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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 419
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Antibiotics (Sulfonamide)
Pharmaceuticals -> Listed in ZINC15
LogP
0.70
0.7
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
190-194 °C
190 - 194 °C
Collision Cross Section
165.3 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
166.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
172.96 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
166.6 Ų [M+H]+ [CCS Type: TW]
169.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
173.22 Ų [M-H]-
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
- 外見
- 粉
- 酸解離定数(Pka)
- 6.16 · 6.16±0.50(Predicted)
- 色
- 白い
- 水溶解度
- 209.8 mg/L · 209.8mg/L(温度表記なし)
- Merck
- 14 · 14,8906
- BRN
- 625453 · 625453
- BCS Class
- 3 · 3/1
- 主な用途
- 臨床検査
- InChI
- 1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
- InChIKey
- PJSFRIWCGOHTNF-UHFFFAOYSA-N
- SMILES
- COc1ncnc(NS(=O)(=O)c2ccc(N)cc2)c1OC
化学的性質
化学的特性White Crystalline Solid
安全と法規制
GHS分類
GHS Classification
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
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
- safety_code
- 26
- Hazard Classifications
- Aquatic Chronic 2Skin Sens. 1
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Pharmacodynamics
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
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
88463U4SM5
SULFADOXINE
Established Pharmacologic Class [EPC] - Sulfonamide
Chemical Structure [CS] - Sulfonamides
Sulfadoxine is a Sulfonamide.
MeSH Pharmacological Classification
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
応用分野
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
上流原料
下流製品
サプライヤー50 社
補足説明
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
関連ノート
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