SULFATHIAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H9N3O2S2
Molecular Weight	255.317
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

NC1=CC=C(C=C1)S(=O)(=O)NC2=NC=CS2

InChI

InChIKey=JNMRHUJNCSQMMB-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C9H9N3O2S2
Molecular Weight	255.317
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Sulfathiazole is a short-acting sulfonamide with properties similar to those of sulfamethoxazole. It is now rarely used systemically due to its toxicity. Sulfathiazole is used with other sulfonamides, usually sulfabenzamide and sulfacetamide, in preparations for the topical treatment of vaginal infections and is also used with other drugs in the treatment of skin infections. Sulfathiazole sodium has been applied topically with other drugs in the treatment of eye infections. Sulfathiazole interferes with nucleic acid synthesis in microorganisms by blocking the conversion of p-aminobenzoic acid to the coenzyme dihydrofolic acid.It has properties similar to sulfamethoxazole.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Escherichia coli 82	Inhibitor 8,504
folic acid biosynthetic process 9	Inhibitor 8,504
Bacterial dihydropteroate synthase 44	Inhibitor 8,504
Escherichia coli 82	Inhibitor 8,504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vaginal infections 8	Curative		Approved 8,583	Sulfathiazole

Doses

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Dose	Population	Adverse events
1 g 6 times / day multiple, oral Recommended	unhealthy	Disc. AE: Dermatitis, Nausea and vomiting... Other AEs: Nitrogen retention, Hematuria...

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AEs

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AE	Significance	Dose	Population
Anemia	1%	1 g 6 times / day multiple, oral Recommended	unhealthy
Conjunctival injection	1%	1 g 6 times / day multiple, oral Recommended	unhealthy
Hematuria	1%	1 g 6 times / day multiple, oral Recommended	unhealthy
Nitrogen retention	1%	1 g 6 times / day multiple, oral Recommended	unhealthy
Burning eyes	2%	1 g 6 times / day multiple, oral Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252	inhibitor 2,438	inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2,057 CYP2E1 1,060 OATP1B1 1,079 CYP2A6 879 CYP1A2 2,153 OATP1B3 961	UGT1A4 399

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 2,333	inhibitor 4,027	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4,027	no [IC50 >10 uM]
CYP2C19 2,141	inhibitor 4,027	no [IC50 >10 uM]
CYP2C9 2,497	inhibitor 4,027	no [IC50 >10 uM]
CYP2D6 2,546	inhibitor 4,027	no [IC50 >10 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
UGT1A4 399	substrate 4,014	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChemIDplus	10135894	https://chem.nlm.nih.gov/chemidplus/id/0010135894
PubChem	23675776	https://pubchem.ncbi.nlm.nih.gov/compound/23675776
SureChEMBL	SCHEMBL11626626	https://www.surechembl.org/chemical/SCHEMBL11626626
Wikidata	Q27292401

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PubMed

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Title	Date	PubMed
Sensitive spectrophotometric determination of nitrite in human saliva and rain water and of nitrogen dioxide in the atmosphere.	2001 Jan-Feb	11234852
Low-level determination of polymorph composition in physical mixtures by near-infrared reflectance spectroscopy.	2001 Mar	11170029
Molecular epidemiology of Salmonella Heidelberg in an equine hospital.	2001 May 3	11278126
Effects of antimicrobials and weaning on porcine serum insulin-like growth factor binding protein levels.	2003 Jun	12817493
Generation of group-specific antibodies against sulfonamides.	2003 Sep 24	13129281

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Patents

Sample Use Guides

In Vivo Use Guide

Adult: Cream (Sulphathiazole 34.2 mg/g, sulphacetamide 28.6 mg/g, sulphabenzamide 37 mg/g and urea 6.4 mg/g): 5g is applied intra-vaginally bid for 4 to 6 days. Thereafter the dosage may be reduced to one-half or one-quarter.

Route of Administration: Topical

In Vitro Use Guide

25 ug/ml of Sulfathiazole is required for inhibition of in vitro cellulose digestion and volatile fatty acid production by ruminal microorganisms.