rifabutin   Click here for help

GtoPdb Ligand ID: 12015

Synonyms: BV100 (for infusion) | 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 antibacterial compounds [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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1992)  |  UK (2003)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). 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
BV100 (for infusion) | LM 427 | Mycobutin® | Rifabutine
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Rifabutin
Other databases
CAS Registry No. 72559-06-9 (source: Scifinder)
ChEMBL Ligand CHEMBL444633
DrugBank Ligand DB00615
DrugCentral Ligand 2376
GtoPdb PubChem SID 464244156
PubChem CID 135398743
Search Google for chemical match using the InChIKey ZWBTYMGEBZUQTK-PVLSIAFMSA-N
Search Google for chemicals with the same backbone ZWBTYMGEBZUQTK
Search PubMed clinical trials rifabutin
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Search PubMed titles/abstracts rifabutin
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