Grundinformationen
- CAS
17479-19-5- Standard-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- Summenformel
- C35H41N5O5
- Durchschnittliche Molmasse
- 611,7 g/mol
- Monoisotopische Masse
- 611,31076943
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- 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
- Lokaler Name
- Dihydroergocristin
- Englischer Name
- dihydroergocristine
- Summenformel
- C35H41N5O5
- Molmasse
- 611.73
Namen und Synonyme
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
Weitere Namen anzeigen
NSC 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
Datenbank-Bezeichner
- CAS
17479-19-5- PubChem CID
- 107715
- DTXSID
DTXSID3046322- ChEMBL
CHEMBL601773- ChEBI
CHEBI:59912- UNII
- 05D48LUM4Z
- EC Number
- 241-493-4
- Nikkaji
- J984I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,3
- Polarare Oberfläche (TPSA)
- 118 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 45
- Formalladung
- 0
- Komplexität
- 1.210
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Melting Point213-215 ºC
Dissociation Constants6.9
Physikochemische Eigenschaften
- Schmelzpunkt
- 199 ℃ · 199℃ (decomposition)
- Siedepunkt
- 899.3 · 899.3±65.0 °C(Predicted)
- Dichte
- 1.41 · 1.41±0.1 g/cm3(Predicted)
- pka
- 6.89 · pKa 6.89±0.07(H2O t=24 I≤0.01) (Uncertain)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302
Chemie und Industrie
Pharmakologische Informationen
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].
MeSH Pharmacological Classification
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
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].
Anbieter8 Anbieter
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
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常州翔龙医药科技有限公司18915873328 18915873328 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
深圳市祥根生物医药有限公司0755-28967200 13631290199 · [email protected]
中梦研（湖北）科技有限公司18062399888; 18062399888 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
上海择睿生物科技有限公司021-54580889 18321124657 · [email protected]
Ergänzende Hinweise
DefinitionChEBI: 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.
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