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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
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

2018
95
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7468
Infectious Diarrheal Disease
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Bacterial DNA-directed RNA polymerase
Approved
7883
AEMCOLO
PubMed

PubMed

TitleDatePubMed
Chemotherapeutic activity of new derivatives of rifamycin.
1966
Inhibition of HIV-1 RNA-dependent DNA polymerase and cellular DNA polymerases alpha, beta and gamma by phosphonoformic acid and other drugs.
1988 Feb
Characterization of the mouse bile salt export pump overexpressed in the baculovirus system.
2001 May
Antibacterial activities of dendritic amphiphiles against nontuberculous mycobacteria.
2012 Mar
Patents

Patents

4005077
4
4174320
9
4431735
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 Mon Oct 21 22:28:35 UTC 2019
Edited
by admin
on Mon Oct 21 22:28:35 UTC 2019
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 Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
WHO-ATC S01AA16
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
WHO-VATC QJ54AB03
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
WHO-ATC J04AB03
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
NCI_THESAURUS C280
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
WHO-ATC S02AA12
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
WHO-VATC QS01AA16
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
WHO-VATC QS02AA12
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
Code System Code Type Description
EVMPD
SUB10310MIG
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY
WIKIPEDIA
Rifamycin
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY
NCI_THESAURUS
C29406
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY
MESH
C023808
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY
ECHA (EC/EINECS)
230-273-3
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY
EPA CompTox
6998-60-3
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY
RXCUI
35616
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M9613
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY Merck Index
PUBCHEM
6324616
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY
CAS
6998-60-3
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY
ChEMBL
CHEMBL437765
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY
INN
2293
Created by admin on Mon Oct 21 22:28:36 UTC 2019 , Edited by admin on Mon Oct 21 22:28:36 UTC 2019
PRIMARY
Related Record Type Details
SOLUTE CARRIER FAMILY 21 MEMBER 3
TRANSPORTER -> INHIBITOR
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.
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.
OATP-B
TRANSPORTER -> INHIBITOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
IC50
MYCOBACTERIUM TUBERCULOSIS
TARGET ORGANISM->INHIBITOR
OATP-8
TRANSPORTER -> 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.
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.
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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