Compound Detail

CHEMBL21

SULFANILAMIDE

💊 Approved Drug

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💊 Approved Drug

Nc1ccc(S(N)(=O)=O)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL21
Name	SULFANILAMIDE
Phase	Approved
Structure Type	MOL
InChI Key	FDDDEECHVMSUSB-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Aniline-p-sulfonic amide Avc NSC-7618 P-aminobenzenesulfamide P-aminobenzenesulfonamide Prontosil i Prontylin Streptocid Sulfamine Sulfanilamida Sulfanilamide Sulfonamide +1 more

Targets

316

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

172.2

MW (Da)

-0.08

ALogP

HBA

HBD

86.2

PSA (Å²)

0.58

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1985
Availability	Discontinued
Chirality	Achiral

Routes of Administration

Topical

USAN Stem

sulfa-

Extended Properties

Molecular Formula	C6H8N2O2S
MW	172.21
Aromatic Rings	1
Heavy Atoms	11
NP-Likeness	-1.27

Mechanism of Action

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

Indications

Bacterial Infections

ATC Classification

D06BA05

sulfanilamide

Level 1: DERMATOLOGICALS

Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE

J01EB06

sulfanilamide

Level 1: ANTIINFECTIVES FOR SYSTEMIC USE

Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

Ki 299 meas. best 7.5

IC50 14 meas. best 7.1

Kd 3 meas. best 5.26

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Carbonic anhydrase 13 CHEMBL3912	Ki	7.5	7.48	32.0	2
Carbonic anhydrase 13 CHEMBL2186	Ki	7.5	7.5	32.0	2
Carbonic anhydrase 12 CHEMBL3242	Ki	7.43	7.43	37.0	12
Unchecked CHEMBL612545	Ki	7.17	5.8644	68.0	55
Carbonic anhydrase 7 CHEMBL2326	Ki	7.16	7.16	70.0	3
HepG2 CHEMBL395	IC50	7.1	7.1	80.0	1
MDA-MB-231 CHEMBL400	IC50	7.05	7.05	90.0	1
Delta carbonic anhydrase CHEMBL3097982	Ki	6.74	6.74	181.0	1
K562 CHEMBL385	IC50	6.7	6.7	200.0	1
Carbonic anhydrase 2 CHEMBL205	Ki	6.62	6.5301	240.0	71
Carbonic anhydrase 9 CHEMBL3594	Ki	6.62	6.5471	238.0	21
Carbonic anhydrase CHEMBL3932	Ki	6.6	6.005	250.0	2
Carbonic anhydrase 2 CHEMBL205	IC50	6.59	5.9775	256.0	4
Carbonic anhydrase 9 CHEMBL3594	IC50	6.54	5.7275	290.0	4
Carbonic anhydrase CHEMBL1649055	Ki	6.52	6.52	300.0	1
Carbonic anhydrase 1 CHEMBL261	Ki	6.52	4.6211	300.0	61
Alpha carbonic anhydrase CHEMBL1075028	Ki	6.44	6.44	364.0	2
Carbonic anhydrase CHEMBL4211	Ki	6.37	6.355	431.0	2
Carbonic anhydrase, alpha family CHEMBL3621035	Ki	6.2	6.2	628.0	1
Carbonate dehydratase CHEMBL3745586	Ki	6.19	6.19	652.0	1
Carbonic anhydrase 2 CHEMBL1697676	Ki	6.12	6.115	765.0	2
Carbonic anhydrase 2 CHEMBL2283	Ki	6.07	5.335	851.1	2
AGAP002992-PA CHEMBL3399914	Ki	6.06	6.06	862.0	1
Carbonic anhydrase 6 CHEMBL3025	Ki	6.03	6.03	941.0	5
Carbonic anhydrase 4 CHEMBL3729	Ki	5.52	5.1375	3000.0	4
Carbonic anhydrase 4 CHEMBL281	Ki	5.52	5.52	3000.0	9
Carbonic anhydrase 5B, mitochondrial CHEMBL3969	Ki	5.44	5.44	3650.0	2
Carbonic anhydrase 14 CHEMBL3510	Ki	5.27	5.27	5400.0	4
Carbonic anhydrase 2 CHEMBL205	Kd	5.26	5.26	5550.0	1
Carbonic anhydrase 2 CHEMBL2283	Kd	5.23	5.23	5880.0	1
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) CHEMBL5767	Ki	5.21	5.18	6240.0	2
Carbonic anhydrase CHEMBL5337	Ki	5.12	5.12	7627.0	3
Astrosclerin-3 CHEMBL1944499	Ki	5.11	5.11	7700.0	1
Carbonic anhydrase CHEMBL6185	Ki	5.1	5.1	8011.0	1
Beta-carbonic anhydrase 1 CHEMBL5631	Ki	5.04	5.02	9230.0	3
Carbonic anhydrase 15 CHEMBL5973	Ki	5.02	5.02	9610.0	2
Protein argonaute-2 CHEMBL4680043	Kd	4.77	4.77	17000.0	1
Carbonic anhydrase CHEMBL5931	Ki	4.73	4.73	18500.0	1
Carbonic anhydrase 2 CHEMBL6068	Ki	4.53	4.53	29600.0	1
Carbonic anhydrase 5A, mitochondrial CHEMBL4789	Ki	4.5	4.5	32000.0	3
Carbonic anhydrase 5A, mitochondrial CHEMBL4789	IC50	4.5	4.5	32000.0	1
Carbonic anhydrase CHEMBL3926	Ki	4.24	4.24	57800.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Ka	5.9	10^4/M	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Carbonic anhydrase 13	Ki	=	32.0	nM	7.5	Inhibition of human recombinant CA13 by stopped flow CO2 hydrase assay	20028100
Carbonic anhydrase 13	Ki	=	32.0	nM	7.5	Ki value against murine carbonic anhydrase XIII	15686895
Carbonic anhydrase 13	Ki	=	32.0	nM	7.5	Inhibitory activity against murine carbonic anhydrase XIII (mCA XIII) by using C...	15203157
Carbonic anhydrase 13	Ki	=	35.0	nM	7.46	Inhibition of human CA13 preincubated for 15 mins by stopped-flow CO2 hydration ...	24300919
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibition of human carbonic anhydrase 12-catalyzed CO2 hydration activity by st...	21852133
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibitory activity against human Carbonic anhydrase XII (hCA XII)	16168653
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibitory activity against catalytic domain of human carbonic anhydrase XII	16039853
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibitory constant against catalytic domain of human carbonic anhydrase XII	16039848
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibition of human recombinant CA12 by CO2 hydration stopped flow assay	18042384
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibition of human recombinant CA12 by stopped flow CO2 hydrase assay	20028100
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibition of human recombinant catalytic domain of carbonic anhydrase 12 preinc...	21470859
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibition of human carbonic anhydrase 12 catalytic domain preincubated for 15 m...	22370338
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibition of human recombinant carbonic anhydrase-12 preincubated for 10 mins b...	28887000
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibition of human recombinant transmembrane tumor associated carbonic anhydras...	24589511
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibition of human CA12 preincubated for 15 mins by stopped-flow CO2 hydration ...	24300919
Carbonic anhydrase 12	Ki	=	37.0	nM	7.43	Inhibition of human catalytic domain of carbonic anhydrase 12 preincubated for 1...	22705188
Unchecked	Ki	=	68.0	nM	7.17	Inhibition of Vibrio cholerae beta carbonic anhydrase pre-incubated for 15 mins ...	33214843
Carbonic anhydrase 7	Ki	=	70.0	nM	7.16	Inhibition of human CA7 preincubated for 15 mins by stopped-flow CO2 hydration m...	24300919
Carbonic anhydrase 7	Ki	=	70.0	nM	7.16	Inhibition of human recombinant CA7 by stopped flow CO2 hydrase assay	20028100
Carbonic anhydrase 7	Ki	=	70.0	nM	7.16	Ki value against human carbonic anhydrase VII	15686895

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	455
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
21332115	10.1021/jm1013242	Unchecked	8
26700575	10.1021/acs.jmedchem.5b01643	Carbonic anhydrase 2	6
10649985	10.1021/jm990479+	ADMET	6
21470859	10.1016/j.bmcl.2011.03.055	Unchecked	4
33132114	10.1016/j.bmcl.2020.127637	Protein argonaute-2	4
21852133	10.1016/j.bmcl.2011.07.090	Unchecked	4
14552772	10.1016/j.bmcl.2003.08.017	Bacillus subtilis	4
15603963	10.1016/j.bmcl.2004.10.076	Escherichia coli	4
26832216	10.1016/j.bmcl.2016.01.023	Unchecked	4
22705188	10.1016/j.bmc.2012.05.037	Unchecked	4
28887000	10.1016/j.bmc.2017.08.047	Unchecked	4
14552772	10.1016/j.bmcl.2003.08.017	Klebsiella pneumoniae	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
14552772	10.1016/j.bmcl.2003.08.017	Escherichia coli	4
17110110	10.1016/j.bmcl.2006.11.001	Salmonella enteritidis	3
15546717	10.1016/j.bmcl.2004.09.085	Carbonic anhydrase	3

Data from ChEMBL 36 via Core Engine