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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL374478
CHEMBL374478
Compound Name RIFAMPIN
ChEMBL Synonyms EREMFAT | L-5103 LEPETIT | BA 411661E | BA-41166E | RIFAMPICIN | L-5103 | RIFAMPIN | RIMACTANE | RIFADIN
Max Phase 4 (Approved)
Trade Names Rifampicin | EREMFAT | RIFAMPIN | RIFADIN | RIMACTANE
Molecular Formula C43H58N4O12

Additional synonyms for CHEMBL374478 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(NC(=O)\C(=C/C=C/[C ...
Download SMILES
Standard InChI InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-4 ...
Download InChI
Standard InChI Key JQXXHWHPUNPDRT-WLSIYKJHSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • Curated Drug Pharmacokinetic Data
  • DrugMatrix
  • HeCaToS Compounds
  • Open TG-GATEs
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL374478

Molecule Features

CHEMBL374478 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:Y 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 PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
ConstipationD003248HP:0002019constipation1ClinicalTrials
Cystic FibrosisD003550Orphanet:586Cystic fibrosis2ClinicalTrials
Essential HypertensionD000075222EFO:1002032primary hypertension1ClinicalTrials
Hypertension, PulmonaryD006976EFO:0001361pulmonary hypertension1ClinicalTrials
InfectionD007239EFO:0000544infection3ClinicalTrials
OnchocerciasisD009855EFO:0007402onchocerciasis2ClinicalTrials
SarcoidosisD012507Orphanet:797Sarcoidosis2ClinicalTrials
TuberculosisD014376Orphanet:3389Tuberculosis4ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
FDA
Tuberculosis, PulmonaryD014397EFO:1000049pulmonary tuberculosis4ClinicalTrials
DailyMed
DailyMed
Arthritis, ReactiveD016918EFO:0007460reactive arthritis3ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus1ClinicalTrials
EndocarditisD004696EFO:0000465endocarditis3ClinicalTrials
MelanomaD008545EFO:0000756melanoma1ClinicalTrials
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials
RhinoscleromaD012226EFO:0007470rhinoscleroma0ClinicalTrials
Venous ThrombosisD020246HP:0004936Venous thrombosis1ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection1ClinicalTrials
NeoplasmsD009369EFO:0000311cancer1ClinicalTrials
Non-alcoholic Fatty Liver DiseaseD065626EFO:1001249non-alcoholic steatohepatitis1ClinicalTrials
Parkinson DiseaseD010300EFO:0002508Parkinson's disease1ClinicalTrials
NauseaD009325EFO:0006911Chemotherapy-induced nausea and vomiting1ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma1ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia1ClinicalTrials
Multiple SclerosisD009103EFO:0003885multiple sclerosis2ClinicalTrials
Multiple System AtrophyD019578EFO:1001050multiple system atrophy3ClinicalTrials
Mycobacterium avium-intracellulare InfectionD015270EFO:0007386Mycobacterium avium complex disease2ClinicalTrials
Renal InsufficiencyD0514371ClinicalTrials
Acquired Immunodeficiency SyndromeD000163EFO:0000765AIDS2ClinicalTrials
Diabetes MellitusD003920EFO:0000400diabetes mellitus1ClinicalTrials
EndometriosisD004715EFO:0001065endometriosis1ClinicalTrials
HypercalcemiaD006934HP:0003072Hypercalcemia1ClinicalTrials
LymphomaD008223EFO:0000574lymphoma1ClinicalTrials
MelanomaD008545EFO:0002617metastatic melanoma1ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease3ClinicalTrials
Coronary Artery DiseaseD003324EFO:0000378coronary artery disease1ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma1ClinicalTrials
NocturiaD0531581ClinicalTrials
SepsisD018805HP:0100806sepsis1ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis1ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma1ClinicalTrials
MeningitisD008581EFO:0000584infectious meningitis2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials

Clinical Data

ClinicalTrials.gov RIFAMPIN
The Cochrane Collaboration RIFAMPIN

Metabolites for CHEMBL374478

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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
823 822.4051 4.34 4 220.15 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
15 6 3 16 6 3


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.96 7.29 2.05 -.46 2 59 0.11

Structural Alerts

There are 11 structural alerts for CHEMBL374478. 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
J04AB02 - rifampicin

ChemSpider ChemSpider:JQXXHWHPUNPDRT-WLSIYKJHSA-N
DailyMed rifampin
PubChem SID: 144204882 SID: 144208583 SID: 144210868 SID: 170464760

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL374478



ACToR 13292-46-1
Atlas rifampicin
BindingDB 50370232
ChEBI 71365 28077
ChemicalBook CB7474473
DrugBank DB01045
eMolecules 511733
EPA CompTox Dashboard DTXSID6021244
FDA SRS VJT6J7R4TR
Guide to Pharmacology 2765
KEGG Ligand C06688
LINCS LSM-43162
Metabolights MTBLC71365 MTBLC28077
MolPort MolPort-002-513-586 MolPort-006-395-891
PDBe RFP
PubChem: Drugs of the Future 24714737
PubChem: Thomson Pharma 14865086 14791501
Rhea 71365
Selleck Rifampin(Rifadin)
SureChEMBL SCHEMBL23490
ZINC ZINC000169621223

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