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

Details

Stereochemistry ABSOLUTE
Molecular Formula C37H47NO12
Molecular Weight 697.7686
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIFAMYCIN

SMILES

CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C4=C(O)C=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)C(O)=C4C(O)=C3C

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 697.7686
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: Rifamycin family of antibiotics originally isolated from the fermentation broths of S. mediterranei. https://www.ncbi.nlm.nih.gov/pubmed/4562808

Approval Year

2018
400
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8360
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

1.54223994E12
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)
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 199
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
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)
n = 420
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 420
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)
n = 619
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 619
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
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
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)
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 199
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)
n = 420
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 420
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)
n = 420
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 420
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/210910s000lbl.pdf
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)
n = 619
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 619
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)
n = 619
Health Status: unhealthy
Condition: travelers’ diarrhea
Age Group: 36.2 years (range: 18 - 87 years)
Sex: M+F
Population Size: 619
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
n = 199
Health Status: unhealthy
Condition: travelers’ diarrhea
Sex: M+F
Population Size: 199
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
1709

inducer
768
substrate
1010

inhibitor
1752
substrate
1193

inhibitor
1837

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A
72

CYP2B6
799

CYP2C8
901

CYP2E1
876

CYP2C19
1463

CYP3A
211

P-gp
1437

BCRP
691

OATP1B1
781

OAT1
595

OAT3
636

OCT2
638

MATE1
304

MATE2
261
CYP1A2
1032

CYP2B6
660

CYP2C8
688

CYP2C19
985

CYP2E1
648

CYP3A5
391

P-gp
1527

BCRP
555
CYP2B6
538

CYP1A2
689

CYP3A4/5
120
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A
121
 no
CYP1A2
1673
 no
CYP2B6
985
 no
CYP2C8
955
 no
CYP2D6
1875
 no
CYP2E1
964
 no
MATE1
306
 no
MATE2
261
 no
OAT1
599
 no
OAT3
638
 no
OCT2
639
 no
CYP3A4/5
330
 yes [EC50 11.1 uM]
BCRP
765
 yes [IC50 34.4 uM]
P-gp
1626
 yes [IC50 6.5 uM]
OATP1B1
796
 yes [Ki 2 uM]
CYP2B6
985
 yes
CYP2C19
1537
 yes
CYP2C9
1803
 yes
CYP3A
295
 yes
CYP3A4
1909
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
555
 no
CYP1A2
1032
 no
CYP2B6
660
 no
CYP2C19
985
 no
CYP2C8
688
 no
CYP2C9
1010
 no
CYP2D6
1193
 no
CYP2E1
648
 no
CYP3A4
1709
 no
CYP3A5
391
 no
P-gp
1527
 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: 192.0
Sourcing

Sourcing

Vendor/AggregatorIDURL
AK Scientific, Inc. (AKSCI)
8248AH
http://www.aksci.com/item_detail.php?cat=8248AH
Aurora Fine Chemicals LLC
A18.030.564
http://online.aurorafinechemicals.com/info?ID=A18.030.564
AvaChem Scientific
2841A
http://www.avachem.com/productSearch.asp?2841A
Clearsynth
CS-O-02237
https://www.clearsynth.com/en/CSO02237.html
Smolecule
S541413
http://www.smolecule.com/products/s541413
THE BioTek
bt-280497
https://www.thebiotek.com/product/inhibitors/bt-280497
TimTec
ST044225
http://www.echemstore.com/st044225-rifamycin-sv-sodium-salt.html
Yuhao Chemical
XJ3218
http://www.chemyuhao.com/6998-60-3.html
eNovation Chemicals
D668777
https://www.enovationchem.com/ProductDetails.asp?ProductID=D668777
iChemical
EBD581134
http://www.ichemical.com/products/6998-60-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
PubMed

PubMed

TitleDatePubMed
The antituberculous activity of rifamycin SV.
1965 Dec
Chemotherapeutic activity of new derivatives of rifamycin.
1966
Potentiation of rifampicin, rifampicin analogs, and tetracycline against animal cells by amphotericin B and polymyxin B.
1973 Jun
Inhibition of HIV-1 RNA-dependent DNA polymerase and cellular DNA polymerases alpha, beta and gamma by phosphonoformic acid and other drugs.
1988 Feb
Multiple intra-articular treatment of rheumatoid arthritis: a randomized prospective study comparing rifamycin SV with pefloxacin.
1992 Feb
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
Patents

Patents

04005077
4
04174320
9
04431735
3
JP2004075665A
2
JP2008001720A
3
JPH07309759A
2
JPS53149999A
3
JPS54110391A
3
JPS54144400A
3
JPS5473798A
2
JPS55164684A
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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 Wed Jul 05 22:34:11 UTC 2023
Edited
by admin
on Wed Jul 05 22:34:11 UTC 2023
Record UNII
DU69T8ZZPA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIFAMYCIN
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
RIFAMYCIN SV [EP IMPURITY]
Common Name English
Rifamycin [WHO-DD]
Common Name English
M-14
Code English
RIFAMYCIN SV
MI  
Common Name English
RIFAMICINE SV
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 [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
RIFAXIMIN IMPURITY C [EP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ04AB03
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
WHO-ATC S01AA16
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
WHO-VATC QJ54AB03
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
WHO-ATC J04AB03
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
NCI_THESAURUS C280
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
WHO-ATC S02AA12
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
FDA ORPHAN DRUG 853821
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
WHO-VATC QS01AA16
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
WHO-VATC QS02AA12
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
Code System Code Type Description
CHEBI
26580
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
SMS_ID
100000080581
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
EVMPD
SUB10310MIG
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
WIKIPEDIA
Rifamycin
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
NCI_THESAURUS
C29406
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
DRUG CENTRAL
4817
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
DRUG BANK
DB11753
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
CHEBI
29673
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
DAILYMED
DU69T8ZZPA
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
MESH
C023808
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
ECHA (EC/EINECS)
230-273-3
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
CHEBI
84571
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID1032014
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
USAN
XX-60
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
RXCUI
35616
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M9613
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY Merck Index
PUBCHEM
6324616
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
CAS
6998-60-3
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
LACTMED
Rifamycin
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
FDA UNII
DU69T8ZZPA
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL437765
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
PRIMARY
INN
2293
Created by admin on Wed Jul 05 22:34:11 UTC 2023 , Edited by admin on Wed Jul 05 22:34:11 UTC 2023
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.
OATP-B
TRANSPORTER -> INHIBITOR
STAPHYLOCOCCUS AUREUS
TARGET ORGANISM->INHIBITOR
METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS
TARGET ORGANISM->INHIBITOR
Structure of RIFALAZIL
DERIVATIVE -> PARENT
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.
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.
SOLUTE CARRIER FAMILY 21 MEMBER 3
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
OATP-8
TRANSPORTER -> INHIBITOR
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.
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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