sulfadiazine ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 100 % 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -1.344 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.374 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 8.260 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 1.799 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 64.960 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 77.050 % High 1
herg hERG pIC50 3.765 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 1.824 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 3.170 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 53.390 % High 1
kinase-safety-class ACVR2A,ACVR2B,ALK,AURKA,AURKB,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK1,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,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PRKCD,PRKDC,SGK1,SIK2,SIK3,STK33,SYK,TEK,TTK,ULK1 52
kinase-selectivity-class AXL,CDK9,ERBB2,GRK2,MAPK7,SIK2,STK33,TEK 8
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.521 High 1
mh-clint Mouse hepatocyte intrinsic clearance 1.879 High 1
mppb Mouse plasma protein binding (% unbound) 83.780 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.352 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 81.220 % High 1
rh-clint Rat hepatocyte intrinsic clearance 0.783 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 94.150 % High 1
rppb Rat plasma protein binding (% unbound) 42.180 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 1011.579 uM High 1

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
Lipase increased 216.86 30.60 50 1946 11061 90615390
Drug hypersensitivity 186.48 30.60 119 1877 463490 90162961
Pancreatitis 129.73 30.60 51 1945 69775 90556676
Drug reaction with eosinophilia and systemic symptoms 92.77 30.60 35 1961 42723 90583728
Cerebral toxoplasmosis 77.84 30.60 15 1981 1390 90625061
Pancytopenia 68.87 30.60 39 1957 120224 90506227
Bone marrow failure 57.84 30.60 23 1973 32198 90594253
Pneumonia aspiration 49.29 30.60 22 1974 40918 90585533
Coma 45.47 30.60 25 1971 72607 90553844
Hepatocellular injury 42.84 30.60 18 1978 28940 90597511
Astigmatism 42.05 30.60 9 1987 1405 90625046
Toxoplasmosis 34.58 30.60 8 1988 1777 90624674
Deafness transitory 33.51 30.60 8 1988 2035 90624416

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
Neuritis 261.76 43.77 69 3914 6151 42611201
Pulmonary vasculitis 261.26 43.77 69 3914 6197 42611155
Neurological symptom 229.41 43.77 69 3914 9922 42607430
Eosinophilic granulomatosis with polyangiitis 212.80 43.77 63 3920 8575 42608777
Respiratory symptom 209.64 43.77 66 3917 11040 42606312
Pulmonary alveolar haemorrhage 206.60 43.77 70 3913 14746 42602606
Total lung capacity abnormal 204.78 43.77 53 3930 4390 42612962
Antineutrophil cytoplasmic antibody positive 195.99 43.77 51 3932 4314 42613038
Forced expiratory volume decreased 185.09 43.77 55 3928 7575 42609777
Vasculitis 177.01 43.77 66 3917 18328 42599024
Sleep disorder due to a general medical condition 172.98 43.77 64 3919 17389 42599963
Obstructive airways disorder 171.57 43.77 70 3913 24689 42592663
Pulmonary fibrosis 166.51 43.77 70 3913 26611 42590741
Mite allergy 160.85 43.77 45 3938 5001 42612351
Dust allergy 158.39 43.77 45 3938 5287 42612065
Mycotic allergy 157.65 43.77 44 3939 4847 42612505
Conjunctivitis allergic 153.81 43.77 45 3938 5866 42611486
Spirometry abnormal 150.92 43.77 43 3940 5103 42612249
Full blood count abnormal 146.05 43.77 66 3917 29810 42587542
Hypothyroidism 144.66 43.77 67 3916 32017 42585335
Lung disorder 135.83 43.77 73 3910 47850 42569502
Normochromic normocytic anaemia 135.02 43.77 45 3938 8986 42608366
Haemoptysis 129.92 43.77 70 3913 46097 42571255
Nodule 120.60 43.77 45 3938 12489 42604863
Asthma 112.92 43.77 71 3912 62243 42555109
Loss of personal independence in daily activities 111.48 43.77 65 3918 49751 42567601
Wheezing 110.91 43.77 67 3916 54714 42562638
Therapeutic product effect incomplete 104.51 43.77 71 3912 70868 42546484
Arteriosclerosis coronary artery 103.22 43.77 45 3938 18632 42598720
Arteriosclerosis 101.56 43.77 44 3939 17945 42599407
Capillaritis 94.99 43.77 25 3958 2203 42615149
Productive cough 69.71 43.77 49 3934 51518 42565834
Anxiety 66.87 43.77 68 3915 118492 42498860
Hypoxia 60.66 43.77 51 3932 69735 42547617
Condition aggravated 60.64 43.77 96 3887 260658 42356694
Toxic epidermal necrolysis 60.00 43.77 35 3948 26715 42590637
Pain in extremity 55.15 43.77 69 3914 150535 42466817
Thrombosis 45.47 43.77 43 3940 68468 42548884

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
Pulmonary vasculitis 304.83 30.54 70 5568 6490 110577171
Neuritis 296.45 30.54 70 5568 7329 110576332
Neurological symptom 262.68 30.54 74 5564 15534 110568127
Eosinophilic granulomatosis with polyangiitis 241.94 30.54 64 5574 10622 110573039
Total lung capacity abnormal 240.41 30.54 54 5584 4529 110579132
Respiratory symptom 234.09 30.54 67 5571 14878 110568783
Pulmonary alveolar haemorrhage 231.20 30.54 71 5567 20079 110563582
Antineutrophil cytoplasmic antibody positive 224.25 30.54 52 5586 5024 110578637
Forced expiratory volume decreased 192.65 30.54 56 5582 13120 110570541
Mite allergy 186.62 30.54 46 5592 5757 110577904
Dust allergy 185.09 30.54 46 5592 5955 110577706
Mycotic allergy 180.43 30.54 45 5593 5909 110577752
Spirometry abnormal 178.93 30.54 44 5594 5453 110578208
Conjunctivitis allergic 178.51 30.54 46 5592 6885 110576776
Vasculitis 176.47 30.54 67 5571 35806 110547855
Obstructive airways disorder 173.68 30.54 71 5567 46078 110537583
Normochromic normocytic anaemia 153.94 30.54 47 5591 13010 110570651
Haemoptysis 150.00 30.54 73 5565 71281 110512380
Full blood count abnormal 147.59 30.54 67 5571 55985 110527676
Sleep disorder due to a general medical condition 145.83 30.54 65 5573 52047 110531614
Hypothyroidism 136.67 30.54 69 5569 72830 110510831
Arteriosclerosis coronary artery 123.80 30.54 47 5591 25071 110558590
Arteriosclerosis 120.83 30.54 46 5592 24721 110558940
Pulmonary fibrosis 120.15 30.54 71 5567 101971 110481690
Nodule 111.88 30.54 47 5591 32584 110551077
Capillaritis 107.77 30.54 25 5613 2414 110581247
Cerebral toxoplasmosis 106.55 30.54 26 5612 3116 110580545
Lung disorder 92.11 30.54 75 5563 179972 110403689
Loss of personal independence in daily activities 84.19 30.54 66 5572 149954 110433707
Therapeutic product effect incomplete 74.24 30.54 73 5565 223732 110359929
Drug reaction with eosinophilia and systemic symptoms 73.46 30.54 48 5590 82047 110501614
Hypoxia 66.28 30.54 54 5584 129461 110454200
Asthma 65.66 30.54 72 5566 250219 110333442
Productive cough 65.64 30.54 51 5587 114254 110469407
Toxic epidermal necrolysis 57.77 30.54 36 5602 56691 110526970
Wheezing 57.73 30.54 68 5570 255162 110328499
Pancytopenia 56.17 30.54 61 5577 209552 110374109
Thrombosis 52.85 30.54 44 5594 108618 110475043
Condition aggravated 46.42 30.54 110 5528 734726 109848935
Anxiety 45.91 30.54 71 5567 345007 110238654
Pulmonary embolism 34.06 30.54 48 5590 214426 110369235
Astigmatism 32.83 30.54 9 5629 1700 110581961
Pain in extremity 31.85 30.54 74 5564 487044 110096617
Deafness transitory 31.80 30.54 8 5630 1085 110582576
Bone marrow failure 31.43 30.54 25 5613 57823 110525838
Pulmonary venous thrombosis 30.75 30.54 6 5632 252 110583409

FDA Adverse Event Reporting System (Pediatric)

None

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 D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D003049 Coccidiostats
CHEBI has role CHEBI:33281 antimicrobial agent
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:35441 antiinfective agent
CHEBI has role CHEBI:35442 antiparasitic agent
CHEBI has role CHEBI:35703 xenobiotic
CHEBI has role CHEBI:35818 coccidiostat
CHEBI has role CHEBI:35820 antiprotozoal drug
CHEBI has role CHEBI:38068 antimalarial
CHEBI has role CHEBI:50502 EC 2.5.1.15 (dihydropteroate synthase) inhibitor
CHEBI has role CHEBI:74234 EC 1.1.1.153 [sepiapterin reductase (<small>L</small>-<i>erythro</i>-7,8-dihydrobiopterin forming)] inhibitor
CHEBI has role CHEBI:78298 environmental contaminant
CHEBI has role CHEBI:88188 drug allergen

Related Drugs by ATC class:

J01EC Intermediate-acting sulfonamides 2 drugs
J01EE Combinations of sulfonamides and trimethoprim, incl. derivatives 7 drugs

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

SpeciesUseRelation
Dogs Systemic antibacterial action against sensitive organisms to surgery Indication
Dogs Systemic antibacterial action against sensitive organisms to debridement Indication
Dogs Control of bacterial infection during the treatment of acute urinary tract infections Indication
Dogs Control of bacterial infection during the treatment of acute bacterial complications of distemper Indication
Dogs Control of bacterial infection during the treatment of acute respiratory tract infections Indication
Dogs Control of bacterial infection during the treatment of acute alimentary tract infections Indication
Dogs Control of bacterial infection during the treatment of wound infections Indication
Dogs Control of bacterial infection during the treatment of abscesses Indication
Horses Systemic antibacterial action against sensitive organisms during treatment of acute strangles Indication
Horses Systemic antibacterial action against sensitive organisms during respiratory infections Indication
Horses Systemic antibacterial action against sensitive organisms during acute urogenital infections Indication
Horses Systemic antibacterial action against sensitive organisms during wound infections Indication
Horses Systemic antibacterial action against sensitive organisms during abscesses Indication

๐Ÿถ Veterinary products

ProductApplicantIngredients
Tribrissen 120 Tablets, Tribrissen 30 Tablets, Tribrissen 480 Tablets, Tribrissen 960 Tablets Intervet Inc. 2
Tribrissen 24% Injection Intervet Inc. 2
Tribrissen 48% Injection Intervet Inc. 2
Di-Trim Tablets Zoetis Inc. 2
Tribrissen 400 Oral Paste Intervet Inc. 2
Di-Trim 24% Zoetis Inc. 2
Di-Trim 48% Injection Zoetis Inc. 2
Di-Trim 400 Paste Zoetis Inc. 2
Tribrissen 60 Oral Suspension Intervet Inc. 2
ReBalance Pegasus Laboratories Inc. 2
EQUISUL-SDT Aurora Pharmaceutical Inc. 2
Uniprim Powder Neogen Corp. 2
Tucoprim Powder Zoetis Inc. 2

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 2B GPCR IC50 4.96 WOMBAT-PK
Dihydrofolate reductase Enzyme IC50 6.89 CHEMBL
5-hydroxytryptamine receptor 2A GPCR IC50 6.03 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
5215 PUBCHEM_CID
12635 IUPHAR_LIGAND_ID
421 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
422 INN_ID
0N7609K889 INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
SULFADIAZINE HUMAN PRESCRIPTION DRUG LABEL 1 42806-757 TABLET 500 mg ORAL ANDA 19 sections
sulfADIAZINE HUMAN PRESCRIPTION DRUG LABEL 1 62135-842 TABLET 500 mg ORAL ANDA 10 sections