スルファドキシン

Sulfadoxine

HCID 17134CAS 2447-57-6

基本情報

標準SMILES
COc1ncnc(NS(=O)(=O)c2ccc(N)cc2)c1OC
InChIKey
PJSFRIWCGOHTNF-UHFFFAOYSA-N
分子式
C12H14N4O4S
平均分子量
310.33 g/mol
単同位体質量
310.07357593

概要

Sulfadoxine is a sulfonamide consisting of pyrimidine having methoxy substituents at the 5- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position. In combination with the antiprotozoal pyrimethamine (CHEBI:8673) it is used as an antimalarial. It has a role as an antibacterial drug and an antimalarial. It is a sulfonamide and a member of pyrimidines.

名称と識別子

優先名称
Sulfadoxine
IUPAC
4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
現地名
スルファドキシン
英語名
Sulfadoxine
分子式
C12H14N4O4S
分子量
310.33

名称と別名

SULFADOXINE2447-57-6SulphadoxineSulfadoxinSulforthomidine4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamideSulphormethoxineSulfadoxinumSulfadoxinaFanzilRo 4-4393Benzenesulfonamide, 4-amino-N-(5,6-dimethoxy-4-pyrimidinyl)-
名称をさらに表示
サナシルオルトスルフィンファナシルスルホルメトキシン4-アミノ-N-(5,6-ジメトキシ-4-ピリミジニル)ベンゼンスルホンアミドスルホルトミジンファンジルスルホルトジメトキシンファナスルフスルファドキシンN-(5,6-ジメトキシピリミジン-4-イル)-4-アミノベンゼンスルホンアミド4-アミノ-N-(5,6-ジメトキシピリミジン-4-イル)ベンゼンスルホンアミドスルファドキシン標準品スルファドキシン (JAN)4-アミノ-N-(2-ヒドロキシ-6-メトキシピリミジン-4-イル)ベンゼン-1-スルホンアミド4-アミノ-N-(5,6-ジメトキシピリミジン-4-イル)ベンゼン-1-スルホンアミドN-(2-ヒドロキシ-6-メトキシピリミジン-4-イル)-4-アミノベンゼンスルホンアミド4-AMINO-N-(5,6-DIMETHOXY-4-PYRIMIDINYL)BENZENESULFONAMIDESulfadimoxineSulfadumoxinewr4873fanasil
Fanasulf4-Sulfanilamido-5,6-dimethoxypyrimidineDTXSID6023608Ro-4-4393N'-(5,6-Dimethoxy-4-pyrimidyl)sulfanilamideRo-44393NSC-759319Sulformethoxine

データベース識別子

CAS
2447-57-6
PubChem CID
17134
DTXSID
DTXSID6023608
ChEMBL
CHEMBL1539、CHEMBL244800
ChEBI
CHEBI:9329
UNII
88463U4SM5
EC Number
219-504-9
Nikkaji
J21.373J

物性

構造計算による物性

XLogP
0.7
極性表面積
125 Ų
水素結合供与体数
2
水素結合受容体数
8
回転可能結合数
5
重原子数
21

実験および物理化学的性質

Drugs · 3 件

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Antibiotics (Sulfonamide)

Pharmaceuticals -> Listed in ZINC15

LogP · 2 件

0.70

0.7

Solubility2.96e-01 g/L
Human Drugs · 2 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point · 2 件

190-194 °C

190 - 194 °C

物理化学的性質

融点
190 · 190-194°C
沸点
298 °C · 298°C (rough estimate)
比重(密度)
1.4006 · 1.4006 (rough estimate)
屈折率
1.627 · 1.6270 (estimate)
貯蔵温度
Keep in dark place,Inert atmosphere,Room temperature
溶解性
エタノールに可溶。水酸化アンモニウム (9:1) 20mg/ml

化学的性質

化学的特性White Crystalline Solid

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (57.7%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 130 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Other Safety InformationIMAP assessments - Benzenesulfonamide, 4-amino-N-(5,6-dimethoxy-4-pyrimidinyl)-: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (57.7%)

安全データ

wgk
2
rtecs
DA9500000
毒性
LD50 in mice (microcrystals, mg/kg): 5200 orally, 2900 s.c., 2900 i.p. (Bhni)
hs_code
29350090
risk_code
36/37/38
hazard_code
Xi

化学と産業

薬理情報

ATC CodeQJ - Antiinfectives for systemic use
Pharmacodynamics · 1 件

Sulfadoxine helps inhibit the enzyme dihydropteroate synthetase which is an enzyme necessary in the conversion of PABA to folic acid. As folic acid is vital to the synthesis, repair, and methylation of DNA which is vital to cell growth in Plasmodium falciparum. With this vital nutrient lacking, the parasite has difficulty in reproducing.

Mechanism of Action · 1 件

Sulfadoxine is a sulfa drug, often used in combination with pyrimethamine to treat malaria. This medicine may also be used to prevent malaria in people who are living in, or will be traveling to, an area where there is a chance of getting malaria. Sulfadoxine targets Plasmodium dihydropteroate synthase and dihydrofolate reductase. Sulfa drugs or Sulfonamides are antimetabolites. They compete with para-aminobenzoic acid (PABA) for incorporation into folic acid. The action of sulfonamides exploits the difference between mammal cells and other kinds of cells in their folic acid metabolism. All cells require folic acid for growth. Folic acid (as a vitamin) diffuses or is transported into human cells. However, folic acid cannot cross bacterial (and certain protozoan) cell walls by diffusion or active transport. For this reason bacteria must synthesize folic acid from p-aminobenzoic acid.

FDA Pharmacological Classification · 5 件

88463U4SM5

SULFADOXINE

Established Pharmacologic Class [EPC] - Sulfonamide

Chemical Structure [CS] - Sulfonamides

Sulfadoxine is a Sulfonamide.

MeSH Pharmacological Classification · 3 件

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)

用途と製造

Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
応用分野 · 2 件

用途高速液体クロマトグラフ法によるスルファドキシン定量用標準品。

説明Sulfadoxin is a sulfonamide antibiotic that inhibits dihydropteroate synthetase (DHPS), an enzyme involved in folic acid synthesis. Sulfadoxin competes with 4-aminobenzoate (PABA), the native substrate of DHPS, and inhibits PABA incorporation into folic acid. Folate is essential for purine and pyrimidine synthesis, therefore, sulfadoxin has antiproliferative activity in non-resistant P. falciparum. Sulfadoxin inhibits growth of P. falciparum in vitro, but potency varies between non-resistant (IC50 = 4 ng/ml) and resistant strains (IC50 = 3,970 ng/ml).

上流・下流製品情報

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]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
補足説明 · 1 件

定義ChEBI: A sulfonamide consisting of pyrimidine having methoxy substituents at the 5- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position. In combination with the antiprotozoal pyrimethamine (CHEBI:8673) it is used as an antimalarial.

関連反応

2 件

関連ノート

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