Rifampicin

Rifampicin

Clinical data
Pregnancy category	AU: C
Routes of administration	Oral, IV
ATC code	J04AB02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	90 to 95%
Metabolism	Hepatic and intestinal wall
Elimination half-life	6 to 7 hours
Excretion	15 to 30% renal 60% faecal
Identifiers
IUPAC name 5,6,9,17,19,21-Hexahydroxy-23-methoxy- 2,4,12,16,18,20,22-heptamethyl- 8-[N-(4-methyl-1-piperazinyl)formimidoyl]- 2,7-(epoxypentadeca[1,11,13]trienimino)- naphtho[2,1-b]furan-1,11(2H)-dione 21-acetate
CAS Number	13292-46-1
PubChem CID	5360416
DrugBank	APRD00207
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C43H58N4O12
Molar mass	822.94 g/mol

WikiDoc Resources for Rifampicin
Articles
Most recent articles on Rifampicin Most cited articles on Rifampicin Review articles on Rifampicin Articles on Rifampicin in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Rifampicin Images of Rifampicin Photos of Rifampicin Podcasts & MP3s on Rifampicin Videos on Rifampicin
Evidence Based Medicine
Cochrane Collaboration on Rifampicin Bandolier on Rifampicin TRIP on Rifampicin
Clinical Trials
Ongoing Trials on Rifampicin at Clinical Trials.gov Trial results on Rifampicin Clinical Trials on Rifampicin at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Rifampicin NICE Guidance on Rifampicin NHS PRODIGY Guidance FDA on Rifampicin CDC on Rifampicin
Books
Books on Rifampicin
News
Rifampicin in the news Be alerted to news on Rifampicin News trends on Rifampicin
Commentary
Blogs on Rifampicin
Definitions
Definitions of Rifampicin
Patient Resources / Community
Patient resources on Rifampicin Discussion groups on Rifampicin Patient Handouts on Rifampicin Directions to Hospitals Treating Rifampicin Risk calculators and risk factors for Rifampicin
Healthcare Provider Resources
Symptoms of Rifampicin Causes & Risk Factors for Rifampicin Diagnostic studies for Rifampicin Treatment of Rifampicin
Continuing Medical Education (CME)
CME Programs on Rifampicin
International
Rifampicin en Espanol Rifampicin en Francais
Business
Rifampicin in the Marketplace Patents on Rifampicin
Experimental / Informatics
List of terms related to Rifampicin

Please Take Over This Page and Apply to be Editor-In-Chief for this topic: There can be one or more than one Editor-In-Chief. You may also apply to be an Associate Editor-In-Chief of one of the subtopics below. Please mail us [1] to indicate your interest in serving either as an Editor-In-Chief of the entire topic or as an Associate Editor-In-Chief for a subtopic. Please be sure to attach your CV and or biographical sketch.

Overview

Rifampicin (INN) (IPA: Template:IPA) or rifampin (USAN) is a bactericidal antibiotic drug of the rifamycin group. It is a semisynthetic compound derived from Amycolatopsis rifamycinica (formerly known as Amycolatopsis mediterranei and Streptomyces mediterranei). Rifampicin may be abbreviated RIF, RMP, RD, RA or R.

Indications

Rifampicin is typically used to treat Mycobacterium infections, including tuberculosis and leprosy; and also has a role in the treatment of methicillin-resistant Staphylococcus aureus (MRSA) in combination with fusidic acid. It is used in prophylactic therapy against Neisseria meningitidis (meningococcal) infection.

It is also used to treat infection by Listeria species, Neisseria gonorrhoeae, Haemophilus influenzae and Legionella pneumophila. For these non-standard indications, sensitivity testing should be done (if possible) before starting rifampicin therapy. Rifampicin resistance develops quickly during treatment and rifampicin monotherapy should not be used to treat these infections — it should be used in combination with other antibiotics. With multidrug therapy (MDT) used as the standard treatment of leprosy, rifampicin is always used in combination with dapsone and clofazimine.

Enterobacteriaceae, Acinetobacter and Pseudomonas species are intrinsically resistant to rifampicin.

Mechanism of action

Rifampicin inhibits DNA-dependent RNA polymerase in bacterial cells by binding its beta-subunit, thus preventing transcription of messenger RNA (mRNA) and subsequent translation to proteins. Its lipophilic nature makes it a good candidate to treat the meningitis form of tuberculosis, which requires distribution to the central nervous system and penetration through the blood-brain barrier.

Adverse effects

Adverse effects are chiefly related to the drug's hepatotoxicity, and patients receiving rifampicin often undergo liver function tests including aspartate aminotransferase (AST).

The most common unwanted effects are fever, gastrointestinal disturbances, rashes and immunological reactions. Liver damage, associated with jaundice, has also been reported and in some rare cases has led to death.

Taking rifampicin can cause certain bodily fluids, such as urine and tears, to become orange-red in color, a benign but sometimes frightening side-effect. This may permanently stain soft contact lenses. It also may be excreted in breast milk, therefore breast feeding should be avoided.

Rifampicin is a potent inducer of hepatic cytochrome P450 enzymes (such as CYP2D6 and CYP3A4) and will increase the metabolism of many drugs that are cleared by the liver through this enzyme system. This results in numerous drug interactions such as reduced efficacy of hormonal contraception.

Preparations

In the U.S., rifampin is marketed as

• Rifadin (Aventis),
• Rifater (in combination with isoniazid and pyrazinamide) (Aventis),
• Rimactane (Novartis).

In the UK, rifampicin is marketed as

• Rifadin (Aventis),
• Rimactane (Sandoz),
• Rifater (in combination with isoniazid and pyrazinamide) (Aventis),
• Rifinah (in combination with isoniazid) (Aventis)
• Rimactazid (in combination with isoniazid) (Sandoz)

In Romania it is marketed as Sinerdol by Sicomed.

In Bulgaria it is marketed as Tubocin by Actavis/Balkanpharma.