Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C43H51N3O11 |
Molecular Weight | 785.8785 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C4=C(C(O)=C3C)C(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)C5=C4N=C6C=C(C)C=CN56
InChI
InChIKey=NZCRJKRKKOLAOJ-XRCRFVBUSA-N
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
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/cdi/rifaximin.html
http://www.rxlist.com/xifaxan-drug.htm
http://www.wikidoc.org/index.php/Special:Search?search=RIFAXIMIN
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/cdi/rifaximin.html
http://www.rxlist.com/xifaxan-drug.htm
http://www.wikidoc.org/index.php/Special:Search?search=RIFAXIMIN
Rifaximin is a structural analog of rifampin and a non-systemic, gastrointestinal site-specific antibiotic. Rifaximin acts by inhibiting bacterial ribonucleic acid (RNA) synthesis and contributes to restore intestinal microflora imbalance. It is FDA approved for the treatment of travelers’ diarrhea, reduction in risk of overt hepatic encephalopathy (HE) recurrence and treatment of irritable bowel syndrome with diarrhea. More common side effects are: black, tarry stools; dizziness or lightheadedness; muscle spasm; rapid breathing; shortness of breath; trouble sleeping. Co-administration of cyclosporine, with XIFAXAN resulted in 83-fold and 124-fold increases in rifaximin mean Cmax in healthy subjects.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL340 |
25.0 µM [IC50] | ||
Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17442842 |
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Target ID: P0A8V2 Gene ID: 948488.0 Gene Symbol: rpoB Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16096056 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | XIFAXAN Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of XIFAXAN and other antibacterial drugs, XIFAXAN when used to treat infection should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. XIFAXAN is a rifamycin antibacterial indicated for: The treatment of patients (≥ 12 years of age) with travelers’ diarrhea (TD) caused by noninvasive strains of ( ) Escherichia coli 1.1 Reduction in risk of overt hepatic encephalopathy (HE) recurrence in patients ≥ 18 years of age ( ) 1.2 Limitations of Use TD: Do not use in patients with diarrhea complicated by fever or blood in the stool or diarrhea due to pathogens other than ( ) Escherichia coli 1.1 1.1 Travelers’ Diarrhea XIFAXAN 200 mg is indicated for the treatment of patients (≥ 12 years of age) with travelers’ diarrhea caused by noninvasive strains of Escherichia coli [see Warnings and Precautions ( ), Clinical Pharmacology ( ) and Clinical Studies ( ) Launch Date2004 |
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Preventing | XIFAXAN Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of XIFAXAN and other antibacterial drugs, XIFAXAN when used to treat infection should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. XIFAXAN is a rifamycin antibacterial indicated for: The treatment of patients (≥ 12 years of age) with travelers’ diarrhea (TD) caused by noninvasive strains of ( ) Escherichia coli 1.1 Reduction in risk of overt hepatic encephalopathy (HE) recurrence in patients ≥ 18 years of age ( ) 1.2 Limitations of Use TD: Do not use in patients with diarrhea complicated by fever or blood in the stool or diarrhea due to pathogens other than ( ) Escherichia coli 1.1 1.1 Travelers’ Diarrhea XIFAXAN 200 mg is indicated for the treatment of patients (≥ 12 years of age) with travelers’ diarrhea caused by noninvasive strains of Escherichia coli [see Warnings and Precautions ( ), Clinical Pharmacology ( ) and Clinical Studies ( ) Launch Date2004 |
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Primary | XIFAXAN Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of XIFAXAN and other antibacterial drugs, XIFAXAN when used to treat infection should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. XIFAXAN is a rifamycin antibacterial indicated for: The treatment of patients (≥ 12 years of age) with travelers’ diarrhea (TD) caused by noninvasive strains of ( ) Escherichia coli 1.1 Reduction in risk of overt hepatic encephalopathy (HE) recurrence in patients ≥ 18 years of age ( ) 1.2 Limitations of Use TD: Do not use in patients with diarrhea complicated by fever or blood in the stool or diarrhea due to pathogens other than ( ) Escherichia coli 1.1 1.1 Travelers’ Diarrhea XIFAXAN 200 mg is indicated for the treatment of patients (≥ 12 years of age) with travelers’ diarrhea caused by noninvasive strains of Escherichia coli [see Warnings and Precautions ( ), Clinical Pharmacology ( ) and Clinical Studies ( ) Launch Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.1 ng/mL |
550 mg single, oral dose: 550 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIFAXIMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
3.4 ng/mL |
550 mg 2 times / day steady-state, oral dose: 550 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
RIFAXIMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.8 ng/mL |
550 mg single, oral dose: 550 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIFAXIMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.1 ng × h/mL |
550 mg single, oral dose: 550 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIFAXIMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
12.3 ng × h/mL |
550 mg 2 times / day steady-state, oral dose: 550 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
RIFAXIMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
22.5 ng × h/mL |
550 mg single, oral dose: 550 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIFAXIMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.8 h |
550 mg single, oral dose: 550 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIFAXIMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
4.8 h |
550 mg single, oral dose: 550 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIFAXIMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
32.5% |
550 mg single, oral dose: 550 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIFAXIMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.4 |
unhealthy, 18-79 n = 320 Health Status: unhealthy Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli Age Group: 18-79 Sex: M+F Population Size: 320 Sources: Page: p.4 |
Disc. AE: Taste loss, Dysentery... AEs leading to discontinuation/dose reduction: Taste loss Sources: Page: p.4Dysentery Weight decrease Anorexia Nausea Nasal passage irritation |
1200 mg 2 times / day multiple, oral Highest studied dose Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: Page: p.478 |
unhealthy, 18–73 n = 99 Health Status: unhealthy Condition: Crohn's disease Age Group: 18–73 Sex: M+F Population Size: 99 Sources: Page: p.478 |
|
800 mg 3 times / day multiple, oral Highest studied dose Dose: 800 mg, 3 times / day Route: oral Route: multiple Dose: 800 mg, 3 times / day Sources: Page: p.207 |
unhealthy, 32-82 n = 17 Health Status: unhealthy Condition: Hepatic Encephalopathy Age Group: 32-82 Sex: M+F Population Size: 17 Sources: Page: p.207 |
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550 mg 3 times / day multiple, oral Studied dose Dose: 550 mg, 3 times / day Route: oral Route: multiple Dose: 550 mg, 3 times / day Sources: Page: p.1119 |
unhealthy, 46.4 n = 2579 Health Status: unhealthy Condition: Diarrhea-Predominant Irritable Bowel Syndrome Age Group: 46.4 Sex: M+F Population Size: 2579 Sources: Page: p.1119 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Anorexia | Disc. AE | 200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.4 |
unhealthy, 18-79 n = 320 Health Status: unhealthy Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli Age Group: 18-79 Sex: M+F Population Size: 320 Sources: Page: p.4 |
Dysentery | Disc. AE | 200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.4 |
unhealthy, 18-79 n = 320 Health Status: unhealthy Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli Age Group: 18-79 Sex: M+F Population Size: 320 Sources: Page: p.4 |
Nasal passage irritation | Disc. AE | 200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.4 |
unhealthy, 18-79 n = 320 Health Status: unhealthy Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli Age Group: 18-79 Sex: M+F Population Size: 320 Sources: Page: p.4 |
Nausea | Disc. AE | 200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.4 |
unhealthy, 18-79 n = 320 Health Status: unhealthy Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli Age Group: 18-79 Sex: M+F Population Size: 320 Sources: Page: p.4 |
Taste loss | Disc. AE | 200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.4 |
unhealthy, 18-79 n = 320 Health Status: unhealthy Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli Age Group: 18-79 Sex: M+F Population Size: 320 Sources: Page: p.4 |
Weight decrease | Disc. AE | 200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.4 |
unhealthy, 18-79 n = 320 Health Status: unhealthy Condition: Travelers’ diarrhea caused by noninvasive strains of Escherichia coli Age Group: 18-79 Sex: M+F Population Size: 320 Sources: Page: p.4 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022554Orig1s000ClinPharmR.pdf#page=23 Page: 23,30 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022554Orig1s000PharmR.pdf#page=9 Page: 9.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Rifaximin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic potential in conditions mediated by gastrointestinal bacteria. | 1995 Mar |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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Rifaximin, a poorly absorbed antibiotic: pharmacology and clinical potential. | 2005 |
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Rifaximin: a new treatment for travelers' diarrhea. | 2005 Feb |
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Rifaximin for the treatment of hepatic encephalopathy. | 2008 Aug |
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Rifaximin pharmacology and clinical implications. | 2009 Jun |
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Rifaximin: a nonsystemic rifamycin antibiotic for gastrointestinal infections. | 2010 Jul |
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Pharmacotherapy of hepatic encephalopathy in cirrhosis. | 2010 Jun |
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Review article: rifaximin, a minimally absorbed oral antibacterial, for the treatment of travellers' diarrhoea. | 2010 Jun |
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Solomonsterols A and B from Theonella swinhoei. The first example of C-24 and C-23 sulfated sterols from a marine source endowed with a PXR agonistic activity. | 2011 Jan 13 |
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Total synthesis and pharmacological characterization of solomonsterol A, a potent marine pregnane-X-receptor agonist endowed with anti-inflammatory activity. | 2011 Jul 14 |
Patents
Sample Use Guides
Travelers’ Diarrhea: The recommended dose is one 200 mg tablet taken orally three times a day for 3 days.
Hepatic Encephalopathy: The recommended dose is one 550 mg tablet taken orally two times a day.
Irritable Bowel Syndrome with Diarrhea: The recommended dose is one 550 mg tablet taken orally three times a day for 14 days.
It can be taken with or without food.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11269233
The activities of rifaximin against enteropathogens were found to be as follows: a MIC50 of 4 to 8 μg/ml and a MIC90 of >8 μg/ml.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
D06AX11
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NDF-RT |
N0000007911
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NDF-RT |
N0000007911
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WHO-VATC |
QD06AX11
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FDA ORPHAN DRUG |
778520
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NDF-RT |
N0000007911
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WHO-VATC |
QA07AA11
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NCI_THESAURUS |
C258
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FDA ORPHAN DRUG |
109497
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WHO-VATC |
QJ51XX01
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WHO-VATC |
QG51AA06
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NDF-RT |
N0000175500
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WHO-ATC |
A07AA11
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NDF-RT |
N0000007911
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LIVERTOX |
NBK548082
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100000091946
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5244
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35619
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80621-81-4
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Rifaximin
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SUB10312MIG
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L36O5T016N
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L36O5T016N
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m9615
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CHEMBL1617
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75246
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C042734
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6436173
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RIFAXIMIN
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ACTIVE MOIETY