File:Rifampicin_structure.svg · Wikimedia Commons · See Wikimedia Commons
rifampicin
Sign in to saveAlso 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,
OverviewAI-generated
Rifampicin is a chemical compound with the formula C₄₃H₅₈N₄O₁₂. Its stylized name is rifAMPin. The substance has a mass of 822.4051232959998 and a weight of 822.9. It carries a charge of 0 and features an xlogp value of 5.6. The compound possesses 6 hydrogen bond donors and 14 hydrogen bond acceptors, with a topological polar surface area of 224.
The molecule is associated with the MCN codes 3003.20.32 and 3004.20.32. Its structure is defined by the canonical SMILES string 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.
In literature, rifampicin is the subject of 38184 PubMed entries. The compound is referenced by 701 other encyclopedia articles.
Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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 Ų
- 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
- Has use
- medication
Show 12 more facts
- chemical formula
- C₄₃H₅₈N₄O₁₂
- Commons category
- Rifampicin
- World Health Organisation international non-proprietary name
- rifampicin
- route of administration
- intravenous infusion and defusion
- subject has role
- essential medicine
- MCN code
- 3004.20.32
- medical condition treated
- staphylococcal infection
- 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
- significant drug interaction
- bazedoxifene
- different from
- rifamycin
via Wikidata · CC0
~21 min read
Encyclopedic overview
22 sectionsContents
- 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
{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477172778 | IUPAC_name = (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-26-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate | image = Rifampicin structure.svg | image_class = skin-invert-image | width = 275 | alt = | image2 = Rifampicin 3D 1i6v.png | image_class2 = bg-transparent | width2 = 225 | alt2 = | USAN = Rifampin
| pronounce = | tradename = Rifadin, others | Drugs.com = | MedlinePlus = a682403 | DailyMedID = Rifampin | pregnancy_AU = C | routes_of_administration = By mouth, Intravenous therapy
Excerpted from Wikipedia’s “rifampicin” article, available under the CC BY-SA 4.0 licence.