Sulfathiazole

Identification

Generic Name
Sulfathiazole
DrugBank Accession Number
DB06147
Background

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.

Except for those formulated for vaginal use, the FDA withdrew its approval for the use of all drug products containing sulfathiazole.1

Type
Small Molecule
Groups
Approved, Vet approved, Withdrawn
Structure
Weight
Average: 255.317
Monoisotopic: 255.013617927
Chemical Formula
C9H9N3O2S2
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
  • Sulfathiazole
  • Sulfathiazolum
  • Sulfatiazol
  • Sulphathiazole

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatBacterial enteritisCombination Product in combination with: Sulfamerazine (DB01581), Sulfadiazine (DB00359)••••••••••••••••••
Used in combination to treatEar infection bacterialCombination Product in combination with: Sulfamerazine (DB01581), Sulfadiazine (DB00359)••••••••••••••••••
Used in combination to treatEar infection bacterialCombination Product in combination with: Sulfadiazine (DB00359), Sulfamerazine (DB01581)••••••••••••••••••
Used in combination to treatEnteritisCombination Product in combination with: Sulfadiazine (DB00359), Sulfamerazine (DB01581)••••••••••••••••••
Used in combination to treatEye infectionsCombination Product in combination with: Sulfadiazine (DB00359), Sulfamerazine (DB01581)••••••••••••••••••
Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

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

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
BenzylpenicillinSulfathiazole may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level.
ChloroprocaineThe therapeutic efficacy of Sulfathiazole can be decreased when used in combination with Chloroprocaine.
Insulin aspartThe risk or severity of hypoglycemia can be increased when Sulfathiazole is combined with Insulin aspart.
Insulin beefThe risk or severity of hypoglycemia can be increased when Sulfathiazole is combined with Insulin beef.
Insulin degludecThe risk or severity of hypoglycemia can be increased when Sulfathiazole is combined with Insulin degludec.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sulfathiazole sodiumPV16N742VM144-74-1IMPWUOJNMQNKON-UHFFFAOYSA-N
International/Other Brands
Norsulfazolum (Galen) / Sulfatiazol (Fecofar)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Gyne-SulfSulfathiazole (3.42 g/100g) + Sulfabenzamide (3.7 g/100g) + Sulfacetamide (2.86 g/100g)CreamVaginalGW Laboratories, Inc.1983-08-031995-09-01US flag
Triple SulfaSulfathiazole (3.42 g/100g) + Sulfabenzamide (3.7 g/100g) + Sulfacetamide (2.86 g/100g)CreamVaginalPhysicians Total Care, Inc.1989-02-012004-06-30US flag

Categories

ATC Codes
G01AE10 — Combinations of sulfonamidesJ01EB07 — SulfathiazoleD06BA02 — Sulfathiazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Azole / Benzenesulfonyl group / Heteroaromatic compound / Hydrocarbon derivative
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)
Affected organisms
Not Available

Chemical Identifiers

UNII
Y7FKS2XWQH
CAS number
72-14-0
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

References

General References
  1. Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
Human Metabolome Database
HMDB0015619
KEGG Drug
D01047
KEGG Compound
C11169
PubChem Compound
5340
PubChem Substance
175427054
ChemSpider
5148
BindingDB
50027796
RxNav
10193
ChEBI
9337
ChEMBL
CHEMBL437
ZINC
ZINC000000121458
PharmGKB
PA165958356
PDBe Ligand
YTZ
Wikipedia
Sulfathiazole
PDB Entries
3tye / 4j7u / 5cp3 / 5g44
MSDS
Download (47 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
OintmentTopical5 g
CreamVaginal
OintmentTopical
PowderTopical
Tablet500 mg
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
Polarizability23.93 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-MSsplash10-0a4i-9310000000-362c90cbc34ebb5b96b1
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0a4i-1960000000-7ebf58709da8be9d0d9d
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0890000000-98343f7b490bd54bd908
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-f6bd9fba4a4fa80d7a68
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0930000000-e6e98e9e3ae3e1e57a9f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2090000000-79efd20a6d612c45f0b5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9000000000-c817a1b7c88d4e78e6a1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-9100000000-7fddf845e08078d01f3a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-159.6536402
predicted
DarkChem Lite v0.1.0
[M-H]-159.8567402
predicted
DarkChem Lite v0.1.0
[M-H]-152.80086
predicted
DeepCCS 1.0 (2019)
[M+H]+160.6658402
predicted
DarkChem Lite v0.1.0
[M+H]+160.7476402
predicted
DarkChem Lite v0.1.0
[M+H]+155.15887
predicted
DeepCCS 1.0 (2019)
[M+Na]+159.6360402
predicted
DarkChem Lite v0.1.0
[M+Na]+161.31227
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]

Drug created at November 19, 2007 17:59 / Updated at March 03, 2024 02:35