Sulfanilamide

Summary

Sulfanilamide (CHEMBL21) is an approved small-molecule EC 4.2.1.1 (carbonic anhydrase) inhibitor (ATC D06BA05); indicated across 1 condition including bacterial infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: D06BA05 (+1 more)
• Indications: 1 condition
• Chemistry: 172.21 Da · C6H8N2O2S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL21
Name	Sulfanilamide
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	5333
ChEBI	CHEBI:45373
ATC	D06BA05, J01EB06
Molecular formula	C6H8N2O2S
Molecular weight	172.21
InChIKey	FDDDEECHVMSUSB-UHFFFAOYSA-N

SMILES: C1=CC(=CC=C1N)S(=O)(=O)N

IUPAC name: 4-aminobenzenesulfonamide

ChEBI definition: A sulfonamide in which the sulfamoyl functional group is attached to aniline at the 4-position.

Pharmacological roles (ChEBI): EC 4.2.1.1 (carbonic anhydrase) inhibitor, antibacterial agent, drug allergen.

Also known as: Aniline-p-sulfonic amide, Avc, NSC-7618, P-aminobenzenesulfamide, P-aminobenzenesulfonamide, Prontosil i, Prontylin, Streptocid, Sulfamine, Sulfanilamida, Sulfanilamide, Sulfonamide

Patent coverage: 55,046 distinct patent families (153,075 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 25 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Ubiquitin carboxyl-terminal hydrolase 2, Thyrotropin receptor, Carbonic anhydrase 2, Carbonic anhydrase 13, Carbonic anhydrase 2, Carbonic anhydrase 7, Carbonic anhydrase 1, Carbonic anhydrase 4, Carbonic anhydrase 6, Carbonic anhydrase 12, Carbonic anhydrase 14, Carbonic anhydrase 9, Carbonic anhydrase 4, Carbonic anhydrase 13, Carbonic anhydrase, Carbonic anhydrase 5B, mitochondrial, Carbonic anhydrase, Protein argonaute-2, Carbonic anhydrase 5A, mitochondrial.

Bioactivity

ChEMBL activities: 160 potent at pChembl ≥ 5 of 231 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
Q9D6N1	7.5	Ki	32	nM	CHEMBL_ACT_1436553
CA13	7.5	Ki	32	nM	CHEMBL_ACT_2949458
Q9D6N1	7.5	Ki	32	nM	CHEMBL_ACT_65537
CA13	7.46	Ki	35	nM	CHEMBL_ACT_13865483
CA12	7.43	Ki	37	nM	CHEMBL_ACT_12712216
CA12	7.43	Ki	37	nM	CHEMBL_ACT_13865484
CA12	7.43	Ki	37	nM	CHEMBL_ACT_1424737
CA12	7.43	Ki	37	nM	CHEMBL_ACT_1425637
CA12	7.43	Ki	37	nM	CHEMBL_ACT_14577861
CA12	7.43	Ki	37	nM	CHEMBL_ACT_1602647
CA12	7.43	Ki	37	nM	CHEMBL_ACT_18217753
CA12	7.43	Ki	37	nM	CHEMBL_ACT_2090968
CA12	7.43	Ki	37	nM	CHEMBL_ACT_2949457
CA12	7.43	Ki	37	nM	CHEMBL_ACT_6256870
CA12	7.43	Ki	37	nM	CHEMBL_ACT_6389206
CA12	7.43	Ki	37	nM	CHEMBL_ACT_8057353
CA7	7.16	Ki	70	nM	CHEMBL_ACT_13865486
CA7	7.16	Ki	70	nM	CHEMBL_ACT_1436552
CA7	7.16	Ki	70	nM	CHEMBL_ACT_2949455
CA2	6.62	Ki	240	nM	CHEMBL_ACT_10946368
CA2	6.62	Ki	240	nM	CHEMBL_ACT_12656009
CA2	6.62	Ki	240	nM	CHEMBL_ACT_12712254
CA9	6.62	Ki	238	nM	CHEMBL_ACT_13865485
CA2	6.62	Ki	240	nM	CHEMBL_ACT_13865491
CA2	6.62	Ki	240	nM	CHEMBL_ACT_13866412
CA2	6.62	Ki	240	nM	CHEMBL_ACT_1436551
CA2	6.62	Ki	240	nM	CHEMBL_ACT_14661431
CA2	6.62	Ki	240	nM	CHEMBL_ACT_15108384
CA2	6.62	Ki	240	nM	CHEMBL_ACT_15143330
CA2	6.62	Ki	240	nM	CHEMBL_ACT_15169414
CA2	6.62	Ki	240	nM	CHEMBL_ACT_15177741
CA2	6.62	Ki	240	nM	CHEMBL_ACT_15674536
CA2	6.62	Ki	240	nM	CHEMBL_ACT_16415147
CA2	6.62	Ki	240	nM	CHEMBL_ACT_16463774
CA2	6.62	Ki	240	nM	CHEMBL_ACT_16478479
CA2	6.62	Ki	240	nM	CHEMBL_ACT_16519957
CA2	6.62	Ki	240	nM	CHEMBL_ACT_16532810
CA2	6.62	Ki	240	nM	CHEMBL_ACT_1655192
CA2	6.62	Ki	240	nM	CHEMBL_ACT_1692927
CA2	6.62	Ki	240	nM	CHEMBL_ACT_1708323
CA2	6.62	Ki	240	nM	CHEMBL_ACT_17997722
CA2	6.62	Ki	240	nM	CHEMBL_ACT_1804119
CA9	6.62	Ki	238	nM	CHEMBL_ACT_1804128
CA2	6.62	Ki	240	nM	CHEMBL_ACT_18160085
CA2	6.62	Ki	240	nM	CHEMBL_ACT_18217717
CA2	6.62	Ki	240	nM	CHEMBL_ACT_19413149
CA2	6.62	Ki	240	nM	CHEMBL_ACT_2090940
CA2	6.62	Ki	240	nM	CHEMBL_ACT_2421880
CA2	6.62	Ki	240	nM	CHEMBL_ACT_2494402
CA2	6.62	Ki	240	nM	CHEMBL_ACT_2495896
CA9	6.62	Ki	238	nM	CHEMBL_ACT_2495898
CA2	6.62	Ki	240	nM	CHEMBL_ACT_2508827
CA2	6.62	Ki	240	nM	CHEMBL_ACT_2684109
CA2	6.62	Ki	240	nM	CHEMBL_ACT_2917339
CA2	6.62	Ki	240	nM	CHEMBL_ACT_2943473
CA2	6.62	Ki	240	nM	CHEMBL_ACT_2949449
CA9	6.62	Ki	238	nM	CHEMBL_ACT_2949456
CA2	6.62	Ki	240	nM	CHEMBL_ACT_3250285
CA2	6.62	Ki	240	nM	CHEMBL_ACT_3400253
CA2	6.62	Ki	240	nM	CHEMBL_ACT_5121747
CA2	6.62	Ki	240	nM	CHEMBL_ACT_5131521
CA2	6.62	Ki	240	nM	CHEMBL_ACT_5233748
CA2	6.62	Ki	240	nM	CHEMBL_ACT_5307586
CA2	6.62	Ki	240	nM	CHEMBL_ACT_6256883
CA2	6.62	Ki	240	nM	CHEMBL_ACT_6320685
CA2	6.62	Ki	240	nM	CHEMBL_ACT_6389172
CA2	6.62	Ki	240	nM	CHEMBL_ACT_8024597
CA2	6.62	Ki	240	nM	CHEMBL_ACT_8056671
CA2	6.62	Ki	240	nM	CHEMBL_ACT_8061130
P40881	6.6	Ki	250	nM	CHEMBL_ACT_1461360
CA2	6.59	IC50	256	nM	CHEMBL_ACT_23172303
CA2	6.58	IC50	260	nM	CHEMBL_ACT_13393748
CA9	6.54	IC50	290	nM	CHEMBL_ACT_13393728
CA9	6.53	Ki	294	nM	CHEMBL_ACT_102956
CA9	6.53	Ki	294	nM	CHEMBL_ACT_12712235
CA9	6.53	Ki	294	nM	CHEMBL_ACT_1424736
CA9	6.53	Ki	294	nM	CHEMBL_ACT_1435031
CA9	6.53	Ki	294	nM	CHEMBL_ACT_1455358
CA9	6.53	Ki	294	nM	CHEMBL_ACT_14577846
CA9	6.53	Ki	294	nM	CHEMBL_ACT_1492199
CA9	6.53	Ki	294	nM	CHEMBL_ACT_1519904
CA9	6.53	Ki	294	nM	CHEMBL_ACT_1602646
CA9	6.53	Ki	294	nM	CHEMBL_ACT_18217735
CA9	6.53	Ki	294	nM	CHEMBL_ACT_2090954
CA9	6.53	IC50	298	nM	CHEMBL_ACT_23172309
CA9	6.53	Ki	294	nM	CHEMBL_ACT_438659
CA9	6.53	Ki	294	nM	CHEMBL_ACT_599111
CA9	6.53	Ki	294	nM	CHEMBL_ACT_6256857
CA9	6.53	Ki	294	nM	CHEMBL_ACT_6389189
CA9	6.53	Ki	294	nM	CHEMBL_ACT_65536
CA9	6.53	Ki	294	nM	CHEMBL_ACT_8057316
CA2	6.53	Ki	296	nM	CHEMBL_ACT_8061149
CA2	6.52	Ki	300	nM	CHEMBL_ACT_1028755
CA2	6.52	Ki	300	nM	CHEMBL_ACT_1092395
CA2	6.52	Ki	300	nM	CHEMBL_ACT_1249527
CA2	6.52	Ki	300	nM	CHEMBL_ACT_1261857
CA2	6.52	Ki	300	nM	CHEMBL_ACT_13286758
CA2	6.52	Ki	300	nM	CHEMBL_ACT_1425636
CA2	6.52	Ki	300	nM	CHEMBL_ACT_1435030
CA2	6.52	Ki	300	nM	CHEMBL_ACT_1437795

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
bacterial infectious disease	4	MONDO:0005113	EFO:0000771

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of CPIC Guideline for aminosalicylic acid, chloramphenicol,	CPIC	G6PD

PharmGKB also curates 0 clinical and 2 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).