기본 정보
- CAS
17479-19-5- 표준 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- 분자식
- C35H41N5O5
- 평균 분자량
- 611.7 g/mol
- 단동위원소 질량
- 611.31076943
개요
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.
이름 및 식별자
- 우선 이름
- 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
- 현지명
- 디하이드로에르고크리스틴
- 영어명
- dihydroergocristine
- 분자식
- C35H41N5O5
- 분자량
- 611.73
이름 및 동의어
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
이름 더 보기
디하이드로에르고크리스틴NSC 409663Dihydroergotamine Mesilate Impurity EDihydro Ergotamine Mesylate Impurity EDihydro Ergotamine Mesylate EP Impurity E (9,10-Dihydroergocristine)9,10α-Dihydro-12'-hydroxy-2'-isopropyl-5'α-benzylergotaman-3',6',18-trione9,10α-Dihydro-12'-hydroxy-2'-isopropyl-5'α-(phenylmethyl)ergotaman-3',6',18-trioneErgotaman-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
물성
구조 계산 물성
- XLogP
- 3.3
- 극성 표면적
- 118 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 45
- 형식 전하
- 0
- 복잡도
- 1,210
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Listed in ZINC15
Melting Point213-215 ºC
Dissociation Constants6.9
물리화학적 성질
- 녹는점
- 199 ℃ · 199℃ (decomposition)
- 끓는 점
- 899.3 · 899.3±65.0 °C(Predicted)
- 밀도
- 1.41 · 1.41±0.1 g/cm3(Predicted)
- 산도 계수 (pKa)
- 6.89 · pKa 6.89±0.07(H2O t=24 I≤0.01) (Uncertain)
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
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.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (100%)
안전 데이터
- 신호 어
- Warning
- 유해·위험 문구
- 암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H302
화학 및 산업
약리 정보
ATC Code
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
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
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
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].
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