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

Stem definitionDrug idCAS RN
anti-infectives, sulfonamides 2529 127-69-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sulfafurazole diolamine
  • sulfisoxazole
  • alphazole
  • soxomide
  • sulfadimethylisoxazole
  • sulfafurazol
  • sulfafurazole
  • sulfaisoxazole
  • sulfazin
  • sulfisoxazol
  • sulfisoxazole dialamine
  • sulphafurazole
  • sulfisoxazole diolamine
A short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms.
  • Molecular weight: 267.30
  • Formula: C11H13N3O3S
  • CLOGP: 0.22
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 98.22
  • ALOGS: -2.93
  • ROTB: 2

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
4 g O
4 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.13 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 49 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 249.52 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 96 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.17 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.08 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 7.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 7, 1971 FDA ALRA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01EB05 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Short-acting sulfonamides
ATC S01AB02 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Sulfonamides
FDA CS M0020790 Sulfonamides
FDA EPC N0000175504 Sulfonamide Antimicrobial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D003049 Coccidiostats
CHEBI has role CHEBI:36047 antibacterial drugs
CHEBI has role CHEBI:88188 allergenic drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Trachoma indication 2576002 DOID:11265
Acute otitis media indication 3110003
Nocardiosis indication 29227009 DOID:2312
Falciparum malaria indication 62676009 DOID:14067
Urinary tract infectious disease indication 68566005
Urethritis due to Chlamydia trachomatis indication 179101003
Meningococcal meningitis indication 192644005
Chlamydial conjunctivitis indication 231861005 DOID:13800
Chancroid indication 266143009 DOID:13778
Infective otitis media indication 312218008
Haemophilus Influenzae Acute Otitis Media indication
Pneumococcal Acute Otitis Media indication
Chlamydia Cervicitis indication
Lymphogranuloma venereum off-label use 186946009 DOID:13819
Urinary tract obstruction contraindication 7163005 DOID:5200
Torsades de pointes contraindication 31722008
Glomerulonephritis contraindication 36171008 DOID:2921
Acute hepatitis contraindication 37871000
Third trimester pregnancy contraindication 41587001
Uremia contraindication 44730006 DOID:4676
Megaloblastic anemia due to folate deficiency contraindication 85649008 DOID:14026
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Cholestatic hepatitis contraindication 95556007
Anemia due to enzyme deficiency contraindication 111577008
Prolonged QT interval contraindication 111975006
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Gastrointestinal obstruction contraindication 126765001
Hearing disorder contraindication 128540005
Liver function tests abnormal contraindication 166603001
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Asthma contraindication 195967001 DOID:2841
Disease of liver contraindication 235856003 DOID:409
Neutropenic disorder contraindication 303011007 DOID:1227
Aplastic anemia contraindication 306058006 DOID:12449
Pseudomembranous enterocolitis contraindication 397683000
Porphyria contraindication 418470004
Slow acetylator due to N-acetyltransferase enzyme variant contraindication 425079005
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 5.0 acidic
pKa2 2.08 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
Histamine H4 receptor GPCR IC50 5.55 WOMBAT-PK
Endothelin-1 receptor GPCR IC50 6.11 CHEMBL
Endothelin B receptor GPCR IC50 4.62 CHEMBL
Dihydropteroate synthase Enzyme INHIBITOR DRUGBANK CHEMBL
Dihydroorotate dehydrogenase (quinone), mitochondrial Enzyme WOMBAT-PK
Endothelin-1 receptor GPCR IC50 6.11 CHEMBL

External reference:

IDSource
4017767 VUID
N0000178993 NUI
D00450 KEGG_DRUG
4299-60-9 SECONDARY_CAS_RN
4017765 VANDF
4017767 VANDF
C0038745 UMLSCUI
CHEBI:102484 CHEBI
CHEMBL453 ChEMBL_ID
DB00263 DRUGBANK_ID
4177 INN_ID
740T4C525W UNII
5344 PUBCHEM_CID
10207 RXNORM
5531 MMSL
5533 MMSL
7990 MMSL
d00120 MMSL
002818 NDDF
002820 NDDF
108866009 SNOMEDCT_US
372858002 SNOMEDCT_US
80732005 SNOMEDCT_US
D013444 MESH_DESCRIPTOR_UI
D013411 MESH_DESCRIPTOR_UI
CHEMBL1200321 ChEMBL_ID

Pharmaceutical products:

None