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 8504		25.0 µM [Ki]
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22974493	Inhibitor 8504		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 8583	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
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
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
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	unhealthy, 9+ Health Status: unhealthy Age Group: 9+ Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/981	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
5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/981	unhealthy, 9+ Health Status: unhealthy Age Group: 9+ Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/981	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

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	unhealthy, 9+ Health Status: unhealthy Age Group: 9+ Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/981
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	unhealthy, 9+ Health Status: unhealthy Age Group: 9+ Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/981
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	unhealthy, 9+ Health Status: unhealthy Age Group: 9+ Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/981
Pain	grade 1, 46%	5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/981	unhealthy, 9+ Health Status: unhealthy Age Group: 9+ Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/981
Pain	grade 2, 33%	5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/981	unhealthy, 9+ Health Status: unhealthy Age Group: 9+ Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/981
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	unhealthy, 9+ Health Status: unhealthy Age Group: 9+ Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/981

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
abcr GmbH	AB523334	http://www.abcr.com/shop/en/AB523334
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
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
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
BioCrick	BCC5237	http://www.biocrick.com/Mafenide-BCC5237.html
BLD Pharm	BD91007	http://www.bldpharm.com/products/138-39-6.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
CSNpharm	CSN19416	https://www.csnpharm.com/products/mafenide.html
Debye Scientific	DB-002011	http://www.debyesci.com/DB-002011.html
eNovation Chemicals	K50765	https://www.enovationchem.com/ProductDetails.asp?ProductID=K50765
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
iChemical	EBD52882	http://www.ichemical.com/products/138-39-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00159775	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00159775
Matrix Scientific	58351	https://www.matrixscientific.com/058351.html
mcule	MCULE-1669556404	https://mcule.com/MCULE-1669556404/
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
Oakwood	79312	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=64486&ExtHyperLink=1
OChem	10843	http://www.ocheminc.com/index.php?act=psearch&pid=009M999
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

PubMed

Title	Date	PubMed
Comparison between topical honey and mafenide acetate in treatment of burn wounds.	2011-09-30	22396671
Activity of topical antimicrobial agents against multidrug-resistant bacteria recovered from burn patients.	2010-12	20542641
Downstream gene activation of the receptor ALX by the agonist annexin A1.	2010-09-17	20862244
Special considerations in paediatric burn patients.	2010-09	21321657
Fungal infections in burns: Diagnosis and management.	2010-09	21321655
Fluid management in major burn injuries.	2010-09	21321653
Topical nanoemulsion therapy reduces bacterial wound infection and inflammation after burn injury.	2010-09	20189619
Detecting extracellular carbonic anhydrase activity using membrane inlet mass spectrometry.	2010-08	20417171
The diversity of wound presentation associated with freon contact frostbite injury.	2010-07-28	20661149
Prophylactic antibiotics for burns patients: systematic review and meta-analysis.	2010-02-15	20156911
A review of the applications of the hydrofiber dressing with silver (Aquacel Ag) in wound care.	2010-02-02	20169033
Systemic absorption of amphotericin B with topical 5% mafenide acetate/amphotericin B solution for grafted burn wounds: is it clinically relevant?	2010-02	19481350
Nanofibers offer alternative ways to the treatment of skin infections.	2010	20798871
Antibiotic-eluting bioresorbable composite fibers for wound healing applications: microstructure, drug delivery and mechanical properties.	2009-10	19416766
A prospective double-blinded comparative analysis of framycetin and silver sulphadiazine as topical agents for burns: a pilot study.	2009-08	19443125
The antimicrobial effect of acetic acid--an alternative to common local antiseptics?	2009-08	19286325
Understanding and managing burn pain: Part 2.	2009-05	19411907
Highly antibiotic-resistant Acinetobacter baumannii clinical isolates are killed by the green tea polyphenol (-)-epigallocatechin-3-gallate (EGCG).	2009-04	19431221
The search for an ideal temporary skin substitute: AWBAT.	2009	19279675
Are topical antimicrobials effective against bacteria that are highly resistant to systemic antibiotics?	2008-12-09	19060725
Comparison of therapeutic antibiotic treatments on tissue-engineered human skin substitutes.	2008-05	18439105
Effects of commonly used topical antimicrobial agents on Acinetobacter baumannii: an in vitro study.	2008-01	18251335
Controlling methicillin resistant Staphyloccocus aureus and Pseudomonas aeruginosa wound infections with a novel biomaterial.	2007-08-22	17710602
Allergic contact dermatitis to mafenide acetate: a case series and review of the literature.	2007-08	17763614
Comparative evaluation of silver-containing antimicrobial dressings and drugs.	2007-06	17651227
Hypochlorous acid as a potential wound care agent: part I. Stabilized hypochlorous acid: a component of the inorganic armamentarium of innate immunity.	2007-04-11	17492050
Management of bioburden with a burn gel that targets nociceptors.	2007-04	17444381
Seven years' experience with Integra as a reconstructive tool.	2007-01-11	17211211
Managing extracavitary prosthetic vascular graft infections: a pathway to success.	2006-12	17122558
Vibrational analyses of sulfamoyl halides NH2SO2X (X is F, Cl and Br).	2006-10	16530000
Topical Sulfamylon cream inhibits DNA and protein synthesis in the skin donor site wound.	2006-05	16701096
Adjuvant dressing for negative pressure wound therapy in burns.	2006-01	16528843
Nanocrystalline silver dressings in wound management: a review.	2006	17722278
Methylamine but not mafenide mimics insulin-like activity of the semicarbazide-sensitive amine oxidase-substrate benzylamine on glucose tolerance and on human adipocyte metabolism.	2005-12	16135411
Comparison of battlefield-expedient topical antimicrobial agents for the prevention of burn wound sepsis in a rat model.	2005-07-12	16006845
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
The potential benefit of 5% Sulfamylon Solution in the treatment of Acinetobacter baumannii-contaminated traumatic war wounds.	2005-02-22	16921408
Wound healing of cutaneous sulfur mustard injuries: strategies for the development of improved therapies.	2005-01-05	16921406
Photosystem II associated carbonic anhydrase activity in higher plants is situated in core complex.	2004-11-05	15527804
Exploring the binding mode of semicarbazide-sensitive amine oxidase/VAP-1: identification of novel substrates with insulin-like activity.	2004-09-23	15369390
Survival benefit conferred by topical antimicrobial preparations in burn patients: a historical perspective.	2004-04	15187754
Silver-sulfadiazine eschar pigmentation mimics invasive wound infection: a case report.	2003-06-07	12792235
Carbonic anhydrase inhibitors: synthesis of water soluble sulfonamides incorporating a 4-sulfamoylphenylmethylthiourea scaffold, with potent intraocular pressure lowering properties.	2002-10	12683750
Dressings for burn injury in a military conflict--change of practice based on current evidence.	2002-09	12469424
Using mafenide acetate in acute and chronic wounds.	2002-09	12298221
Comparative evaluation of topical antiseptic/antimicrobial treatment on aspects of wound repair in the porcine model.	2002-09	12298220
Topical mafenide hydrochloride aqueous spray in initial management of massive contaminated wounds with devitalized tissue.	2002-03-06	11875802
Mafenide acetate allergy presenting as recurrent chondritis.	2002-02	11910229
An in vivo comparison of topical agents on wound repair.	2001-09-01	11698839
Off-label drug use in WOC nursing: issues related to use of mafenide acetate to treat infected chronic wounds.	2001-09	11557929

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

D06BA03

Preferred 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

Classification Tree Code System Code

NDF-RT

N0000175512