バモロロン
Vamorolone
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基本情報
- CAS
13209-41-1- 標準SMILES
C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)C3=CC[C@]2(C)[C@@]1(O)C(=O)CO- InChIKey
ZYTXTXAMMDTYDQ-DGEXFFLYSA-N- 分子式
- C22H28O4
- 平均分子量
- 356.5 g/mol
- 単同位体質量
- 356.19875937
概要
Vamorolone is a 3-oxo-1,4-steroid that is pregna-1,4,9(11)-trien-17-ol substituted by oxo, oxo, and hydroxy groups at positions 3, 20, and 21, respectively. It is approved by the FDA for the treatment of patients with Duchenne muscular dystrophy aged 2 years and older. It has a role as an anti-inflammatory drug, an immunosuppressive agent and a glucocorticoid receptor agonist. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a 17alpha-hydroxy steroid, a 21-hydroxy steroid, a 20-oxo steroid, a corticosteroid and a 3-oxo-Delta(1),Delta(4)-steroid.
名称と識別子
- 優先名称
- Vamorolone
- IUPAC
- (8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
- 現地名
- バモロロン
- 英語名
- Dexamethasone EP Impurity E
- 分子式
- C22H28O4
- 分子量
- 356.46
名称と別名
vamorolone13209-41-1AgamreeVBP-15 free alcoholvamorolonaVBP-1517,21-Dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dionevamorolonum(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one9,11-dehydro dexamethasone8XP29XMB43(16alpha)-17,21-dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione
名称をさらに表示
17,21-ジヒドロキシ-16α-メチルプレグナ-1,4,9(11)-トリエン-3,20-ジオンバモロロン3-オキソ-16α-メチル-17-ヒドロキシ-17β-(2-ヒドロキシアセチル)アンドロスタ-1,4,9(11)-トリエン16α-メチル-17,21-ジヒドロキシプレグナ-1,4,9(11)-トリエン-3,20-ジオン(1R,2R,3aS,3bS,9aS,11aS)-1-ヒドロキシ-1-(2-ヒドロキシアセチル)-2,9a,11a-トリメチル-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,11H,11aH-シクロペンタ[a]フェナントレン-7-オンDexamethasone EP Imp EDexamethasone impurity EDexamethasone Impurity LCarbamazepine Impurity 22Vamorolone, 10 mM in DMSO(8S,10S,13S,14S,16R,17R)-17-hydroxy16α-Methyl-9,11-dehydro PrednisoloneTobramycin and dexamethasone impurity C
DTXSID60927527(8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta(a)phenanthren-3-oneRefChem:901612DTXCID601356317(1R,2R,3aS,3bS,9aS,11aS)-1-hydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,11H,11aH-cyclopenta(a)phenanthren-7-one236-177-8Dexamethasone EP Impurity EVBP15
データベース識別子
- CAS
13209-41-1- PubChem CID
- 3035000
- DTXSID
DTXSID60927527- ChEMBL
CHEMBL2348780- ChEBI
CHEBI:228304- UNII
- 8XP29XMB43
- EC Number
- 236-177-8
- Nikkaji
- J213.750J
物性
構造計算による物性補完中
- XLogP
- 2.7
- 極性表面積
- 74.6 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 2
- 重原子数
- 26
- 形式電荷
- 0
- 複雑度
- 775
実験および物理化学的性質
Human Drugs
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine (Orphan designations)
FDA approved drugs -> Active ingredient
物理化学的性質
- 融点
- 228 · 228-231 °C(Solv: acetone (67-64-1); hexane (110-54-3))
- 沸点
- 548.3 · 548.3±50.0 °C(Predicted)
- 比重(密度)
- 1.24 · 1.24±0.1 g/cm3(Predicted)
- 貯蔵温度
- Refrigerator
- 溶解性
- クロロホルム（微量）、ジオキサン（微量）、酢酸エチル（微量）
- 外見
- 個体
- 酸解離定数(Pka)
- 12.53 · 12.53±0.70(Predicted)
- 色
- ペールイエロー
- InChIKey
- ZYTXTXAMMDTYDQ-JBFVNPOPNA-N
- SMILES
- C1(=O)C=C2[C@](C)(C=C1)C1[C@]([H])([C@@]3([H])[C@@](CC=1)(C)[C@@](O)(C(=O)CO)[C@H](C)C3)CC2 |&1:4,9,11,13,17,23,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。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Warning
H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (33.3%)
安全データ
- wgk
- WGK 3
- Hazard Classifications
- Eye Irrit. 2Skin Sens. 1
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
H - Systemic hormonal preparations, excl. sex hormones and insulins
QH - Systemic hormonal preparations, excl. sex hormones and insulin
Protein BindingThe _in vitro_ protein binding of vamorolone is 88.1%.
PharmacodynamicsIn clinical studies, treatment with vamorolone induced a dose-dependent decrease in morning cortisol levels and a dose-dependent increase in leukocyte and lymphocyte counts.
Mechanism of Action
Vamorolone is a synthetic corticosteroid that acts as an agonist at the glucocorticoid receptor to exert anti-inflammatory and immunosuppressive effects. It is also an antagonist of the mineralocorticoid receptor. The precise mechanism by which vamorolone exerts its therapeutic effects in patients with DMD is unclear.
Biological Half-LifeThe terminal elimination half-life of vamorolone is approximately 2 hours.
Metabolism/Metabolites
Vamorolone is subject to multiple metabolic pathways, including glucuronidation, hydroxylation, and reduction. Its metabolism is mediated through CYP3A4, CYP3A5, CYP2C8, UGT1A3, UGT2B7, and UGT2B17. Glucuronides - formed via direct glucuronidation and hydrogenation with subsequent glucuronidation - are the main metabolites in the plasma and urine.
FDA Pharmacological Classification
8XP29XMB43
VAMOROLONE
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Vamorolone is a Corticosteroid. The mechanism of action of vamorolone is as a Corticosteroid Hormone Receptor Agonist.
Absorption, Distribution and Excretion
Following oral administration with food, the median Tmax of vamorolone is approximately 2 hours. The co-administration of vamorolone with a high-fat, high-calorie meal reduced Cmax by 18%, increased AUC by 13%, and delayed Tmax by one hour. The co-administration of vamorolone with a low-fat, low-calorie meal reduced Cmax by 4%, increased AUC by 14%, and delayed Tmax by one hour.
Approximately 30% of a given vamorolone dose is excreted in the feces (15.4% as unchanged parent drug) and 48% is excreted in the urine (<1% as unchanged parent drug).
Based on population pharmacokinetic analysis, the apparent volume of distribution of vamorolone when administered with a meal to a 20 kg patient with DMD is 162 L.
Based on population pharmacokinetic analysis, the clearance of vamorolone when administered with a meal to a 20 kg patient with DMD is 58 L/h.
応用分野
使用A related intermediate of Prednisolone (P703740).
上流・下流製品情報
下流製品
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