rifabutin   Click here for help

GtoPdb Ligand ID: 12015

Synonyms: LM 427 | Mycobutin® | Rifabutine
Approved drug
rifabutin is an approved drug (FDA (1992), UK (2003))
Compound class: Synthetic organic
Comment: Rifabutin is a derivative of rifamycin S and belongs to the ansamycin group of antibiotics [1]. It is on the World Health Organization's Model List of Essential Medicines (link provided in the Classification table, under the Summary tab below) for use as an oral antituberculosis medication.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 5
Rotatable bonds 5
Topological polar surface area 209.04
Molecular weight 846.44
XLogP 5.13
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(c(c3C)O)c(O)c(=NC(=O)/C(=C\C=C\[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)C)/C)c1=NC3(Nc21)CCN(CC3)CC(C)C
Isomeric SMILES C[C@H]1/C=C/C=C(\C(=O)N=c2c(c3c(c4c2=NC2(N4)CCN(CC2)CC(C)C)c2c(c(c3O)C)O[C@@](C2=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)O)/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/h12-15,20,22-23,25-27,30,37-38,41,48,52-55H,16-19,21H2,1-11H3/b13-12+,20-15+,24-14-,47-36?/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1
InChI Key ZWBTYMGEBZUQTK-PVLSIAFMSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1992), UK (2003))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23-dioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(32),2,4,9,19,21,24,26,30-nonaene-28,4'-piperidine]-13-yl] acetate
International Nonproprietary Names Click here for help
INN number INN
5668 rifabutin
Synonyms Click here for help
LM 427 | Mycobutin® | Rifabutine
Database Links Click here for help
CAS Registry No. 72559-06-9 (source: Scifinder)
ChEMBL Ligand CHEMBL444633
DrugBank Ligand DB00615
DrugCentral Ligand 2376
GtoPdb PubChem SID 464244156
PubChem CID 135398743
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UniChem Compound Search for chemical match using the InChIKey ZWBTYMGEBZUQTK-PVLSIAFMSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZWBTYMGEBZUQTK-PVLSIAFMSA-N
Wikipedia Rifabutin