2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid

• ChemBase ID: 674
• Molecular Formular: C18H14N4O5S
• Molecular Mass: 398.39256
• Monoisotopic Mass: 398.06849057
• SMILES: c1(S(=O)(=O)Nc2ccccn2)ccc(cc1)/N=N/c1cc(c(cc1)O)C(=O)O
• Canonical SMILES: OC(=O)c1cc(/N=N/c2ccc(cc2)S(=O)(=O)Nc2ccccn2)ccc1O
• InChI: InChI=1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25)/b21-20+
• InChIKey: NCEXYHBECQHGNR-QZQOTICOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid; 2-hydroxy-5-(2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl)benzoic acid
• IUPAC Traditional name: sulfasalazine; @sulfasalazine
• Brand Name: Accucol; Alti-Sulfasalazine; Asulfidine; Azlufidine EN-Tabs; Azopyrin; Azopyrine; Azulfidine; Azulfidine EN-Tabs; Benzosulfa; Colo-Pleon; PMS-Sulfasalazine; Pms-Sulfasalazine E.C.; Reupirin; Rorasul; S.A.S. Enteric-500; Salazopiridazin; Salazopyridin; Salazopyrin; Salazopyrin EN-Tabs; Salazosulfapyridin; Salazosulfapyridine; Salicylazosulfapyridine; Salisulf; Sulcolon; W-T Sasp Oral; More...
• Synonyms: Sulfasalazine; 5-[4-(2-Pyridylsulfamoyl)phenylazo]salicylic acid; Sulphasalazine; Sulfasalazin; 2-Hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]benzoic Acid; 5-[[p-(2-Pyridylsulfamoyl)phenyl]azo]salicylic Acid; 5-[p-(2-Pyridylsulfamyl)phenylazo]salicylic Acid; Azopyrin; Azopyrine; Azulfidine; Azulfidine EN; Benzosulfa; Colo-Pleon; NSC 203730; NSC 667219; Reupirin; Salazopyridin; Salazopyrin; Salazopyrine; Salazosulfapyridin; Salazosulfapyridine; Salicylazosulfapyridine; Salisulf; 2-hydroxy-5-(2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl)benzoic acid; Sulfasalazine; 2-HYDROXY-(5-([4-(2-PYRIDINYLAMINO)SULFONYL]PHENYL)AZO)BENZOIC ACID; 5-(p-(2-Pyridinylsulfamoyl)Phenylazo)Salicylic Acid; Sulfasalazine (Azulfidine); 5-[对-(2-吡啶胺磺酰基)苯]偶氮水杨酸; 柳氮磺胺吡啶; More...

Database IDs

• CAS Number: 599-79-1
• EC Number: 209-974-3
• MDL Number: MFCD00057363
• Beilstein Number: 356241
• PubChem SID: 46505451; 160964137
• PubChem CID: 5359476

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.2977388
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.9754564
• LogD (pH = 7.4): 0.2490507
• Log P: 3.9374347
• Molar Refractivity: 104.6029 cm^3
• Polarizability: 38.550716 Å^3
• Polar Surface Area: 141.31 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.92
• LOG S: -3.93
• Solubility (Water): 4.64e-02 g/l

PROPERTIES

Physical Property

• Solubility: Dichlormethane; DMSO
• Apperance: Orange Solid
• Melting Point: 240°C; 249-251°C; 260 - 265°C; 260-265 °C (dec.)(lit.)
• Hydrophobicity(logP): 2.5; 3.88

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: VO6250000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 22-29/56-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Target: Others

Product Information

• Purity: ~95%; ≥98%; 95%; 97%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H14N4O5S

DETAILS

MP Biomedicals - 02191144

Purity: ~95%

DrugBank - DB08518

Drug information: experimental

DrugBank - DB00795

• Drug Groups: approved
• Description: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see mesalamine) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907)
• Indication: For the treatment of Crohn's disease and rheumatoid arthritis as a second-line agent.
• Pharmacology: Sulfasalazine is an anti-inflammatory indicated for the treatment of ulcerative colitis and rheumatoid arthritis.
• Affected Organisms: Humans and other mammals
• Half Life: 5-10 hours
• Elimination: The majority of 5-ASA stays within the colonic lumen and is excreted as 5-ASA and acetyl-5-ASA with the feces.
• Distribution: * 7.5 ± 1.6 L
• Clearance: * 1 L/h [IV administration]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - S0883

包装
10, 50, 100 g in glass bottle

Toronto Research Chemicals - S699084

Sulfasalazine is an anti-inflammatory (gastrointestinal). Sulfasalazine has been used in granulomatous colitis.

REFERENCES

• Schroder, H., et al.: Clin. Pharmacol. Ther.,13, 539 (1972)
• McDonnell, J.P., et al.: Anal. Profiles Drug Subs., 5, 515 (1972)
• Klotz, U., et al.: Clin. Pharmacokinet.,10, 285 (1972)