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Dihydroergocornine

Dihydroergocornine structure

CAS No:
25447-65-8
Formula:
C31H41N5O5
Chemical Name:
Dihydroergocornine
Synonyms:
Ergotaman-3′,6′,18-trione,9,10-dihydro-12′-hydroxy-2′,5′-bis(1-methylethyl)-,(5′α,10α)-;Ergocornine,9,10-dihydro-;Ergocornine,dihydro-;Indolo[4,3-fg]quinoline,ergotaman-3′,6′,18-trione deriv.;8H-Oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine,ergotaman-3′,6′,18-trione deriv.;(5′α,10α)-9,10-Dihydro-12′-hydroxy-2′,5′-bis(1-methylethyl)ergotaman-3′,6′,18-trione;Dihydroergocornine;9,10-Dihydroergocornine;DHO 180;5611-87-0;17479-17-3;53176-61-7
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Dihydroergocornine is ergocornine in which a single bond replaces the double bond between positions 9 and 10. It derives from an ergocornine. It derives from a hydride of an ergotaman.|Dihydroergocornine is one of the dihydrogenated ergot compounds that present very large hypotensive effects. It is an artificial derivative of the crude extract of ergot and later purified, ergocornine. The formation of dihydroergocornine implies the hydrogenation of the double bonds in the lysergic acid. Dihydroergocornine presents a formula of 9,10 alpha-dihydro-12'-hydroxy-2',5'alpha-bis(1-methylethyl)-ergotaman-3',6',18-trione. It is found as one of the components in the ergoloid mesylate mixture. To know more about this mixture please refer to [DB01049]|A 9,10alpha-dihydro derivative of ERGOTAMINE that contains isopropyl sidechains at the 2' and 5' positions of the molecule.

Dihydroergocornine Basic Attributes

Molecular Weight：

563.7 g/mol

Exact Mass：

563.69

EC Number：

246-992-0

UNII：

IK4C1OC8NE

DSSTox ID：

DTXSID1044013

Characteristics

PSA：

118 Å²

XLogP3：

2.33

Melting Point：

185-187 °C (decomp)

Boiling Point：

Decomposes

Safety Information

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Toxicity

Toxicity Summary：

Dihydroergocornine effect on fertility was tested in preclinical studies. The reported effect was a decreased weight gain in neonates. Overdosing has also been reported to present effects of fall of blood pressure and a decrease in heart rate to 13 beats per minute. To know more about the pharmacokinetics please visit [DB01049].

Protein Binding：

To know more about the pharmacokinetics please visit [DB01049].

Drug Information

Drug Indication：

To know more about the approved indications please visit [DB01049]

Pharmacology：

It is reported that dihydroergocornine administration, in non-toxic doses, presents sympatholytic and hypotensive properties which are observed as a significantly decreased mean arterial pressure. In the brain, the activity of dihydroergocornine was observed as a decrease in cerebral blood flow, cerebral vascular resistance and oxygen uptake. The effect in the brain seems to allow a cerebral metabolic homeostasis. To know more about the pharmacology please visit [DB01049]

MeSH：

Drugs that bind to and activate dopamine receptors. (See all compounds classified as Dopamine Agonists.)

Absorption：

Dihydroergocornine absorption in man after oral administration is very rapid when compared to the mixture or most of the components. The time to reach maximum plasma concentration or 0.57 ng-eq/ml is 1.4 hours. It presents an absorption half-life of 0.32 hours. The absorption percentage is of about 25% which corresponds to the registered absorption presented in the ergoloid mixture. To know more about the pharmacokinetics please visit [DB01049].|When orally administered, dihydroergocornine is almost completely eliminated via feces. The urinary secretion accounts only for 2.5% of the administered dose. On the other hand, when administered intravenously, the renal excretion can account for approximately 10% of the administered dose. To know more about the pharmacokinetics please visit [DB01049].|To know more about the pharmacokinetics please visit [DB01049].|No pharmacokinetic related to the clearance rate was found in current literature.

Metabolism/Metabolites：

The biotransformation of dihydroergocornine occurs via oxidation and cleavage of the proline in the peptide portion of the molecule as well as by the splitting of the amide bond yielding dihydrolysergic acid amide. Some of the derivate metabolites retain the essential ring structure of the ergot alkaloid. To know more about the pharmacokinetics please visit [DB01049].

Biological Half-Life：

To know more about the pharmacokinetics please visit [DB01049].

Mechanism of Action：

The mechanism of action by which dihydroergocornine exerts its effects are not entirely defined. However, it is reported that dihydroergocornine has central and peripheral effects. The fall in blood pressure seems to be related to the stimulation of the vasodilator center. It has been demonstrated that dihydroergocornine possesses potent adrenolytic and sympathicolytic actions. The effect of dihydroergocornine is related to the inhibitory effect against the serotonin and noradrenaline receptors in which dihydroergocornine seems to be very potent against a stimulation-induced noradrenaline overflow. It also presents a stimulatory effect in arterial and venous smooth muscle when administered at slightly higher concentrations than the necessary for the inhibitory effect.

MeSH Entry Terms：

Dihydroergocornine

Computed Properties

Molecular Weight:563.7
XLogP3:2.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:563.31076943
Monoisotopic Mass:563.31076943
Topological Polar Surface Area:118
Heavy Atom Count:41
Complexity:1120
Defined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes