Compound Detail

CHEMBL374478

RIFAMPIN

💊 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(C)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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL374478
Name	RIFAMPIN
Phase	Approved
Structure Type	MOL
InChI Key	JQXXHWHPUNPDRT-WLSIYKJHSA-N
Therapeutic	✓ Yes

Known Names

Abrifam BA 41166/E BA 411661E BA-41166/E BA-41166E Eremfat L-5103 L-5103 LEPETIT L-5103-LEPETIT NIH-10782 NSC-113926 Rifa +17 more

Targets

153

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

823.0

MW (Da)

4.34

ALogP

HBA

HBD

220.2

PSA (Å²)

0.11

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1971
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product

USAN Stem	-pin; rifa-
USAN Year	1968

Extended Properties

Molecular Formula	C43H58N4O12
MW	822.95
Aromatic Rings	2
Heavy Atoms	59
NP-Likeness	1.66

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 Alzheimer Disease Arthritis, Reactive Diarrhea Endocarditis Enterocolitis, Pseudomembranous Infections Leprosy Meningitis Multiple System Atrophy Acquired Immunodeficiency Syndrome Buruli Ulcer Cystic Fibrosis Multiple Sclerosis Mycobacterium avium-intracellulare Infection Onchocerciasis Sarcoidosis Anti-Neutrophil Cytoplasmic Antibody-Associated Vasculitis Arthritis, Rheumatoid

ATC Classification

J04AB02

rifampicin

Level 1: ANTIINFECTIVES FOR SYSTEMIC USE

Level 2: ANTIMYCOBACTERIALS

Activity Summary

IC50 105 meas. best 9.14

EC50 30 meas. best 7.7

Ki 16 meas. best 5.96

Kd 2 meas. best 4.92

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Mycobacterium tuberculosis CHEMBL360	IC50	9.14	7.6522	0.7	23
Mycobacterium tuberculosis variant bovis CHEMBL613086	IC50	8.0	7.02	10.0	2
Unchecked CHEMBL612545	IC50	7.94	6.657	11.5	20
Mycobacterium tuberculosis CHEMBL360	EC50	7.7	7.7	20.0	2
Enoyl-[acyl-carrier-protein] reductase [NADH] CHEMBL1849	IC50	7.52	7.52	30.0	1
Enterococcus faecium CHEMBL357	EC50	6.89	6.405	130.0	2
Staphylococcus aureus CHEMBL352	EC50	6.82	6.73	150.0	2
Plasmodium falciparum CHEMBL364	IC50	6.72	6.0014	190.0	7
Nuclear receptor subfamily 1 group I member 2 CHEMBL3401	EC50	6.72	5.9371	190.0	14
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	IC50	6.52	5.935	300.0	4
Acinetobacter baumannii CHEMBL614425	EC50	6.33	6.11	470.0	2
Hepatocyte CHEMBL613690	EC50	6.01	6.01	980.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	Ki	5.96	5.365	1100.0	2
Cytochrome P450 2B6 CHEMBL4729	EC50	5.89	5.89	1300.0	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	Ki	5.85	5.575	1400.0	2
Solute carrier organic anion transporter family member 1A4 CHEMBL1781860	Ki	5.85	5.845	1400.0	2
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	5.82	5.82	1500.0	1
Mycolicibacterium smegmatis CHEMBL613088	IC50	5.73	5.5333	1870.0	3
Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL4358	IC50	5.53	5.53	2949.0	1
Pseudomonas aeruginosa CHEMBL348	EC50	5.28	5.195	5200.0	2
Klebsiella pneumoniae subsp. pneumoniae CHEMBL613207	EC50	5.27	5.27	5400.0	1
Enterobacter cloacae CHEMBL349	EC50	5.21	5.135	6200.0	2
Alpha-synuclein CHEMBL6152	IC50	5.15	4.74	7100.0	2
Caspase-1 CHEMBL4801	IC50	5.08	5.08	8319.0	1
Klebsiella pneumoniae CHEMBL350	EC50	4.96	4.96	11000.0	1
Bile salt export pump CHEMBL6020	IC50	4.95	4.72	11300.0	4
Albumin CHEMBL3253	Kd	4.92	4.92	12000.0	1
Bile salt export pump CHEMBL2073674	Ki	4.92	4.92	11900.0	1
Solute carrier organic anion transporter family member 1A1 CHEMBL1781859	Ki	4.74	4.74	18200.0	1
Plasmodium yoelii CHEMBL612889	IC50	4.65	4.65	22200.0	1
Lanosterol 14-alpha demethylase CHEMBL3849	IC50	4.52	4.52	30000.0	1
Bile salt export pump CHEMBL2073674	IC50	4.46	4.46	34700.0	1
ATP-binding cassette sub-family C member 4 CHEMBL1743128	IC50	4.38	4.38	41900.0	1
ADMET CHEMBL612558	Ki	4.3	4.15	50000.0	2
Solute carrier organic anion transporter family member 1A2 CHEMBL1743123	Ki	4.29	4.29	51000.0	1
ATP-binding cassette sub-family C member 2 CHEMBL5748	IC50	4.28	4.28	53000.0	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	4.25	4.25	56000.0	1
Solute carrier organic anion transporter family member 2B1 CHEMBL1743124	Ki	4.2	4.2	63000.0	1
Solute carrier organic anion transporter family member 2B1 CHEMBL1743124	IC50	4.19	4.19	65000.0	1
ATP-binding cassette sub-family C member 3 CHEMBL5918	IC50	4.16	4.16	69000.0	1
Glutathione S-transferase omega-1 CHEMBL3174	IC50	4.12	4.12	75000.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.02	4.02	96000.0	1
Vero CHEMBL391	IC50	4.01	4.01	97900.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	79700.0	ng.hr.mL-1	Homo sapiens
AUC	48500.0	ng.hr.mL-1	Homo sapiens
AUC	6400.0	ng.hr.mL-1	Homo sapiens
AUC	13200.0	ng.hr.mL-1	Homo sapiens
AUC	29700.0	ng.hr.mL-1	Homo sapiens
AUC	48200.0	ng.hr.mL-1	Mus musculus
AUC	45700.0	ng.hr.mL-1	Homo sapiens
AUC	41700.0	ng.hr.mL-1	Homo sapiens
AUC	13.1	ug ml-1	Homo sapiens
AUC	24.5	ug ml-1	Homo sapiens
AUC	100.0	ug ml-1	Homo sapiens
AUC	171.0	ug ml-1	Homo sapiens
AUC	44000.0	ng.hr.mL-1	Homo sapiens
AUC	-	ng.hr.mL-1	-
AUC	14000.0	ng.hr.mL-1	-
AUC	-	ng.hr.mL-1	-
AUC	122000.0	ng.hr.mL-1	-
AUC	7000.0	ng.hr.mL-1	-
AUC	7000.0	ng.hr.mL-1	-
AUC	14000.0	ng.hr.mL-1	-
AUC	14000.0	ng.hr.mL-1	-
AUC	112000.0	ng.hr.mL-1	Homo sapiens
AUC	49000.0	ng.hr.mL-1	Homo sapiens
AUC	50600.0	ng.hr.mL-1	Homo sapiens
AUC	24760.0	ng.hr.mL-1	Mus musculus
AUC	40280.0	ng.hr.mL-1	Oryctolagus cuniculus
AUC	6.22	-	Cavia porcellus
AUC	4600.0	ng.hr.mL-1	Cavia porcellus
AUC	64400.0	ng.hr.mL-1	-
AUC	19650.0	ng.hr.mL-1	Staphylococcus aureus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Mycobacterium tuberculosis	IC50	=	0.72	nM	9.14	Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 afte...	28993106
Mycobacterium tuberculosis	IC50	=	0.72	nM	9.14	Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 expr...	28763645
Mycobacterium tuberculosis	IC50	=	2.4	nM	8.62	Antitubercular activity against dormant stage of Mycobacterium tuberculosis H37R...	30910461
Mycobacterium tuberculosis	IC50	=	2.4	nM	8.62	Antitubercular activity against Mycobacterium tuberculosis H37Ra ATCC 25177 dorm...	28411559
Mycobacterium tuberculosis	IC50	=	4.1	nM	8.39	Antitubercular activity against fluorescent reporter strain of Mycobacterium tub...	26191372
Mycobacterium tuberculosis	IC50	=	4.6	nM	8.34	Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 afte...	28763645
Mycobacterium tuberculosis	IC50	=	4.6	nM	8.34	Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 afte...	28993106
Mycobacterium tuberculosis	IC50	=	4.7	nM	8.33	Antitubercular activity against Mycobacterium tuberculosis H37Rv INH-R2 ATCC 358...	27437078
Mycobacterium tuberculosis	IC50	=	8.4	nM	8.08	Antitubercular activity against Mycobacterium tuberculosis H37Rv INH-R1 harborin...	27437078
Mycobacterium tuberculosis variant bovis	IC50	=	10.0	nM	8.0	Antimycobacterial activity against Mycobacterium bovis BCG assessed as growth in...	-
Mycobacterium tuberculosis	IC50	=	10.0	nM	8.0	Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 expr...	33075682
Unchecked	IC50	=	11.5	nM	7.94	Inhibition of Escherichia coli RNA polymerase using Kool NC-45 universal RNA pol...	20660693
Unchecked	IC50	=	12.0	nM	7.92	Inhibition of wild type Escherichia coli RNA polymerase after 10 mins by rolling...	23679862
Mycobacterium tuberculosis	IC50	=	13.0	nM	7.89	Antitubercular activity against Mycobacterium tuberculosis H37Rv FQ-R1 harboring...	27437078
Unchecked	IC50	=	14.0	nM	7.85	Inhibition of Escherichia coli switch region of RNA polymerase after 1 hr by tra...	25798859
Unchecked	IC50	=	15.0	nM	7.82	Inhibition of wild type Staphylococcus aureus RNA polymerase assessed as reducti...	27336583
Unchecked	IC50	=	15.0	nM	7.82	Inhibition of Staphylococcus aureus wild-type RNA polymerase RpoB	18443108
Unchecked	IC50	=	16.0	nM	7.8	Inhibition of Escherichia coli RNA polymerase core enzyme by transcription assay	24112046
Unchecked	IC50	=	17.0	nM	7.77	Inhibition of wild type Mycobacterium tuberculosis RNA polymerase after 10 mins ...	23679862
Mycobacterium tuberculosis	EC50	=	20.0	nM	7.7	Antitubercular activity against Mycobacterium tuberculosis H37Rv by microdilutio...	23352268

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1400
-	10.6019/CHEMBL3885881	Rattus norvegicus	196
18559647	10.1128/aac.00342-08	Clostridioides difficile	160
31022550	10.1016/j.ejmech.2019.04.034	Pseudomonas aeruginosa	43
18443108	10.1128/aac.01649-07	Staphylococcus aureus	41
33826327	10.1021/acs.jmedchem.0c01833	Mycobacterium tuberculosis	38
18591267	10.1128/aac.00405-08	Escherichia coli	36
19188385	10.1128/aac.01619-08	Staphylococcus aureus	36
20606072	10.1128/aac.00315-10	Neisseria meningitidis	34
19223616	10.1128/aac.01605-07	Staphylococcus aureus	31
19546358	10.1128/aac.00206-09	Staphylococcus aureus	27
17846127	10.1128/aac.01259-06	Acinetobacter baumannii	26
18391026	10.1128/aac.00461-07	Homo sapiens	26
17452486	10.1128/aac.01550-06	Homo sapiens	25
17724157	10.1128/aac.01533-06	Mycobacterium tuberculosis	22
17158933	10.1128/aac.01052-06	Staphylococcus lugdunensis	22
20713672	10.1128/aac.00470-10	Staphylococcus aureus	22
31281018	10.1016/j.bmcl.2019.07.001	Mycobacteroides abscessus	22
18378710	10.1128/aac.01486-07	Mycobacterium tuberculosis	21
20516287	10.1128/aac.00287-10	Mycobacterium tuberculosis	21

Data from ChEMBL 36 via Core Engine