Compound Detail

CHEMBL1191

SULFAMETHIZOLE

💊 Approved Drug

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💊 Approved Drug

Cc1nnc(NS(=O)(=O)c2ccc(N)cc2)s1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1191
Name	SULFAMETHIZOLE
Phase	Approved
Structure Type	MOL
InChI Key	VACCAVUAMIDAGB-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Methazol Microsul NSC-757327 Proklar Sulfamethizol Sulfamethizole Sulfametizol Sulphamethylthiadiazole Tetracid Thiosulfil Urolucosil

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

270.3

MW (Da)

1.23

ALogP

HBA

HBD

98.0

PSA (Å²)

0.82

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1953
Availability	Withdrawn
Chirality	Achiral

Routes of Administration

Oral

Flags

Withdrawn Natural Product

USAN Stem

sulfa-

Extended Properties

Molecular Formula	C9H10N4O2S2
MW	270.34
Aromatic Rings	2
Heavy Atoms	17
NP-Likeness	-2.20

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Bacterial dihydropteroate synthase inhibitor	INHIBITOR	Dihydropteroate synthase	✓	✓

Indications

Bacterial Infections Eye Infections Osteomyelitis

ATC Classification

B05CA04

sulfamethizole

Level 1: BLOOD AND BLOOD FORMING ORGANS

Level 2: BLOOD SUBSTITUTES AND PERFUSION SOLUTIONS

D06BA04

sulfamethizole

Level 1: DERMATOLOGICALS

Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE

J01EB02

sulfamethizole

Level 1: ANTIINFECTIVES FOR SYSTEMIC USE

Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

S01AB01

sulfamethizole

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Drug Warnings

Withdrawn

General Warning

adverse reactions and low sales

Country: Sweden Year: 1984

Activity Summary

IC50 3 meas. best 4.24

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
No relevant target CHEMBL2362975	IC50	4.24	4.24	57455.0	1
Unchecked CHEMBL612545	IC50	4.06	4.06	86564.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
No relevant target	IC50	=	57455.0	nM	4.24	PubChem BioAssay. Counterscreen for inhibitors of RecBCD: Absorbance-based cell-...	-
Unchecked	IC50	=	86564.0	nM	4.06	PubChem BioAssay. Absorbance-based bacterial cell-based high throughput dose res...	-

Literature References

PubMed	DOI	Target Context	# Activities
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
14552772	10.1016/j.bmcl.2003.08.017	Escherichia coli	4
14552772	10.1016/j.bmcl.2003.08.017	Klebsiella pneumoniae	4
14552772	10.1016/j.bmcl.2003.08.017	Bacillus subtilis	4
15603963	10.1016/j.bmcl.2004.10.076	Escherichia coli	4
15603963	10.1016/j.bmcl.2004.10.076	Bacillus subtilis	4
15603963	10.1016/j.bmcl.2004.10.076	Klebsiella pneumoniae	4
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
37468498	10.1038/s41467-023-40064-9	Cannabinoid receptor 1	3
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	2
37468498	10.1038/s41467-023-40064-9	Gamma-aminobutyric acid receptor subunit alpha-1	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
-	10.6019/CHEMBL3301361	No relevant target	2
26948801	10.1016/j.drudis.2016.02.015	Homo sapiens	2
21601448	10.1016/j.bmcl.2011.04.133	No relevant target	2
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2

Data from ChEMBL 36 via Core Engine