sulfathiazole 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
anti-infectives, sulfonamides 2527 72-14-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sulfathiazole
  • norsulfasol
  • norsulfazol
  • norsulfazole
  • sulfanilamidothiazole
  • sulfathiazol
  • sulphathiazole
  • thiozamide
  • thiazamide
A sulfathiazole compound that is used as a short-acting anti-infective agent. It is no longer commonly used systemically due to its toxicity, but may still be applied topically in combination with other drugs for the treatment of vaginal and skin infections, and is still used in veterinary medicine.
  • Molecular weight: 255.31
  • Formula: C9H9N3O2S2
  • CLOGP: 0.73
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 85.08
  • ALOGS: -2.44
  • ROTB: 2

  • Status: OFM

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

Drug dosage:

None

ADMET properties:

None

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.104 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.862 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 19.498 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 2.307 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 35.100 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 45.580 % High 1
herg hERG pIC50 4.025 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 2.028 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 3.793 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 24.830 % High 1
kinase-safety-class ACVR2A,ACVR2B,AKT3,ALK,AURKA,AURKB,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,CHEK1,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GRK3,GSK3B,ITK,JAK1,JAK2,MAP2K6,MAP3K1,MAP3K21,MAP3K7,MAP4K1,MAPK12,MAPK7,MAPK9,MARK4,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIK3CD,PIM2,PRKCD,PRKDC,SGK1,SIK2,SIK3,STK33,SYK,TEK,TTK,ULK1 54
kinase-selectivity-class ACVR2A,AURKA,AXL,CDK1,CDK9,DDR1,DYRK1B,EPHB4,ERBB2,GRK2,JAK1,MAP2K3,MAP2K6,MAP3K7,MAP4K1,MAPK12,MAPK7,MARK4,PDK4,PRKDC,SGK1,SIK2,SIK3,STK33,SYK,TEK,TTK,ULK1 28
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.807 High 1
mh-clint Mouse hepatocyte intrinsic clearance 4.603 High 1
mppb Mouse plasma protein binding (% unbound) 42.850 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.905 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 33.440 % High 1
rh-clint Rat hepatocyte intrinsic clearance 1.679 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 92.340 % High 1
rppb Rat plasma protein binding (% unbound) 17.090 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 939.723 uM High 1

Approvals:

DateAgencyCompanyOrphan
Sept. 12, 1945 FDA ORTHO MCNEIL PHARM

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
Subcutaneous drug absorption impaired 253.25 81.63 105 23920 13440 90590982
General symptom 241.88 81.63 104 23921 14564 90589858
Rash vesicular 223.47 81.63 105 23920 18092 90586330
Breast cancer stage II 221.62 81.63 130 23895 35204 90569218
Pustular psoriasis 218.46 81.63 104 23921 18452 90585970
Back disorder 211.70 81.63 113 23912 25518 90578904
Myositis 209.55 81.63 110 23915 24018 90580404
Dislocation of vertebra 180.46 81.63 136 23889 55832 90548590
Adjustment disorder with depressed mood 178.77 81.63 136 23889 56617 90547805
Folliculitis 148.74 81.63 224 23801 204129 90400293
Wound infection 146.27 81.63 160 23865 106242 90498180
Hypocholesterolaemia 144.66 81.63 57 23968 6392 90598030
X-ray abnormal 138.97 81.63 107 23918 45317 90559105
Joint range of motion decreased 135.12 81.63 173 23852 135470 90468952
Irritable bowel syndrome 130.94 81.63 213 23812 207235 90397187
Anti-cyclic citrullinated peptide antibody positive 129.68 81.63 228 23797 236205 90368217
Muscle injury 123.35 81.63 190 23835 176464 90427958
Disability 122.50 81.63 95 23930 40650 90563772
Impaired healing 122.21 81.63 221 23804 233978 90370444
Wound 121.72 81.63 256 23769 302724 90301698
Pericarditis 118.82 81.63 237 23788 269914 90334508
Blood cholesterol increased 118.48 81.63 204 23821 207808 90396614
Hypercholesterolaemia 117.09 81.63 139 23886 100753 90503669
Swollen joint count increased 115.75 81.63 145 23880 111061 90493361
Lower respiratory tract infection 111.53 81.63 221 23804 250438 90353984
Rheumatoid factor positive 107.93 81.63 176 23849 171474 90432948
Drug ineffective 105.36 81.63 128 23897 1384170 89220252
Liver injury 103.35 81.63 172 23853 170395 90434027
Pemphigus 103.17 81.63 251 23774 326613 90277809
Peripheral venous disease 103.00 81.63 119 23906 83802 90520620
Glossodynia 101.46 81.63 247 23778 321532 90282890
Rheumatic fever 98.98 81.63 159 23866 152962 90451460
Helicobacter infection 97.29 81.63 197 23828 226653 90377769
Grip strength decreased 95.19 81.63 120 23905 92456 90511966
Type 2 diabetes mellitus 92.55 81.63 181 23844 203063 90401359
Duodenal ulcer perforation 92.32 81.63 190 23835 221098 90383324
Blister 91.54 81.63 206 23819 254792 90349630
Fluid retention 90.27 81.63 114 23911 87977 90516445
Walking aid user 90.16 81.63 75 23950 35431 90568991
Ill-defined disorder 89.50 81.63 169 23856 184722 90419700
Synovitis 89.28 81.63 239 23786 329513 90274909
Psoriatic arthropathy 85.93 81.63 188 23837 228147 90376275
Memory impairment 85.39 81.63 172 23853 197072 90407350
Fall 85.30 81.63 13 24012 481797 90122625
Amnesia 84.68 81.63 123 23902 108382 90496040
Hand deformity 84.49 81.63 219 23806 296143 90308279
Migraine 83.58 81.63 167 23858 190225 90414197
Pulmonary fibrosis 82.64 81.63 121 23904 107382 90497040
Delirium 82.46 81.63 119 23906 104240 90500182
Lupus vulgaris 82.28 81.63 79 23946 44980 90559442

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

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
Hypocholesterolaemia 177.57 86.65 57 16262 6364 110566616
Peripheral venous disease 165.02 86.65 120 16199 83997 110488983
Breast cancer stage II 154.17 86.65 77 16242 27298 110545682
Lupus vulgaris 146.98 86.65 80 16239 33803 110539177
Adjustment disorder with depressed mood 137.93 86.65 84 16235 43799 110529181
General symptom 137.31 86.65 51 16268 8795 110564185
Subcutaneous drug absorption impaired 136.90 86.65 49 16270 7610 110565370
Dislocation of vertebra 135.66 86.65 83 16236 43638 110529342
Bursitis 134.56 86.65 128 16191 129790 110443190
Wound infection 131.50 86.65 111 16208 96354 110476626
Folliculitis 129.55 86.65 141 16178 167512 110405468
Wound 124.76 86.65 163 16156 234274 110338706
Back disorder 121.21 86.65 60 16259 20862 110552118
Joint range of motion decreased 120.42 86.65 117 16202 121715 110451265
Bone erosion 118.81 86.65 78 16241 46293 110526687
Taste disorder 116.36 86.65 88 16231 65299 110507681
Pemphigus 115.42 86.65 150 16169 214420 110358560
Breast cancer stage III 113.95 86.65 94 16225 79023 110493957
Pericarditis 112.94 86.65 150 16169 218964 110354016
Glossodynia 112.93 86.65 151 16168 221853 110351127
Irritable bowel syndrome 107.93 86.65 127 16192 164088 110408892
Anti-cyclic citrullinated peptide antibody positive 106.99 86.65 133 16186 181851 110391129
Pustular psoriasis 106.44 86.65 48 16271 13557 110559423
Rash vesicular 106.15 86.65 49 16270 14603 110558377
Exostosis 105.01 86.65 72 16247 45884 110527096
Impaired healing 104.97 86.65 137 16182 196580 110376400
Blepharospasm 104.70 86.65 77 16242 54774 110518206
Night sweats 102.27 86.65 112 16207 133871 110439109
Musculoskeletal pain 101.62 86.65 130 16189 182893 110390087
Retinitis 96.78 86.65 60 16259 32267 110540713
Psoriatic arthropathy 94.22 86.65 130 16189 196631 110376349
Type 2 diabetes mellitus 93.87 86.65 123 16196 177109 110395871
Liver injury 93.36 86.65 113 16206 150300 110422680
Nail disorder 92.24 86.65 73 16246 57862 110515118
Product quality issue 91.31 86.65 82 16237 77217 110495763
Laryngitis 91.16 86.65 64 16255 42347 110530633
X-ray abnormal 87.75 86.65 60 16259 38057 110534923
Hypercholesterolaemia 87.42 86.65 86 16233 90751 110482229

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC D06BA02 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
CHEMOTHERAPEUTICS FOR TOPICAL USE
Sulfonamides
ATC J01EB07 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Short-acting sulfonamides
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:35441 antiinfective agent
CHEBI has role CHEBI:35703 xenobiotic
CHEBI has role CHEBI:50502 EC 2.5.1.15 (dihydropteroate synthase) inhibitor
CHEBI has role CHEBI:78298 environmental contaminant
CHEBI has role CHEBI:88188 drug allergen

Related Drugs by ATC class:

D06BA Sulfonamides 5 drugs
J01EB Short-acting sulfonamides 7 drugs

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Vulvovaginitis indication 53277000 DOID:2273
Gardnerella Vaginalis Bacterial Vaginosis indication
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
Breastfeeding (mother) contraindication 413712001
Porphyria contraindication 418470004




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.16 acidic
pKa2 2.48 Basic
pKa3 1.61 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
Endothelin-1 receptor GPCR IC50 4.16 WOMBAT-PK
Dihydropteroate synthase Enzyme INHIBITOR IC50 5.60 CHEMBL CHEMBL
Endothelin-1 receptor GPCR IC50 4.16 CHEMBL
Transcriptional activator protein LasR Transcription factor IC50 5.05 CHEMBL

External reference:

IDSource
4018558 VUID
N0000178992 NUI
D01047 KEGG_DRUG
4018558 VANDF
C0038722 UMLSCUI
CHEBI:9337 CHEBI
YTZ PDB_CHEM_ID
CHEMBL437 ChEMBL_ID
DB06147 DRUGBANK_ID
D000077589 MESH_DESCRIPTOR_UI
5340 PUBCHEM_CID
12699 IUPHAR_LIGAND_ID
428 INN_ID
Y7FKS2XWQH UNII
10193 RXNORM
5529 MMSL
002815 NDDF
16867004 SNOMEDCT_US
387093005 SNOMEDCT_US

Pharmaceutical products:

None