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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL444633
CHEMBL444633
Compound Name RIFABUTIN
ChEMBL Synonyms LM-427 | RIFABUTIN | ANSAMYCIN | MYCOBUTIN
Max Phase 4 (Approved)
Trade Names RIFABUTIN | MYCOBUTIN
Molecular Formula C46H62N4O11

Additional synonyms for CHEMBL444633 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C)c(O)c4C(=O)C(=C5NC6(CCN(CC(C)C ...
Download SMILES
Standard InChI InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-3 ...
Download InChI
Standard InChI Key ATEBXHFBFRCZMA-VXTBVIBXSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL444633

Molecule Features

CHEMBL444633 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Bacterial DNA-directed RNA polymerase inhibitor Bacterial DNA-directed RNA polymerase PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials
Mycobacterium avium-intracellulare InfectionD015270EFO:0007386Mycobacterium avium complex disease2ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection1ClinicalTrials
TuberculosisD014376Orphanet:3389Tuberculosis1ClinicalTrials
InfectionD007239EFO:0000544infection3ClinicalTrials
Tuberculosis, PulmonaryD014397EFO:1000049pulmonary tuberculosis2ClinicalTrials

Clinical Data

ClinicalTrials.gov RIFABUTIN
The Cochrane Collaboration RIFABUTIN

Metabolites for CHEMBL444633

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
847 846.4415 4.62 4 205.55 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
14 5 2 15 5 2


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
3.31 9.5 4.49 1.92 1 61 0.26

Structural Alerts

There are 5 structural alerts for CHEMBL444633. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J04 - ANTIMYCOBACTERIALS
J04A - DRUGS FOR TREATMENT OF TUBERCULOSIS
J04AB - Antibiotics
J04AB04 - rifabutin

ChemSpider ChemSpider:ATEBXHFBFRCZMA-VXTBVIBXSA-N
DailyMed rifabutin
PubChem SID: 144204563 SID: 144207956
Wikipedia Rifabutin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL444633



ACToR 72559-06-9
Brenda 135623
ChEBI 45367
ChemicalBook CB0702764
DrugBank DB00615
DrugCentral 2376
eMolecules 3717994 29541954
EPA CompTox Dashboard DTXSID0033960
FDA SRS 1W306TDA6S
KEGG Ligand C07235
LINCS LSM-43193
Nikkaji J342.306I
PDBe RBT
PharmGKB PA451249
PubChem 6323490
PubChem: Drugs of the Future 12012943
PubChem: Thomson Pharma 14791636
Selleck Rifabutin(Mycobutin)
SureChEMBL SCHEMBL36043
ZINC ZINC000169621215

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/ATEBXHFBFRCZMA-VXTBVIBXSA-N spacer
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