3-({4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}carbamoyl)propanoic acid

• ChemBase编号: 102766
• 分子式: C13H13N3O5S2
• 平均质量: 355.38942
• 单一同位素质量: 355.02966253
• SMILES: OC(=O)CCC(=O)Nc1ccc(cc1)S(=O)(=O)Nc1nccs1
• Canonical SMILES: O=C(Nc1ccc(cc1)S(=O)(=O)Nc1nccs1)CCC(=O)O
• InChI: InChI=1S/C13H13N3O5S2/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)
• InChIKey: SKVLYVHULOWXTD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-({4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}carbamoyl)propanoic acid
• IUPAC传统名: 3-({4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}carbamoyl)propanoic acid; succinylsulfathiazole
• 别名: Succinylsulfathiazole; Succinylsulphathiazole; Kaoxidin; Sulfasuxidine; Colistatin; SUCCINYLSULFATHIAZOLE

登记号

• CAS号: 116-43-8
• EC号: 204-141-0
• MDL号: MFCD00022437
• Beilstein号: 349989
• PubChem SID: 162090073; 24899811
• PubChem CID: 5315

理论计算性质

• Acid pKa: 3.3619187
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): -1.2780585
• LogD (pH = 7.4): -3.0957887
• Log P: 0.866527
• 摩尔折射率: 83.3282 cm^3
• 极化性: 32.270557 Å^3
• 极化表面积: 125.46 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: WM4767000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 42/43
• 安全公开号: 22-36/37-45
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H317
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

药理学性质

• 生物活性机理: Dihydrofolate reductase inhibitor; Dihydrofolate synthesis inhibitor;; Folate antagonist

产品相关信息

• 纯度: ≥99%
• 应用领域: Antidiarrheic; Antiseptic; Intestinal antibacterial agent

详细说明

MP Biomedicals - 02102976

Crystalline

Sigma Aldrich - S8752

Application
Succinylsulfathiazole is used to block the synthesis of folic acid. It is used to study folate deficiency1. It is used to suppress folate production by bacteria in the intestine2.
Biochem/physiol Actions
Succinylsulfathiazole is a competitive inhibitor of dihydropteroate synthetase. It is a dihydrofolate reductase (DHFR) inhibitor.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S8752.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

参考文献

• Poth, E.J. et al., Arch. Surg. (Chicago), 1942, 44, 187-222, (pharmacol)
• Moore, M.L. et al., J.A.C.S., 1942, 64, 1572-1576, (synth)
• U.S. Pat., 1944, Sharp and Dohme, 2 324 013; CA, 38, 2193, (synth)
• Phillips, M.A., Chem. Ind. (London), 1945, 247, (synth)
• Kram, T.C., J. Pharm. Sci., 1972, 61, 254, (hplc)
• Moustafa, M.A. et al., J. Pharm. Sci., 1974, 63, 1103-1109, (polymorph)
• Chang, C.J. et al., J. Med. Chem., 1975, 18, 505, (nmr)
• Rodier, N. et al., Acta Cryst. B, 1978, 34, 218-221, (cryst struct)
• Burger, A. et al., Sci. Pharm., 1989, 57, 293-305, (polymorph, struct, props)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 204
• Bourne, S.A. et al., J. Pharm. Sci., 1994, 83, 887-892, (cryst struct solvates)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 3391