Compound Detail

CHEMBL419

MAFENIDE

💊 Approved Drug

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💊 Approved Drug

NCc1ccc(S(N)(=O)=O)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL419
Name	MAFENIDE
Phase	Approved
Structure Type	MOL
InChI Key	TYMRLRRVMHJFTF-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

4-homosulfanilamide D06BA03 Mafenida Mafenide NSC-34632 Sulfamylon

Targets

207

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

186.2

MW (Da)

-0.21

ALogP

HBA

HBD

86.2

PSA (Å²)

0.67

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1969
Availability	Prescription
Chirality	Achiral

Routes of Administration

Topical

Flags

Natural Product

USAN Year

1967

Extended Properties

Molecular Formula	C7H10N2O2S
MW	186.24
Aromatic Rings	1
Heavy Atoms	12
NP-Likeness	-1.14

Indications

Osteomyelitis

ATC Classification

D06BA03

mafenide

Level 1: DERMATOLOGICALS

Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE

Activity Summary

Ki 205 meas. best 9.52

IC50 2 meas. best 5.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Carbonic anhydrase 12 CHEMBL3242	Ki	9.52	9.52	0.3	4
Carbonic anhydrase 13 CHEMBL2186	Ki	7.39	7.39	41.0	2
Carbonic anhydrase 7 CHEMBL2326	Ki	7.12	7.12	75.0	1
Unchecked CHEMBL612545	Ki	7.09	5.8885	80.6	41
Alpha carbonic anhydrase CHEMBL1075028	Ki	7.08	7.08	82.5	2
Carbonic anhydrase 9 CHEMBL3594	Ki	6.99	6.99	103.0	10
Carbonic anhydrase 2 CHEMBL205	Ki	6.77	6.7198	170.0	51
Carbonic anhydrase, alpha family CHEMBL3621035	Ki	6.7	6.7	202.0	1
Carbonic anhydrase CHEMBL3932	Ki	6.46	5.765	350.0	2
Carbonate dehydratase CHEMBL3745586	Ki	6.46	6.46	350.0	1
Delta carbonic anhydrase CHEMBL3097982	Ki	6.37	6.37	424.0	1
Carbonic anhydrase CHEMBL5931	Ki	6.36	6.36	433.0	1
Carbonic anhydrase CHEMBL1649055	Ki	6.29	6.29	508.0	1
Carbonic anhydrase CHEMBL4211	Ki	6.08	6.07	830.0	2
Carbonic anhydrase CHEMBL6185	Ki	6.06	6.06	865.0	1
Carbonic anhydrase 15 CHEMBL5973	Ki	6.01	6.01	970.0	1
Astrosclerin-3 CHEMBL1944499	Ki	6.01	6.01	973.0	1
Carbonic anhydrase CHEMBL5337	Ki	5.96	5.96	1109.0	2
Carbonic anhydrase 4 CHEMBL281	Ki	5.55	5.55	2800.0	8
Carbonic anhydrase 4 CHEMBL3729	Ki	5.55	5.31	2800.0	2
Carbonic anhydrase 14 CHEMBL3510	Ki	5.5	5.5	3200.0	2
Carbonic anhydrase 2 CHEMBL205	IC50	5.4	5.4	4000.0	1
Carbonic anhydrase 6 CHEMBL3025	Ki	5.32	5.32	4800.0	3
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) CHEMBL5767	Ki	5.13	5.13	7330.0	1
Beta-carbonic anhydrase 1 CHEMBL5631	Ki	5.06	5.06	8690.0	2
Carbonic anhydrase 5B, mitochondrial CHEMBL3969	Ki	4.91	4.91	12300.0	1
AGAP002992-PA CHEMBL3399914	Ki	4.87	4.87	13600.0	1
Carbonic anhydrase 2 CHEMBL1697676	Ki	4.73	4.73	18490.0	1
Carbonic anhydrase 1 CHEMBL261	Ki	4.6	4.5952	25000.0	46
Carbonic anhydrase 5A, mitochondrial CHEMBL4789	IC50	4.56	4.56	27600.0	1
Carbonic anhydrase 5A, mitochondrial CHEMBL4789	Ki	4.56	4.56	27600.0	1
Carbonic anhydrase CHEMBL3926	Ki	4.54	4.54	28500.0	1
Carbonic anhydrase 2 CHEMBL6068	Ki	4.51	4.51	30700.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Carbonic anhydrase 12	Ki	=	0.3	nM	9.52	Inhibition of human recombinant CA12 by stopped flow CO2 hydration assay	20201556
Carbonic anhydrase 12	Ki	=	0.3	nM	9.52	Inhibition of human carbonic anhydrase 12 catalytic domain preincubated for 15 m...	22370338
Carbonic anhydrase 12	Ki	=	0.3	nM	9.52	Inhibitory constant against catalytic domain of human carbonic anhydrase XII	16039848
Carbonic anhydrase 12	Ki	=	0.3	nM	9.52	Ki value against human carbonic anhydrase XII (hCA XII)	15686894
Carbonic anhydrase 13	Ki	=	41.0	nM	7.39	Inhibitory activity against murine carbonic anhydrase XIII (mCA XIII) by using C...	15203157
Carbonic anhydrase 13	Ki	=	41.0	nM	7.39	Ki value against murine carbonic anhydrase XIII	15686895
Carbonic anhydrase 7	Ki	=	75.0	nM	7.12	Ki value against human carbonic anhydrase VII	15686895
Unchecked	Ki	=	80.6	nM	7.09	Inhibition of recombinant Vibrio cholerae gamma-carbonic anhydrase preincubated ...	26972117
Unchecked	Ki	=	80.6	nM	7.09	Inhibition of Vibrio cholerae Gamma-carbonic anhydrase assessed as reduction in ...	28025002
Alpha carbonic anhydrase	Ki	=	82.5	nM	7.08	Inhibition of Stylophora pistillata carbonic anhydrase by stopped-flow CO2 hydra...	21208801
Alpha carbonic anhydrase	Ki	=	82.5	nM	7.08	Inhibition of cloned Stylophora pistillata alpha-CA expressed in human HEK293 ce...	19520577
Unchecked	Ki	=	93.6	nM	7.03	Inhibition of recombinant Enterobacter sp. B13 beta carbonic anhydrase incubated...	26920803
Carbonic anhydrase 9	Ki	=	103.0	nM	6.99	Inhibitory constant against human Carbonic anhydrase IX	15837325
Carbonic anhydrase 9	Ki	=	103.0	nM	6.99	Inhibition of human recombinant carbonic anhydrase 9 catalytic domain by stopped...	19193158
Carbonic anhydrase 9	Ki	=	103.0	nM	6.99	Inhibitory activity against human carbonic anhydrase IX expressed in Escherichia...	15454239
Carbonic anhydrase 9	Ki	=	103.0	nM	6.99	Inhibition of catalytic domain of human recombinant CA IX	17228881
Carbonic anhydrase 9	Ki	=	103.0	nM	6.99	Inhibitory activity against human cloned carbonic anhydrase isozyme IX, by CO2 h...	12643899
Carbonic anhydrase 9	Ki	=	103.0	nM	6.99	Inhibitory constant against catalytic domain of human carbonic anhydrase IX	16039848
Carbonic anhydrase 9	Ki	=	103.0	nM	6.99	Inhibitory activity against human tumor-associated transmembrane carbonic anhydr...	15149691
Carbonic anhydrase 9	Ki	=	103.0	nM	6.99	Inhibitory activity against human carbonic anhydrase IX (hCA IX) by using CO2 hy...	15203157

Literature References

PubMed	DOI	Target Context	# Activities
15369390	10.1021/jm0499211	Unchecked	9
26832216	10.1016/j.bmcl.2016.01.023	Unchecked	4
20201556	10.1021/jm901888x	Unchecked	4
26174556	10.1016/j.bmcl.2015.06.079	Unchecked	3
15546717	10.1016/j.bmcl.2004.09.085	Carbonic anhydrase	3
25129169	10.1016/j.bmc.2014.07.048	Unchecked	3
26972117	10.1016/j.bmcl.2016.03.014	Unchecked	3
24792813	10.1016/j.bmc.2014.04.006	Unchecked	3
25773015	10.1016/j.bmc.2015.02.045	Unchecked	3
17482815	10.1016/j.bmcl.2007.04.063	Unchecked	2
14971907	10.1021/jm031057+	Unchecked	2
26850377	10.1016/j.bmc.2016.01.037	Unchecked	2
21757360	10.1016/j.bmc.2011.06.038	Unchecked	2
22424239	10.1021/jm300203r	Carbonic anhydrase 2	2
21251841	10.1016/j.bmc.2010.12.048	Unchecked	2
24314394	10.1016/j.bmcl.2013.11.021	Unchecked	2
22883029	10.1016/j.bmc.2012.07.024	Unchecked	2
22424239	10.1021/jm300203r	NON-PROTEIN TARGET	2
19846301	10.1016/j.bmcl.2009.10.009	Carbonic anhydrase 2	2
15686931	10.1016/j.bmcl.2004.12.009	Carbonic anhydrase 4	2

Data from ChEMBL 36 via Core Engine