SUCCINYLSULFATHIAZOLE MONOHYDRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H13N3O5S2.H2O
Molecular Weight	373.405
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of SUCCINYLSULFATHIAZOLE MONOHYDRATE

SMILES

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

InChI

InChIKey=QZIZYTCUSHTEBJ-UHFFFAOYSA-N

InChI=1S/C13H13N3O5S2.H2O/c17-11(5-6-12(18)19)15-9-1-3-10(4-2-9)23(20,21)16-13-14-7-8-22-13;/h1-4,7-8H,5-6H2,(H,14,16)(H,15,17)(H,18,19);1H2

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
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

Molecular Formula	C13H13N3O5S2
Molecular Weight	355.389
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 8,297
folic acid biosynthetic process 9	Inhibitor 8,297
Bacterial dihydropteroate synthase 44	Inhibitor 8,297
Escherichia coli 82	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vaginal infections 8	Curative		Approved 8,429	Sulfathiazole

Doses

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Dose	Population	Adverse events
1 g 6 times / day multiple, oral Recommended	unhealthy n = 100	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 n = 100
Conjunctival injection	1%	1 g 6 times / day multiple, oral Recommended	unhealthy n = 100
Hematuria	1%	1 g 6 times / day multiple, oral Recommended	unhealthy n = 100
Nitrogen retention	1%	1 g 6 times / day multiple, oral Recommended	unhealthy n = 100
Burning eyes	2%	1 g 6 times / day multiple, oral Recommended	unhealthy n = 100

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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
Determination of the onset of crystallization of N1-2-(thiazolyl)sulfanilamide (sulfathiazole) by UV-Vis and calorimetry using an automated reaction platform; subsequent characterization of polymorphic forms using dispersive Raman spectroscopy.	2001 Aug	11506030
Characterization of dextran-producing Leuconostoc strains.	2001 Mar	11264750
Polymorph control of sulfathiazole in supercritical CO2.	2001 May	11465426
Molecular epidemiology of Salmonella Heidelberg in an equine hospital.	2001 May 3	11278126
Nuclease activity of [Cu(sulfathiazolato)(2)(benzimidazole)(2)]2MeOH. Synthesis, properties and crystal structure.	2002 Apr 10	11931960

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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.