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Succinylsulfathiazole

Succinylsulfathiazole structure

CAS No:
116-43-8
Formula:
C13H13N3O5S2
Chemical Name:
Succinylsulfathiazole
Synonyms:
Butanoic acid,4-oxo-4-[[4-[(2-thiazolylamino)sulfonyl]phenyl]amino]-;Succinanilic acid,4′-(2-thiazolylsulfamoyl)-;4-Oxo-4-[[4-[(2-thiazolylamino)sulfonyl]phenyl]amino]butanoic acid;Kaoxidin;Kaoxidine;2-(N4-Succinylsulfanilamido)thiazole;Succinylsulfathiazole;Succinylsulphathiazole;Sulfasuccithiazole;Sulfasuxidine;Sulfenterone;Thiacyl;4′-(2-Thiazolylsulfamoyl)succinanilic acid;p-2-Thiazolylsulfamylsuccinanilic acid;Sulfasuccidine;Colistatin;Cremosuxidine;Rolsul;Sulfadigesin;Sulfasuccidin;Sulfasuccinil;NSC 14193;NSC 163939;3-([4-[(1,3-Thiazol-2-yl)sulfamoyl]phenyl]carbamoyl)propanoic acid;1391-00-0
Categories:
Organic Chemistry > Amides

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Description

Succinylsulfathiazole is a sulfonamide, it is an ultra long acting drug.

N-succinylsulfathiazole is a member of 1,3-thiazoles. It derives from a sulfathiazole.

Succinylsulfathiazole Basic Attributes

Molecular Weight：

355.39

Exact Mass：

355.39

EC Number：

204-141-0

UNII：

RSS8647O4S

NSC Number：

758161|163939|14193

DSSTox ID：

DTXSID7045281

ATC Code：

A - Alimentary tract and metabolism

HScode：

2935009090

Characteristics

PSA：

162

XLogP3：

-0.7

Appearance：

white to off-white

Density：

1.6±0.1 g/cm3

Melting Point：

193.5 °C

Refractive Index：

1.679

Water Solubility：

1 M NaOH: soluble 50mg/mL

Collision Cross Section：

182.4 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

3249

wgk germany：

hazard class code：

42/43

safety instructions：

22-36/37-45

RTECS Number：

WM4767000

Marks：

Precautionary statement(s)：

P280

Hazard Statements：

H317

GHS Classification：

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 41 companies from 4 notifications to the ECHA C&L Inventory.

Drug Information

MeSH Entry Terms：

4'-(2-thiazolylsulfamoyl)succinanilic acid

Succinylsulfathiazole Use and Manufacturing

Methods of Manufacturing

Compound 27j was synthesized by the method outlined in FIG. 1. Briefly, Compound 27j was synthesized by first complexing succinic anhydride with sulfathiazole by reacting these compounds at room temperature for 6 hours in tetrahydrofuran (THF) in the presence of triethylamine (TEA) to produce succinylsulfathiazole as a white solid (67percent yield). The succinylsulfathiazole was then reacted for 2 hours at room temperature with O-(N-succinimidyl)-1, 1, 3, 3-tetramethyluronium tetrafluoroborate (TSTU) in dichloromethane in the presence of TEA to produce the corresponding succinimidyl ester, which was reacted with 1-(4-aminobutyl)-2-{1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl}acetamide in dichloromethane in the presence of TEA at room temperature for 16 hours to produce Compound 27j as a yellow gummy mass (45percent yield). Compound 27j was characterized by NMR, two-dimensional NMR, and mass spectroscopy.

Uses

Succinylsulfathiazole is a sulfonamide antibiotic that was shown to inhibit bacteria that are responsible for folate production. Succinylsulfathiazole was used in various folate deficiency studies to block the synthesis of folic acid.

Use Classification：

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Computed Properties

Molecular Weight:355.4
XLogP3:-0.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:7
Exact Mass:355.02966287
Monoisotopic Mass:355.02966287
Topological Polar Surface Area:162
Heavy Atom Count:23
Complexity:526
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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