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
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
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 |
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
PubMed
Title | Date | PubMed |
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Chemotherapeutic activity of new derivatives of rifamycin. | 1966 |
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Inhibition of HIV-1 RNA-dependent DNA polymerase and cellular DNA polymerases alpha, beta and gamma by phosphonoformic acid and other drugs. | 1988 Feb |
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Characterization of the mouse bile salt export pump overexpressed in the baculovirus system. | 2001 May |
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Antibacterial activities of dendritic amphiphiles against nontuberculous mycobacteria. | 2012 Mar |
Sample Use Guides
The recommended dosage of AEMCOLO (rifamycin) delayed-release tablets is 388 mg (two tablets) orally twice daily for three days
Route of Administration:
Oral
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
Edited
Mon Oct 21 22:28:35 UTC 2019
by
admin
on
Mon Oct 21 22:28:35 UTC 2019
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Record UNII |
DU69T8ZZPA
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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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
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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
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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
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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
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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
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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
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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
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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
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Code System | Code | Type | Description | ||
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SUB10310MIG
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Rifamycin
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C29406
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C023808
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230-273-3
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6998-60-3
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35616
Created by
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PRIMARY | RxNorm | ||
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M9613
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PRIMARY | Merck Index | ||
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6324616
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6998-60-3
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PRIMARY | |||
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CHEMBL437765
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PRIMARY | |||
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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
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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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.
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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.
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TARGET ORGANISM->INHIBITOR | |||
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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.
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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.
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TARGET ORGANISM->INHIBITOR |
Other
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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.
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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.
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
IC50
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TARGET ORGANISM->INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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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.
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TRANSPORTER -> SUBSTRATE | |||
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EXCRETED UNCHANGED |
After IV administration of rifamycin SV, > 90% of the dose is excreted as unchanged drug in feces via biliary secretion8
FECAL
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR |
IC50
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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.
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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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.
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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.
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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.
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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.
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |