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ジヒドロエルゴクリスチン

Dihydroergocristine

HCID 107715
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
17479-19-5
標準SMILES
CC(C)[C@@]1(NC(=O)[C@@H]2C[C@@H]3c4cccc5[nH]cc(c45)C[C@H]3N(C)C2)O[C@@]2(O)[C@@H]3CCCN3C(=O)[C@H](Cc3ccccc3)N2C1=O
InChIKey
DEQITUUQPICUMR-HJPBWRTMSA-N
分子式
C35H41N5O5
平均分子量
611.7 g/mol
単同位体質量
611.31076943

概要

Dihydroergocristine is ergocristine in which a single bond replaces the double bond between positions 9 and 10. It is used as the mesylate salt for the symptomatic treatment of mental deterioration associated with cerebrovascular insufficiency and in peripheral vascular disease. It has a role as a vasodilator agent and an adrenergic antagonist. It is functionally related to an ergocristine. It derives from a hydride of an ergotaman.

名称と識別子

優先名称
Dihydroergocristine
IUPAC
(6aR,9R,10aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
現地名
ジヒドロエルゴクリスチン
英語名
dihydroergocristine
分子式
C35H41N5O5
分子量
611.73

名称と別名

Dihydroergocristine17479-19-59,10-DihydroergocristineDHECGNF-Pf-3462DTXSID304632205D48LUM4ZDTXCID1026322CHEBI:59912Erotaman-3',6',18-trione, 9,10-dihydro-12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'alpha,10alpha)-(10alphaH)-5'alpha-benzyl-12'-hydroxy-3',6',18-trioxo-2'-(propan-2-yl)-9,10-dihydroergotamanRefChem:133803
名称をさらに表示
9,10α-ジヒドロ-12'-ヒドロキシ-2'-イソプロピル-5'α-(フェニルメチル)エルゴタマン-3',6',18-トリオン9,10-ジヒドロエルゴクリスチンジヒドロエルゴクリスチン9,10α-ジヒドロ-12'-ヒドロキシ-2'-イソプロピル-5'α-ベンジルエルゴタマン-3',6',18-トリオン(5'α,10α)-9,10-ジヒドロ-12'-ヒドロキシ-2'-(1-メチルエチル)-5'-(フェニルメチル)エルゴタマン-3',6',18-トリオン(2R,4R,7R)-N-[(1S,2S,4R,7S)-7-ベンジル-2-ヒドロキシ-5,8-ジオキソ-4-(プロパン-2-イル)-3-オキサ-6,9-ジアザトリシクロ[7.3.0.02,6]ドデカン-4-イル]-6-メチル-6,11-ジアザテトラシクロ[7.6.1.02,7.012,16]ヘキサデカ-1(16),9,12,14-テトラエン-4-カルボキサミド(5′α,10α)-9,10-ジヒドロ-12′-ヒドロキシ-2′-(1-メチルエチル)-5′-(フェニルメチル)エルゴタマン-3′,6′,18-トリオン9,10α-ジヒドロ-12′-ヒドロキシ-2′-イソプロピル-5′α-ベンジルエルゴタマン-3′,6′,18-トリオン

物性

構造計算による物性

XLogP
3.3
極性表面積
118 Ų
水素結合供与体数
3
水素結合受容体数
6
回転可能結合数
5
重原子数
45
形式電荷
0
複雑度
1,210

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
Melting Point213-215 ºC
Dissociation Constants6.9

物理化学的性質

融点
199 ℃ · 199℃ (decomposition)
沸点
899.3 · 899.3±65.0 °C(Predicted)
比重(密度)
1.41 · 1.41±0.1 g/cm3(Predicted)
酸解離定数(Pka)
6.89 · pKa 6.89±0.07(H2O t=24 I≤0.01) (Uncertain)

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 · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P301+P317, P304+P340, P317, P330, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

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 H302

化学と産業

薬理情報

ATC Code · 2 件

C - Cardiovascular system

QC - Cardiovascular system

Protein BindingDihydroergocristine can be found in a bound state to plasma proteins in a proportion of even 68% of the administered dose. To know more about dihydroergocristine as part of the ergoloid mesylate mixture, please visit [DB01049].
Pharmacodynamics · 1 件

Dihydroergocristine has been shown to present effect on memory and cognition. This activity in the brain is been reported by an increase in glutathione in age-related brain states. The reported effect on serotonin and adrenergic receptors has also been correlated to an inhibition of platelet aggregation. It has also been reported that individuals exposed to dihydroergocristine may present an amphoteric vasoregulating activity either hypotensive in hypertensive individuals or hypertensive in hypotensive individuals. This action is performed by promoting a dilating action in the contracted arteries and a tonic action in the dilated arteries and arterioles. The vasoregulating effect causes an increase in cerebral blood flow and oxygen consumption by the brain, which correlates with the brain protective function of dihydroergocristine. In Alzheimer studies, dihydroergocristine reduced the amyloid-beta levels in different cell types. To know more about dihydroergocristine as part of the ergoloid mesylate mixture, please visit [DB01049].

Mechanism of Action · 1 件

Dihydroergocristine mechanism of action seems to be related to a noncompetitive antagonistic activity in the serotonin receptors as well as a double partial agonist/antagonist activity in dopaminergic and adrenergic receptors. In Alzheimer studies, dihydroergocristine act as a direct inhibitor of γ-secretase.

Biological Half-LifeThe half-life of dihydroergocristine has only been studied as part of the therapeutic mixture, please refer to [DB01049].
Metabolism/Metabolites · 1 件

The major metabolite of dihydroergocristine is 8'-hydroxy-dihydroergocristine is produced in the liver. The modification of dihydroergocristine in the body is very extensive and it has been observed as an almost complete absence of the unchanged drug. To know more about dihydroergocristine as part of the ergoloid mesylate mixture, please visit [DB01049].

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
9,10α-ジヒドロ-12′-ヒドロキシ-2′-イソプロピル-5′α-(フェニルメチル)エルゴタマン-3′,6′,18-トリオン
NSC 409663
Dihydroergotamine Mesilate Impurity E
Dihydro Ergotamine Mesylate Impurity E
Dihydro Ergotamine Mesylate EP Impurity E (9,10-Dihydroergocristine)
9,10α-Dihydro-12'-hydroxy-2'-isopropyl-5'α-benzylergotaman-3',6',18-trione
9,10α-Dihydro-12'-hydroxy-2'-isopropyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione
Ergotaman-3',6',18-trione, 9,10-dihydro-12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'α,10α)-
N-(7-benzyl-2-hydroxy-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo(7.3.0.0^(2,6))dodecan-4-yl)-6-methyl-6,11-diazatetracyclo(7.6.1.0^(2,7).0^(12,16))hexadeca-1(16),9,12,14-tetraene-4-carboxamide241-493-4Ergotaman-3',6',18-trione, 9,10alpha-dihydro-12'-hydroxy-2'-(1-methylethyl)-5'alpha-(phenylmethyl)-DihydroergocristinCHEMBL601773(6aR,9R,10aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamideNCGC00017401-02(6aR,9R,10aR)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-isopropyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

データベース識別子

CAS
17479-19-5
PubChem CID
107715
DTXSID
DTXSID3046322
ChEMBL
CHEMBL601773
ChEBI
CHEBI:59912
UNII
05D48LUM4Z
EC Number
241-493-4
Nikkaji
J984I
MeSH Pharmacological Classification · 2 件

Drugs used to cause dilation of the blood vessels.

Drugs that bind to but do not activate ADRENERGIC RECEPTORS. Adrenergic antagonists block the actions of the endogenous adrenergic transmitters EPINEPHRINE and NOREPINEPHRINE.

Absorption, Distribution and Excretion · 4 件

Dihydroergocristine presents an absorption in the digestive tract of about 25% of the administered dose. When dihydroergocristine was orally administered in humans and the peak plasma concentration of 0.28 mcg/l was achieved after 0.46 hours. In the same report, the AUC was reported to be 0.39 mcg/l.h. To know more about dihydroergocristine as part of the ergoloid mesylate mixture, please visit [DB01049].

The most important elimination route of dihydroergocristine is in via the bile and it accounts for over 85% of the eliminated dose. Urine elimination accounts only for 5% of the administered dose. To know more about dihydroergocristine as part of the ergoloid mesylate mixture, please visit [DB01049].

Dihydroergocristine presents a large volume of distribution of 52 l/kg. To know more about dihydroergocristine as part of the ergoloid mesylate mixture, please visit [DB01049].

Dihydroergocristine presents a high systemic clearance rate of 2.65 l/h.hg. To know more about dihydroergocristine as part of the ergoloid mesylate mixture, please visit [DB01049].

サプライヤー8 社

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中梦研（湖北）科技有限公司18062399888; 18062399888 · [email protected]
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上海择睿生物科技有限公司021-54580889 18321124657 · [email protected]
補足説明 · 1 件

定義ChEBI: Ergocristine in which a single bond replaces the double bond between positions 9 and 10. It is used as the mesylate salt for the symptomatic treatment of mental deterioration associated with cerebrovascular insufficiency and in peripheral vascular disease.