Rifabutin

Rifabutin
Clinical data
Trade names	Mycobutin
AHFS/Drugs.com	Monograph
MedlinePlus	a693009
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth
ATC code	J04AB04 (WHO) ;
Legal status
Legal status	CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	85%
Protein binding	85%
Metabolism	Liver
Elimination half-life	28 to 62 hours (mean)
Excretion	Kidney and fecal
Identifiers
	IUPAC name (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	72559-06-9 ;
PubChem CID	6323490;
DrugBank	DB00615 ;
ChemSpider	10482168 ;
UNII	1W306TDA6S;
KEGG	D00424 ;
ChEBI	CHEBI:45367 ;
ChEMBL	ChEMBL444633 ;
CompTox Dashboard (EPA)	DTXSID0033960 ;
ECHA InfoCard	100.133.627
Chemical and physical data
Formula	C46H62N4O11
Molar mass	847.019 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:ATEBXHFBFRCZMA-VXTBVIBXSA-N ;
	(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]

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]

^ ^a ^b ^c ^d ^e ^f "Rifabutin". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
^ 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.

[AHFS2016-1] ^ ^a ^b ^c ^d ^e ^f "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.

[WHO21st-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.

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Clinical data

Trade names	Mycobutin^[1]
AHFS/Drugs.com	Monograph
MedlinePlus	a693009
Pregnancy category	AU: C
Routes of administration	By mouth
ATC code	J04AB04 (WHO)
Legal status
Legal status	CA: ℞-only^[2] UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	85%
Protein binding	85%
Metabolism	Liver
Elimination half-life	28 to 62 hours (mean)
Excretion	Kidney and fecal
Identifiers
IUPAC name (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	72559-06-9^Y
PubChem CID	6323490
DrugBank	DB00615^Y
ChemSpider	10482168^Y
UNII	1W306TDA6S
KEGG	D00424^Y
ChEBI	CHEBI:45367^Y
ChEMBL	ChEMBL444633^Y
CompTox Dashboard (EPA)	DTXSID0033960
ECHA InfoCard	100.133.627
Chemical and physical data
Formula	C₄₆H₆₂N₄O₁₁
Molar mass	847.019 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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 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^Y Key:ATEBXHFBFRCZMA-VXTBVIBXSA-N^Y
(verify)