mafenide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
anti-infectives, sulfonamides 1624 138-39-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mafenide
  • 4-(Aminosulfonyl)benzylamine
  • 4-Homosulfanilamide
  • 4-Sulfamoylbenzylamine
  • ambamide
  • benzamsulfonamide
  • homosulfanilamide
  • malfamin
  • maphenid
  • maphenide
  • p-Sulfamoylbenzylamine
  • mafenide acetate
  • m,afenide hydrochloride
  • m,afenide HCl
A sulfonamide that inhibits the enzyme CARBONIC ANHYDRASE and is used as a topical anti-bacterial agent, especially in burn therapy.
  • Molecular weight: 186.23
  • Formula: C7H10N2O2S
  • CLOGP: -0.74
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 86.18
  • ALOGS: -1.56
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
Jan. 24, 1969 FDA MYLAN INSTITUTIONAL

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC D06BA03 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
CHEMOTHERAPEUTICS FOR TOPICAL USE
Sulfonamides
FDA EPC N0000175511 Methylated Sulfonamide Antibacterial
FDA Chemical/Ingredient N0000175512 Methylated Sulfonamides
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000891 Anti-Infective Agents, Local
MeSH PA D002257 Carbonic Anhydrase Inhibitors
MeSH PA D004791 Enzyme Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Burn Wound Infections indication
Disorder of lung contraindication 19829001 DOID:850
Metabolic acidosis contraindication 59455009
Kidney disease contraindication 90708001 DOID:557
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.03 acidic
pKa2 8.54 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 4.56 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.77 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 5.49 CHEMBL
Carbonic anhydrase 7 Enzyme Ki 7.12 CHEMBL
Carbonic anhydrase 12 Enzyme Ki 9.52 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 6.99 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 5.55 CHEMBL
Carbonic anhydrase 1 Enzyme Ki 6.77 CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme Ki 4.91 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 5.32 CHEMBL
Dihydropteroate synthase Enzyme INHIBITOR CHEMBL CHEMBL
Delta carbonic anhydrase Unclassified Ki 6.37 CHEMBL
Carbonic anhydrase Enzyme Ki 6.36 CHEMBL
Carbonic anhydrase Enzyme Ki 4.55 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 7.39 CHEMBL
Carbonic anhydrase Enzyme Ki 6.08 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 6.01 CHEMBL
Alpha carbonic anhydrase Unclassified Ki 7.08 CHEMBL
Probable transmembrane carbonic anhydrase (Carbonate dehydratase) (Carbonic dehydratase); Transmembrane carbonic anhydrase Enzyme Ki 5.13 CHEMBL
Astrosclerin-3 Unclassified Ki 6.01 CHEMBL
Carbonic anhydrase Enzyme Ki 6.77 CHEMBL
Carbonic anhydrase Enzyme Ki 6.46 CHEMBL
Beta-carbonic anhydrase 1 Enzyme Ki 5.06 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 4.51 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 5.55 CHEMBL
Carbonic anhydrase Unclassified Ki 4.87 CHEMBL
Carbonic anhydrase Unclassified Ki 6.29 CHEMBL
Carbonic anhydrase Enzyme Ki 6.06 CHEMBL

External reference:

IDSource
4018256 VUID
N0000146586 NUI
C0024452 UMLSCUI
D01166 KEGG_DRUG
58447S8P4L UNII
2393 INN_ID
84737005 SNOMEDCT_US
4018256 VANDF
6572 RXNORM
372876009 SNOMEDCT_US
004960 NDDF
3998 PUBCHEM_CID
CHEBI:6633 CHEBI
CHEMBL419 ChEMBL_ID
13009-99-9 SECONDARY_CAS_RN
DB06795 DRUGBANK_ID
CHEMBL1201161 ChEMBL_ID
D008272 MESH_DESCRIPTOR_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Mafenide acetate HUMAN PRESCRIPTION DRUG LABEL 1 49884-902 POWDER, FOR SOLUTION 50 g TOPICAL ANDA 11 sections
Mafenide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 50742-310 POWDER, FOR SOLUTION 50 g TOPICAL ANDA 12 sections
Sulfamylon HUMAN PRESCRIPTION DRUG LABEL 1 51079-623 CREAM 85 mg TOPICAL NDA 10 sections
Sulfamylon HUMAN PRESCRIPTION DRUG LABEL 1 51079-624 POWDER, FOR SOLUTION 50 g TOPICAL NDA 11 sections