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Revision as of 12:57, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456849125 of page Rifabutin for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 05:54, 23 December 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,178 edits infobox 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
⚫ | verifiedrevid = 464382389
| Verifiedfields = changed
⚫ | IUPAC_name = (9''S'',12''E'',14''S'',15''R'',16''S'',17''R'',18''R'',19''R'',20''S'',<br />21''S'',22''E'',24''Z'')-6,16,18,20-tetrahydroxy-1'-<br />isobutyl-14-methoxy-7,9,15,17,19,21,25-<br />hepta-methyl-spirotrienimino)-2''H''-furo--naphth<br />imidazol-2,4'-piperidin]-5,10,26-(3''H'',9''H'')-<br />trione-16-acetate
⚫ | verifiedrevid = 408990442
| image = Rifabutin structure.svg
⚫ | IUPAC_name = (9''S'',12''E'',14''S'',15''R'',16''S'',17''R'',18''R'',19''R'',20''S'',<br>21''S'',22''E'',24''Z'')-6,16,18,20-tetrahydroxy-1'-<br>isobutyl-14-methoxy-7,9,15,17,19,21,25-<br>hepta-methyl-spirotrienimino)-2''H''-furo--naphth<br>imidazol-2,4'-piperidin]-5,10,26-(3''H'',9''H'')-<br>trione-16-acetate
| image = Rifabutin.png | width = 300


<!--Clinical data--> <!--Clinical data-->
| tradename = Mycobutin | tradename = Mycobutin<ref name=AHFS2016/>
| Drugs.com = {{drugs.com|monograph|rifabutin}} | Drugs.com = {{drugs.com|monograph|rifabutin}}
| MedlinePlus = a693009 | MedlinePlus = a693009
| pregnancy_AU = C
| pregnancy_category = C <small>(Australia)</small>, B <small>(United States)</small>
⚫ | routes_of_administration = ]
| legal_status = ] <small>(UK)</small>, ℞-only <small>(U.S.)<small>
⚫ | ATC_prefix = J04
⚫ | routes_of_administration = Oral
⚫ | ATC_suffix = AB04
| ATC_supplemental = {{ATC|J04|AM11}}

| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=Health Canada | date=February 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=24 March 2024}}</ref>
| legal_UK = POM
| legal_US = Rx-only


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 85% | bioavailability = 85%
| protein_bound = 85% | protein_bound = 85%
| metabolism = ] | metabolism = ]
| elimination_half-life = 28 to 62 hours (mean) | elimination_half-life = 28 to 62 hours (mean)
| excretion = ] and fecal | excretion = ] and fecal


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 72559-06-9 | CAS_number = 72559-06-9
⚫ | ATC_prefix = J04
⚫ | ATC_suffix = AB04
| PubChem = 6323490 | PubChem = 6323490
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10482168 | ChemSpiderID = 10482168
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1W306TDA6S | UNII = 1W306TDA6S
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00424 | KEGG = D00424
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 45367 | ChEBI = 45367
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
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<!--Chemical data--> <!--Chemical data-->
| C=46 | H=62 | N=4 | O=11 | C=46 | H=62 | N=4 | O=11
| SMILES = C1/C=C\C=C(/C(=O)NC2=C3C(=NC4(N3)CCN(CC4)CC(C)C)C5=C6C(=C(C(=C5C2=O)O)C)O(C6=O)(O/C=C\((((((1O)C)O)C)OC(=O)C)C)OC)C)\C
| molecular_weight = 847.005 ]/]
| smiles = CC(C)CN1CCC2(CC1)/N=C\3/c4c6C(=O)5(C)O/C=C/(OC)(C)(OC(C)=O)(C)(O)(C)(O)(C)\C=C\C=C(\C)C(=O)N\C(=C/3/N2)C(=O)c4c(O)c(C)c6O5
| InChI = 1/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
| InChIKey = ATEBXHFBFRCZMA-VXTBVIBXBQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
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| StdInChIKey = ATEBXHFBFRCZMA-VXTBVIBXSA-N | StdInChIKey = ATEBXHFBFRCZMA-VXTBVIBXSA-N
}} }}
<!-- Definition and medical uses -->
'''Rifabutin''' ('''Rfb''') is an ] used to treat ] and prevent and treat ].<ref name=AHFS2016/> It is typically only used in those who cannot tolerate ] such as people with ] on ].<ref name=AHFS2016/> For active tuberculosis it is used with other ]s.<ref name=AHFS2016/> For latent tuberculosis it may be used by itself when the exposure was with ].<ref name=AHFS2016/>

<!-- Society and culture -->
Rifabutin was approved for medical use in the United States in 1992.<ref name=AHFS2016>{{cite web|title=Rifabutin|url=https://www.drugs.com/monograph/rifabutin.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220231139/https://www.drugs.com/monograph/rifabutin.html|archive-date=20 December 2016}}</ref> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref>

==Medical uses==
Rifabutin is now recommended as first-line treatment for ] (TB),<ref>{{cite book|publisher=World Health Organization|title=Guidelines for the programmatic management of drug-resistant tuberculosis: emergency update 2008 (WHO/HTM/TB/2008.402)|year=2008|location=Geneva, Switzerland|isbn=978-92-4-154758-1|url=https://www.who.int/tb/publications/2008/programmatic_guidelines_for_mdrtb/en/index.html|page=ix|url-status=dead|archive-url=https://web.archive.org/web/20081018020405/http://www.who.int/tb/publications/2008/programmatic_guidelines_for_mdrtb/en/index.html|archive-date=2008-10-18}}</ref> but ] 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 ], ], rash, ], and ].<ref name=AHFS2016/> Other side effects include muscles pains and ].,<ref name=AHFS2016/> 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 ] it has not been well studied in this population.<ref name=AHFS2016/> Rifabutin is in the ] family of medications.<ref name=AHFS2016/> It works by blocking ] production in bacteria.<ref>{{cite journal | vauthors = Rockwood N, Cerrone M, Barber M, Hill AM, Pozniak AL | title = Global access of rifabutin for the treatment of tuberculosis - why should we prioritize this? | journal = Journal of the International AIDS Society | volume = 22 | issue = 7 | pages = e25333 | date = July 2019 | pmid = 31318176 | pmc = 6637439 | doi = 10.1002/jia2.25333 | quote = Rifabutin is a rifamycin, which like rifampicin, works via inhibition of DNA‐dependent RNA synthesis in prokaryotes. }}</ref>

==History==
Scientists at the Italian drug company Achifar discovered rifabutin in 1975. (Eventually Archifar became part of ] Carlo Erba, a unit of the conglomerate Montedison which was subsequently bought by ]) This company's Adria Laboratories subsidiary filed for ] (FDA) approval of rifabutin under the brand name Mycobutin in the early 1990s and the drug gained FDA approval in December 1992.{{cn|date=August 2022}}

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 '']'', '']'', and '']''.{{cn|date=December 2022}}

== References ==
{{Reflist}}

{{Antimycobacterials}}
{{Nucleic acid inhibitors}}
{{Portal bar|Medicine}}

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