Identification

Name
Sulfathiazole
Accession Number
DB06147
Type
Small Molecule
Groups
Approved, 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
Product Ingredients
IngredientUNIICASInChI Key
Sulfathiazole sodiumPV16N742VM144-74-1IMPWUOJNMQNKON-UHFFFAOYSA-N
International/Other Brands
Norsulfazolum (Galen) / Sulfatiazol (Fecofar)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Sultrin Triple Sulfa CrmSulfathiazole (3.42 %) + Sulfabenzamide (3.7 %) + Sulfacetamide (2.86 %) + Urea (0.64 %)CreamVaginalOrtho Pharmaceutical, Division Of Janssen Ortho Inc.1946-12-311999-04-14Canada
Categories
UNII
Y7FKS2XWQH
CAS number
72-14-0
Weight
Average: 255.317
Monoisotopic: 255.013617927
Chemical Formula
C9H9N3O2S2
InChI Key
JNMRHUJNCSQMMB-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
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ADihydropteroate synthetase
inhibitor
Plasmodium falciparum
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not 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 elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

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

Affected organisms
Not Available
Pathways
Not 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, Investigational
MecamylamineThe risk or severity of adverse effects can be increased when Sulfathiazole is combined with Mecamylamine.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB15619
KEGG Drug
D01047
KEGG Compound
C11169
PubChem Compound
5340
PubChem Substance
175427054
ChemSpider
5148
BindingDB
50027796
ChEBI
9337
ChEMBL
CHEMBL437
PharmGKB
PA165958356
HET
YTZ
Wikipedia
Sulfathiazole
ATC Codes
J01EB07 — SulfathiazoleD06BA02 — SulfathiazoleG01AE10 — Combinations of sulfonamides
PDB Entries
3tye / 4j7u / 5cp3 / 5g44
MSDS
Download (47 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CreamVaginal
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-3d0cdd49066827cafa83
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0090000000-f7971b44ce4287715041
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0pb9-2940000000-2d9aef67398dcb851e42
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-5900000000-f03cbf45fd1ef6844bea
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4j-9500000000-1d1e5ab23f50f3e1a8ef
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-9100000000-02aff95420f40ac161b7
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-01ot-9000000000-518c1b2f38e7b707d3d8
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0090000000-4629341fc578b9d3ca3f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0pb9-2950000000-54cf4b489c407b1da7bf
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-3900000000-d906641906d22ec2d590
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4j-9800000000-f53d35a00a8692390b26
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-9100000000-7587cac1009d6df32f99
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-01ot-9000000000-38916267be638c54890a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-886ee9e3260c7b7583cb
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0090000000-67d88e77f2bf9487a1ec
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0pb9-4980000000-f023f391d35f708b88c6
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4j-7900000000-b7781621336d485b51d5
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9200000000-c1ee875d073a3fcaacfb
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-01ot-9000000000-a27aed083057f42e702f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-1900000000-7bc90f2d7a5426c57962
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-3774b8582bc3da622e77
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0190000000-cc1537eecf8f0928f6c7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1920000000-67b406efe7f4806206eb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-55c7124e6f14eb2ea11b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-6900000000-94d2498bc052ec461bc7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-052f-9700000000-45924fb72059e9fa4024
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05mo-9400000000-a6a660b7015f1d8cbc77
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0190000000-4b7e9c0118744272d725
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1920000000-1e9a52902d5d0a38e802
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-d12381393c6cd6606766
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-6900000000-8b7994467e53f12a507d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-052f-9700000000-4ec9e7d8c2f2d5e27a13
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05mo-9400000000-e9b1b4264f1999e97c2a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0900000000-a8e0f7a8e8482fe318bc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0090000000-cc86c80d75169a2b4e87
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0930000000-3817d3a71879f5a4adf0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4l-5900000000-de5d143210a83861101f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-052f-9600000000-56dd863571d7db9713e2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9300000000-fc5599d98abe799aedbb
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0a4i-0900000000-f577c37bf9009f56b5a3
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-1960000000-7ebf58709da8be9d0d9d

Taxonomy

Description
This compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Aminobenzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Aniline and substituted anilines / Organosulfonamides / Thiazoles / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organic oxides
show 1 more
Substituents
Aminobenzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Organosulfonic acid amide / Azole / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl / Thiazole / Aminosulfonyl compound
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
substituted 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 December 01, 2017 17:17