Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL437765

RIFAMYCIN
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(O)c(cc(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 CHEMBL437765
Name RIFAMYCIN
Phase Approved
Structure Type MOL
InChI Key HJYYPODYNSCCOU-ODRIEIDWSA-N
Therapeutic ✓ Yes

Known Names

CB-01-11 M-14 Rifamicina Rifamicine sv Rifamycin Rifamycine Rifomycin Rifomycin sv
14
Targets
23
Activities
3
Assay Types
5
PK Parameters
20
Publications
8
Known Names
5
Indications

Molecular Properties

697.8
MW (Da)
4.75
ALogP
12
HBA
6
HBD
201.3
PSA (Ų)
0.14
QED
3
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2018
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -mycin; rifa-
USAN Year 2009

Extended Properties

Molecular Formula C37H47NO12
MW 697.78
Aromatic Rings 2
Heavy Atoms 50
NP-Likeness 2.39

Indications

Eye Infections Tuberculosis Diarrhea Dysentery Irritable Bowel Syndrome

ATC Classification

A07AA13
rifamycin
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
D06AX15
rifamycin
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
J04AB03
rifamycin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOBACTERIALS
S01AA16
rifamycin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S02AA12
rifamycin
Level 1: SENSORY ORGANS
Level 2: OTOLOGICALS

Activity Summary

IC50 14 meas. best 8.07
Ki 8 meas. best 5.7
Kd 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 8.07 6.285 8.6 2
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
IC50 6.64 6.64 230.0 1
Plasmodium falciparum
CHEMBL364
IC50 6.26 6.26 550.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 6.0 6.0 990.0 1
Leishmania donovani
CHEMBL367
IC50 5.82 5.82 1500.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
Ki 5.7 5.7 2000.0 1
Solute carrier organic anion transporter family member 2B1
CHEMBL1743124
Ki 5.52 5.52 3000.0 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
Ki 5.52 5.52 3000.0 1
Bile salt export pump
CHEMBL2073674
IC50 5.51 5.51 3100.0 1
Bile salt export pump
CHEMBL2073674
Ki 5.42 5.42 3800.0 1
Bile salt export pump
CHEMBL6020
IC50 5.2 5.0433 6300.0 3
Solute carrier organic anion transporter family member 1A1
CHEMBL1781859
Ki 5.18 5.18 6600.0 1
Solute carrier organic anion transporter family member 1A4
CHEMBL1781860
Ki 5.14 5.14 7300.0 1
Solute carrier organic anion transporter family member 1A2
CHEMBL1743123
Ki 4.96 4.96 11000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.8 4.59 15680.0 2
Bile salt export pump
CHEMBL6020
Ki 4.51 4.51 31000.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.3 4.3 49950.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 80.0 mL.min-1.kg-1 -
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
Cmax 2780.0 nM Homo sapiens
T1/2 0.33 hr -
Vd 1.2 L.kg-1 -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 8.6 nM 8.07 Inhibition of Escherichia coli RNA polymerase using Kool NC-45 universal RNA pol... 20660693
Solute carrier organic anion transporter family member 1B1 IC50 = 230.0 nM 6.64 TP_TRANSPORTER: inhibition of estradiol-17beta-glucuronide uptake(estradiol-17be... 15616150
Plasmodium falciparum IC50 = 550.0 nM 6.26 DNDI: Malaria in Vitro, 72 hour -
Trypanosoma brucei rhodesiense IC50 = 990.0 nM 6.0 DNDI: HAT in Vitro, 72 hour -
Leishmania donovani IC50 = 1500.0 nM 5.82 DNDI: Leish (axenic) in Vitro, 72 hour -
Solute carrier organic anion transporter family member 1B1 Ki = 2000.0 nM 5.7 TP_TRANSPORTER: inhibition of BSP uptake in Xenopus laevis oocytes 12085361
Solute carrier organic anion transporter family member 2B1 Ki = 3000.0 nM 5.52 TP_TRANSPORTER: inhibition of BSP uptake in Xenopus laevis oocytes 12085361
Solute carrier organic anion transporter family member 1B3 Ki = 3000.0 nM 5.52 TP_TRANSPORTER: inhibition of BSP uptake in Xenopus laevis oocytes 12085361
Bile salt export pump IC50 = 3100.0 nM 5.51 Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of S... 21965623
Bile salt export pump Ki = 3800.0 nM 5.42 TP_TRANSPORTER: inhibition of Taurocholate uptake in membrane vesicles from Bsep... 10648470
Bile salt export pump IC50 = 6300.0 nM 5.2 Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells ass... 21965623
Solute carrier organic anion transporter family member 1A1 Ki = 6600.0 nM 5.18 TP_TRANSPORTER: inhibition of E217betaG uptake in Xenopus laevis oocytes 10869292
Solute carrier organic anion transporter family member 1A4 Ki = 7300.0 nM 5.14 TP_TRANSPORTER: inhibition of E217betaG uptake in Xenopus laevis oocytes 10869292
Bile salt export pump IC50 = 9500.0 nM 5.02 Inhibition of recombinant human BSEP expressed in baculovirus infected sf9 cell ... 24799086
Solute carrier organic anion transporter family member 1A2 Ki = 11000.0 nM 4.96 TP_TRANSPORTER: inhibition of BSP uptake in Xenopus laevis oocytes 12085361
Bile salt export pump IC50 = 12200.0 nM 4.91 TP_TRANSPORTER: increase in dihydrofluorescein intracellular accumulation (dihyd... 12739759
NON-PROTEIN TARGET IC50 = 15680.0 nM 4.8 DNDI: Cytotoxicity in Vitro, 72 hour, in rat skeletal myoblast cells -
Bile salt export pump Ki = 31000.0 nM 4.51 TP_TRANSPORTER: inhibition of Taurocholate uptake(Rifampicin SV 30uM, 50 % of co... 12404239
Unchecked IC50 = 31640.0 nM 4.5 Inhibition of synthetic amyloid beta-42 oligomerization by ELISA 17284452
NON-PROTEIN TARGET IC50 = 41620.0 nM 4.38 DNDI: Cytotoxicity in Vitro, 96 hour, in mouse macrophages (infected-amastigotes... -

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
25205189 10.1016/j.bmcl.2014.08.032 NON-PROTEIN TARGET 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
24874895 10.1021/jm500571f Mycobacterium tuberculosis 6
17284452 10.1074/jbc.m608207200 Unchecked 4
- 10.1584/jpestics.28.183 Streptomyces acidiscabies 4
- 10.1584/jpestics.28.183 Streptomyces scabiei 4
17826091 10.1016/j.bmcl.2007.08.048 Staphylococcus aureus 3
2299623 10.1021/jm00164a013 Rattus norvegicus 3
11311053 10.1021/jm000407e ADMET 3
2329569 10.1021/jm00167a029 Mycobacterium avium 3
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.1584/jpestics.28.183 Streptomyces alboniger 3
2329569 10.1021/jm00167a029 Staphylococcus aureus 3
21965623 10.1124/dmd.111.040758 Bile salt export pump 2
- 10.6019/CHEMBL3392926 NON-PROTEIN TARGET 2
12739759 10.1023/a:1023278211849 Bile salt export pump 2
9632365 10.1021/jm970791o Escherichia coli 2
9632365 10.1021/jm970791o Nucleic Acid 2
- 10.6019/CHEMBL3392926 Leishmania donovani 2

Data from ChEMBL 36 via Core Engine