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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(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)C=C(O)C4=C3C2=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

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

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AEMCOLO
PubMed

PubMed

TitleDatePubMed
New derivatives of rifamycin SV.
1965
The antituberculous activity of rifamycin SV.
1965 Dec
Chemotherapeutic activity of new derivatives of rifamycin.
1966
A new series of semisynthetic rifamycins. N derivatives of 4-amino-4-deoxyrifamycin SV.
1971 Aug
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
Interactions of rifamycin SV and rifampicin with organic anion uptake systems of human liver.
2002 Jul
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

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.
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
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
RIFOCIN
Brand Name English
RIFOMYCIN SV
Common Name English
Classification Tree Code System Code
WHO-VATC QJ04AB03
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
WHO-ATC S01AA16
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
WHO-VATC QJ54AB03
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
WHO-ATC J04AB03
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
WHO-ATC S02AA12
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
WHO-VATC QS01AA16
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
WHO-VATC QS02AA12
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
Code System Code Type Description
EVMPD
SUB10310MIG
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY
NCI_THESAURUS
C29406
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY
MESH
C023808
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY
ECHA (EC/EINECS)
230-273-3
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY
EPA CompTox
6998-60-3
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY
RXCUI
35616
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY RxNorm
MERCK INDEX
M9613
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY Merck Index
PUBCHEM
6324616
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY SWITZERF
CAS
6998-60-3
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY
ChEMBL
CHEMBL437765
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY
INN
2293
Created by admin on Tue Mar 06 12:11:06 UTC 2018 , Edited by admin on Tue Mar 06 12:11:06 UTC 2018
PRIMARY