Rifaximin

Identification

Summary

Rifaximin is a rifamycin-based non-systemic antibiotic used for the treatment of gastrointestinal bacterial infections, such as traveler's diarrhea and irritable bowel syndrome, and reduction of overt hepatic encephalopathy recurrence in adults.

Brand Names
Xifaxan, Zaxine
Generic Name
Rifaximin
DrugBank Accession Number
DB01220
Background

Rifaximin 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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 785.8785
Monoisotopic: 785.352359489
Chemical Formula
C43H51N3O11
Synonyms
  • Rifamycin L 105
  • Rifamycin L 105SV
  • Rifaxidin
  • Rifaximin
  • Rifaximina
  • Rifaximine
  • Rifaximinun

Pharmacology

Indication

Rifaximin 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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofBacterial infection••••••••••••
Treatment ofHepatic encephalopathy••• •••••
Prophylaxis ofHepatic encephalopathy•••••••••••••••••
Treatment ofIrritable bowel syndrome•••••••••••••••••
Management ofRecurrent clostridium difficile infection••• •••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Rifaximin 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 action

Rifaximin 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 binding blocks translocation, which stops transcription.

TargetActionsOrganism
ADNA-directed RNA polymerase subunit beta
inhibitor
Escherichia coli (strain K12)
NNuclear receptor subfamily 1 group I member 2
agonist
Humans
Absorption

Low absorption in both the fasting state and when administered within 30 minutes of a high-fat breakfast.

Volume of distribution

Not Available

Protein binding

Not 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 elimination

In 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-life

Approximately 6 hours.

Clearance

Not Available

Adverse Effects
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Toxicity

LD50 > 2 g/kg (orally, in rats)

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbrocitinibThe serum concentration of Rifaximin can be increased when it is combined with Abrocitinib.
AcebutololThe metabolism of Acebutolol can be increased when combined with Rifaximin.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Rifaximin.
AdagrasibThe serum concentration of Rifaximin can be increased when it is combined with Adagrasib.
AfatinibThe serum concentration of Rifaximin can be increased when it is combined with Afatinib.
Food Interactions
  • Take with or without food. Fatty meals may increase the systemic AUC of rifaximin, but do not impact Cmax. Rifaximin is an antibacterial used for local action in the gastrointestinal tract; therefore, changes in systemic exposure may not significantly impact efficacy.

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Product Images
International/Other Brands
Normix / Rifacol / Xifaxsan
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
XifaxanTablet200 mg/1OralCarilion Materials Management2004-07-25Not applicableUS flag
XifaxanTablet200 mg/1OralPhysicians Total Care, Inc.2008-12-14Not applicableUS flag
XifaxanTablet550 mg/1OralSalix Pharmaceuticals, Inc.2010-05-01Not applicableUS flag
XifaxanTablet550 mg/1OralCarton Service, Incorporated2010-05-012017-07-13US flag
XifaxanTablet200 mg/1OralDispensing Solutions, Inc.2004-07-25Not applicableUS flag

Categories

ATC Codes
A07AA11 — RifaximinD06AX11 — Rifaximin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolactams
Sub Class
Not Available
Direct Parent
Macrolactams
Alternative Parents
Naphthofurans / Naphthols and derivatives / Benzimidazoles / Benzofurans / Coumarans / Imidazo[1,2-a]pyridines / Aryl alkyl ketones / Methylpyridines / Ketals / N-substituted imidazoles
show 14 more
Substituents
1-naphthol / Acetal / Alcohol / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Azole / Benzenoid / Benzimidazole
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
acetate ester, organic heterohexacyclic compound, lactam, semisynthetic derivative, macrocycle, cyclic ketal, rifamycin (CHEBI:75246)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
L36O5T016N
CAS number
80621-81-4
InChI Key
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[23.10.1.1^{4,7}.0^{5,35}.0^{26,34}.0^{27,32}]heptatriaconta-1,3,5(35),9,19,21,25(36),26(34),28,30,32-undecaen-13-yl acetate
SMILES
CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C)C(O)=C4C(O)=C(NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C1=C(N=C5C=C(C)C=CN15)C4=C3C2=O

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. [Article]
  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. [Article]
  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. [Article]
  4. Pakyz AL: Rifaximin: a new treatment for travelers' diarrhea. Ann Pharmacother. 2005 Feb;39(2):284-9. Epub 2004 Dec 14. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  9. Scarpignato C, Pelosini I: Rifaximin, a poorly absorbed antibiotic: pharmacology and clinical potential. Chemotherapy. 2005;51 Suppl 1:36-66. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  13. Romero-Gomez M: Pharmacotherapy of hepatic encephalopathy in cirrhosis. Expert Opin Pharmacother. 2010 Jun;11(8):1317-27. doi: 10.1517/14656561003724721. [Article]
  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. [Article]
  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 . [Article]
  16. Rifaximin Australian Public Assessment Report [File]
Human Metabolome Database
HMDB15351
KEGG Drug
D02554
PubChem Compound
6436173
PubChem Substance
46508705
ChemSpider
10482302
BindingDB
50347620
RxNav
35619
ChEBI
75246
ChEMBL
CHEMBL1617
ZINC
ZINC000169621200
Therapeutic Targets Database
DAP001006
PharmGKB
PA164752443
PDBe Ligand
RXM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Rifaximin
PDB Entries
6bee
FDA label
Download (478 KB)
MSDS
Download (58.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceAscites / Cirrhosis of the Liver1
4CompletedBasic ScienceCirrhosis of the Liver / Hepatoencephalopathy, Early Fatal Progressive1
4CompletedBasic ScienceCommon Variable Immune Deficiency (CVID)1
4CompletedBasic ScienceDiarrhoea Predominant Irritable Bowel Syndrome1
4CompletedPreventionChronic Kidney Disease (CKD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Diversified Healthcare Services Inc.
  • Patheon Inc.
  • Physicians Total Care Inc.
  • Salix Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral200.000 mg
Tablet, film coatedOral
Granule, for suspensionOral
Ointment
Granule, for suspensionOral100 MG/5ML
SuspensionOral1.2000 g
SuspensionOral2 g
Capsule, liquid filledOral550 mg
Capsule, liquid filledOral200 mg
Capsule, liquid filledOral20000000 mg
Powder, for suspensionOral2 g
Granule, for suspensionOral2 G/100ML
TabletOral100 MG
Tablet, film coatedOral200 mg
CreamTopical
Tablet, coatedOral550 mg
Solution / dropsOral5 %
Tablet, coatedOral400 mg
Tablet, coatedOral200 mg
TabletOral200 mg/1
TabletOral550 mg/1
Tablet, film coatedOral550 mg
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)Region
US7928115No2011-04-192029-07-24US flag
US8741904No2014-06-032026-02-27US flag
US7612199No2009-11-032024-06-19US flag
US8853231No2014-10-072024-06-19US flag
US8158644No2012-04-172024-06-19US flag
US8193196No2012-06-052027-09-02US flag
US7906542No2011-03-152025-06-01US flag
US8158781No2012-04-172024-06-19US flag
US7045620No2006-05-162024-06-19US flag
US8518949No2013-08-272026-02-27US flag
US8835452No2014-09-162024-06-19US flag
US7902206No2011-03-082024-06-19US flag
US8829017No2014-09-092029-07-24US flag
US8642573No2014-02-042029-10-02US flag
US8969398No2015-03-032029-10-02US flag
US8946252No2015-02-032029-07-24US flag
US7915275No2011-03-292025-02-23US flag
US8309569No2012-11-132029-07-18US flag
US7718608No2010-05-182019-08-11US flag
US7452857No2008-11-182019-08-11US flag
US6861053No2005-03-012019-08-11US flag
US7605240No2009-10-202019-08-11US flag
US7935799No2011-05-032019-08-11US flag
US9271968No2016-03-012026-02-27US flag
US9421195No2016-08-232030-03-10US flag
US9629828No2017-04-252029-07-24US flag
US10314828No2019-06-112029-10-02US flag
US10335397No2019-07-022029-10-02US flag
US10456384No2019-10-292029-02-26US flag
US10709694No2020-07-142029-07-24US flag
US10703763No2020-07-072026-02-27US flag
US10765667No2020-09-082029-02-26US flag
US11564912No2009-02-262029-02-26US flag
US11779571No2009-02-262029-02-26US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00738 mg/mLALOGPS
logP4.94ALOGPS
logP4.59Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)6.69Chemaxon
pKa (Strongest Basic)5.88Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count11Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area198.38 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity216.69 m3·mol-1Chemaxon
Polarizability82.04 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-0000000900-ff32d840ddcdd131918d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01wf-1000001900-8e5ff3fe8a673b1e476e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-002o-0000001900-99e865ce1e4d016e1151
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-b081b597fec5db0ee9a4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0lec-3000000900-b659019e754fa62de7ab
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0000000900-38e6a4feb1f9dcd82650
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-289.6224029
predicted
DarkChem Lite v0.1.0
[M-H]-270.00867
predicted
DeepCCS 1.0 (2019)
[M+H]+288.1678029
predicted
DarkChem Lite v0.1.0
[M+H]+271.7324
predicted
DeepCCS 1.0 (2019)
[M+Na]+277.91818
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
Uniprot Name
DNA-directed RNA polymerase subunit beta
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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 . [Article]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
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 an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  2. Hoffman JT, Hartig C, Sonbol E, Lang M: Probable interaction between warfarin and rifaximin in a patient treated for small intestine bacterial overgrowth. Ann Pharmacother. 2011 May;45(5):e25. doi: 10.1345/aph.1P578. Epub 2011 Apr 19. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Rana R, Chen Y, Ferguson SS, Kissling GE, Surapureddi S, Goldstein JA: Hepatocyte nuclear factor 4{alpha} regulates rifampicin-mediated induction of CYP2C genes in primary cultures of human hepatocytes. Drug Metab Dispos. 2010 Apr;38(4):591-9. doi: 10.1124/dmd.109.030387. Epub 2010 Jan 19. [Article]
  2. Edwards RJ, Price RJ, Watts PS, Renwick AB, Tredger JM, Boobis AR, Lake BG: Induction of cytochrome P450 enzymes in cultured precision-cut human liver slices. Drug Metab Dispos. 2003 Mar;31(3):282-8. [Article]
  3. Rifaximin FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48