スガマデクス
Sugammadex
基本情報
- CAS
343306-71-8- 標準SMILES
O=C(O)CCSC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]9[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]9CSCCC(=O)O)O[C@@H]8CSCCC(=O)O)O[C@@H]7CSCCC(=O)O)O[C@@H]6CSCCC(=O)O)O[C@@H]5CSCCC(=O)O)O[C@@H]4CSCCC(=O)O)O[C@@H]3CSCCC(=O)O- InChIKey
WHRODDIHRRDWEW-VTHZAVIASA-N- 分子式
- C72H112O48S8
- 平均分子量
- 2,002.2 g/mol
- 単同位体質量
- 2,000.4088747
概要
Sugammadex is an octasaccharide derivative that is gamma-cyclodextrin in which all eight primary hydroxy groups are replaced by 2-(carboxyethyl)sulfanyl groups. Used (as the octasodium salt) for reversal of neuromuscular blockade induced by rocuronium and vecuronium in adults undergoing surgery. It has a role as a neuromuscular agent. It is an organic sulfide and an octasaccharide derivative. It is functionally related to a gamma-cyclodextrin. It is a conjugate acid of a sugammadex(8-).
名称と識別子
- 優先名称
- Sugammadex
- IUPAC
- 3-[[(1S,3S,5S,6S,8S,10S,11S,13S,15S,16S,18S,20S,21S,23S,25S,26S,28S,30S,31S,33S,35S,36S,38S,40S,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-10,15,20,25,30,35,40-heptakis(2-carboxyethylsulfanylmethyl)-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.23,6.28,11.213,16.218,21.223,26.228,31.233,36]hexapentacontan-5-yl]methylsulfanyl]propanoic acid
- 現地名
- スガマデクス
- 英語名
- SUGAMMADEX
- 分子式
- C72H112O48S8
- 分子量
- 2002.15
名称と別名
Sugammadex343306-71-8361LPM2T56CHEBI:90953DTXSID90895043sugammadexumRefChem:58917V03AB35DTXCID901324600Gamma-cyclodextrin, 6A,6B,6C,6D,6E,7F,6G,6H-octakis-S-(2-carboxyethyl)-6A,6B,6C,6D,6E,7F,6G,6H-octathio-3-(((1S,3S,5S,6S,8S,10S,11S,13S,15S,16S,18S,20S,21S,23S,25S,26S,28S,30S,31S,33S,35S,36S,38S,40S,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-10,15,20,25,30,35,40-heptakis(2-carboxyethylsulfanylmethyl)-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo(36.2.2.23,6.28,11.213,16.218,21.223,26.228,31.233,36)hexapentacontan-5-yl)methylsulfanyl)propanoic acidSuggmadex Sodium
名称をさらに表示
1-O,4-[[6-(2-カルボキシエチルチオ)-4,6-ジデオキシ-α-D-グルコピラノース-4,1-O-ジイル][6-(2-カルボキシエチルチオ)-4,6-ジデオキシ-α-D-グルコピラノース-4,1-O-ジイル][6-(2-カルボキシエチルチオ)-4,6-ジデオキシ-α-D-グルコピラノース-4,1-O-ジイル][6-(2-カルボキシエチルチオ)-4,6-ジデオキシ-α-D-グルコピラノース-4,1-O-ジイル][6-(2-カルボキシエチルチオ)-4,6-ジデオキシ-α-D-グルコピラノース-4,1-O-ジイル][6-(2-カルボキシエチルチオ)-4,6-ジデオキシ-α-D-グルコピラノース-4,1-O-ジイル][6-(2-カルボキシエチルチオ)-4,6-ジデオキシ-α-D-グルコピラノース-4,1-O-ジイル]]-6-(2-カルボキシエチルチオ)-4,6-ジデオキシ-α-D-グルコピラノース
物性
構造計算による物性
- XLogP
- -10.5
- 極性表面積
- 972 Ų
- 水素結合供与体数
- 24
- 水素結合受容体数
- 56
- 回転可能結合数
- 40
- 重原子数
- 128
- 形式電荷
- 0
- 複雑度
- 2,830
実験および物理化学的性質
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antidotes; Gamma-Cyclodextrins; Neuromuscular Blockade
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
物理化学的性質
- 融点
- 208 °C · >208°C (dec.)
- 比重(密度)
- 1.559 · 1.559±0.06 g/cm3(Predicted)
- 貯蔵温度
- Inert atmosphere,Room Temperature
- 溶解性
- 水性酸（わずかに）、水（わずかに、超音波処理）
- 酸解離定数(Pka)
- 3.42 · 3.42±0.10(Predicted)
- 外見
- 個体
- 色
- ホワイト～ペールベージュ
- 安定性
- 吸湿性
- InChIKey
- WHRODDIHRRDWEW-JLBXVEOTNA-N
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。
毒性情報
Adverse EffectsThe most commonly reported adverse reactions after sugammadex administration is nausea and vomiting, headache, itching, procedural pain, and dysgeusia.
Toxicity Summary
Sugammadex is biologically inactive and is generally well tolerated. However, concerns related to anaphylaxis caused the Food and Drug Administration to delay approval for sugammadex for years. An early manufacturer-sponsored study found a 0.3% incidence of anaphylaxis. The study involved 299 subjects, and one subject who received the largest dose, 16 mg/kg, had an anaphylactic reaction. Sugammadex has been approved in the United States since 2015, in Japan since 2010, and in the European Union since 2008. The actual rate of anaphylaxis appears to be much lower, perhaps similar to the incidence of anaphylaxis from rocuronium. Reassuringly, anaphylaxis does not seem to be more common with repeated exposure. The risk of anaphylaxis appears to be higher when higher doses are administered. The most common clinical symptoms of anaphylaxis are skin changes (flushing, rash, erythema, and urticaria) and hypotension.
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- 危険有害性情報
- コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H315
化学と産業
薬理情報
ATC Code
V03AB35
V - Various
Protein BindingSugammadex does not bind plasma proteins.
Mechanism of Action
Sugammadex is a modified gamma-cyclodextrin which forms very tight water soluble complexes at a 1:1 ratio with steroidal neuromuscular blocking drugs (rocuronium > vecuronium >> pancuronium). Sugammadex creates a concentration gradient which favors movement of rocurionium from the neuromuscular junction into the plasma, which quickly reverses rocuronium-induced neuromuscular blockade. The free rocuronium in the plasma are then bound tightly to sugammadex, assisting the diffusion of the remaining rocuronium molecules out of the neuromuscular junction and increasing bound and free rocuronium in the plasma.
Biological Half-LifeAbout 2 hours
Metabolism/MetabolitesNo metabolites of sugammadex were observed during clinical studies.
FDA Pharmacological Classification
361LPM2T56
SUGAMMADEX
Chemical Structure [CS] - gamma-Cyclodextrins
SUGAMMADEX
gamma-Cyclodextrins [CS]
Absorption, Distribution and Excretion
Sugammadex is administered intravenously.
Renal excretion of unchanged product. >90 of dose is excreted within 24 hours. 0.02% is excreted in feces and air.
At steady state, the volume of distribution is 11-14 L in adult patients with normal renal function.
88L/min
応用分野
用途拮抗薬ロクロニウムの拮抗薬
説明Sugammadex is a selective relaxant binding agent indicated for reversal of neuromuscular blockade induced by rocuronium bromide and vecuronium bromide during surgery in adults. Rocuronium bromide and vecuronium bromide are neuromuscular blocking medications that cause temporary paralysis and are especially useful for general anesthesia, ventilation, or tracheal intubation that patients may require for surgery. Sugammadex provides a new treatment option to reverse the effects of those medications and possibly help patients recover sooner post-surgery. Sugammadex (brand name Bridion) is marketed by Merck Sharp and Dohme, and was approved by the United States FDA on December 15, 2015.
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