sulfadimidine ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
anti-infectives, sulfonamides 2502 57-68-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sulfadimidine
  • sulfamethazine
  • sulfadimerazine
  • sulfadimethyldiazine
  • sulfamethazine sodium
  • sulfamethazine sodium salt
  • sodium sulfamethazine
  • sulfamethazine bisulfate
A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.
  • Molecular weight: 278.33
  • Formula: C12H14N4O2S
  • CLOGP: 1.10
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 97.97
  • ALOGS: -3.08
  • ROTB: 2

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
4 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 153.98 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 86.50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -0.192 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 3.565 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 19.454 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 0.953 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 59.770 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 73.680 % High 1
herg hERG pIC50 3.865 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 1.045 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 3.105 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 52.300 % 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,KIT,MAP3K1,MAP3K21,MAP3K7,MAP4K1,MAPK12,MAPK7,MAPK9,MARK4,MTOR,NTRK2,PAK4,PDK2,PDK4,PDPK1,PIK3CB,PIK3CD,PIM2,PRKCD,PRKDC,SGK1,SIK2,SIK3,STK33,SYK,TEK,TTK,ULK1 54
kinase-selectivity-class ACVR2A,AURKA,AXL,BRAF,CDK9,DDR1,DYRK1B,EPHB4,ERBB2,FGFR1,GRK2,JAK1,MAP2K6,MAP4K1,MAPK7,MARK4,SIK2,SIK3,STK33,SYK,TEK,ULK1 22
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 9.057 High 1
mh-clint Mouse hepatocyte intrinsic clearance 3.162 High 1
mppb Mouse plasma protein binding (% unbound) 61.970 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 6.668 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 68.530 % High 1
rh-clint Rat hepatocyte intrinsic clearance 0.984 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 93.750 % High 1
rppb Rat plasma protein binding (% unbound) 31.270 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 676.083 uM High 1

Approvals:

DateAgencyCompanyOrphan
Aug. 16, 1949 FDA LEDERLE

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01EB03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Short-acting sulfonamides
ATC J01EE05 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
SULFONAMIDES AND TRIMETHOPRIM
Combinations of sulfonamides and trimethoprim, incl. derivatives
MeSH PA D000890 Anti-Infective Agents
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:35703 xenobiotic
CHEBI has role CHEBI:36047 antibacterial drug
CHEBI has role CHEBI:50502 EC 2.5.1.15 (dihydropteroate synthase) inhibitor
CHEBI has role CHEBI:50903 carcinogenic agent
CHEBI has role CHEBI:52214 ligand
CHEBI has role CHEBI:78298 environmental contaminant
CHEBI has role CHEBI:88188 drug allergen

Related Drugs by ATC class:

J01EB Short-acting sulfonamides 7 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
Third trimester pregnancy contraindication 41587001
Megaloblastic anemia due to folate deficiency contraindication 85649008 DOID:14026
Kidney disease contraindication 90708001 DOID:557
Anemia due to enzyme deficiency contraindication 111577008
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




๐Ÿถ Veterinary Drug Use

SpeciesUseRelation
Cattle Bacterial pneumonia Indication
Cattle Respiratory disease complex caused by Pasteurella species Indication
Cattle Colibacillosis caused by Escherichia coli Indication
Cattle Necrotic pododermatitis (foot rot) caused by Fusobacterium necrophorum Indication
Cattle Diphtheria caused by Fusobacterium necrophorum Indication
Cattle Acute metritis caused by Streptococcus species Indication
Cattle Acute mastitis caused by Streptococcus species Indication
Chickens Infectious coryza caused by Avibacterium paragallinarium Indication
Chickens Coccidiosis cased by Eimeria tenella Indication
Chickens Pullorum disease caused by Salmonella Pullorum Indication
Chickens Coccidiosis cased by Eimeria necatrix Indication
Chickens Cholera caused by Pasteurella multocida Indication
Swine Colibacillosis caused by Escherichia coli Indication
Swine Bacterial pneumonia caused by Pasteurella multocida Indication
Turkeys Coccidiosis caused by Eimeria adenoeides Indication
Turkeys Coccidiosis caused by Eimeria adenoeides Indication
Cattle Bacterial pneumonia Indication
Cattle Bovine respiratory disease complex caused by Pasteurella species Indication
Cattle Colibacillosis caused by Escherichia coli Indication
Cattle Necrotic pododermatitis (foot rot) caused by Fusobacterium necrophorum Indication
Cattle Diphtheria caused by Fusobacterium necrophorum Indication
Cattle Acute metritis caused by Streptococcus species Indication
Cattle Acute mastitis caused by Streptococcus species Indication
Chickens Coryza caused by Avibacterium paragallinarum Indication
Chickens Coccidiosis caused by Eimeria tenella Indication
Chickens Coccidiosis caused by Eimeria necatrix Indication
Chickens Cholera caused by Pasteurella multocida Indication
Chickens Pullorum disease caused by Salmonella Pullorum Indication
Swine Colibacillosis caused by Escherichia coli Indication
Swine Bacterial pneumonia caused by Pasteurella species Indication
Turkeys Coccidiosis caused by Eimeria meleagrimitis Indication
Turkeys Coccidiosis caused by Eimeria adenoeides Indication

๐Ÿถ Veterinary products

ProductApplicantIngredients
Sulmet Drinking Water Solution, 12.5% Huvepharma EOOD 1
Sulmet Solution Injectable Huvepharma EOOD 1
Aureomix S 40/40 Granular Zoetis Inc. 2
Aureo S 700 Granular, Aureo S 700 Zoetis Inc. 2
Tylan 5 Sulfa-G, Tylan 10 Sulfa-G, Tylan 20 Sulfa-G, Tylan 40 Sulfa-G Elanco US Inc. 2
AUREOMIX S 700-A Zoetis Inc. 2
AUREOMIX S 700-D Zoetis Inc. 2
Aureomix S 700-G Zoetis Inc. 2
Aureomix S 700-E Zoetis Inc. 2
Aureomix 700-F Zoetis Inc. 2
Aureomix S 700-C Zoetis Inc. 2
AUREOMIX S 700-B Zoetis Inc. 2
AUREOMIX S 700-H Zoetis Inc. 2
Sulfamethazine Spanbolet II Zoetis Inc. 1
Chloronex Sulmet Huvepharma EOOD 2
Tylan 10 Sulfa-G, Tylan 40 Sulfa-G Zoetis Inc. 2
PoultrySulfa Huvepharma EOOD 3
Sustain III Bolus, Sustain III Calf Bolus Bimeda Animal Health Limited 1
Sulmet Oblets Huvepharma EOOD 1
Sulmet Soluble Powder Huvepharma EOOD 1
Calfspan Zoetis Inc. 1
Pennchlor S 40/40 Pharmgate Inc. 2
Sulfamethazine Sustained Release Bolus Huvepharma EOOD 1
Veta-Meth Lloyd Inc. 1
Sulka-S Bolus Zoetis Inc. 1
Aureo S 700 and Bovatec Zoetis Inc. 3
Pennchlor S Pharmgate Inc. 2
SMZ-Med 454 Bimeda Animal Health Limited 1

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.24 acidic
pKa2 2.88 Basic
pKa3 2.27 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
Lactoylglutathione lyase Enzyme WOMBAT-PK
Dihydropteroate synthase Enzyme INHIBITOR CHEMBL CHEMBL

External reference:

IDSource
4017499 VUID
N0000145884 NUI
D02436 KEGG_DRUG
4017499 VANDF
C0038686 UMLSCUI
CHEBI:102265 CHEBI
CHEMBL446 ChEMBL_ID
DB01582 DRUGBANK_ID
5327 PUBCHEM_CID
12642 IUPHAR_LIGAND_ID
1981-58-4 SECONDARY_CAS_RN
10178 RXNORM
NOCODE MMSL
002817 NDDF
324417001 SNOMEDCT_US
40036000 SNOMEDCT_US
D013418 MESH_DESCRIPTOR_UI
24540-76-9 SECONDARY_CAS_RN
1068 INN_ID
48U51W007F UNII

Pharmaceutical products:

None