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

Stem definitionDrug idCAS RN
anti-infectives, sulfonamides 2500 68-35-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sulfadiazine sodium
  • sulfadiazine
  • sulfadiazin
  • sulfapyrimidine
  • sulfazine
  • sulphadiazine
One of the short-acting SULFONAMIDES used in combination with PYRIMETHAMINE to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.
  • Molecular weight: 250.28
  • Formula: C10H10N4O2S
  • CLOGP: 0.10
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 97.97
  • ALOGS: -2.62
  • ROTB: 2

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.60 g O

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) 57 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 684.95 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.29 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.55 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.44 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 7 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Aug. 11, 1941 FDA LEDERLE

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 143.48 27.12 98 1788 265144 53082036
Pneumonia aspiration 141.57 27.12 51 1835 34250 53312930
Lipase increased 133.42 27.12 36 1850 9342 53337838
Coma 122.12 27.12 54 1832 61729 53285451
Gastrooesophageal reflux disease 101.27 27.12 52 1834 82611 53264569
Drug reaction with eosinophilia and systemic symptoms 82.31 27.12 34 1852 32766 53314414
Pancreatitis 80.46 27.12 37 1849 46105 53301075
Somnolence 76.34 27.12 56 1830 167678 53179502
Underdose 39.79 27.12 18 1868 21504 53325676
Cerebral toxoplasmosis 37.06 27.12 8 1878 807 53346373
Astigmatism 35.18 27.12 8 1878 1023 53346157
Hepatocellular injury 31.30 27.12 17 1869 29969 53317211
Infection protozoal 29.68 27.12 4 1882 21 53347159

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
Toxic epidermal necrolysis 63.81 29.51 27 1516 20566 32491417
Cerebral toxoplasmosis 49.09 29.51 12 1531 1560 32510423
Stevens-Johnson syndrome 43.30 29.51 20 1523 18689 32493294

Pharmacologic Action:

SourceCodeDescription
ATC J01EC02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Intermediate-acting sulfonamides
ATC J01EE02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC J01EE06 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Combinations of sulfonamides and trimethoprim, incl. derivatives
FDA CS M0020790 Sulfonamides
FDA EPC N0000175503 Sulfonamide Antibacterial
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:33281 antibiotics
CHEBI has role CHEBI:35441 anti-infective drugs
CHEBI has role CHEBI:35703 Xenobiotic
CHEBI has role CHEBI:35818 anticoccidial agent
CHEBI has role CHEBI:35820 antiprotozoal agent
CHEBI has role CHEBI:50502 dihydropteroate synthase inhibitor
CHEBI has role CHEBI:74234 7,8-dihydrobiopterin:NADP(+) oxidoreductase
CHEBI has role CHEBI:78298 environmental contaminants
CHEBI has role CHEBI:88188 allergenic drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Chorioretinitis indication 46627006 DOID:8886
Skin ulcer indication 46742003
Ulcerative colitis indication 64766004 DOID:8577
Congenital toxoplasmosis indication 73893000 DOID:13336
Toxoplasmosis indication 187192000 DOID:9965
Toxoplasmosis associated with acquired immunodeficiency syndrome indication 421666009
Rheumatic Fever Prevention indication
Burn Wound Infections indication
Encephalitis due to Toxoplasmosis indication
Minor Bacterial Skin Infections indication
Collagenous colitis off-label use 19311003 DOID:0060183
Psoriasis with arthropathy off-label use 33339001
Crohn's disease off-label use 34000006
Rheumatoid arthritis off-label use 69896004 DOID:7148
Systemic sclerosis off-label use 89155008 DOID:418
Juvenile rheumatoid arthritis off-label use 410795001
Toxoplasmosis Prevention off-label use
Urinary tract obstruction contraindication 7163005 DOID:5200
Third trimester pregnancy contraindication 41587001
Leukopenia contraindication 84828003 DOID:615
Megaloblastic anemia due to folate deficiency contraindication 85649008 DOID:14026
Kidney disease contraindication 90708001 DOID:557
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Gastrointestinal obstruction contraindication 126765001
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Superimposed infection contraindication 193198003
Asthma contraindication 195967001 DOID:2841
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Aplastic anemia contraindication 306058006 DOID:12449
Breastfeeding (mother) contraindication 413712001
Porphyria contraindication 418470004
Slow acetylator due to N-acetyltransferase enzyme variant contraindication 425079005

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.6 acidic
pKa2 2.03 Basic
pKa3 1.41 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
5-hydroxytryptamine receptor 2A GPCR IC50 6.03 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR IC50 4.96 WOMBAT-PK
Aurora kinase A Kinase IC50 4.68 CHEMBL
High affinity choline transporter 1 Transporter IC50 4.24 WOMBAT-PK
Dihydropteroate synthase Enzyme INHIBITOR CHEMBL CHEMBL
Dihydroorotate dehydrogenase (quinone), mitochondrial Enzyme WOMBAT-PK

External reference:

IDSource
D00587 KEGG_DRUG
547-32-0 SECONDARY_CAS_RN
4017497 VANDF
C0038675 UMLSCUI
CHEBI:9328 CHEBI
CHEMBL439 ChEMBL_ID
CHEMBL1200351 ChEMBL_ID
DB00359 DRUGBANK_ID
D013411 MESH_DESCRIPTOR_UI
421 INN_ID
5215 PUBCHEM_CID
422 INN_ID
0N7609K889 UNII
10171 RXNORM
13920 MMSL
2022 MMSL
5523 MMSL
7798 MMSL
87818 MMSL
d00118 MMSL
002814 NDDF
014626 NDDF
371400009 SNOMEDCT_US
74523009 SNOMEDCT_US
768490003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Sulfadiazine HUMAN PRESCRIPTION DRUG LABEL 1 0185-0757 TABLET 500 mg ORAL ANDA 18 sections
SULFADIAZINE HUMAN PRESCRIPTION DRUG LABEL 1 42806-757 TABLET 500 mg ORAL ANDA 19 sections