rifampicin

Also known as BA-41166E, BA-411661E, L-5103, 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin sv, RFP, L-5103-LEPETIT, rifampin, 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin SV

Rifampicin, also known as rifampin, is an ansamycin antibiotic used to treat several types of bacterial infections, including tuberculosis (TB), Mycobacterium avium complex, leprosy, and Legionnaires' disease. It is almost always used together with other antibiotics with two notable exceptions: when given as a "preferred treatment that is strongly recommended" for latent TB infection; and when used as post-exposure prophylaxis to prevent Haemophilus influenzae type b and meningococcal disease in people who have been exposed to those bacteria. Before treating a person for a long period of time,

Chemical data

Formula: C43H58N4O12
Molecular weight: 822.9 g/mol
IUPAC name: (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-13-acetyloxy-15,17,27,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-(4-methylpiperazin-4-ium-1-yl)iminomethyl]-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-2-olate
SMILES: C[C@H]1/C=C/C=C(\C(=O)NC2=C(C(=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=N/N5CC[NH+](CC5)C)/C
InChIKey: JQXXHWHPUNPDRT-WLSIYKJHSA-N
XLogP: 5.6
Polar surface area: 224 Å²
H-bond donors: 6
H-bond acceptors: 14
Formal charge: 0

via PubChem

Research

38,184 papers

Pharmacokinetic interactions with rifampicin : clinical relevance.Clinical pharmacokinetics · 2003
[Rifampicin-glucocorticoid combinations].La Revue de medecine interne · 1998
Clinical pharmacokinetics of rifampicin.Clinical pharmacokinetics · 1978
Rifampicin bioavailability: a review of its pharmacology and the chemotherapeutic necessity for ensuring optimal absorption.The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease · 1999
Impact of diabetes mellitus on rifampicin's plasma concentration and bioavailability in patients with tuberculosis: A systematic review and meta-analysis study.Therapie · 2023

via PubMed

Wikidata facts

Mass: 822.4051232959998

Show 7 more facts

chemical formula: C₄₃H₅₈N₄O₁₂
Commons category: Rifampicin
World Health Organisation international non-proprietary name: rifampicin
MCN code: 3004.20.32
isomeric SMILES: CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)\C(=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(=O)C)[C@@H]1C)\C)c(\C=N\N5CCN(C)CC5)c(O)c4c3C2=O
stylized name: rifAMPin
canonical SMILES: COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(c(C=NN5CCN(C)CC5)c(O)c4c3C2=O)NC(=O)C(C)=CC=CC(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C1C

Sources (4)

via Wikidata · CC0

~21 min read

Article

22 sections

Contents

Medical uses
Mycobacteria
Other bacteria and protozoans
Viruses
Pathogen susceptibility
Primary biliary cholangitis
Hidradenitis suppurativa
Adverse effects
Chemical structure
Interactions
Pharmacology
Mechanism of action
Mechanism of resistance
Resistance in tuberculosis
Pharmacokinetics
Use in biotechnology
History
Society and culture
Cancer-causing impurities
Names
References
External links

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