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Compound Detail

CHEMBL444633

RIFABUTIN
💊 Approved Drug
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💊 Approved Drug
CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C2=NC3(CCN(CC(C)C)CC3)NC2=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL444633
Name RIFABUTIN
Phase Approved
Structure Type MOL
InChI Key ATEBXHFBFRCZMA-VXTBVIBXSA-N
Therapeutic ✓ Yes

Known Names

Ansamycin LM 427 LM-427 MYCOBUTIN Rifabutin Rifabutin component of talicia Rifabutina Rifabutine
4
Targets
6
Activities
1
Assay Types
30
PK Parameters
20
Publications
8
Known Names
11
Indications
1
Mechanisms

Molecular Properties

847.0
MW (Da)
4.62
ALogP
14
HBA
5
HBD
205.6
PSA (Ų)
0.26
QED
2
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1992
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem rifa-
USAN Year 1993

Extended Properties

Molecular Formula C46H62N4O11
MW 847.02
Aromatic Rings 1
Heavy Atoms 61
NP-Likeness 1.73

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial DNA-directed RNA polymerase inhibitor INHIBITOR Bacterial DNA-directed RNA polymerase ✓ ✓

Indications

HIV Infections HIV Infections Mycobacterium avium-intracellulare Infection Tuberculosis Crohn Disease Infections Mycobacterium Infections Mycoses Lung Diseases Tuberculosis, Pulmonary Osteomyelitis

ATC Classification

J04AB04
rifabutin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOBACTERIALS

Activity Summary

IC50 6 meas. best 4.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.8 4.8 15900.0 1
Programmed cell death protein 1/Programmed cell death 1 ligand 1
CHEMBL4523993
 IC50 4.6 4.6 25000.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.57 4.57 26700.0 3
ATP-binding cassette sub-family C member 2
CHEMBL5748
 IC50 4.3 4.3 49800.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6110.0 ng.hr.mL-1 Homo sapiens
AUC 5810.0 ng.hr.mL-1 Homo sapiens
AUC 47100.0 ng.hr.mL-1 Homo sapiens
AUC 411.0 ng.hr.mL-1 Homo sapiens
AUC 7740.0 ng.hr.mL-1 Homo sapiens
AUC 4600.0 ng.hr.mL-1 Homo sapiens
AUC 12700.0 ng.hr.mL-1 Homo sapiens
AUC 90820.0 ng.hr.mL-1 Mus musculus
AUC 109350.0 ng.hr.mL-1 Mus musculus
AUC 2059.11 ng.hr.mL-1 Homo sapiens
AUC 6600.0 ng.hr.mL-1 Mus musculus
CL 80.0 mL.min-1.kg-1 -
CL 2.4 mL.min-1.kg-1 Homo sapiens
CL 2.0 mL.min-1.kg-1 Homo sapiens
CL 2.4 mL.min-1.kg-1 Homo sapiens
CL 2.4 mL.min-1.kg-1 Homo sapiens
CL 1.02 ml/hr Mus musculus
CL 11.68 ml/hr Mus musculus
Cmax 369.53 nM Homo sapiens
Cmax 316.4 nM Homo sapiens
Cmax 8606.64 nM Homo sapiens
Cmax 28.33 nM Homo sapiens
Cmax 164.1 nM Homo sapiens
Cmax 1.38 ug/10^6 cells Homo sapiens
Cmax 2.03 ug/10^6 cells Homo sapiens
Cmax 1.65 ug Mus musculus
Cmax 0.32 ug Mus musculus
Cmax 4096.72 nM Mus musculus
Cmax 1877.17 nM Mus musculus
Cmax 684.9 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
ATP-binding cassette sub-family C member 4 IC50 = 15900.0 nM 4.8 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Programmed cell death protein 1/Programmed cell death 1 ligand 1 IC50 = 25000.0 nM 4.6 Inhibition of biotinylated human PD-I /His-tagged PD-L1 (unknown origin) interac... 37196547
Bile salt export pump IC50 = 26700.0 nM 4.57 Inhibition of human BSEP expressed in fall armyworm sf9 cell plasma membrane ves... 20829430
Bile salt export pump IC50 = 26700.0 nM 4.57 Inhibition of recombinant human BSEP expressed in baculovirus infected sf9 cell ... 24799086
Bile salt export pump IC50 = 26700.0 nM 4.57 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
ATP-binding cassette sub-family C member 2 IC50 = 49800.0 nM 4.3 Inhibition of human MRP2 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 514
18056271 10.1128/aac.00724-07 Homo sapiens 65
31103404 10.1016/j.bmc.2019.04.032 Mycobacterium leprae 26
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22100303 10.1016/j.ejmech.2011.10.041 Mycobacterium tuberculosis 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
36948128 10.1016/j.ejmech.2023.115257 ADMET 14
35175750 10.1021/acs.jmedchem.1c02045 Helicobacter pylori 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
23215016 10.1021/jm301116j No relevant target 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
23215016 10.1021/jm301116j Lipid bilayer 8
20070106 10.1021/jm901371v Homo sapiens 8
16987658 10.1016/j.bmcl.2006.08.090 Mycobacterium tuberculosis 7
31103404 10.1016/j.bmc.2019.04.032 ADMET 6
19119013 10.1016/j.bmc.2008.12.006 Mycobacterium tuberculosis 6
18955515 10.1128/aac.01302-08 Mycobacterium tuberculosis variant bovis 5
17189695 10.1016/j.bmcl.2006.12.026 Staphylococcus aureus 5
18591268 10.1128/aac.00153-08 Mus musculus 4
17210775 10.1128/aac.00055-06 Mycobacterium tuberculosis 4

Data from ChEMBL 36 via Core Engine