Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H10N2O2S.ClH |
| Molecular Weight | 222.692 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NCC1=CC=C(C=C1)S(N)(=O)=O
InChI
InChIKey=SIACJRVYIPXFKS-UHFFFAOYSA-N
InChI=1S/C7H10N2O2S.ClH/c8-5-6-1-3-7(4-2-6)12(9,10)11;/h1-4H,5,8H2,(H2,9,10,11);1H
DescriptionCurator'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
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 |
|---|---|---|---|
Target ID: CHEMBL261 |
25.0 µM [Ki] | ||
Target ID: CHEMBL205 |
17.1 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | SULFAMYLON Approved UseSULFAMYLON® 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 Date1969 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
197 μg/mL |
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 |
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 |
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 |
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: Page: p.1447 |
unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: Page: p.1447 |
Other AEs: Pain, Pain... Other AEs: Pain (grade 3, 58%) Sources: Page: p.1447Pain (grade 2, 33%) Pain (grade 1, 8%) |
5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: Page: p.1447 |
unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: Page: p.1447 |
Other AEs: Pain, Pain... Other AEs: Pain (grade 3, 12.5%) Sources: Page: p.1447Pain (grade 2, 33%) Pain (grade 1, 46%) |
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: Page: p.1447 |
unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: 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: Page: p.1447 |
unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: 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: Page: p.1447 |
unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: Page: p.1447 |
| Pain | grade 1, 46% | 5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: Page: p.1447 |
unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: Page: p.1447 |
| Pain | grade 2, 33% | 5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: Page: p.1447 |
unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: Page: p.1447 |
| Pain | grade 3, 12.5% | 5 % single, topical Recommended Dose: 5 % Route: topical Route: single Dose: 5 % Sources: Page: p.1447 |
unhealthy, 9+ n = 24 Health Status: unhealthy Condition: burns Age Group: 9+ Sex: M+F Population Size: 24 Sources: Page: p.1447 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Carbonic anhydrase inhibitors: synthesis of water soluble sulfonamides incorporating a 4-sulfamoylphenylmethylthiourea scaffold, with potent intraocular pressure lowering properties. | 2002 Oct |
|
| Dressings for burn injury in a military conflict--change of practice based on current evidence. | 2002 Sep |
|
| Silver-sulfadiazine eschar pigmentation mimics invasive wound infection: a case report. | 2003 May-Jun |
|
| Survival benefit conferred by topical antimicrobial preparations in burn patients: a historical perspective. | 2004 Apr |
|
| Photosystem II associated carbonic anhydrase activity in higher plants is situated in core complex. | 2004 Nov 5 |
|
| 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 |
|
| Wound healing of cutaneous sulfur mustard injuries: strategies for the development of improved therapies. | 2005 Jan 5 |
|
| Comparison of battlefield-expedient topical antimicrobial agents for the prevention of burn wound sepsis in a rat model. | 2005 Jul-Aug |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Nanocrystalline silver dressings in wound management: a review. | 2006 |
|
| Adjuvant dressing for negative pressure wound therapy in burns. | 2006 Jan |
|
| Vibrational analyses of sulfamoyl halides NH2SO2X (X is F, Cl and Br). | 2006 Oct |
|
| Allergic contact dermatitis to mafenide acetate: a case series and review of the literature. | 2007 Aug |
|
| Controlling methicillin resistant Staphyloccocus aureus and Pseudomonas aeruginosa wound infections with a novel biomaterial. | 2007 Jul-Aug |
|
| Effects of commonly used topical antimicrobial agents on Acinetobacter baumannii: an in vitro study. | 2008 Jan |
|
| Comparison of therapeutic antibiotic treatments on tissue-engineered human skin substitutes. | 2008 May |
|
| Highly antibiotic-resistant Acinetobacter baumannii clinical isolates are killed by the green tea polyphenol (-)-epigallocatechin-3-gallate (EGCG). | 2009 Apr |
|
| A prospective double-blinded comparative analysis of framycetin and silver sulphadiazine as topical agents for burns: a pilot study. | 2009 Aug |
|
| Are topical antimicrobials effective against bacteria that are highly resistant to systemic antibiotics? | 2009 Jan-Feb |
|
| Understanding and managing burn pain: Part 2. | 2009 May |
|
| Detecting extracellular carbonic anhydrase activity using membrane inlet mass spectrometry. | 2010 Aug |
|
| Activity of topical antimicrobial agents against multidrug-resistant bacteria recovered from burn patients. | 2010 Dec |
|
| Prophylactic antibiotics for burns patients: systematic review and meta-analysis. | 2010 Feb 15 |
|
| A review of the applications of the hydrofiber dressing with silver (Aquacel Ag) in wound care. | 2010 Feb 2 |
|
| Special considerations in paediatric burn patients. | 2010 Sep |
|
| Fungal infections in burns: Diagnosis and management. | 2010 Sep |
|
| Topical nanoemulsion therapy reduces bacterial wound infection and inflammation after burn injury. | 2010 Sep |
|
| Downstream gene activation of the receptor ALX by the agonist annexin A1. | 2010 Sep 17 |
|
| Comparison between topical honey and mafenide acetate in treatment of burn wounds. | 2011 Sep 30 |
Sample Use Guides
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
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.
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NCI_THESAURUS |
C29577
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m6982
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138-37-4
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67313
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CHEMBL419
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205-325-3
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3527
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3J751V0284
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SUB02999MIG
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C76107
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100000086175
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DTXSID6045296
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ACTIVE MOIETY
SUBSTANCE RECORD
