MAFENIDE

First approved in 1948

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H10N2O2S
Molecular Weight	186.231
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCC1=CC=C(C=C1)S(N)(=O)=O

InChI

InChIKey=TYMRLRRVMHJFTF-UHFFFAOYSA-N

InChI=1S/C7H10N2O2S/c8-5-6-1-3-7(4-2-6)12(9,10)11/h1-4H,5,8H2,(H2,9,10,11)

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/19832lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/4948236 | http://www.rxlist.com/sulfamylon-cream-drug.htm | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=570ce479-d902-4394-bbae-41dfe16c5485

Mafenide is a sulfonamide-type medication used as an antibiotic. It is indicated for use as an adjunctive topical antimicrobial agent to control bacterial infection when used under moist dressings over meshed autografts on excised burn wounds. Mafenide is not antagonized by pABA, serum, pus or tissue exudates, and there is no correlation between bacterial sensitivities to mafenide and to the sulfonamides. A single case of bone marrow depression and a single case of an acute attack of porphyria have been reported following therapy with mafenide acetate. Fatal hemolytic anemia with disseminated intravascular coagulation, presumably related to a glucose-6-phosphate dehydrogenase deficiency, has been reported following therapy with mafenide acetate. Other adverse reactions are: pain or burning sensation, rash and pruritis, erythema, skin maceration from prolonged wet dressings, facial edema, swelling, hives, blisters, eosinophilia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Carbonic anhydrase I 62 Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22974493	Inhibitor 8297		25.0 µM [Ki]
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22974493	Inhibitor 8297		17.1 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Burn 40 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/19832lbl.pdf	Primary		Approved 8429	SULFAMYLON Approved Use SULFAMYLON® For 5% Topical Solution is indicated for use as an adjunctive topical antimicrobial agent to control bacterial infection when used under moist dressings over meshed autografts on excised burn wounds. Launch Date 1969

C_max

Value	Dose	Analyte	Population
197 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/19832lbl.pdf	77 g single, topical dose: 77 g route of administration: Topical experiment type: SINGLE co-administered:	MAFENIDE blood	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
26 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/19832lbl.pdf	14 g single, topical dose: 14 g route of administration: Topical experiment type: SINGLE co-administered:	MAFENIDE blood	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
10 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/19832lbl.pdf	14 g single, topical dose: 14 g route of administration: Topical experiment type: SINGLE co-administered:	CARZENIDE blood	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
340 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1998/19832lbl.pdf	77 g single, topical dose: 77 g route of administration: Topical experiment type: SINGLE co-administered:	CARZENIDE blood	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
11.2 % single, topical Highest studied dose Dose: 11.2 % Route: topical Route: single Dose: 11.2 % Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447	unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447	Other AEs: Pain, Pain... Other AEs: Pain (grade 3, 58%) Pain (grade 2, 33%) Pain (grade 1, 8%) Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447
5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447	unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447	Other AEs: Pain, Pain... Other AEs: Pain (grade 3, 12.5%) Pain (grade 2, 33%) Pain (grade 1, 46%) Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447

AEs

AE	Significance	Dose	Population
Pain	grade 1, 8%	11.2 % single, topical Highest studied dose Dose: 11.2 % Route: topical Route: single Dose: 11.2 % Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447	unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447
Pain	grade 2, 33%	11.2 % single, topical Highest studied dose Dose: 11.2 % Route: topical Route: single Dose: 11.2 % Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447	unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447
Pain	grade 3, 58%	11.2 % single, topical Highest studied dose Dose: 11.2 % Route: topical Route: single Dose: 11.2 % Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447	unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447
Pain	grade 1, 46%	5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447	unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447
Pain	grade 2, 33%	5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447	unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447
Pain	grade 3, 12.5%	5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447	unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/981 Page: p.1447

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY456202	https://www.001chemical.com/chem/138-39-6
AA Blocks	AA0017QF	http://www.aablocks.com/goods/Goods/detail?id=AA0017QF
AEchem Scientific Corp., USA	AE1-017732	http://www.aechemsc.com/info_products/AE1-017732.php
AK Scientific, Inc. (AKSCI)	W3020	http://www.aksci.com/item_detail.php?cat=W3020
Acadechem	ACDS-033172	http://www.acadechemical.com/product/107871
Achemtek	0104-020837	http://www.achemtek.com/13009-99-9
Achemtek	0104-029365	http://www.achemtek.com/138-39-6
Alfa Chemistry	138-39-6	https://www.alfa-chemistry.com/4-aminomethyl-benzenesulfonamide-cas-138-39-6-item-290151.htm
Alinda	ALBB-014887	http://alinda.ru/finechem_en_.html?i=ALBB-014887
Allbio Pharm Co., Ltd	AD10338	http://www.allbiopharm.com/product/n/AD10338
Ambinter	Amb1655464	http://www.ambinter.com/reference/1655464
Angel Pharmatech	AG185879	http://www.angelpharmatech.com/138-39-6.html
Anward	ANW-51240	http://www.anward.com/pro_result/37691
Ark Pharm	AK-22175	http://www.arkpharminc.com/products/138-39-6.html
Aronis	ARONIS24095	http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=1222
Aurora Fine Chemicals LLC	A00.740.600	http://online.aurorafinechemicals.com/info?ID=A00.740.600
Aurora Fine Chemicals LLC	K00.351.100	http://online.aurorafinechemicals.com/info?ID=K00.351.100
Aurum Pharmatech LLC	S-2285	http://www.Aurumpharmatech.com/Product/ProductDetails/S_2285
BLD Pharm	BD91007	http://www.bldpharm.com/products/138-39-6.html
BioCrick	BCC5237	http://www.biocrick.com/Mafenide-BCC5237.html
CSNpharm	CSN19416	https://www.csnpharm.com/products/mafenide.html
Chem Scene	CS-2838	http://www.chemscene.com/138-39-6.html
ChemMol	80101229	http://www.chemmol.com/chemmol/80101229.html
ChemReagents	80081027	http://www.chemreagents.com/Product/Product.asp?ProductID=80081027
Chemspace	CSSB00000737900	https://chem-space.com/CSSB00000737900
Debye Scientific	DB-002011	http://www.debyesci.com/DB-002011.html
Finetech	FT-0682668	http://www.finetechnology-ind.com/prod/detail/pub/138-39-6.html
Glentham Life Sciences	GK6511	http://www.glentham.com/products/product/GK6511/
Hairui	HR147397	http://www.hairuichem.com/en/product/138-39-6.html
Lab Network	LN00159775	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00159775
Matrix Scientific	58351	https://www.matrixscientific.com/058351.html
MedChem Express	HY-B0614	https://www.medchemexpress.com/mafenide.html
Molcore	MC456202	https://www.molcore.com/product/138-39-6
MuseChem	I001481	https://www.musechem.com/product/I001481.html
Nextpeptide	NP183955	http://www.nextpeptide.com/138-39-6.html
OChem	10843	http://www.ocheminc.com/index.php?act=psearch&pid=009M999
Oakwood	79312	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=64486&ExtHyperLink=1
Sinfoo Biotech	S017515	http://www.sinfoobiotech.com/product/1020913
Smolecule	S534376	http://www.smolecule.com/products/s534376
THE BioTek	bt-274677	https://www.thebiotek.com/product/inhibitors/bt-274677
abcr GmbH	AB523334	http://www.abcr.com/shop/en/AB523334
eNovation Chemicals	K50765	https://www.enovationchem.com/ProductDetails.asp?ProductID=K50765
iChemical	EBD52882	http://www.ichemical.com/products/138-39-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-1669556404	https://mcule.com/MCULE-1669556404/

PubMed

Title	Date	PubMed
Antifungal activity of Ag(I) and Zn(II) complexes of aminobenzolamide (5-sulfanilylamido-1,3,4-thiadiazole-2-sulfonamide) derivatives.	2000	11140608
Topical mafenide hydrochloride aqueous spray in initial management of massive contaminated wounds with devitalized tissue.	2001 Jul-Sep	11875802
An in vivo comparison of topical agents on wound repair.	2001 Sep 1	11698839
Mafenide acetate allergy presenting as recurrent chondritis.	2002 Feb	11910229
Using mafenide acetate in acute and chronic wounds.	2002 Sep	12298221
Photosystem II associated carbonic anhydrase activity in higher plants is situated in core complex.	2004 Nov 5	15527804
Methylamine but not mafenide mimics insulin-like activity of the semicarbazide-sensitive amine oxidase-substrate benzylamine on glucose tolerance and on human adipocyte metabolism.	2005 Dec	16135411
The potential benefit of 5% Sulfamylon Solution in the treatment of Acinetobacter baumannii-contaminated traumatic war wounds.	2005 Feb 22	16921408
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Managing extracavitary prosthetic vascular graft infections: a pathway to success.	2006 Dec	17122558
Hypochlorous acid as a potential wound care agent: part I. Stabilized hypochlorous acid: a component of the inorganic armamentarium of innate immunity.	2007 Apr 11	17492050
Allergic contact dermatitis to mafenide acetate: a case series and review of the literature.	2007 Aug	17763614
Effects of commonly used topical antimicrobial agents on Acinetobacter baumannii: an in vitro study.	2008 Jan	18251335
Are topical antimicrobials effective against bacteria that are highly resistant to systemic antibiotics?	2009 Jan-Feb	19060725
Nanofibers offer alternative ways to the treatment of skin infections.	2010	20798871
Systemic absorption of amphotericin B with topical 5% mafenide acetate/amphotericin B solution for grafted burn wounds: is it clinically relevant?	2010 Feb	19481350
Downstream gene activation of the receptor ALX by the agonist annexin A1.	2010 Sep 17	20862244
The diversity of wound presentation associated with freon contact frostbite injury.	2010 Sep-Oct	20661149
Comparison between topical honey and mafenide acetate in treatment of burn wounds.	2011 Sep 30	22396671

Patents

Sample Use Guides

In Vivo Use Guide

The grafted area should be covered with one layer of fine mesh gauze. An eight-ply burn dressing should be cut to the size of the graft and wetted with Mafenide 5% solution using an irrigation syringe and/or irrigation tubing until leaking is noticeable.

Route of Administration: Topical

In Vitro Use Guide

The action of mafenide is primarily bacteriostatic and it has been demonstrated to be active in vitro in concentrations of 5 mg/ml or less against a variety of Gram-positive and Gram-negative organisms. Ps. aeruginosa is the most sensitive; with 32 of 41 strains the minimum inhibitory concentration (MIC) was 0.2 to 1 mg/ml and with the remaining 9 strains the MIC was 2 to 5 mg/ml. In other studies the mean MIC was 0.31 mg/ml (range 0.075 to 5 mg/ml) for 55 strains of Ps. aeruginosa isolated from clinical material (Thompson et al., 1969) and 1.25 mg/ml for 7 strains of Ps. Aeruginosa.

Name

Type

Language

MAFENIDE

Official Name

English

NSC-34632

Code

English

MAFENIDE [VANDF]

Common Name

English

4-(AMINOMETHYL)BENZENESULFONAMIDE

Systematic Name

English

BENZENESULFONAMIDE, 4-(AMINOMETHYL)-

Systematic Name

English

Mafenide [WHO-DD]

Common Name

English

MAFENIDE [USAN]

Common Name

English

.ALPHA.-AMINO-P-TOLUENESULFONAMIDE

Common Name

English

MAFENIDE [MI]

Common Name

English

mafenide [INN]

Common Name

English

MAFENIDE [MART.]

Common Name

English

D06BA03

Code

English

Classification Tree Code System Code

NDF-RT

N0000175512