スルファダイアジン

Sulfadiazine

HCID 5215CAS 68-35-9

基本情報

標準SMILES
Nc1ccc(S(=O)(=O)Nc2ncccn2)cc1
InChIKey
SEEPANYCNGTZFQ-UHFFFAOYSA-N
分子式
C10H10N4O2S
平均分子量
250.28 g/mol
単同位体質量
250.05244656

概要

Sulfadiazine is a sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position. It has a role as an antimicrobial agent, an antiinfective agent, a xenobiotic, a coccidiostat, an antiprotozoal drug, an EC 2.5.1.15 (dihydropteroate synthase) inhibitor, an EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor, an environmental contaminant and a drug allergen. It is a sulfonamide, a member of pyrimidines, a substituted aniline and a sulfonamide antibiotic. It is functionally related to a sulfanilamide. It is a conjugate acid of a sulfadiazinate.

名称と識別子

優先名称
Sulfadiazine
IUPAC
4-amino-N-pyrimidin-2-ylbenzenesulfonamide
現地名
スルファダイアジン
英語名
Sulfadiazine
分子式
C10H10N4O2S
分子量
250.28

名称と別名

sulfadiazine68-35-9SulphadiazineSulfapyrimidineSulfadiazinAdiazineCoco-Diazine2-SulfanilamidopyrimidineSulfolexBenzenesulfonamide, 4-amino-N-2-pyrimidinyl-2-Sulfanilylaminopyrimidine4-amino-N-pyrimidin-2-ylbenzenesulfonamide
名称をさらに表示
スルファジアジンアジアジン2-スルファニルアミノピリミジンクレモジアジンテラジア4-アミノ-N-(ピリミジン-2-イル)ベンゼンスルホンアミドデベナールピリマールホニージアジンN-(2-ピリミジニル)-4-アミノベンゼンスルホンアミドエスカジアジンジアジン2-(スルファニリルアミノ)ピリミジン4-アミノ-N-(2-ピリミジニル)ベンゼンスルホンアミドスルファピリミジンスルファジアジン標準品N-(2-ピリミジニル)スルファニルアミドスルファジアジンスルファピリミジンスルファジアジン (JAN)2-(スルファニルアミド)ピリミジンSulfadiazine,(S)SulfadiazeneDiazinSulfoseTerfonylDiazoloneNeotrizinesuldadiazine
N(1)-2-pyrimidylsulfanilamideN(sup 1)-2-Pyrimidinylsulfanilamide4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamideN(1)-2-pyrimidinylsulfanilamide4-AMINO-N-2-PYRIMIDINYLBENZENESULFONAMIDEDTXSID7044130CHEBI:9328NSC35600

データベース識別子

CAS
68-35-9
PubChem CID
5215
DTXSID
DTXSID7044130
ChEMBL
CHEMBL439
ChEBI
CHEBI:9328
UNII
0N7609K889
EC Number
200-685-8
Nikkaji
J1.418D

物性

構造計算による物性

XLogP
-0.1
極性表面積
106 Ų
水素結合供与体数
2
水素結合受容体数
6
回転可能結合数
3
重原子数
17

実験および物理化学的性質

Drugs · 4 件

Pharmaceuticals -> Antibiotics (Sulfonamide)

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

SpringerMaterials PropertiesFusion temperature
LogP · 2 件

-0.2

-0.04

Solubility6.01e-01 g/L
Human Drugs · 3 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Anti-infective medicines

Animal Drugs · 3 件

Active Ingredients (Sulfadiazine) -> FDA Greenbook

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

物理化学的性質

融点
253 °C · 253 °C (dec.) (lit.)
沸点
512.6 · 512.6±52.0 °C(Predicted)
比重(密度)
1.378 · 1.3780 (rough estimate)
屈折率
1.644 · 1.6440 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
ジメチルスルホキシドに可溶。

化学的性質

化学的特性White to slightly yellow crystalline pow

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 1.2% (2 of 171) of reports.

Danger

H302 (98.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P233, P260, P261, P263, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P391, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 171 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 2 件

Status: Active Update: 23-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17511

Sulphadiazine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (98.2%)

毒性情報

Hepatotoxicity · 1 件

Sulfadiazine, like other sulfonamides, causes a characteristic idiosyncratic liver injury which has features of drug-allergy or hypersensitivity. The typical onset is sudden development of fever and rash followed by jaundice within a few days or weeks of starting the medication. The pattern of injury is typically mixed, although fatal cases are often hepatocellular and prolonged cholestatic cases have also been described. Eosinophilia or atypical lymphocytosis are also common and the clinical pattern can be considered a part of DRESS syndrome (drug rash with eosinophilia and systemic symptoms). Cases of Stevens Johnson syndrome due to sulfadiazine have also been described. Sulfonamides such as sulfadiazine have been linked to many cases of acute liver failure and as a class, the sulfonamides still rank in the top 5 to 10 causes of drug induced, idiosyncratic fulminant hepatic failure. However, most cases of sulfonamide induced liver injury resolve rapidly, usually within 2 to 4 weeks unless cholestasis is severe. Onset of injury is more rapid with rechallenge and can appear within a day or reexposure. Patients with hepatic injury due to sulfadiazine may have a history of previous exposure to the drug without injury. Sulfonamides such as sulfadiazine can also cause mild and transient ALT elevations that do not progress to jaundice or more severe liver injury either alone or as a part of a generalized hypersensitivity reaction. Sulfonamides have also been linked to hepatic granulomas.

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Sulfadiazine

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

安全データ

F
10
wgk
3
tsca
TSCA listed
rtecs
WP1925000
ridadr
3249
毒性
LD50 oral in mouse: 1500mg/kg

化学と産業

薬理情報

ATC Code · 4 件

J01EC02

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

J01EC02

Pharmacodynamics · 1 件

Sulfadiazine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of <i>p</i>-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.

Mechanism of Action · 1 件

Sulfadiazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

Metabolism/MetabolitesSulfadiazine has known human metabolites that include Sulfadiazine hydroxylamine.
FDA Pharmacological Classification · 6 件

0N7609K889

SULFADIAZINE

Established Pharmacologic Class [EPC] - Sulfonamide Antibacterial

Chemical Structure [CS] - Sulfonamides

Sulfadiazine is a Sulfonamide Antibacterial.

SULFADIAZINE

MeSH Pharmacological Classification · 3 件

Substances that are destructive to protozoans.

Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals.

Substances that inhibit the growth or reproduction of BACTERIA.

用途と製造

UsesUse (kg) in Switzerland (2009): >250
Use Classification · 3 件

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Pharmaceuticals -> Antiinfectives for systemic use -> Antibacterials for systemic use -> Sulfonamides and trimethoprims -> Intermediate-acting sulfonamides -> Antibiotics

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

General Manufacturing InformationBenzenesulfonamide, 4-amino-N-2-pyrimidinyl-: ACTIVE
応用分野 · 5 件

解説スルファダイアジンは,サルファ剤の一種。ぶどう球菌・大腸菌などに抗菌力を持ち、皮膚の細菌感染症や肺炎・赤痢などに用いる。小学館 デジタル大辞泉について 情報 | 凡例

用途スルファジアジン(Sulfadiazine)は、サルファ薬の一つ。感染源の細菌細胞内での葉酸の合成を阻害することによって殺す効果があり、尿路感染症(UTIs)の治療に使われる。 スルファジアジンとピリメタミンとの組み合わせは、トキソプラズマ(Toxoplasma gondii)が原因のトキソプラズマ症の治療に使われる。

用途細菌性下痢症、ヘモフィルス感染症 (豚) 。

使用It is used in the form of silver salts (sulfadiazine silver) as an external antibacterial agent, primarily for treating burns. It is believed that the presence of the silver ion in the molecule facilitates increased antimicrobial and wound-healing action.

一般的な説明Sulfadiazine’s plasma half-life is 17 hours. It is a white,odorless crystalline powder soluble in water to the extentof 1:8,100 at 37°C and 1:13,000 at 25°C, in human serumto the extent of 1:620 at 37°C, and sparingly soluble in alcoholand acetone. It is readily soluble in dilute mineralacids and bases. Its pKa is 6.3.

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

補足説明

定義ChEBI: A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.

関連反応

36 件

関連ノート

読み込み中…