Rifampicin

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Image:Rifampicin.png
Rifampicin
Systematic (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
Identifiers
CAS number	13292-46-1
ATC code	J04 AB02
PubChem	5360416
DrugBank	APRD00207
Chemical data
Formula	C₄₃H₅₈N₄O₁₂
Mol. weight	822.94 g/mol
Pharmacokinetic data
Bioavailability	90 to 95%
Metabolism	Hepatic and intestinal wall
Half life	6 to 7 hours
Excretion	15 to 30% renal 60% faecal
Therapeutic considerations
Pregnancy cat.	C(AU)
Legal status	S4(AU) POM(UK)
Routes	Oral, IV

Rifampicin (INN) (IPA: [rɪˈfampəsɪn]) or rifampin (USAN) is a bactericidal<ref name = Katzung>Trevor A, Katzung B, Masters S (2004). Katzung and Trevor's Pharmacology. McGraw-Hill. ISBN 0-07-142290-0.</ref> antibiotic drug of the rifamycin group. It is a semisynthetic compound derived from Streptomyces mediterranei. Rifampicin may be abbreviated RIF, RMP, RD or R.

1 Indications
2 Mechanism of action
3 Adverse effects
4 Preparations
5 References

[edit] 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.

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

[edit] 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.

[edit] 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, tears and semen, to become orange-red in color. This may permanently stain soft contact lenses. It also may be excreted in breast milk, therefore breast feeding should be avoided.

Rifampicin is an 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 the oral contraceptive pill.

[edit] 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.

[edit] References

Antimycobacterials (J04) edit
Tuberculosis:	Aminosalicylic acid, Calcium aminosalicylate, Capreomycin, Cycloserine, Ethambutol, Ethionamide, Isoniazid, Morinamide, Protionamide, Pyrazinamide, Rifabutin, Rifampicin, Rifamycin, Rifapentin, Sodium aminosalicylate, Terizidone, Tiocarlide
Leprosy:	Aldesulfone sodium, Clofazimine, Dapsone