基本情報
- CAS
109889-09-0- 標準SMILES
CN1[C@@H]2CCC[C@H]1CC(NC(=O)c1nn(C)c3ccccc13)C2- InChIKey
MFWNKCLOYSRHCJ-AGUYFDCRSA-N- 分子式
- C18H24N4O
- 平均分子量
- 312.4 g/mol
- 単同位体質量
- 312.1950114
概要
Granisetron is a monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 1-methyl-1H-indazole-3-carboxylic acid with the primary amino group of (3-endo)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine. A selective 5-HT3 receptor antagonist, it is used (generally as the monohydrochloride salt) to manage nausea and vomiting caused by cancer chemotherapy and radiotherapy, and to prevent and treat postoperative nausea and vomiting. It has a role as a serotonergic antagonist and an antiemetic. It is a monocarboxylic acid amide, a member of indazoles and a tertiary amino compound.
名称と識別子
- 優先名称
- Granisetron (JAN/USAN/INN)
- IUPAC
- 1-methyl-N-[(1R,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]indazole-3-carboxamide
- 現地名
- グラニセトロン
- 英語名
- Granisetron
- 分子式
- C18H24N4O
- 分子量
- 312.41
名称と別名
Granisetron (JAN/USAN/INN)RefChem:1086176granisetron109889-09-0SancusoSustolexo-GranisetronKevatrilBRL-43694GranisetronumAPF5301364914-39-5
名称をさらに表示
1-メチル-N-[(1R,5S)-9-メチル-9-アザビシクロ[3.3.1]ノナン-3α-イル]-1H-インダゾール-3-カルボアミドグラニステロン1-メチル-N-[(1α,3β,5α)-9-メチル-9-アザビシクロ[3.3.1]ノナン-3-イル]-1H-インダゾール-3-カルボアミド1-メチル-N-[(1β,3α,5β)-9-メチル-9-アザビシクロ[3.3.1]ノナン-3-イル]-1H-インダゾール-3-カルボアミドN-[(1β,5β)-9-メチル-9-アザビシクロ[3.3.1]ノナン-3α-イル]-1-メチル-1H-インダゾール-3-カルボアミドグラニセトロン1-メチル-N-[(1β,5β)-9-メチル-9-アザビシクロ[3.3.1]ノナン-3α-イル]-1H-インダゾール-3-カルボアミドグラニセトロン (JAN)1-メチル-N-[(1R,3r,5S)-9-メチル-9-アザビシクロ[3.3.1]ノナン-3-イル]-1H-インダゾール-3-カルボキサミドBRL 43964GRANESETRONGranisteronGramisetronGranisetron 99%Granisetron USP/EP/BPgranisetron(base,HCl)GRANISETRON(FREE BASE)
Kytril1-methyl-N-[(1S,5R)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]indazole-3-carboxamideGranisetron EP Impurity FAPF 530WZG3J2MCOLBRL 436941-methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamideCHEBI:5537
物性
構造計算による物性
- XLogP
- 2.8
- 極性表面積
- 50.2 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 2
- 重原子数
- 23
- 形式電荷
- 0
- 複雑度
- 442
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsPharmaceuticals
物理化学的性質
- 沸点
- 532 · 532.0±40.0 °C(Predicted)
- 比重(密度)
- 1.33 · 1.33±0.1 g/cm3(Predicted)
- 貯蔵温度
- Inert atmosphere,Room Temperature
- 溶解性
- 25 ℃: · 25℃: DMSO
- 外見
- Powder
- 酸解離定数(Pka)
- 12.34 · 12.34±0.20(Predicted)
- 色
- White to off-white
- InChI
- InChI=1/C18H24N4O/c1-21-13-6-5-7-14(21)11-12(10-13)19-18(23)17-15-8-3-4-9-16(15)22(2)20-17/h3-4,8-9,12-14H,5-7,10-11H2,1-2H3,(H,19,23)/t12-,13+,14-/i2D3
- InChIKey
- MFWNKCLOYSRHCJ-JQHPXDLNNA-N
- SMILES
- C1(C(=O)N[C@H]2C[C@@]3([H])CCC[C@@]([H])(C2)N3C)C2C=CC=CC=2N(C([2H])([2H])[2H])N=1 |&1:4,6,11,r|
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
- hs_code
- 2933399090
化学と産業
薬理情報
Protein Binding65%
Pharmacodynamics
Granisetron is a selective inhibitor of type 3 serotonergic (5-HT<sub>3</sub>) receptors. Granisetron has little or no affinity for other serotonin receptors, including 5-HT 1 , 5-HT 1A , 5-HT 1B/C , or 5-HT 2 ; for alpha 1 -, alpha 2 -, or beta-adrenoreceptors; for dopamine D 2 receptors; for histamine H 1 receptors; for benzodiazepine receptors; for picrotoxin receptors; or for opioid receptors. In most human studies, granisetron has had little effect on blood pressure, heart rate, or electrocardiogram (ECG). The drug is structurally and pharmacologically related to ondansetron, another selective inhibitor of 5-HT<sub>3</sub> receptors. The serontonin 5-HT<sub>3</sub> receptors are located on the nerve terminals of the vagus in the periphery, and centrally in the chemoreceptor trigger zone of the area postrema. The temporal relationship between the emetogenic action of emetogenic drugs and the release of serotonin, as well as the efficacy of antiemetic agents suggest that chemotherapeutic agents release serotonin from the enterochromaffin cells of the small intestine by causing degenerative changes in the GI tract. The serotonin then stimulates the vagal and splanchnic nerve receptors that project to the medullary vomiting center, as well as the 5-HT3 receptors in the area postrema, thus initiating the vomiting reflex, causing nausea and vomiting.
Mechanism of Action
Granisetron is a potent, selective antagonist of 5-HT<sub>3</sub> receptors. The antiemetic activity of the drug is brought about through the inhibition of 5-HT3 receptors present both centrally (medullary chemoreceptor zone) and peripherally (GI tract). This inhibition of 5-HT3 receptors in turn inhibits the visceral afferent stimulation of the vomiting center, likely indirectly at the level of the area postrema, as well as through direct inhibition of serotonin activity within the area postrema and the chemoreceptor trigger zone.
Biological Half-Life4-6 hours in healthy patients, 9-12 hours in cancer patients
Metabolism/Metabolites
Primarily hepatic; undergoes N -demethylation and aromatic ring oxidation followed by conjugation. Animal studies suggest that some of the metabolites may have 5-HT 3 receptor antagonist activity.
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…