基本情報
- CAS
129-46-4- 標準SMILES
Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1- InChIKey
FIAFUQMPZJWCLV-UHFFFAOYSA-N- 分子式
- C51H40N6O23S6
- 平均分子量
- 1,297.3 g/mol
- 単同位体質量
- 1,296.0469086
概要
Suramin is a member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years. It has a role as an antinematodal drug, an antineoplastic agent, a trypanocidal drug, an EC 2.7.11.13 (protein kinase C) inhibitor, a GABA-gated chloride channel antagonist, an angiogenesis inhibitor, a GABA antagonist, a ryanodine receptor agonist, an apoptosis inhibitor and a purinergic receptor P2 antagonist. It is a member of phenylureas, a secondary carboxamide and a naphthalenesulfonic acid. It is functionally related to a naphthalene-1,3,5-trisulfonic acid. It is a conjugate acid of a suramin(6-).
名称と識別子
- 優先名称
- Suramin
- IUPAC
- 8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic acid
- 現地名
- スラミンヘキサナトリウム
- 英語名
- Suramin sodium
- 分子式
- C51H34N6Na6O23S6
- 分子量
- 1429.17
名称と別名
suraminSuramine145-63-1FourneauFarmaBelganylMetaretDTXSID1046344NSC-34936FARMA-9396032D45BEM1,3,5-naphthalenetrisulfonic acid, 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-
名称をさらに表示
ゲルマニンスラミンナトリウムアントリポールナフリドナトリウム8,8'-[カルボニルビス[イミノ(3,1-フェニレン)カルボニルイミノ(4-メチル-3,1-フェニレン)カルボニルイミノ]]ビス(1,3,5-ナフタレントリスルホン酸トリナトリウム)8,8'-[カルボニルビス[イミノ-3,1-フェニレンカルボニルイミノ(4-メチル-3,1-フェニレン)カルボニルイミノ]]ビス(1,3,5-ナフタレントリスルホン酸)ヘキサナトリウムナガニンスラミンヘキサナトリウムモラニルスラミンナトリウム塩8,8'-[カルボニルビス[イミノ-3,1-フェニレンカルボニルイミノ(4-メチル-3,1-フェニレン)カルボニルイミノ]]ビス(1,3,5-ナフタレントリスルホン酸トリナトリウム)スラミン六ナトリウムスラミン六ナトリウム塩スラミン ナトリウム塩8,8′-[カルボニルビス[イミノ(3,1-フェニレン)カルボニルイミノ(4-メチル-3,1-フェニレン)カルボニルイミノ]]ビス(1,3,5-ナフタレントリスルホン酸トリナトリウム)8,8′-[カルボニルビス[イミノ-3,1-フェニレンカルボニルイミノ(4-メチル-3,1-フェニレン)カルボニルイミノ]]ビス(1,3,5-ナフタレントリスルホン酸)ヘキサナトリウム
物性
構造計算による物性
- XLogP
- 1.5
- 極性表面積
- 534 Ų
- 水素結合供与体数
- 12
- 水素結合受容体数
- 23
- 回転可能結合数
- 16
- 重原子数
- 86
- 形式電荷
- 0
- 複雑度
- 3,020
実験および物理化学的性質
Solubility8.72e-03 g/L
Physical DescriptionSolid
物理化学的性質
- 融点
- 260 °C · >260°C (dec.)
- 貯蔵温度
- 0 · 0-6°C
- 溶解性
- 2 O: · H2O: >10mg/mL
- 外見
- 結晶性粉末
- 色
- 白い
- PH
- pH(10g/l, 25℃) : 5.0～8.0
- 水溶解度
- 溶ける
- BRN
- 3694087 · 3694087
- 安定性
- 吸湿性
- InChIKey
- VAPNKLKDKUDFHK-UHFFFAOYSA-H
化学的性質
化学的特性White crystalline powder
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- F
- 3-10
- wgk
- 3
- rtecs
- QM7000000
- 毒性
- LD50 in mice (mg/kg): ~620 i.v. (Hawking)
- hs_code
- 29242998
- safety_code
- 22-24/25
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Protein BindingApproximately 99.7%
Mechanism of Action
The mechanism is unknown, but the trypanocidal activity may be due to the inhibition of enzymes involved with the oxidation of reduced nicotinamide-adenine dinucleotide (NADH), which functions as a co-enzyme in many cellular reactions, such as respiration and glycolysis, in the trypanosome parasite. Suramin's action in the treatment of onchocerciasis is macrofilaricidal and partially microfilaricidal. It may also act as an antagonist of P2 receptors and as an agonist of Ryanodine receptors. It also can inhibit follicle-stimulating hormone receptors.
Biological Half-LifeApproximately 36 to 60 days
Metabolism/MetabolitesLittle or no metabolism
MeSH Pharmacological Classification
Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA.
Absorption, Distribution and ExcretionPoorly absorbed from the gastrointestinal tract.
Cellular LocationsCytoplasm
応用分野
説明Introduced into therapy for the treatment of early trypanosomiasis in the 1920s, suramin, a bis-hexasulfonatednaphthylurea, is still considered to be the drug of choice for treatment of non-CNS-associated African trypanosomiasis.
使用Suramin sodium is a compound with a dyelike structure. Suramin is most effective against T. b. rhodesiense, but has also been used against T. b. gambiense infection. The compound causes side effects such as nausea, photophobia, and peripheral neuropathy which disappear shortly after conclusion of administration. Because the drug is unable to pass the bloodbrain barrier, prompt treatment of patients is essential. Suramin in combination with tryparsamide is an alternative that has been investigated.
関連反応
0 件
現在のフィルター条件では反応記録がありません。
化合物ノート
読み込み中…