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

• ChemBase ID: 104523
• Molecular Formular: C17H13N3O5S2
• Molecular Mass: 403.43222
• Monoisotopic Mass: 403.02966253
• SMILES: OC(=O)c1c(cccc1)C(=O)Nc1ccc(cc1)S(=O)(=O)Nc1nccs1
• Canonical SMILES: O=C(c1ccccc1C(=O)O)Nc1ccc(cc1)S(=O)(=O)Nc1nccs1
• InChI: InChI=1S/C17H13N3O5S2/c21-15(13-3-1-2-4-14(13)16(22)23)19-11-5-7-12(8-6-11)27(24,25)20-17-18-9-10-26-17/h1-10H,(H,18,20)(H,19,21)(H,22,23)
• InChIKey: PBMSWVPMRUJMPE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}carbamoyl)benzoic acid
• IUPAC Traditional name: 2-({4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}carbamoyl)benzoic acid; phthalylsulphathiazole
• Synonyms: Colicitina; Phthazol; Sulfathalidin; Thalazole; Phthalylsulfathiazole; 2-[[[4-[(2-Thiazolylamino)sulfonyl]-phenyl]amino]-carbonyl]benzoic acid; PHTHALYLSULFATHIAZOLE; 2-[[[4-[(2-Thiazolylamino)sulfonyl]phenylamino]carbonyl]benzoic acid; N4-Phthalylsulfathiazole; 2-[[[4-[(2-噻唑氨基)磺酰基]苯氨基]羰基]苯甲酸; N4-酞磺胺噻唑

Database IDs

• CAS Number: 85-73-4
• EC Number: 201-627-4
• MDL Number: MFCD00005318
• Beilstein Number: 359901
• PubChem SID: 162091594; 24870549
• PubChem CID: 4806

CALCULATED PROPERTIES

• Acid pKa: 2.912309
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.010286049
• LogD (pH = 7.4): -1.4816947
• Log P: 2.5534215
• Molar Refractivity: 100.3616 cm^3
• Polarizability: 38.04544 Å^3
• Polar Surface Area: 125.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 240 °C (dec.)(lit.); 272-277°C (decomposes)

Safety Information

• Storage Condition: Room Temperature (15-30°C), Protect from light
• RTECS: TH8575000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Mechanism of Action: Folic acid biosynthesis antagonist

Product Information

• Grade: VETRANAL™, analytical standard
• Application(s): Antibacterial (intestinal) agent; Antiseptic
• Empirical Formula (Hill Notation): C17H13N3O5S2

DETAILS

MP Biomedicals - 02156250

Crystalline

Sigma Aldrich - 46901

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 649A, (ir)
• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 744A, (nmr)
• Shell, J.W. et al., Mikrochim. Acta, 1957, 145, (props)
• Freytag, B., Arzneim.-Forsch., 1960, 10, 165, (pharmacol)
• Tanaka, Y. et al., Chem. Pharm. Bull., 1965, 13, 399, (ir)
• Walash, M.I. et al., J. Pharm. Sci., 1972, 61, 277, (tlc)
• Ganju, A. et al., Indian Chem. J., 1973, 8, 33, (synth)
• Cobb, P.H. et al., J. Chromatogr., 1976, 123, 443, (ir)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 192
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5594, (synonyms)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PHY750