RIFAMYCIN

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 Search

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

Molecular Formula	C37H47NO12
Molecular Weight	697.7686
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA-directed RNA polymerase 11	Inhibitor 6502	Infectious Diarrheal Disease

Conditions

Condition	Modality	Targets	Highest Phase	Product
Infectious Diarrheal Disease 10	Primary	Bacterial DNA-directed RNA polymerase	Approved 7817	AEMCOLO

PubMed

Title	Date	PubMed
New derivatives of rifamycin SV.	1965	4956802
The antituberculous activity of rifamycin SV.	1965 Dec	4958120
Chemotherapeutic activity of new derivatives of rifamycin.	1966	5985258
A new series of semisynthetic rifamycins. N derivatives of 4-amino-4-deoxyrifamycin SV.	1971 Aug	4398855
Potentiation of rifampicin, rifampicin analogs, and tetracycline against animal cells by amphotericin B and polymyxin B.	1973 Jun	4352361
Inhibition of HIV-1 RNA-dependent DNA polymerase and cellular DNA polymerases alpha, beta and gamma by phosphonoformic acid and other drugs.	1988 Feb	2452149
Multiple intra-articular treatment of rheumatoid arthritis: a randomized prospective study comparing rifamycin SV with pefloxacin.	1992 Feb	1568518
Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds.	1997 Sep-Oct	9403935
Characterization of the mouse bile salt export pump overexpressed in the baculovirus system.	2001 May	11343252
Interactions of rifamycin SV and rifampicin with organic anion uptake systems of human liver.	2002 Jul	12085361
Differential interaction of 3-hydroxy-3-methylglutaryl-coa reductase inhibitors with ABCB1, ABCC2, and OATP1B1.	2005 Apr	15616150
Antibacterial activities of dendritic amphiphiles against nontuberculous mycobacteria.	2012 Mar	22209468

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.

Substance Class	Chemical Created by `admin` on `Tue Mar 06 12:11:06 UTC 2018` Edited by `admin` on `Tue Mar 06 12:11:06 UTC 2018`
Record UNII	DU69T8ZZPA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RIFAMYCIN

Official Name

English

M-14

Code

English

RIFAMYCIN [WHO-DD]

Common Name

English

RIFAMYCIN SV

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