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Sulfamerazine

Sulfamerazine structure

CAS No:
127-79-7
Formula:
C11H12N4O2S
Chemical Name:
Sulfamerazine
Synonyms:
Benzenesulfonamide,4-amino-N-(4-methyl-2-pyrimidinyl)-;Sulfanilamide,N1-(4-methyl-2-pyrimidinyl)-;4-Amino-N-(4-methyl-2-pyrimidinyl)benzenesulfonamide;RP 2632;Cremomerazine;Methylpyrimal;N1-(4-Methyl-2-pyrimidinyl)sulfanilamide;Methylsulfazine;Percoccide;Pyralcid;Pyrimal m;2643RP;Sulfamerazine;Sulfamethyldiazine;2-Sulfa-4-methylpyrimidine;2-Sulfanilamido-4-methylpyrimidine;Sumedine;Veta-Merazine;Romezin;A 310;Sulfameradine;N-(4-Methyl-2-pyrimidyl)sulfanilamide;Sulphamerazine;Metilsulfazin;Metilsulfadiazin;Pirimal-M;Sulfamerazin;Debenal-M;Kelamerazine;2632RP;Septacil;Mesulfa;Mebacid;2-(4-Aminobenzenesulfonamido)-4-methylpyrimidine;Spanbolet II;NSC 27259;N-(4-Methylpyrimidin-2-yl)-4-aminobenzenesulfonamide;99482-27-6
Categories:
Organic Chemistry > Amides

Description

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

Solid

Sulfamerazine is a sulfonamide consisting of pyrimidine with a methyl substituent at the 4-position and a 4-aminobenzenesulfonamido group at the 2-position. It has a role as an antiinfective agent and a drug allergen. It is a member of pyrimidines, a sulfonamide and a sulfonamide antibiotic. It derives from a sulfanilamide.|A sulfanilamide that is used as an antibacterial agent.|Sulfamerazine is a long-acting sulfanilamide antibacterial agent. Sulfamerazine inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for the binding site on dihydropteroate synthase.

Sulfamerazine Basic Attributes

Molecular Weight：

264.3

Exact Mass：

264.30

BRN：

249133

EC Number：

204-866-2

UNII：

UR1SAB295F

NSC Number：

757325|27259

DSSTox ID：

DTXSID0023612

NCI Thesaurus Code：

C61959

ATC Code：

D - Dermatologicals|J - Antiinfectives for systemic use

HScode：

2935904000

Characteristics

PSA：

106

XLogP3：

0.1

Appearance：

Solid

Density：

1.3425 g/cm³

Melting Point：

236 °C

Boiling Point：

519.1±52.0 °C(Predicted)

Flash Point：

267.8±30.7 °C

Refractive Index：

1.6440 (estimate)

Water Solubility：

3.04e-01 g/L

Storage Conditions：

0-6°C

Vapor Pressure：

7.03E-11mmHg at 25°C

Toxicity：

Subcutaneous-rat LD50: 1890 mg/kg; peritoneal-mouse LD50: 1400 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxides and sulfur oxide fumes

Collision Cross Section：

156.3 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|154.8 Å² [M+H]+ [CCS Type: TW]|159 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|168.3 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|161.33 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36/37

RTECS Number：

WP0750000

Marks：

Storage features：

Warehouse ventilated, low temperature and dry

Precautionary statement(s)：

P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (97.87%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 48 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

moderately toxic

Toxicity Summary：

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.

Drug Information

Drug 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.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

Rapidly absorbed following oral administration.

Metabolism/Metabolites：

Sulfamerazine has known human metabolites that include N(4)-Acetylsulfamerazine.

Mechanism of Action：

Sulfamerazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamerazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.

MeSH Entry Terms：

Mebacid

Sulfamerazine Use and Manufacturing

Uses

Antibacterial.

Manufacturing Info：

Benzenesulfonamide, 4-amino-N-(4-methyl-2-pyrimidinyl)-: INACTIVE

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Computed Properties

Molecular Weight:264.31
XLogP3:0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:264.06809681
Monoisotopic Mass:264.06809681
Topological Polar Surface Area:106
Heavy Atom Count:18
Complexity:360
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 127-79-7

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