Compound Detail
CHEMBL1660
RIFAPENTINE 💊 Approved Drug
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💊 Approved Drug
CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(c(/C=N/N5CCN(C6CCCC6)CC5)c(O)c4c3C2=O)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
Basic Information
| ChEMBL ID | CHEMBL1660 |
| Name | RIFAPENTINE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | WDZCUPBHRAEYDL-GZAUEHORSA-N |
| Therapeutic | ✓ Yes |
4
Targets
4
Activities
1
Assay Types
16
PK Parameters
20
Publications
12
Known Names
4
Indications
1
Mechanisms
Molecular Properties
877.0
MW (Da)
5.65
ALogP
15
HBA
6
HBD
220.2
PSA (Ų)
0.09
QED
4
Ro5 Violations
5
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1998 |
| Availability | Prescription |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Bacterial DNA-directed RNA polymerase inhibitor | INHIBITOR | Bacterial DNA-directed RNA polymerase | ✓ | ✓ |
Indications
Tuberculosis Tuberculosis, Pulmonary HIV Infections Osteomyelitis
ATC Classification
J04AB05
rifapentine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOBACTERIALS
Activity Summary
IC50 4 meas. best 5.0
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Bile salt export pump CHEMBL6020 | IC50 | 5.0 | 5.0 | 9910.0 | 1 |
| ATP-binding cassette sub-family C member 2 CHEMBL5748 | IC50 | 4.79 | 4.79 | 16300.0 | 1 |
| ATP-binding cassette sub-family C member 4 CHEMBL1743128 | IC50 | 4.45 | 4.45 | 35900.0 | 1 |
| ATP-binding cassette sub-family C member 3 CHEMBL5918 | IC50 | 4.09 | 4.09 | 80900.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 512900.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 410200.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 319000.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 346001.05 | ng.hr.mL-1 | Homo sapiens |
| Cmax | 24970.35 | nM | Homo sapiens |
| Cmax | 24172.22 | nM | Homo sapiens |
| Cmax | 11401.99 | nM | Homo sapiens |
| F | 70.0 | % | Homo sapiens |
| T1/2 | 18.5 | hr | Homo sapiens |
| T1/2 | 14.8 | hr | Homo sapiens |
| T1/2 | 13.0 | hr | Homo sapiens |
| Tmax | 5.08 | hr | Homo sapiens |
| Tmax | 4.77 | hr | Homo sapiens |
| Tmax | 4.8 | hr | Homo sapiens |
| Vd | 40.7 | l | Homo sapiens |
| Vd | 43.7 | l | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| Bile salt export pump | IC50 | = | 9910.0 | nM | 5.0 | Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... | 23956101 |
| ATP-binding cassette sub-family C member 2 | IC50 | = | 16300.0 | nM | 4.79 | Inhibition of human MRP2 overexpressed in Sf9 cell membrane vesicles assessed as... | 23956101 |
| ATP-binding cassette sub-family C member 4 | IC50 | = | 35900.0 | nM | 4.45 | Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... | 23956101 |
| ATP-binding cassette sub-family C member 3 | IC50 | = | 80900.0 | nM | 4.09 | Inhibition of human MRP3 overexpressed in Sf9 insect cell membrane vesicles asse... | 23956101 |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| - | 10.6019/CHEMBL3885881 | Rattus norvegicus | 278 |
| 18765687 | 10.1128/aac.00554-08 | Homo sapiens | 18 |
| 22194678 | 10.1371/journal.pcbi.1002310 | Hepatotoxicity | 14 |
| 17606690 | 10.1128/aac.00343-07 | Staphylococcus epidermidis | 5 |
| - | 10.6019/CHEMBL4495565 | SARS-CoV-2 | 4 |
| 19075046 | 10.1128/aac.00749-08 | Homo sapiens | 4 |
| 23956101 | 10.1093/toxsci/kft176 | Unchecked | 4 |
| - | 10.6019/CHEMBL4495564 | Replicase polyprotein 1ab | 2 |
| 28628823 | 10.1016/j.ejmech.2017.06.005 | Mycobacterium tuberculosis | 2 |
| 26948801 | 10.1016/j.drudis.2016.02.015 | Homo sapiens | 2 |
| 23956101 | 10.1093/toxsci/kft176 | Homo sapiens | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | D(1A) dopamine receptor | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | Prostaglandin G/H synthase 1 | 2 |
| - | 10.6019/CHEMBL4808148 | Histone deacetylase 6 | 2 |
| 19075046 | 10.1128/aac.00749-08 | Mycobacterium tuberculosis | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | Thromboxane A2 receptor | 2 |
| 23956101 | 10.1093/toxsci/kft176 | ATP-binding cassette sub-family C member 2 | 1 |
| 23956101 | 10.1093/toxsci/kft176 | Bile salt export pump | 1 |
| 38318365 | 10.1016/j.isci.2024.108907 | Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | 1 |
| 18268091 | 10.1128/aac.00897-07 | Mycobacterium tuberculosis | 1 |
Data from ChEMBL 36 via Core Engine