U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C37H47NO12
Molecular Weight 697.77
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIFAMYCIN

SMILES

C[C@@]1([H])/C(/[H])=C(\[H])/C(/[H])=C(/C)\C(=Nc2cc(c3c(c(c(C)c4c3C(=O)[C@@](C)(O/C(/[H])=C(\[H])/[C@@]([H])([C@@]([H])(C)[C@]([H])([C@]([H])(C)[C@@]([H])([C@]([H])(C)[C@@]1([H])O)O)OC(=O)C)OC)O4)O)c2O)O)O

InChI

InChIKey=HJYYPODYNSCCOU-ODRIEIDWSA-N
InChI=1S/C37H47NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1

HIDE SMILES / InChI
Molecular Formula C37H47NO12
Molecular Weight 697.77
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Rifamycin SV is a derivative of antibiotic rifamycin B (the natural fermentation product of S. mediterranei broths). The primary target of rifampicin on whole bacteria is the synthesis of RNA. Rifamycin belongs to the ansamycin class of antibacterial drugs and acts by inhibiting the beta subunit of the bacterial DNA-dependent RNA polymerase, blocking one of the steps in DNA transcription. This results in inhibition of bacterial synthesis and consequently growth of bacteria. Rifampicin exhibits bactericidal activity on Gram-positive and Gram-negative bacteria and on mycobacteria. Rifamycin SV MMX® (AEMCOLO), a non-absorbable rifamycin antibiotic formulated using the multi-matrix system, was designed to exhibit its pharmacological action on the distal small intestine and colon. AEMCOLO is indicated for the treatment of travelers’ diarrhea (TD) caused by non-invasive strains of Escherichia coli in adults.

Originator

Sensi et al., 1959
2
Sources: Sensi P., Margalith P., Timbal M.T. Farmaco (Ed. Sci.) 1959;14:146 |Sensi P., Greco, A.M., Ballotta, R. Antimicrob. Ag. Chemother. 1959;60:262-70
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/4562808

Approval Year

2018
97
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7701
Travelers’ diarrhea
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Bacterial DNA-directed RNA polymerase
Approved
7997
AEMCOLO

Approved Use

AEMCOLO is a rifamycin antibacterial indicated for the treatment of travelers’ diarrhea caused by noninvasive strains of Escherichia coli in adults

Launch Date

1542240000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
36025 ng/mL
OTHER GOV
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RIFAMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
8.72 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
388 mg 2 times / day multiple, oral
dose: 388 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
RIFAMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11865.21 ng × h/mL
OTHER GOV
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RIFAMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.04 h
OTHER GOV
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RIFAMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
388 mg 2 times / day multiple, oral
dose: 388 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
RIFAMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
unhealthy, 36.2 years (range: 18 - 87 years)
Health Status: unhealthy
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
Disc. AE: Abdominal pain, Pyrexia...
AEs leading to
discontinuation/dose reduction:
Abdominal pain (0.5%)
Pyrexia (0.3%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
unhealthy, 36.2 years (range: 18 - 87 years)
Health Status: unhealthy
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
Other AEs: Headache, Dyspepsia...
Other AEs:
Headache (3.3%)
Dyspepsia (<2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
unhealthy, 36.2 years (range: 18 - 87 years)
Health Status: unhealthy
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
Other AEs: Constipation...
Other AEs:
Constipation (3.5%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Other AEs: Abdominal distension, Arthralgia...
Other AEs:
Abdominal distension (0.5%)
Arthralgia (0.5%)
Muscle spasms (1%)
Fatigue (1%)
Bronchitis (1%)
Nasopharyngitis (0.5%)
Parasitic gastroenteritis (1%)
Pharyngitis (0.5%)
Urinary tract infection (1%)
Dysmenorrhea (1.5%)
Dysuria (1%)
Dizziness (0.5%)
Conjunctivitis (1%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
400 mg 2 times / day multiple, oral
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (1%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
AEs

AEs

AESignificanceDosePopulation
Pyrexia 0.3%
Disc. AE
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
unhealthy, 36.2 years (range: 18 - 87 years)
Health Status: unhealthy
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
Abdominal pain 0.5%
Disc. AE
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
unhealthy, 36.2 years (range: 18 - 87 years)
Health Status: unhealthy
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
Headache 3.3%
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
unhealthy, 36.2 years (range: 18 - 87 years)
Health Status: unhealthy
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
Dyspepsia <2%
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
unhealthy, 36.2 years (range: 18 - 87 years)
Health Status: unhealthy
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
Constipation 3.5%
388 mg 2 times / day multiple, oral
Recommended
Dose: 388 mg, 2 times / day
Route: oral
Route: multiple
Dose: 388 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
unhealthy, 36.2 years (range: 18 - 87 years)
Health Status: unhealthy
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
Abdominal distension 0.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Arthralgia 0.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Dizziness 0.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Nasopharyngitis 0.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Pharyngitis 0.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Bronchitis 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Conjunctivitis 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Dysuria 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Fatigue 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Muscle spasms 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Parasitic gastroenteritis 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Urinary tract infection 1%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Dysmenorrhea 1.5%
400 mg 2 times / day multiple, oral
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Diarrhea 1%
Disc. AE
400 mg 2 times / day multiple, oral
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210910Orig1s000MultidisciplineR.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1470

inducer
657
substrate
865

inhibitor
1318
substrate
1038

inhibitor
1421

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A
66

CYP2B6
679

CYP2C8
761

CYP2E1
761

CYP2C19
1215

CYP3A
175

P-gp
1089

BCRP
574

OATP1B1
698

OAT1
547

OAT3
570

OCT2
582

MATE1
290

MATE2
258
CYP1A2
892

CYP2B6
575

CYP2C8
586

CYP2C19
830

CYP2E1
567

CYP3A5
346

P-gp
1223

BCRP
461
CYP2B6
486

CYP1A2
618

CYP3A4/5
107
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A
105
 no
CYP1A2
1406
 no
CYP2B6
845
 no
CYP2C8
810
 no
CYP2D6
1455
 no
CYP2E1
841
 no
MATE1
291
 no
MATE2
258
 no
OAT1
551
 no
OAT3
572
 no
OCT2
583
 no
CYP3A4/5
277
 yes [EC50 11.1 uM]
BCRP
639
 yes [IC50 34.4 uM]
P-gp
1255
 yes [IC50 6.5 uM]
OATP1B1
713
 yes [Ki 2 uM]
CYP2B6
845
 yes
CYP2C19
1277
 yes
CYP2C9
1362
 yes
CYP3A
244
 yes
CYP3A4
1462
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
461
 no
CYP1A2
892
 no
CYP2B6
575
 no
CYP2C19
830
 no
CYP2C8
586
 no
CYP2C9
865
 no
CYP2D6
1038
 no
CYP2E1
567
 no
CYP3A4
1470
 no
CYP3A5
346
 no
P-gp
1223
 yes
unlikely
Comment: Co-administration of rifamycin SV MMX with P-gp inhibitors is not expected to result in a clinically relevant increase in the systemic exposure of rifamycin SV based on the following: i) poor drug solubility; ii) wide safety margin in relation to systemic exposures observed with i.v. rifamycin SV, iii) limited 3-day treatment duration; and iv) colonic release (P-gp levels lower in colon and distal to site of most oral drugs’ absorption (i.e., duodenum and jejunum).
Page: 192
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubChem
6324616
https://pubchem.ncbi.nlm.nih.gov/compound/6324616
PubMed

PubMed

TitleDatePubMed
Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds.
1997 Sep-Oct
Characterization of the mouse bile salt export pump overexpressed in the baculovirus system.
2001 May
Differential interaction of 3-hydroxy-3-methylglutaryl-coa reductase inhibitors with ABCB1, ABCC2, and OATP1B1.
2005 Apr
Antibacterial activities of dendritic amphiphiles against nontuberculous mycobacteria.
2012 Mar
Patents

Patents

04005077
4
04174320
9
04431735
3
JP2004075665A
2
JP2008001720A
3
JPH07309759A
2
JPS53149999A
3
JPS54110391A
3
JPS54144400A
3
JPS5473798A
2
JPS55164684A
3
JPS5569589A
3
JPS5618986A
2
JPS5653682A
3
JPS574994A
3
JPS5772984A
2
JPS58146587A
3

Sample Use Guides

In Vivo Use Guide
The recommended dosage of AEMCOLO (rifamycin) delayed-release tablets is 388 mg (two tablets) orally twice daily for three days
Route of Administration: Oral
In Vitro Use Guide
Rifamycin SV demonstrated similar antimicrobial activity levels against the Enterobacteriaceae, with MIC₅₀ values ranging from 32 to 128 μg/ml for all but one strain (an enterotoxigenic Escherichia coli at >512 μg/ml). For non-Enterobacteriaceae strains, MIC₅₀ values ranged from 2 to 8 μg/ml, with the exception of Campylobacter spp., for which all strains had MIC values of >512 μg/ml. Rifamycin SV also demonstrated excellent activity (MIC₅₀ of ≤ 0.03 μg/ml) against most C. difficile strains (including one hypervirulent NAP1 strain), and this activity was even superior to the potency observed for vancomycin, metronidazole, and rifaximin.
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:54:49 UTC 2021
Edited
by admin
on Sat Jun 26 11:54:49 UTC 2021
Record UNII
DU69T8ZZPA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIFAMYCIN
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
M-14
Code English
RIFAMYCIN [WHO-DD]
Common Name English
RIFAMYCIN SV
MI  
Common Name English
RIFAMICINE SV
Common Name English
RIFAXIMIN IMPURITY C [EP]
Common Name English
5,6,9,17,19,21-HEXAHYDROXY-23-METHOXY-2,4,12,16,18,20,22-HEPTAMETHYL-2,7-(EPOXYPENTADECA(1,11,13)TRIENIMINO)NAPHTHO(2,1-B)FURAN-1,11(2H)-DIONE 21-ACETATE
Common Name English
RIFAMYCIN SV [EP]
Common Name English
RIFAMYCIN [USAN]
Common Name English
RIFAMYCIN SV, AN ANTIBIOTIC PRODUCED BY CERTAIN STRAINS OF STREPTOMYCES MEDITERRANEI, OR THE SAME SUBSTANCE PRODUCED BY ANY OTHER MEANS
Common Name English
RIFAMYCIN [INN]
Common Name English
RIFAMYCIN SV [MI]
Common Name English
RIFOMYCIN SV
Common Name English
Classification Tree Code System Code
WHO-VATC QJ04AB03
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-ATC S01AA16
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-VATC QJ54AB03
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-ATC J04AB03
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
NCI_THESAURUS C280
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-ATC S02AA12
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-VATC QS01AA16
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
WHO-VATC QS02AA12
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
Code System Code Type Description
EVMPD
SUB10310MIG
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
WIKIPEDIA
Rifamycin
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
NCI_THESAURUS
C29406
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
DRUG CENTRAL
4817
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
DRUG BANK
DB11753
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
MESH
C023808
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
ECHA (EC/EINECS)
230-273-3
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
EPA CompTox
6998-60-3
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
RXCUI
35616
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M9613
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY Merck Index
PUBCHEM
6324616
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
CAS
6998-60-3
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
LACTMED
Rifamycin
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
FDA UNII
DU69T8ZZPA
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL437765
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
INN
2293
Created by admin on Sat Jun 26 11:54:50 UTC 2021 , Edited by admin on Sat Jun 26 11:54:50 UTC 2021
PRIMARY
Related Record Type Details
OAT-3
TRANSPORTER -> INHIBITOR
Rifamycin is an inhibitor of renal transporters organic anion transporter (OAT) 3, multidrug and toxin extrusion (MATE) 1, and MATE2-K transporters in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose, clinically relevant inhibition of these transporters in vivo is unlikely.
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INDUCER
Rifamycin is an inducer of CYP3A4 and CYP2B6 but not CYP1A2 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose, clinically relevant induction of these enzymes in vivo is unlikely.
STAPHYLOCOCCUS AUREUS
TARGET ORGANISM->INHIBITOR
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
CYTOCHROME P450 2C8
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
ESCHERICHIA COLI
TARGET ORGANISM->INHIBITOR
Other
CYTOCHROME P450 2B6
METABOLIC ENZYME -> INDUCER
Rifamycin is an inducer of CYP3A4 and CYP2B6 but not CYP1A2 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose, clinically relevant induction of these enzymes in vivo is unlikely.
SOLUTE CARRIER FAMILY 21 MEMBER 3
TRANSPORTER -> INHIBITOR
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> INHIBITOR
Rifamycin is an inhibitor of renal transporters organic anion transporter (OAT) 3, multidrug and toxin extrusion (MATE) 1, and MATE2-K transporters in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose, clinically relevant inhibition of these transporters in vivo is unlikely.
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
IC50
MYCOBACTERIUM TUBERCULOSIS
TARGET ORGANISM->INHIBITOR
CYTOCHROME P450 2B6
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
OATP-B
TRANSPORTER -> INHIBITOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Structure of RIFAMYCIN
EXCRETED UNCHANGED
After IV administration of rifamycin SV, > 90% of the dose is excreted as unchanged drug in feces via biliary secretion8
FECAL
Structure of RIFAMYCIN SODIUM
SALT/SOLVATE -> PARENT
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
IC50
CYTOCHROME P450 2D6
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
CYTOCHROME P450 3A4
METABOLIC ENZYME -> NON-SUBSTRATE
MATE-2
TRANSPORTER -> INHIBITOR
Rifamycin is an inhibitor of renal transporters organic anion transporter (OAT) 3, multidrug and toxin extrusion (MATE) 1, and MATE2-K transporters in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose, clinically relevant inhibition of these transporters in vivo is unlikely.
OATP-8
TRANSPORTER -> INHIBITOR
CYTOCHROME P450 2C19
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
CYTOCHROME P450 1A2
METABOLIC ENZYME -> INHIBITOR
Rifamycin is an inhibitor of CYP1A2, 2B6, 2C8, 2C9, 2C19, 2D6 and 3A4/5 in vitro, however, based on systemic concentrations of rifamycin observed after administration of the recommended dose clinically relevant inhibition of these enzymes in vivo is unlikely.
Related Record Type Details
Structure of RIFAXIMIN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of RIFAMYCIN S
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of RIFAMYCIN
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