4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide

• ChemBase ID: 1361
• Molecular Formular: C11H12N4O2S
• Molecular Mass: 264.30358
• Monoisotopic Mass: 264.06809664
• SMILES: S(=O)(=O)(Nc1nc(ccn1)C)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1nccc(n1)C
• InChI: InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
• InChIKey: QPPBRPIAZZHUNT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide
• IUPAC Traditional name: 4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide; sulfamerazine
• Synonyms: 4-Amino-N-(4-methyl-2-pyrimidinyl)benzenesulfonamide; N1-(4-Methylpyrimidin-2-yl)sulfanilamide; Sulfamerazine; Cremomerazine; Mesulfa; N-(4-Methyl-2-pyrimidyl)sulfanilamide; Sulfameradine; Sulfamerazin; RP 2632; 2-Sulfanilamido-4-methylpyrimidine; 4-Methylsulfadiazine; Sulfamethyldiazine; N(1)-(4-Methyl-2-pyrimidinyl)sulfanilamide; Sulfamerazine; 4-氨基-N-(4-甲基-2-嘧啶基)苯磺酰胺; N1-(4-甲基嘧啶-2-基)磺胺; 磺胺甲嘧啶; 磺胺甲基嘧啶

Database IDs

• CAS Number: 127-79-7
• EC Number: 204-866-2
• MDL Number: MFCD00023212
• Beilstein Number: 249133
• Merck Index: 148913
• PubChem SID: 46505036; 24870500; 160964821; 24899818
• PubChem CID: 5325
• CHEBI ID: 102130
• ATC CODE: D06BA06; QJ01EQ17; J01ED07
• CHEMBL: 438
• Chemspider ID: 5134
• DrugBank ID: DB01581
• KEGG ID: D02435
• Unique Ingredient Identifier: UR1SAB295F
• Wikipedia Title: Sulfamerazine

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.991748
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.506311
• LogD (pH = 7.4): 0.078416295
• Log P: 0.518631
• Molar Refractivity: 68.7924 cm^3
• Polarizability: 26.346254 Å^3
• Polar Surface Area: 97.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.44
• LOG S: -2.94
• Solubility (Water): 3.04e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.202 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO
• Apperance: White Solid
• Melting Point: 234-236°C; 234-238°C
• Hydrophobicity(logP): 0.14 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Refrigerator
• RTECS: WP0750000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: Others
• Mechanism of Action: Folic acid biosynthesis antagonist

Product Information

• Purity: ≥99.0%; 98+%
• Grade: ReagentPlus®; VETRANAL™, analytical standard
• Salt Data: Free Base
• Suitability: suitable for 1694 per US EPA
• Application(s): Antiseptic
• Empirical Formula (Hill Notation): C11H12N4O2S

DETAILS

DrugBank - DB01581

• Drug Groups: approved
• Description: A sulfanilamide that is used as an antibacterial agent. [PubChem]
• Indication: A sulfanilamide that is used as an antibacterial agent. It can be used to treat bronchitis, prostatitis and urinary tract infections.
• Pharmacology: Sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis in bacteria.
• Toxicity: Sulfamerazine may cause nausea, vomiting, diarrhea and hypersensitivity reactions. Hematologic effects such as anemia, agranulocytosis, thrombocytopenia and hemolytic anemia in patients with glucose-6-phosphate dehydrogenase deficiency may also occur. Sulfamethoxazole may displace bilirubin from albumin binding sites causing jaundice or kernicterus in newborns.
• Absorption: Rapidly absorbed following oral administration.
• External Links: Wikipedia

Sigma Aldrich - S8876

Packaging
50, 250, 500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 46826

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

Toronto Research Chemicals - S689000

Antibacterial.

REFERENCES

• Woolfenden, R.D.G., et al.: Anal. Profiles Drug Subs., 6, 515 (1977)
• Roblin, R.O. et al., J.A.C.S., 1940, 62, 2002, (synth)
• Sprague, J.M. et al., J.A.C.S., 1941, 63, 3028, (synth)
• Moriguchi, I. et al., Chem. Pharm. Bull., 1969, 17, 2554, (pharmacol)
• Pogorzhel'skaya, N.A. et al., Zh. Org. Khim., 1969, 5, 1179, (synth)
• Chang, C.J. et al., J. Med. Chem., 1975, 18, 505, (nmr)
• Przybylski, M. et al., Adv. Mass Spectrom. Biochem. Med., Proc. Int. Symp. Mass Spectrom. Biochem. Med. 2nd, 3rd, 1976, 1, 309, (ms)
• Woolfenden, R.D.G., Anal. Profiles Drug Subst., 1977, 6, 515, (rev, synth, props, anal)
• Acharya, K.R. et al., J. Crystallogr. Spectrosc. Res., 1982, 12, 369, (cryst struct)
• Bult, A., Pharm. Weekbl., Sci. Ed., 1983, 5, 77, (cmr, tautom)
• Maury, L. et al., Farmaco, Ed. Prat., 1986, 41, 26, (ir, uv, Raman)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1930
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 205
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ALF250; SJW475