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基本情報
- CAS
1350462-55-3- 標準SMILES
C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@H](C(C)(C)C)NC(=O)O[C@@H]1C[C@H]1CCCCCc1nc3ccc(OC)cc3nc1O2)C(=O)NS(=O)(=O)C1CC1- InChIKey
OBMNJSNZOWALQB-NCQNOWPTSA-N- 分子式
- C38H50N6O9S
- 平均分子量
- 766.9 g/mol
- 単同位体質量
- 766.33599818
概要
Grazoprevir is an azamacrocyclic compound that is a hepatitis C protease inhibitor used in combination with elbasvir (under the brand name Zepatier) for treatment of chronic HCV genotypes 1 or 4 infection in adults. It has a role as an antiviral drug, a hepatoprotective agent and a hepatitis C protease inhibitor. It is a carbamate ester, a lactam, an aromatic ether, a quinoxaline derivative, a member of cyclopropanes, an azamacrocycle and a N-sulfonylcarboxamide.
名称と識別子
- 優先名称
- Grazoprevir
- IUPAC
- (1R,18R,20R,24S,27S)-24-tert-butyl-N-[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamide
- 現地名
- グラゾプレビル水和物
- 英語名
- MK 5172 hydrate
- 分子式
- C38H50N6O9S.H2O
- 分子量
- 784.91868
名称と別名
Grazoprevir1350514-68-9MK5172MK-5172 ANHYDROUS(1R,18R,20R,24S,27S)-24-tert-butyl-N-[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamideCHEBI:132975DTXSID50159234MK-5172 MONOHYDRATEDTXSID00159229grazoprevirum(1R,18R,20R,24S,27S)-24-tert-butyl-N-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl)-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo(24.2.1.03,12.05,10.018,20)nonacosa-3,5(10),6,8,11-pentaene-27-carboxamideRefChem:782705
名称をさらに表示
グラゾプレビル水和物グラゾプレビル水和物 (JAN)(2R,4S,7S,11R,13R)-N-[(1R,2S)-1-シクロプロピルスルホニルカルバモイル-2-エテニルシクロプロパン-1-イル]-7-tert-ブチル-5,8-ジアザ-6,9-ジオキソ-1-オキサ-2,5-メタノ-11,13-シクロ-1,18-(7-メトキシキノキサリン-2,3-ジイル)オクタデカン-4-カルボアミド/水,(1:1)(1aR,5S,8S,10R,22aR)-5-tert-ブチル-N-[(1R,2S)-1-(シクロプロパンスルホニルカルバモイル)-2-ビニルシクロプロピル]-14-メトキシ-3,6-ジオキソ-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-テトラデカヒドロ-8H-7,10-メタノシクロプロパ[18,19][1,10,3,6]ジオキサジアザシクロノナデシノ[11,12-b]キノキサリン-8-カルボキサミド-水(1/1)
物性
構造計算による物性補完中
- XLogP
- 4.7
- 極性表面積
- 204 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 11
- 回転可能結合数
- 8
- 重原子数
- 54
- 形式電荷
- 0
- 複雑度
- 1,580
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antiviral Agents; Protease Inhibitors
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
物理化学的性質
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- 50 mg/mL · DMSO : 50 mg/mL (63.70 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)
- 外見
- Powder
- 色
- White to off-white
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。
GHS分類
GHS Classification
Warning
H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
P260, P319, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 35 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesSTOT RE 2 (100%)
毒性情報
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 H373
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingGrazoprevir is more than 98.8% bound to plasma proteins. It binds both human serum albumin and α1-acid glycoprotein.
PharmacodynamicsGrazoprevir is classified as a direct-acting antiviral (DAA) and prevents viral replication in HCV genotypes 1a, 1b, and 4.
Mechanism of Action
Grazoprevir is a second generation NS3/4a protease inhibitor used to inhibit viral HCV replication. NS3/4a protease is an integral part of viral replication and mediates the cleavage the virally encoded polyprotein to mature proteins (NS3, NS4A, NS4B, NS5A and NS5B). Grazoprevir inhibits the NS3/4protease enzymes of HCV genotype 1a, 1B, and 4 with IC50 values of 7pM, 4pM, and 62pM, respectively.
Biological Half-LifeThe geometric mean apparent terminal half-life for Grazoprevir is 31 hours in HCV-infected subjects.
Metabolism/MetabolitesGrazoprevir is partially eliminated by oxidative metabolism meditated by CYP3A. No circulating metabolites of have been detected in human plasma.
FDA Pharmacological Classification
8YE81R1X1J
GRAZOPREVIR ANHYDROUS
Mechanisms of Action [MoA] - HCV NS3/4A Protease Inhibitors
Established Pharmacologic Class [EPC] - Hepatitis C Virus NS3/4A Protease Inhibitor
Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors
Mechanisms of Action [MoA] - Cytochrome P450 3A Inhibitors
MeSH Pharmacological Classification
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
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