Rifamycin

Overview

The rifamycins are a group of antibiotics that are synthesized either naturally by the bacterium Amycolatopsis rifamycinica or artificially. They are a subclass of the larger family of ansamycins. Rifamycins are particularly effective against mycobacteria, and are therefore used to treat tuberculosis, leprosy, and mycobacterium avium complex (MAC) infections. WP

The rifamycin group includes the classic rifamycin drugs as well as the rifamycin derivatives rifampicin (or rifampin), rifabutin, rifapentine, rifalazil and rifaximin. Rifamycin, sold under the trade name Aemcolo, is approved in the United States for treatment of travelers' diarrhea in some circumstances.[1][2][3] WP

The name "rifamycin" (originally "rifomycin") was derived from the 1955 French film Rififi.[4] WP

Pharmacology

Mechanism of action

The antibacterial activity of rifamycins relies on the inhibition of bacterial DNA-dependent RNA synthesis. This is due to the high affinity of rifamycins for the prokaryotic RNA polymerase. The selectivity of the rifamycins depends on the fact that they have a very poor affinity for the analogous mammalian enzyme. Crystal structure data of the antibiotic bound to RNA polymerase indicates that rifamycin blocks synthesis by causing strong steric clashes with the growing oligonucleotide ("steric-occlusion" mechanism). If rifamycin binds the polymerase after the chain extension process has started, no inhibition is observed on the biosynthesis, consistent with a steric-occlusion mechanism. Single step high level resistance to the rifamycins occurs as the result of a single amino acid change in the bacterial DNA dependent RNA polymerase.[5][6][7] WP

Chemistry

Formula

C37H47NO12 PC

CAS number

6998-60-3 PC

Molar mass (g/mol)

697.8 PC

IUPAC name (computed by PubChem)

[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate PC

SMILES

C[C@H]1/C=C/C=C(\C(=O)NC2=CC(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C PC

InChIKey

HJYYPODYNSCCOU-ODRIEIDWSA-N PC

PubChem CID

6324616

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Lin SW, Lin CJ, Yang JC. Rifamycin SV MMX for the treatment of traveler's diarrhea. Expert Opinion on Pharmacotherapy. August 2017. doi:10.1080/14656566.2017.1353079 · PMID 28697313
2. Journal / agency FDA approves new drug to treat travelers' diarrhea. 16 November 2018
3. Journal / agency Drug Approval Package: Aemcolo (rifamycin). 21 December 2018
4. Journal / agency Sensi, P. History of the Development of Rifampin. Clinical Infectious Diseases. 1983. doi:10.1093/clinids/5.Supplement_3.S402 · PMID 6635432
5. Journal / agency Calvori C, Frontali L, Leoni L, Tecce G. Effect of rifamycin on protein synthesis. Nature. July 1965. doi:10.1038/207417a0 · PMID 4957347
6. Journal / agency Campbell EA, Korzheva N, Mustaev A, Murakami K, Nair S, Goldfarb A, Darst SA. Structural mechanism for rifampicin inhibition of bacterial rna polymerase. Cell. March 2001. doi:10.1016/S0092-8674(01)00286-0 · PMID 11290327
7. Journal / agency Feklistov A, Mekler V, Jiang Q, Westblade LF, Irschik H, Jansen R, Mustaev A, Darst SA, Ebright RH. Rifamycins do not function by allosteric modulation of binding of Mg2+ to the RNA polymerase active center. Proceedings of the National Academy of Sciences of the United States of America. September 2008. doi:10.1073/pnas.0802822105 · PMID 18787125 · PMC2567451

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.