CAS 127-79-7|4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide|sulfamerazine|Sulfamerazine|N1-(4-甲基嘧啶-2-基)磺胺|4-氨基-N-(4-甲基-2-嘧啶基)苯磺酰胺|N1-(4-Methylpyrimidin-2-yl)sulfanilamide|...

General Information

Structure

Molecular Formula

C₁₁H₁₂N₄O₂S

Molecular Mass

264.30358

Exact Mass

264.06809664

Charge

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

Canonic Smiles

Nc1ccc(cc1)S(=O)(=O)Nc1nccc(n1)C

Isomeric Smiles

S(=O)(=O)(Nc1nc(ccn1)C)c1ccc(N)cc1

Calculated Properties

JChem

LogD (pH = 7.4)

0.08

LogD (pH = 5.5)

0.51

Log P

0.52

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

6.99

Polar Surface Area

97.97

Polarizability

26.47

Molar Refractivity

68.79

LOG S

-2.66

Data Source

Names and Identifiers

IUPAC Traditional name

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

IUPAC name

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

Synonyms

Sulfamerazine4-氨基-N-(4-甲基-2-嘧啶基)苯磺酰胺N1-(4-甲基嘧啶-2-基)磺胺4-Amino-N-(4-methyl-2-pyrimidinyl)benzenesulfonamideN1-(4-Methylpyrimidin-2-yl)sulfanilamide磺胺甲嘧啶SulfamerazineRP 2632SulfamerazinMesulfaCremomerazineSulfameradineN-(4-Methyl-2-pyrimidyl)sulfanilamide2-Sulfanilamido-4-methylpyrimidineSulfamethyldiazine磺胺甲基嘧啶4-MethylsulfadiazineN(1)-(4-Methyl-2-pyrimidinyl)sulfanilamide2-Sulfa-4-methylpyrimidineN(1)-(4-Methyl-2-pyrimidinyl)sulfanilamideN-(4-Methyl-2-pyrimidyl)sulfanilamideSulfamethyldiazine2-(4-Aminobenzenesulfonamido)-4-methylpyrimidine2-(Sulfanilamido)-4-methylpyrimidineSulphamerazine(p-Aminobenzolsulfonyl)-2-amino-4-methylpyrimidin2-(p-Aminobenzolsulfonamido)-4-methylpyrimidinesulfamerazine4-Amino-N-(4-methyl-2-pyrimidinyl)-benzenesulfonamide

API Name

Sulfamerazine

International Nonproprietary Name (INN)

sulfamerazinasulfamerazinumsulfamerazine

Names and Identifiers

Registration numbers

PubChem SID

16096482146505036248705002489981885307740

PubChem CID

Chemspider ID

CHEBI ID

Wikipedia Title

ATC CODE

D06BA06QJ01EQ17J01ED07

Unique Ingredient Identifier

KEGG ID

CHEMBL

DrugBank ID

CAS Number

Beilstein Number

MDL Number

Merck Index

EC Number

PubMed Citation Links

2362744411431418130375792434548245088836864729

Drug Central Database

2,510

MetaboLights Database

MTBLS1642MTBLS1693MTBLS4967MTBLS1918

LINCS Database

LSM-5979

Patent number

US2407966

BRENDA Database

1.14.14.192.3.1.52.5.1.15

SureChEMBL Database

CompTox Database

ACToR Database

IEDB Database

Gmelin ID

BindingDB Database

KEGG DRUG Database

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

0.14 [HANSCH,C ET AL. (1995)]

Solubility

0.202 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

DMSO

Melting Point

234-236°C

234-238°C

Apperance

White Solid

Safety Information

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Pharmacology Properties

Folic acid biosynthesis antagonist

Others

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Wikipedia

Sulfamerazine

Sigma Aldrich

S8876

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

46826

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

TRC

S689000

Antibacterial.

ChEBI

CHEBI:102130

A sulfonamide consisting of pyrimidine with a methyl substituent at the 4-position and a 4-aminobenzenesulfonamido group at the 2-position.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

• 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)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1930

• Woolfenden, R.D.G., Anal. Profiles Drug Subst., 1977, 6, 515, (rev, synth, props, anal)

• Sprague, J.M. et al., J.A.C.S., 1941, 63, 3028, (synth)

• Moriguchi, I. et al., Chem. Pharm. Bull., 1969, 17, 2554, (pharmacol)

• 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)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 205

• Maury, L. et al., Farmaco, Ed. Prat., 1986, 41, 26, (ir, uv, Raman)

• Pogorzhel'skaya, N.A. et al., Zh. Org. Khim., 1969, 5, 1179, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ALF250; SJW475

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

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

IUPAC name

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

Synonyms

API Name

Sulfamerazine

International Nonproprietary Name (INN)

sulfamerazinasulfamerazinumsulfamerazine

Registration numbers

PubChem SID

16096482146505036248705002489981885307740

PubChem CID

Chemspider ID

CHEBI ID

Wikipedia Title

ATC CODE

D06BA06QJ01EQ17J01ED07

Unique Ingredient Identifier

KEGG ID

CHEMBL

DrugBank ID

CAS Number

Beilstein Number

MDL Number

Merck Index

EC Number

PubMed Citation Links

2362744411431418130375792434548245088836864729

Drug Central Database

2,510

MetaboLights Database

MTBLS1642MTBLS1693MTBLS4967MTBLS1918

LINCS Database

LSM-5979

Patent number

US2407966

BRENDA Database

1.14.14.192.3.1.52.5.1.15

SureChEMBL Database

CompTox Database

ACToR Database

IEDB Database

Gmelin ID

BindingDB Database

KEGG DRUG Database

Molecule Details

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

Absorption

Rapidly absorbed following oral administration.

External Links

• [Wikipedia]

Wikipedia

Sulfamerazine

Sigma Aldrich

S8876

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

46826

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

TRC

S689000

Antibacterial.

ChEBI

CHEBI:102130

A sulfonamide consisting of pyrimidine with a methyl substituent at the 4-position and a 4-aminobenzenesulfonamido group at the 2-position.

References

PubChem Literature

From Data Sources

• 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)

• 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)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1930

• Woolfenden, R.D.G., Anal. Profiles Drug Subst., 1977, 6, 515, (rev, synth, props, anal)

• Sprague, J.M. et al., J.A.C.S., 1941, 63, 3028, (synth)

• Moriguchi, I. et al., Chem. Pharm. Bull., 1969, 17, 2554, (pharmacol)

• 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)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 205

• Maury, L. et al., Farmaco, Ed. Prat., 1986, 41, 26, (ir, uv, Raman)

• Pogorzhel'skaya, N.A. et al., Zh. Org. Khim., 1969, 5, 1179, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ALF250; SJW475

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

0.14 [HANSCH,C ET AL. (1995)]

Solubility

0.202 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

DMSO

Melting Point

234-236°C

234-238°C

Apperance

White Solid

Safety Information

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Pharmacology Properties

Folic acid biosynthesis antagonist

Others

Molecule

ID:1361