Identification
NameSulfathiazole
Accession NumberDB06147
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

Sulfathiazole is a short-acting sulfa drug. It used to be a common oral and topical antimicrobial until less toxic alternatives were discovered. It is still occasionally used, sometimes in combination with sulfabenzamide and sulfacetamide.

Structure
Thumb
Synonyms
2-(P-Aminobenzenesulfonamido)thiazole
2-(P-Aminobenzenesulphonamido)thiazole
2-(Sulfanilylamino)thiazole
2-Sulfanilamidothiazol
2-Sulfanilamidothiazole
2-Sulfonamidothiazole
4-Amino-N-2-thiazolylbenzenesulfonamide
N(1)-2-Thiazolylsulfanilamide
N1-2-Thiazolylsulfanilamide
Sulfanilamidothiazole
Sulfathiazol
Sulfathiazolum
Sulfatiazol
Sulphathiazole
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Sulfathiazole sodiumPV16N742VM 144-74-1IMPWUOJNMQNKON-UHFFFAOYSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
NorsulfazolumGalen
SulfatiazolFecofar
Brand mixturesNot Available
Categories
UNIIY7FKS2XWQH
CAS number72-14-0
WeightAverage: 255.317
Monoisotopic: 255.013617927
Chemical FormulaC9H9N3O2S2
InChI KeyJNMRHUJNCSQMMB-UHFFFAOYSA-N
InChI
InChI=1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12)
IUPAC Name
4-amino-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CS1
Pharmacology
Indication

Sulfathiazole is effective against a wide range of gram positive and gram negative pathogenic microorganisms. Although no longer used in humans, it is used in cattle.

Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Dihydropteroate synthetaseProteinyes
inhibitor
Plasmodium falciparumQ27738 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Metabolism of sulfonamide drugs in animals includes conjugation at the N4-position (acetyl, sulfate, glucuronic acid, and glucose), conjugation at the N1-position (sulfate and glucuronic acid), removal of the p-amino group (formation of the desamino metabolite), ring hydroxylation, and conjugation of the ring hydroxylation products. Dietary nitrite enhances the production of the desamino metabolite of sulfathiazole. The intermediate leading to the desamino metabolite of sulfamethazine is weakly mutagenic in the Ames test (Nelson et al., 1987; Paulson et al., 1987).

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity

Acute oral toxicity (LD50): 4500 mg/kg [Mouse].

Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Sulfathiazole.Approved
MecamylamineThe risk or severity of adverse effects can be increased when Sulfathiazole is combined with Mecamylamine.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ01EB07 — SulfathiazoleD06BA02 — SulfathiazoleG01AE10 — Combinations of sulfonamides
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (47 KB)
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)189 °CPhysProp
water solubility373 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.05HANSCH,C ET AL. (1995)
pKa7.2BUDAVARI,S ET AL. (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.921 mg/mLALOGPS
logP0.88ALOGPS
logP0.98ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.93ChemAxon
pKa (Strongest Basic)2.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.08 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.27 m3·mol-1ChemAxon
Polarizability23.96 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9087
Blood Brain Barrier+0.946
Caco-2 permeable-0.6975
P-glycoprotein substrateNon-substrate0.9186
P-glycoprotein inhibitor INon-inhibitor0.9445
P-glycoprotein inhibitor IINon-inhibitor0.8896
Renal organic cation transporterNon-inhibitor0.8926
CYP450 2C9 substrateNon-substrate0.8236
CYP450 2D6 substrateNon-substrate0.9083
CYP450 3A4 substrateNon-substrate0.7952
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9338
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7817
Ames testNon AMES toxic0.9151
CarcinogenicityNon-carcinogens0.9034
BiodegradationNot ready biodegradable0.9776
Rat acute toxicity1.7929 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9396
hERG inhibition (predictor II)Non-inhibitor0.9101
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-3d0cdd49066827cafa83View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-f7971b44ce4287715041View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0pb9-2940000000-2d9aef67398dcb851e42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-5900000000-f03cbf45fd1ef6844beaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-9500000000-1d1e5ab23f50f3e1a8efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-02aff95420f40ac161b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01ot-9000000000-518c1b2f38e7b707d3d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-4629341fc578b9d3ca3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0pb9-2950000000-54cf4b489c407b1da7bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-3900000000-d906641906d22ec2d590View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-9800000000-f53d35a00a8692390b26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-7587cac1009d6df32f99View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01ot-9000000000-38916267be638c54890aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-886ee9e3260c7b7583cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-67d88e77f2bf9487a1ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0pb9-4980000000-f023f391d35f708b88c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4j-7900000000-b7781621336d485b51d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9200000000-c1ee875d073a3fcaacfbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01ot-9000000000-a27aed083057f42e702fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentAminobenzenesulfonamides
Alternative ParentsBenzenesulfonyl compounds / Aniline and substituted anilines / Primary aromatic amines / Organosulfonamides / Thiazoles / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Organopnictogen compounds / Organic oxides
SubstituentsAminobenzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Primary aromatic amine / Organosulfonic acid amide / Azole / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Heteroaromatic compound / Aminosulfonyl compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorssubstituted aniline, sulfonamide, 1,3-thiazole, sulfonamide antibiotic (CHEBI:9337 ) / a small molecule (CPD-11285 )

Targets

Kind
Protein
Organism
Plasmodium falciparum
Pharmacological action
yes
Actions
inhibitor
General Function:
Dihydropteroate synthase activity
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q27738
Uniprot Name:
Dihydropteroate synthetase
Molecular Weight:
43370.845 Da
References
  1. Nichols BP, Guay GG: Gene amplification contributes to sulfonamide resistance in Escherichia coli. Antimicrob Agents Chemother. 1989 Dec;33(12):2042-8. [PubMed:2694948 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Uniprot Name:
Aromatase
Molecular Weight:
57882.48 Da
References
  1. Ji K, Choi K, Lee S, Park S, Khim JS, Jo EH, Choi K, Zhang X, Giesy JP: Effects of sulfathiazole, oxytetracycline and chlortetracycline on steroidogenesis in the human adrenocarcinoma (H295R) cell line and freshwater fish Oryzias latipes. J Hazard Mater. 2010 Oct 15;182(1-3):494-502. doi: 10.1016/j.jhazmat.2010.06.059. Epub 2010 Jun 19. [PubMed:20630653 ]
Drug created on November 19, 2007 10:59 / Updated on June 11, 2017 16:42