Stereochemistry | ABSOLUTE |
Molecular Formula | C37H46NO12.Na |
Molecular Weight | 719.7504 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].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=YVOFSHPIJOYKSH-NLYBMVFSSA-M
InChI=1S/C37H47NO12.Na/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);/q;+1/p-1/b11-10+,14-13+,17-12-;/t16-,18+,19+,20+,25-,29-,30+,33+,37-;/m0./s1
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
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Drug as perpetrator
Drug as victim
Sourcing
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.