DIHYDRO-.ALPHA.-ERGOCRYPTINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H43N5O5
Molecular Weight	577.7143
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DIHYDRO-.ALPHA.-ERGOCRYPTINE

SMILES

CC(C)C[C@@H]1N2C(=O)[C@](NC(=O)[C@@H]3C[C@H]4[C@@H](CC5=CNC6=C5C4=CC=C6)N(C)C3)(O[C@@]2(O)[C@@H]7CCCN7C1=O)C(C)C

InChI

InChIKey=PBUNVLRHZGSROC-VTIMJTGVSA-N

InChI=1S/C32H43N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,15,17-18,20,22,24-26,33,41H,7,10-14,16H2,1-5H3,(H,34,38)/t20-,22-,24-,25+,26+,31-,32+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C32H43N5O5
Molecular Weight	577.7143
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Dihydro-alpha-ergocryptine is an ergot alkaloid that has an agonist activity on D2 dopaminergic receptors and a partial agonist activity on D1 receptors. It also demonstrated antagonistic activity towards alpha-adrenergic receptors. The drug was approved by FDA in combination with other alkaloids (dihydroergocornine, dihydroergocristine and dihydro-beta-ergocryptine mesylate salts) under the name Hydergine for the treatment of dimentia and cerebrovascular insufficiency.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adrenergic receptor alpha 65	Antagonist 2,849	3.1 nM [Kd]
D(2) dopamine receptor 58	Agonist 2,752	4.7 nM [Ki]
D(1A) dopamine receptor 18	Partial Agonist 297	35.4 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dementia 27	Primary		Approved 8,583	HYDERGINE
Cerebrovascular insufficiency 15	Primary		Approved 8,583	HYDERGINE

Doses

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Dose	Population	Adverse events
40 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 47-70 years
60 mg 1 times / day multiple, oral	unhealthy, 64 ±1.5 years	Disc. AE: Nausea, Hypotension...

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AEs

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AE	Significance	Dose	Population
Cramps	1 patient Disc. AE	60 mg 1 times / day multiple, oral	unhealthy, 64 ±1.5 years
Erythema	1 patient Disc. AE	60 mg 1 times / day multiple, oral	unhealthy, 64 ±1.5 years
Itching	1 patient Disc. AE	60 mg 1 times / day multiple, oral	unhealthy, 64 ±1.5 years
Nausea	1 patient Disc. AE	60 mg 1 times / day multiple, oral	unhealthy, 64 ±1.5 years
Tremor	1 patient Disc. AE	60 mg 1 times / day multiple, oral	unhealthy, 64 ±1.5 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 substrate 1,946 inducer 1,087	substrate 1,193	substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
K+ channels 73	CYP1A1 389 CYP1A2 1,197 CYP1B1 104 CYP2A6 626 CYP2C8 810 CYP2C18 149 CYP2C19 1,119 CYP2E1 729	CYP2E1 131

Drug as perpetrator

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Target	Modality	Activity
CYP2E1 1,146	inducer 1,966	likely
CYP3A4 2,633	inducer 1,966	likely
K+ channels 73	inhibitor 4,027	unlikely
CYP3A4 2,633	inhibitor 4,027	yes

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Drug as victim

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Target	Modality	Activity
CYP1A1 389	substrate 4,014	no
CYP1A2 1,197	substrate 4,014	no
CYP1B1 104	substrate 4,014	no
CYP2A6 626	substrate 4,014	no
CYP2C18 149	substrate 4,014	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
Alfa Chemistry	ACM17479195
Bosche Scientific	D2294
Compound Cloud	114948
Compound Cloud	159729
Hangzhou APIChem Technology	AC-13189

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PubMed

PubMed

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Title	Date	PubMed
New detection of brain dopamine receptors with (3H)dihydroergocryptine.	1977 Sep	410026
Evidence for two alpha-adrenergic binding sites in liver plasma membranes. Studies with [3H]epinephrine and [3H]dihydroergocryptine.	1979 Jun 10	35537
Effects of trypsin on binding of [3H]epinephrine and [3H]-dihydroergocryptine to rat liver plasma membranes. Evidence for interconversion of binding sites.	1980 Jun 25	6247349
Binding of [3H]-prazosin and [3H]-dihydroergocryptine to rat cardiac alpha-adrenoceptors.	1981 May	6269682
The binding characteristics of [3H]-dihydroergocryptine on intact human platelets.	1982 May	6805543

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Sample Use Guides

In Vivo Use Guide

The recommended dosage (in form of hydergine tablets containing dihydroergocornine, dihydroergocristine, dihydro-alpha-ergocryptine and dihydro-beta-ergocryptine mesylate salts in an approximate weight ratio of 1:1:1) in the US is 1 mg three times daily. In Europe and Japan, up to 12 mg of hydergine daily have been used without serious adverse effects.

Route of Administration: Oral

In Vitro Use Guide

Primary cultures of rat cerebellar granule cells were exposed to toxic concentrations (100 uM) of glutamate in Mg2+-free buffer. Repeated addition of dihydro-alpha-ergocryptine (100 nM-1 uM, once a day from the second day in culture, last addition 3 hr before the glutamate pulse) protected cerebellar granule cells against the toxic action of glutamate.

Substance Class	Chemical
Record UNII	202229IR8Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

12'-HYDROXY-2'-(1-METHYLETHYL)-5'.ALPHA.-(2-METHYLPROPYL)-9,10.ALPHA.-DIHYDROERGOTAMAN-3',6',18-TRIONE

Preferred Name

English

DIHYDRO-.ALPHA.-ERGOCRYPTINE

Common Name

English

ERGOTAMAN-3',6',18-TRIONE, 9,10-DIHYDRO-12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(2-METHYLPROPYL)-, (5'.ALPHA.,10.ALPHA.)-

Common Name

English

9,10-DIHYDROERGOCRYPTINE

Common Name

English

DIHYDRO-ALPHA-ERGOCRYPTINE

Common Name

English

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Classification Tree

Code System

Code

Adrenergic Antagonist

NCI_THESAURUS

C29713

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Code System

Code

Type

Description

EPA CompTox

DTXSID5048689

PRIMARY

FDA UNII

202229IR8Y

PRIMARY

CAS

25447-66-9

PRIMARY

NCI_THESAURUS

C75932

PRIMARY

DAILYMED

202229IR8Y

PRIMARY

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Related Record

Type

Details


					Z4I7BU58DN

DIHYDRO-.ALPHA.-ERGOCRYPTINE MESYLATE

SALT/SOLVATE -> PARENT

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Sample Use Guides

Drug as perpetrator