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

Stem definitionDrug idCAS RN
anti-infectives, sulfonamides 2521 63-74-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sulfanilamide
  • 4-Aminobenzene-1-sulfonamide
  • 4-Aminobenzenesulfonamide
  • sulfamidyl
  • sulfamine
  • sulfana
  • sulfanalone
  • sulfanidyl
  • sulfonamide
  • sulfonylamide
  • sulphanilamide
  • sulphonamide
Sulfanilamide has been a useful ingredient of vaginal formulations for about four decades. It blocks certain metabolic processes essential for the growth of susceptible bacteria.
  • Molecular weight: 172.20
  • Formula: C6H8N2O2S
  • CLOGP: -0.57
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 86.18
  • ALOGS: -1.22
  • ROTB: 1

  • Status: OFM

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

Drug dosage:

None

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
June 5, 1965 FDA MEDA PHARMS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 133.32 77.39 45 153 265197 53083671

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC D06BA05 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
CHEMOTHERAPEUTICS FOR TOPICAL USE
Sulfonamides
ATC J01EB06 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Short-acting sulfonamides
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:23018 carbonate dehydratase inhibitor
CHEBI has role CHEBI:33282 antibacterials
CHEBI has role CHEBI:88188 allergenic drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Vulvovaginitis indication 53277000 DOID:2273
Candidal vulvovaginitis indication 72605008 DOID:2272
Kidney disease contraindication 90708001 DOID:557
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Disease of liver contraindication 235856003 DOID:409
Porphyria contraindication 418470004

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.33 acidic
pKa2 2.14 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 1 Enzyme Ki 6.52 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 5.52 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 6.62 CHEMBL
Carbonic anhydrase 12 Enzyme Ki 7.43 CHEMBL
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 4.49 CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme Ki 5.44 CHEMBL
Carbonic anhydrase 7 Enzyme Ki 7.15 CHEMBL
Carbonic anhydrase 3 Enzyme Ki 6.01 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 6.03 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 5.27 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 7.49 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.62 CHEMBL
Dihydropteroate synthase Enzyme INHIBITOR CHEMBL CHEMBL
Carbonic anhydrase Enzyme Ki 6.37 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 7.49 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 5.52 CHEMBL
Carbonic anhydrase Enzyme Ki 6.60 CHEMBL
Carbonic anhydrase Enzyme Ki 4.24 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 5.02 CHEMBL
Carbonic anhydrase Enzyme Ki 4.73 CHEMBL
Carbonic anhydrase Enzyme Ki 6.62 CHEMBL
Probable transmembrane carbonic anhydrase (Carbonate dehydratase) (Carbonic dehydratase); Transmembrane carbonic anhydrase Enzyme Ki 5.20 CHEMBL
Carbonic anhydrase Enzyme Ki 5.10 CHEMBL
Alpha carbonic anhydrase Enzyme Ki 6.44 CHEMBL
Carbonic anhydrase Enzyme Ki 6.52 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.11 CHEMBL
Astrosclerin-3 Enzyme Ki 5.11 CHEMBL
Beta-carbonic anhydrase 1 Enzyme Ki 5.03 CHEMBL
Delta carbonic anhydrase Unclassified Ki 6.74 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 4.53 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.07 CHEMBL
Carbonic anhydrase Enzyme Ki 6.06 CHEMBL
Carbonic anhydrase, alpha family Unclassified Ki 6.20 CHEMBL
Carbonate dehydratase Enzyme Ki 6.19 CHEMBL

External reference:

IDSource
4018615 VUID
N0000146928 NUI
D08543 KEGG_DRUG
4018615 VANDF
C0038702 UMLSCUI
CHEBI:45373 CHEBI
SAN PDB_CHEM_ID
CHEMBL21 ChEMBL_ID
DB00259 DRUGBANK_ID
D000077145 MESH_DESCRIPTOR_UI
5333 PUBCHEM_CID
426 INN_ID
21240MF57M UNII
10184 RXNORM
2053 MMSL
5527 MMSL
002833 NDDF
386569003 SNOMEDCT_US
387406002 SNOMEDCT_US
56436005 SNOMEDCT_US
763875007 SNOMEDCT_US

Pharmaceutical products:

None