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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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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/)
No information available.
Summary of Clinical Use Click here for help
Rifabutin can be used as a monotherapy to treat latent tuberculosis, or in combination with other antimycobacterial medications for active infection. It is most commonly used in people with HIV/AIDS who are taking antiretroviral drugs and who are unable to be prescribed rifampicin.
BV100 is an intravenous formulation of rifabutin that is being developed by BioVersys AG as a treatment for carbapenem-resistant Acinetobacter baumannii infections [2]. It has completed a number of Phase 1 clinical trials and has progressed to Phase 2 evaluation (NCT05685615).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT05685615 PK of BV100 in Patients VABP Suspected or Confirmed to be Due to CRAB Phase 2 Interventional BioVersys AG
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com