Rifabutin

Last updated
Rifabutin
Rifabutin structure.svg
Clinical data
Trade names Mycobutin [1]
AHFS/Drugs.com Monograph
MedlinePlus a693009
Pregnancy
category
  • AU:C
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 85%
Protein binding 85%
Metabolism Liver
Elimination half-life 28 to 62 hours (mean)
Excretion Kidney and fecal
Identifiers
  • (9S,12E,14S,15R,16S,17R,18R,19R,20S,
    21S,22E,24Z)-6,16,18,20-tetrahydroxy-1'-
    isobutyl-14-methoxy-7,9,15,17,19,21,25-
    hepta-methyl-spiro[9,4-(epoxypentadeca
    [1,11,13]trienimino)-2H-furo-[2',3':7,8]-naphth
    [1,2-d]imidazol-2,4'-piperidin]-5,10,26-(3H,9H)-
    trione-16-acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.133.627 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C46H62N4O11
Molar mass 847.019 g·mol−1
3D model (JSmol)
  • C[C@H]1/C=C\C=C(/C(=O)NC2=C3C(=NC4(N3)CCN(CC4)CC(C)C)C5=C6C(=C(C(=C5C2=O)O)C)O[C@@](C6=O)(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
  • InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49,52-54H,16-19,21H2,1-11H3,(H,47,57)/b13-12+,20-15+,24-14-/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1 Yes check.svgY
  • Key:ATEBXHFBFRCZMA-VXTBVIBXSA-N Yes check.svgY
   (verify)

Rifabutin (Rfb) is an antibiotic used to treat tuberculosis and prevent and treat Mycobacterium avium complex. [1] It is typically only used in those who cannot tolerate rifampin such as people with HIV/AIDS on antiretrovirals. [1] For active tuberculosis it is used with other antimycobacterial medications. [1] For latent tuberculosis it may be used by itself when the exposure was with drug-resistant TB. [1]

Contents

Rifabutin was approved for medical use in the United States in 1992. [1] It is on the World Health Organization's List of Essential Medicines. [3]

Medical uses

Rifabutin is now recommended as first-line treatment for tuberculosis (TB), [4] but rifampicin was used more widely because of its cheaper cost. However, due to the expiration of patents, prices are now similar.

Adverse effects

Common side effects include abdominal pain, nausea, rash, headache, and low blood neutrophil levels. [1] Other side effects include muscles pains and uveitis., [1] especially when hitting Bartonella and Babesia colonies in the capillaries of the ciliary body in the eye anterior chamber. While no harms have been found during pregnancy it has not been well studied in this population. [1] Rifabutin is in the rifamycin family of medications. [1] It works by blocking RNA production in bacteria. [5]

History

Scientists at the Italian drug company Achifar discovered rifabutin in 1975. (Eventually Archifar became part of Farmitalia Carlo Erba, a unit of the conglomerate Montedison which was subsequently bought by Pharmacia) This company's Adria Laboratories subsidiary filed for Food and Drug Administration (FDA) approval of rifabutin under the brand name Mycobutin in the early 1990s and the drug gained FDA approval in December 1992.[ citation needed ]

Rifabutin is primarily bactericidal antibiotic drug used to treat tuberculosis. Its effect on bacteria is based on the DNA-dependent RNA polymerase blocking drug rifamycin S, a semi-synthetic derivative. It is effective, for example, in highly resistant mycobacteria, Gram-positive bacteria (and some are effective against Gram-negative bacteria), but also against Mycobacterium tuberculosis , M. leprae , and M. avium intracellulare .[ citation needed ]

Related Research Articles

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Tuberculosis (TB), also known colloquially as the "white death", or historically as consumption, is a contagious disease usually caused by Mycobacterium tuberculosis (MTB) bacteria. Tuberculosis generally affects the lungs, but it can also affect other parts of the body. Most infections show no symptoms, in which case it is known as latent tuberculosis. Around 10% of latent infections progress to active disease that, if left untreated, kill about half of those affected. Typical symptoms of active TB are chronic cough with blood-containing mucus, fever, night sweats, and weight loss. Infection of other organs can cause a wide range of symptoms.

<span class="mw-page-title-main">Clarithromycin</span> Antibiotic medication

Clarithromycin, sold under the brand name Biaxin among others, is an antibiotic used to treat various bacterial infections. This includes strep throat, pneumonia, skin infections, H. pylori infection, and Lyme disease, among others. Clarithromycin can be taken by mouth as a tablet or liquid or can be infused intravenously.

<span class="mw-page-title-main">Streptomycin</span> Aminoglycoside antibiotic

Streptomycin is an antibiotic medication used to treat a number of bacterial infections, including tuberculosis, Mycobacterium avium complex, endocarditis, brucellosis, Burkholderia infection, plague, tularemia, and rat bite fever. For active tuberculosis it is often given together with isoniazid, rifampicin, and pyrazinamide. It is administered by injection into a vein or muscle.

<span class="mw-page-title-main">Isoniazid</span> Antibiotic for treatment of tuberculosis

Isoniazid, also known as isonicotinic acid hydrazide (INH), is an antibiotic used for the treatment of tuberculosis. For active tuberculosis, it is often used together with rifampicin, pyrazinamide, and either streptomycin or ethambutol. For latent tuberculosis, it is often used alone. It may also be used for atypical types of mycobacteria, such as M. avium, M. kansasii, and M. xenopi. It is usually taken by mouth, but may be used by injection into muscle.

<span class="mw-page-title-main">Rifamycin</span> Group of antibiotics

The rifamycins are a group of antibiotics that are synthesized either naturally by the bacterium Amycolatopsis rifamycinica or artificially. They are a subclass of the larger family of ansamycins. Rifamycins are particularly effective against mycobacteria, and are therefore used to treat tuberculosis, leprosy, and mycobacterium avium complex (MAC) infections.

<span class="mw-page-title-main">Rifampicin</span> Antibiotic medication

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, measurements of liver enzymes and blood counts are recommended. Rifampicin may be given either by mouth or intravenously.

<span class="mw-page-title-main">Management of tuberculosis</span> Disease treatment

Management of tuberculosis refers to techniques and procedures utilized for treating tuberculosis (TB), or simply a treatment plan for TB.

<span class="mw-page-title-main">Ethambutol</span> Chemical compound

Ethambutol is a medication primarily used to treat tuberculosis. It is usually given in combination with other tuberculosis medications, such as isoniazid, rifampicin and pyrazinamide. It may also be used to treat Mycobacterium avium complex, and Mycobacterium kansasii. It is taken by mouth.

<span class="mw-page-title-main">4-Aminosalicylic acid</span> Anti-tuberculosis and anti-inflammatory drug

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<span class="mw-page-title-main">Amikacin</span> Antibiotic medication

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<i>Mycobacterium avium-intracellulare</i> infection Medical condition

Mycobacterium avium-intracellulare infection (MAI) is an atypical mycobacterial infection, i.e. one with nontuberculous mycobacteria or NTM, caused by Mycobacterium avium complex (MAC), which is made of two Mycobacterium species, M. avium and M. intracellulare. This infection causes respiratory illness in birds, pigs, and humans, especially in immunocompromised people. In the later stages of AIDS, it can be very severe. It usually first presents as a persistent cough. It is typically treated with a series of three antibiotics for a period of at least six months.

<span class="mw-page-title-main">Rifapentine</span> Chemical compound

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<span class="mw-page-title-main">Ethionamide</span> Chemical compound

Ethionamide is an antibiotic used to treat tuberculosis. Specifically it is used, along with other antituberculosis medications, to treat active multidrug-resistant tuberculosis. It is no longer recommended for leprosy. It is taken by mouth.

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Extensively drug-resistant tuberculosis (XDR-TB) is a form of tuberculosis caused by bacteria that are resistant to some of the most effective anti-TB drugs. XDR-TB strains have arisen after the mismanagement of individuals with multidrug-resistant TB (MDR-TB).

<span class="mw-page-title-main">Multidrug-resistant tuberculosis</span> Medical condition

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<span class="mw-page-title-main">Pretomanid</span> Chemical compound

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References

  1. 1 2 3 4 5 6 7 8 9 10 "Rifabutin". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  2. "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  3. World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  4. Guidelines for the programmatic management of drug-resistant tuberculosis: emergency update 2008 (WHO/HTM/TB/2008.402). Geneva, Switzerland: World Health Organization. 2008. p. ix. ISBN   978-92-4-154758-1. Archived from the original on 2008-10-18.
  5. Rockwood N, Cerrone M, Barber M, Hill AM, Pozniak AL (July 2019). "Global access of rifabutin for the treatment of tuberculosis - why should we prioritize this?". Journal of the International AIDS Society. 22 (7): e25333. doi:10.1002/jia2.25333. PMC   6637439 . PMID   31318176. Rifabutin is a rifamycin, which like rifampicin, works via inhibition of DNA‐dependent RNA synthesis in prokaryotes.