Dihydroergocryptine
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Dihydroergocryptine
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CAS No:
25447-66-9
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Formula:
C32H43N5O5
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Chemical Name:
Dihydroergocryptine
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Synonyms:
Ergotaman-3′,6′,18-trione,9,10-dihydro-12′-hydroxy-2′-(1-methylethyl)-5′-(2-methylpropyl)-,(5′α,10α)-;Ergocryptine,dihydro-;8H-Oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine,ergotaman-3′,6′,18-trione deriv.;Indolo[4,3-fg]quinoline,ergotaman-3′,6′,18-trione deriv.;(5′α,10α)-9,10-Dihydro-12′-hydroxy-2′-(1-methylethyl)-5′-(2-methylpropyl)ergotaman-3′,6′,18-trione;Dihydroergocryptine;9,10-Dihydroergocryptine;9,10-Dihydroergokryptine;Dihydro-α-ergocryptine;Dihydro-α-ergocriptine;α-Dihydroergokryptine;Dihydro-α-ergocryptin;Dihydroergocriptine;9,10-Dihydro-α-ergocryptine;Almirid;5611-86-9;17479-14-0;26913-94-0;73465-91-5;148043-09-8;187458-06-6
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CAS No:
Description
Dihydro-alpha-ergocryptine is alpha-Ergocryptine in which a single bond replaces the double bond between positions 9 and 10. It derives from an alpha-ergocryptine. It derives from a hydride of an ergotaman.|Alpha-dihydroergocryptine is usually referred to the mixture of the alpha and beta dihydroergocryptine. These two compounds are differentiated in the position of a methyl group. This structural difference is due to a proteinogenic amino acid replacement from leucine to isoleucine. Both compounds are hydrogenated ergot derivatives. Alpha-dihydroergocryptine approved drug product is as a part of an ergoloid mixture. To know more about this mixture, please visit [DB01049]|A 9,10alpha-dihydro derivative of ERGOTAMINE that contains an isopropyl sidechain at the 2' position and an alpha-isobutyl sidechain at 5'alpha position of the molecule.
Characteristics
121.70000
3.17460
1.36g/cm3
180 °C (decomp)
848.7ºC at 760 mmHg
467.1ºC
1.667
1.26E-30mmHg at 25°C
Toxicity
Alpha-dihydroergocryptine does not have effect in fertility and it does not present mutagenic potential. To know more about the ergoloid mesylate mixture please visit [DB01049].
Alpha-dihydroergocryptine is highly bound to proteins and it has been reported to present a high affinity for intact human platelets. To know more about the ergoloid mesylate mixture please visit [DB01049].
Drug Information
Alpha-dihydroergocryptine has been studied for the early treatment of Parkinson disease as well as for its use in migraine prophylaxis, treatment of low blood pressure and peripheral vascular disorder. To know more about the ergoloid mesylate mixture and its uses please visit [DB01049].
The effect of alpha-dihydroergocryptine in dopamine receptors was tested in PD patients and seem to generate a significant clinical improvement in the tested patients as well as to reduce motor complications and side effects. In long-term clinical trials with Parkinson disease patients, the administration of alpha-dihydroergocryptine and levodopa, the symptoms were reposted to improve or completely vanish in 80% of the tested individuals. All the registered effects of alpha-dihydroergocryptine suggest a potential neuroprotective effect of this drug and some reports have indicated that this activity may be related to the activation of NF-kB. The effect of alpha-dihydroergocryptine in the dopamine D2 receptor also reduces prolactin plasma levels and induce hypotension. To know more about the ergoloid mesylate mixture please visit [DB01049].
Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)|Drugs that bind to and activate dopamine receptors. (See all compounds classified as Dopamine Agonists.)
Alpha-dihydroergocryptine is rapidly absorbed but it presents a very low bioavailability as it is part of a first-pass hepatic metabolism and thus less of 5% of the administered dose reaches blood circulation. The peak plasma concentration is attained after 30-120 minutes. The absorption of alpha-dihydroergocryptine is not affected by the co-administration with food. When administered in repeated oral doses the Cmax after 1 hour was registered to be 2157 pg/ml. To know more about the ergoloid mesylate mixture please visit [DB01049].|Alpha-dihydroergocryptine is eliminated mainly by feces and to present a very low urinary excretion. To know more about the ergoloid mesylate mixture please visit [DB01049].|In preclinical studies, the volume of distribution after intravenous or oral administration was registered to be 11.054 L and 218.630 L respectively. To know more about the ergoloid mesylate mixture please visit [DB01049].|In preclinical studies, the clearance rate after intravenous or oral administration was registered to be 1.129 L/h and 25.98 L/h respectively. To know more about the ergoloid mesylate mixture please visit [DB01049].
Alpha-dihydroergocryptine presents a linear metabolism with the formation of active metabolites and the metabolism kinetics of this compound has no interference with L-dopa. It is highly metabolized with a rate of 2.4 ng/min/mg protein in the microsomal system and a formation of eight different metabolites. the metabolism of alpha-dihydroergocryptine seems to be highly marked by the action of CYP 3A4. To know more about the ergoloid mesylate mixture please visit [DB01049].
Alpha-dihydroergocryptine has been studied in Parkinson disease models and it has shown a half-life of 12-16 hours. To know more about the ergoloid mesylate mixture please visit [DB01049].
Alpha-dihydroergocryptine is an established high-affinity ligand to alpha 1 and alpha 2 adrenoreceptors in a number of tissues as well as a dopamine ligand in the brain. It is reported to be a potent agonist of the dopamine D2 receptor and a partial agonist of the dopamine receptors D1 and D3. To know more about the ergoloid mesylate mixture please visit [DB01049] and to know more about the isomer please visit [DB11275].
Almirid
Computed Properties
Molecular Weight:577.7
XLogP3:3.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:577.32641949
Monoisotopic Mass:577.32641949
Topological Polar Surface Area:118
Heavy Atom Count:42
Complexity:1130
Defined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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