it is combined with Aminohippuric acid.Approved
AmiodaroneThe serum concentration of Rifaximin can be increased when it is combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Rifaximin can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Rifaximin can be increased when it is combined with Amlodipine.Approved
AmprenavirThe serum concentration of Rifaximin can be increased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Rifaximin can be increased when it is combined with Amsacrine.Approved
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Rifaximin.Approved, Investigational
AstemizoleThe serum concentration of Rifaximin can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe serum concentration of Rifaximin can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Rifaximin can be increased when it is combined with Atenolol.Approved
AtorvastatinThe serum concentration of Rifaximin can be increased when it is combined with Atorvastatin.Approved
AzelastineThe serum concentration of Rifaximin can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Rifaximin can be increased when it is combined with Azithromycin.Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Rifaximin.Investigational
BenzocaineThe serum concentration of Rifaximin can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Rifaximin can be increased when it is combined with Bepridil.Approved, Withdrawn
BiperidenThe serum concentration of Rifaximin can be increased when it is combined with Biperiden.Approved
BosutinibThe serum concentration of Rifaximin can be increased when it is combined with Bosutinib.Approved
BromocriptineThe serum concentration of Rifaximin can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Rifaximin can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe serum concentration of Rifaximin can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe serum concentration of Rifaximin can be increased when it is combined with Cabazitaxel.Approved
CaffeineThe serum concentration of Rifaximin can be increased when it is combined with Caffeine.Approved
CanagliflozinThe serum concentration of Rifaximin can be increased when it is combined with Canagliflozin.Approved
CandesartanThe serum concentration of Rifaximin can be increased when it is combined with Candesartan.Approved
CaptoprilThe serum concentration of Rifaximin can be increased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Rifaximin can be increased when it is combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Rifaximin can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Rifaximin can be increased when it is combined with Caspofungin.Approved
ChloroquineThe serum concentration of Rifaximin can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Rifaximin can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Rifaximin can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Rifaximin can be increased when it is combined with Chlorprothixene.Approved, Withdrawn
CholesterolThe serum concentration of Rifaximin can be increased when it is combined with Cholesterol.Experimental
CilazaprilThe serum concentration of Rifaximin can be increased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Rifaximin can be increased when it is combined with Cimetidine.Approved
CiprofloxacinThe serum concentration of Rifaximin can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe serum concentration of Rifaximin can be increased when it is combined with Citalopram.Approved
ClarithromycinThe serum concentration of Rifaximin can be increased when it is combined with Clarithromycin.Approved
ClofazimineThe serum concentration of Rifaximin can be increased when it is combined with Clofazimine.Approved, Investigational
ClomipramineThe serum concentration of Rifaximin can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe serum concentration of Rifaximin can be increased when it is combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Rifaximin can be increased when it is combined with Cobicistat.Approved
ColchicineThe serum concentration of Rifaximin can be increased when it is combined with Colchicine.Approved
ColforsinThe serum concentration of Rifaximin can be increased when it is combined with Colforsin.Experimental
CrizotinibThe serum concentration of Rifaximin can be increased when it is combined with Crizotinib.Approved
CyclophosphamideThe serum concentration of Rifaximin can be increased when it is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Rifaximin can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DaclatasvirThe serum concentration of Rifaximin can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Rifaximin can be increased when it is combined with Dactinomycin.Approved
DasatinibThe serum concentration of Rifaximin can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Rifaximin can be increased when it is combined with Daunorubicin.Approved
DesipramineThe serum concentration of Rifaximin can be increased when it is combined with Desipramine.Approved
DesloratadineThe serum concentration of Rifaximin can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Rifaximin can be increased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe serum concentration of Rifaximin can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Rifaximin can be increased when it is combined with Diclofenac.Approved, Vet Approved
DigoxinThe serum concentration of Rifaximin can be increased when it is combined with Digoxin.Approved
DihydroergotamineThe serum concentration of Rifaximin can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Rifaximin can be increased when it is combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Rifaximin can be increased when it is combined with Dipyridamole.Approved
DoxazosinThe serum concentration of Rifaximin can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Rifaximin can be increased when it is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Rifaximin can be increased when it is combined with Doxorubicin.Approved, Investigational
DronabinolThe serum concentration of Rifaximin can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe serum concentration of Rifaximin can be increased when it is combined with Dronedarone.Approved
ElbasvirThe serum concentration of Rifaximin can be increased when it is combined with Elbasvir.Approved
EnalaprilThe serum concentration of Rifaximin can be increased when it is combined with Enalapril.Approved, Vet Approved
EnzalutamideThe serum concentration of Rifaximin can be increased when it is combined with Enzalutamide.Approved
ErgonovineThe serum concentration of Rifaximin can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Rifaximin can be increased when it is combined with Ergotamine.Approved
ErythromycinThe serum concentration of Rifaximin can be increased when it is combined with Erythromycin.Approved, Vet Approved
EstramustineThe serum concentration of Rifaximin can be increased when it is combined with Estramustine.Approved
EtoposideThe serum concentration of Rifaximin can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Rifaximin can be increased when it is combined with Etravirine.Approved
FelodipineThe serum concentration of Rifaximin can be increased when it is combined with Felodipine.Approved, Investigational
FentanylThe serum concentration of Rifaximin can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Rifaximin can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Rifaximin can be increased when it is combined with Fidaxomicin.Approved
FluconazoleThe serum concentration of Rifaximin can be increased when it is combined with Fluconazole.Approved
FluoxetineThe serum concentration of Rifaximin can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Rifaximin can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Rifaximin can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Rifaximin can be increased when it is combined with Flurazepam.Approved, Illicit
FluvoxamineThe serum concentration of Rifaximin can be increased when it is combined with Fluvoxamine.Approved, Investigational
GefitinibThe serum concentration of Rifaximin can be increased when it is combined with Gefitinib.Approved, Investigational
GenisteinThe serum concentration of Rifaximin can be increased when it is combined with Genistein.Investigational
GlyburideThe serum concentration of Rifaximin can be increased when it is combined with Glyburide.Approved
GlycerolThe serum concentration of Rifaximin can be increased when it is combined with Glycerol.Experimental
Gramicidin DThe serum concentration of Rifaximin can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Rifaximin can be increased when it is combined with Grepafloxacin.Withdrawn
HaloperidolThe serum concentration of Rifaximin can be increased when it is combined with Haloperidol.Approved
HydrocortisoneThe serum concentration of Rifaximin can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe serum concentration of Rifaximin can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of Rifaximin can be increased when it is combined with Imatinib.Approved
ImipramineThe serum concentration of Rifaximin can be increased when it is combined with Imipramine.Approved
IndinavirThe serum concentration of Rifaximin can be increased when it is combined with Indinavir.Approved
IndomethacinThe serum concentration of Rifaximin can be increased when it is combined with Indomethacin.Approved, Investigational
IsavuconazoniumThe serum concentration of Rifaximin can be increased when it is combined with Isavuconazonium.Approved, Investigational
ItraconazoleThe serum concentration of Rifaximin can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Rifaximin can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Rifaximin can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Rifaximin can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe serum concentration of Rifaximin can be increased when it is combined with Ketoconazole.Approved, Investigational
LansoprazoleThe serum concentration of Rifaximin can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Rifaximin can be increased when it is combined with Lapatinib.Approved, Investigational
LevofloxacinThe serum concentration of Rifaximin can be increased when it is combined with Levofloxacin.Approved, Investigational
LidocaineThe serum concentration of Rifaximin can be increased when it is combined with Lidocaine.Approved, Vet Approved
LisinoprilThe serum concentration of Rifaximin can be increased when it is combined with Lisinopril.Approved, Investigational
LomitapideThe serum concentration of Rifaximin can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Rifaximin can be increased when it is combined with Loperamide.Approved
LopinavirThe serum concentration of Rifaximin can be increased when it is combined with Lopinavir.Approved
LoratadineThe serum concentration of Rifaximin can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Rifaximin can be increased when it is combined with Losartan.Approved
LovastatinThe serum concentration of Rifaximin can be increased when it is combined with Lovastatin.Approved, Investigational
MaprotilineThe serum concentration of Rifaximin can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Rifaximin can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineThe serum concentration of Rifaximin can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Rifaximin can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Rifaximin can be increased when it is combined with Meprobamate.Approved, Illicit
MethadoneThe serum concentration of Rifaximin can be increased when it is combined with Methadone.Approved
MetoprololThe serum concentration of Rifaximin can be increased when it is combined with Metoprolol.Approved, Investigational
MibefradilThe serum concentration of Rifaximin can be increased when it is combined with Mibefradil.Withdrawn
MiconazoleThe serum concentration of Rifaximin can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Rifaximin can be increased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Rifaximin can be increased when it is combined with Mifepristone.Approved, Investigational
MitomycinThe serum concentration of Rifaximin can be increased when it is combined with Mitomycin.Approved
MitoxantroneThe serum concentration of Rifaximin can be increased when it is combined with Mitoxantrone.Approved, Investigational
MorphineThe serum concentration of Rifaximin can be increased when it is combined with Morphine.Approved, Investigational
NaltrexoneThe serum concentration of Rifaximin can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Rifaximin can be increased when it is combined with Naringenin.Experimental
NelfinavirThe serum concentration of Rifaximin can be increased when it is combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Rifaximin can be increased when it is combined with Neostigmine.Approved, Vet Approved
NicardipineThe serum concentration of Rifaximin can be increased when it is combined with Nicardipine.Approved
NifedipineThe serum concentration of Rifaximin can be increased when it is combined with Nifedipine.Approved
NilotinibThe serum concentration of Rifaximin can be increased when it is combined with Nilotinib.Approved, Investigational
NisoldipineThe serum concentration of Rifaximin can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Rifaximin can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Rifaximin can be increased when it is combined with Nitrendipine.Approved
OmeprazoleThe serum concentration of Rifaximin can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
P-NitrophenolThe serum concentration of Rifaximin can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe serum concentration of Rifaximin can be increased when it is combined with Paclitaxel.Approved, Vet Approved
Palmitic AcidThe serum concentration of Rifaximin can be increased when it is combined with Palmitic Acid.Experimental
PantoprazoleThe serum concentration of Rifaximin can be increased when it is combined with Pantoprazole.Approved
ParoxetineThe serum concentration of Rifaximin can be increased when it is combined with Paroxetine.Approved, Investigational
PerindoprilThe serum concentration of Rifaximin can be increased when it is combined with Perindopril.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Rifaximin.Approved
PimozideThe serum concentration of Rifaximin can be increased when it is combined with Pimozide.Approved
PonatinibThe serum concentration of Rifaximin can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe serum concentration of Rifaximin can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Rifaximin can be increased when it is combined with Pravastatin.Approved
PrazosinThe serum concentration of Rifaximin can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Rifaximin can be increased when it is combined with Prednisone.Approved, Vet Approved
ProbenecidThe serum concentration of Rifaximin can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Rifaximin can be increased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Rifaximin can be increased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Rifaximin can be increased when it is combined with Propafenone.Approved
PropranololThe serum concentration of Rifaximin can be increased when it is combined with Propranolol.Approved, Investigational
ProtriptylineThe serum concentration of Rifaximin can be increased when it is combined with Protriptyline.Approved
QuercetinThe serum concentration of Rifaximin can be increased when it is combined with Quercetin.Experimental
QuinacrineThe serum concentration of Rifaximin can be increased when it is combined with Quinacrine.Approved
QuinidineThe serum concentration of Rifaximin can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Rifaximin can be increased when it is combined with Quinine.Approved
RanitidineThe serum concentration of Rifaximin can be increased when it is combined with Ranitidine.Approved
ReboxetineThe serum concentration of Rifaximin can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Rifaximin can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Rifaximin can be increased when it is combined with Reserpine.Approved
RifampicinThe serum concentration of Rifaximin can be increased when it is combined with Rifampicin.Approved
RilpivirineThe serum concentration of Rifaximin can be increased when it is combined with Rilpivirine.Approved
RitonavirThe serum concentration of Rifaximin can be increased when it is combined with Ritonavir.Approved, Investigational
RolapitantThe serum concentration of Rifaximin can be increased when it is combined with Rolapitant.Approved
SaquinavirThe serum concentration of Rifaximin can be increased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Rifaximin.Approved
ScopolamineThe serum concentration of Rifaximin can be increased when it is combined with Scopolamine.Approved
SelegilineThe serum concentration of Rifaximin can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Rifaximin can be increased when it is combined with Sertraline.Approved
SimeprevirThe serum concentration of Rifaximin can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Rifaximin can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Rifaximin can be increased when it is combined with Sirolimus.Approved, Investigational
SorafenibThe serum concentration of Rifaximin can be increased when it is combined with Sorafenib.Approved, Investigational
SpironolactoneThe serum concentration of Rifaximin can be increased when it is combined with Spironolactone.Approved
StaurosporineThe serum concentration of Rifaximin can be increased when it is combined with Staurosporine.Experimental
SulfinpyrazoneThe serum concentration of Rifaximin can be increased when it is combined with Sulfinpyrazone.Approved
SumatriptanThe serum concentration of Rifaximin can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Rifaximin can be increased when it is combined with Sunitinib.Approved, Investigational
TacrineThe serum concentration of Rifaximin can be increased when it is combined with Tacrine.Withdrawn
TacrolimusThe serum concentration of Rifaximin can be increased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Rifaximin can be increased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Rifaximin can be increased when it is combined with Taurocholic Acid.Experimental
TelmisartanThe serum concentration of Rifaximin can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Rifaximin can be increased when it is combined with Temsirolimus.Approved
TerazosinThe serum concentration of Rifaximin can be increased when it is combined with Terazosin.Approved
TerfenadineThe serum concentration of Rifaximin can be increased when it is combined with Terfenadine.Withdrawn
TestosteroneThe serum concentration of Rifaximin can be increased when it is combined with Testosterone.Approved, Investigational
TicagrelorThe serum concentration of Rifaximin can be increased when it is combined with Ticagrelor.Approved
TolvaptanThe serum concentration of Rifaximin can be increased when it is combined with Tolvaptan.Approved
TrifluoperazineThe serum concentration of Rifaximin can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Rifaximin can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimThe serum concentration of Rifaximin can be increased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Rifaximin can be increased when it is combined with Trimipramine.Approved
TroleandomycinThe serum concentration of Rifaximin can be increased when it is combined with Troleandomycin.Approved
VenlafaxineThe serum concentration of Rifaximin can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Rifaximin can be increased when it is combined with Verapamil.Approved
VinblastineThe serum concentration of Rifaximin can be increased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Rifaximin can be increased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Rifaximin can be increased when it is combined with Vinorelbine.Approved, Investigational
ZimelidineThe serum concentration of Rifaximin can be increased when it is combined with Zimelidine.Withdrawn
Food InteractionsNot 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 CodesD06AX11A07AA11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (478 KB)
MSDSDownload (58.4 KB)
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
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

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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on December 05, 2016 02:43