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| {{drugbox |
| | #REDIRECT[[Rifampin]] |
| |image=
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| |width=280
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| |IUPAC_name = 5,6,9,17,19,21-Hexahydroxy-23-methoxy-<br>2,4,12,16,18,20,22-heptamethyl-<br>8-[''N''-(4-methyl-1-piperazinyl)formimidoyl]-<br>2,7-(epoxypentadeca[1,11,13]trienimino)-<br>naphtho[2,1-''b'']furan-1,11(2''H'')-dione 21-acetate
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| |CAS_number = 13292-46-1
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| | ATC_prefix=J04
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| | ATC_suffix=AB02
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| | PubChem=5360416
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| | DrugBank=APRD00207
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| | C = 43 | H = 58 | N = 4 | O = 12
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| |molecular_weight = 822.94 g/mol
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| |bioavailability = 90 to 95%
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| |metabolism = [[Liver|Hepatic]] and intestinal wall
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| |elimination_half-life = 6 to 7 hours
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| |excretion = 15 to 30% [[Kidney|renal]]<br />60% [[faeces|faecal]]
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| |pregnancy_AU = C
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| |legal_AU = S4
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| |legal_UK = POM
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| |routes_of_administration = Oral, [[Intravenous therapy|IV]]
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| }}
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| {{SI}}
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| ==Overview==
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| '''Rifampicin''' ([[International Nonproprietary Name|INN]]) ([[International Phonetic Alphabet|IPA]]: {{IPA|[rɪˈfampəsɪn]}}) or '''rifampin''' ([[United States Adopted Name|USAN]]) is a [[bactericidal]]<ref name = Katzung>{{cite book | author = Trevor A, Katzung B, Masters S | title = Katzung and Trevor's Pharmacology | publisher = McGraw-Hill | location = | year = 2004 | id = ISBN 0-07-142290-0}}</ref> [[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'''.
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| ==Indications==
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| 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.
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| 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 [[antibiotic resistance|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]].
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| ''[[Enterobacteriaceae]]'', ''[[Acinetobacter]]'' and ''[[Pseudomonas]]'' species are intrinsically resistant to rifampicin.
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| ==Mechanism of action==
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| 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]].
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| ==Adverse effects==
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| [[Adverse drug reaction|Adverse effect]]s are chiefly related to the drug's [[hepatotoxicity]], and patients receiving rifampicin often undergo [[liver function tests]] including [[aspartate aminotransferase]] (AST).
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| 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.
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| 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.
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| 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 interaction]]s such as reduced efficacy of [[hormonal contraception]].
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| ==Preparations==
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| In the U.S., rifampin is marketed as
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| * Rifadin ([[Aventis]]),
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| * Rifater (in combination with [[isoniazid]] and [[pyrazinamide]]) (Aventis),
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| * Rimactane ([[Novartis]]).
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| In the UK, rifampicin is marketed as
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| * Rifadin (Aventis),
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| * Rimactane ([[Sandoz]]),
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| * Rifater (in combination with [[isoniazid]] and [[pyrazinamide]]) (Aventis),
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| * Rifinah (in combination with isoniazid) (Aventis)
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| * Rimactazid (in combination with isoniazid) (Sandoz)
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| In Romania it is marketed as Sinerdol by Sicomed.
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| In Bulgaria it is marketed as Tubocin by Actavis/Balkanpharma.
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| ==References==
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| <div class="references-small">
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| <references/>
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| </div>
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| {{Antimycobacterials}}
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| [[Category:Rifamycin antibiotics]]
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| [[Category:Leprosy]]
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| [[Category:Tuberculosis]]
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| [[es:Rifampicina]]
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| [[fr:Rifampicine]]
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| [[pl:Rifampicyna]]
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| [[tr:Rifampisin]] | |
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| {{WH}}
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| {{WS}}
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