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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H43N5O5.CH4O3S
Molecular Weight 673.82
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDRO-.ALPHA.-ERGOCRYPTINE MESYLATE

SMILES

CS(O)(=O)=O.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=TZGKQIBPZOZAKF-PJLVGBPESA-N
InChI=1S/C32H43N5O5.CH4O3S/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;1-5(2,3)4/h6,8-9,15,17-18,20,22,24-26,33,41H,7,10-14,16H2,1-5H3,(H,34,38);1H3,(H,2,3,4)/t20-,22-,24-,25+,26+,31-,32+;/m1./s1

HIDE SMILES / InChI
Molecular Formula C32H43N5O5
Molecular Weight 577.7143
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1951
105
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 3.1 nM [Kd]
D(2) dopamine receptor
58
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
Agonist
2752
 4.7 nM [Ki]
D(1A) dopamine receptor
18
Target ID: P21728
Gene ID: 1812.0
Gene Symbol: DRD1
Target Organism: Homo sapiens (Human)
Partial Agonist
297
 35.4 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
HYDERGINE

Approved Use

For the treatment of senility and cerebrovascular insufficiency.

Launch Date

1977
Primary
Approved
8583
HYDERGINE

Approved Use

For the treatment of senility and cerebrovascular insufficiency.

Launch Date

1977
Doses

Doses

DosePopulationAdverse events​
40 mg 2 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/16618013
unhealthy, 47-70 years
Health Status: unhealthy
Age Group: 47-70 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/16618013
Sources:
https://pubmed.ncbi.nlm.nih.gov/16618013
60 mg 1 times / day multiple, oral
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
unhealthy, 64 ±1.5 years
Health Status: unhealthy
Age Group: 64 ±1.5 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
Disc. AE: Nausea, Hypotension...
AEs leading to
discontinuation/dose reduction:
Nausea (1 patient)
Hypotension (2 patients)
Tremor (1 patient)
Cramps (1 patient)
Itching (1 patient)
Erythema (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
AEs

AEs

AESignificanceDosePopulation
Cramps 1 patient
Disc. AE
60 mg 1 times / day multiple, oral
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
unhealthy, 64 ±1.5 years
Health Status: unhealthy
Age Group: 64 ±1.5 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
Erythema 1 patient
Disc. AE
60 mg 1 times / day multiple, oral
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
unhealthy, 64 ±1.5 years
Health Status: unhealthy
Age Group: 64 ±1.5 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
Itching 1 patient
Disc. AE
60 mg 1 times / day multiple, oral
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
unhealthy, 64 ±1.5 years
Health Status: unhealthy
Age Group: 64 ±1.5 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
Nausea 1 patient
Disc. AE
60 mg 1 times / day multiple, oral
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
unhealthy, 64 ±1.5 years
Health Status: unhealthy
Age Group: 64 ±1.5 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
Tremor 1 patient
Disc. AE
60 mg 1 times / day multiple, oral
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
unhealthy, 64 ±1.5 years
Health Status: unhealthy
Age Group: 64 ±1.5 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
Hypotension 2 patients
Disc. AE
60 mg 1 times / day multiple, oral
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
unhealthy, 64 ±1.5 years
Health Status: unhealthy
Age Group: 64 ±1.5 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252

substrate
1946

inducer
1087
substrate
1193
substrate
1388

OverviewOther

Other InhibitorOther SubstrateOther Inducer
K+ channels
73
CYP1A1
389

CYP1A2
1197

CYP1B1
104

CYP2A6
626

CYP2C8
810

CYP2C18
149

CYP2C19
1119

CYP2E1
729
CYP2E1
131
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2E1
1146
 likely
CYP3A4
2633
 likely
K+ channels
73
 unlikely
CYP3A4
2633
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A1
389
 no
CYP1A2
1197
 no
CYP1B1
104
 no
CYP2A6
626
 no
CYP2C18
149
 no
CYP2C19
1119
 no
CYP2C8
810
 no
CYP2C9
1193
 no
CYP2D6
1388
 no
CYP2E1
729
 no
CYP3A4
1946
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
Alfa Chemistry
ACM17479195
Bosche Scientific
D2294
Compound Cloud
114948
Compound Cloud
159729
Hangzhou APIChem Technology
AC-13189
ZINC
ZINC000003929793
http://zinc15.docking.org/substances/ZINC000003929793
PubMed

PubMed

TitleDatePubMed
Preparation and characterization of conjugates of recombinant CD4 and deglycosylated ricin A chain using different cross-linkers.
1990-01-01
Variations in circulating catecholamines fail to alter human platelet alpha-2-adrenergic receptor number or affinity for [3H]yohimbine or [3H]dihydroergocryptine.
1984-09
Effect of 781094, a new selective alpha-adrenoceptor antagonist, on the aggregatory responses of human blood platelets and on binding of [3H]-dihydroergocryptine to these cells.
1983-06
The binding characteristics of [3H]-dihydroergocryptine on intact human platelets.
1982-05
Binding of [3H]-prazosin and [3H]-dihydroergocryptine to rat cardiac alpha-adrenoceptors.
1981-05
Effects of trypsin on binding of [3H]epinephrine and [3H]-dihydroergocryptine to rat liver plasma membranes. Evidence for interconversion of binding sites.
1980-06-25
Evidence for two alpha-adrenergic binding sites in liver plasma membranes. Studies with [3H]epinephrine and [3H]dihydroergocryptine.
1979-06-10
Binding of [3H]-dihydroergocryptine to alpha-adrenoceptors on intact human platelets [proceedings].
1979-05
New detection of brain dopamine receptors with (3H)dihydroergocryptine.
1977-09
Identification of alpha-adrenergic receptors in uterine smooth muscle membranes by [3H]dihydroergocryptine binding.
1976-11-25
Studies on the hypotensive action of dihydroergokryptine (DHK) and epinephrine-reversal in the dog and cat.
1957-09

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
Created
by admin
on Mon Mar 31 17:56:26 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:26 GMT 2025
Record UNII
Z4I7BU58DN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDRO-.ALPHA.-ERGOCRYPTINE MESYLATE
Common Name English
DIHYDROERGOCRYPTINE ALFA-MESILATE
WHO-DD  
Preferred Name English
ERGOTAMAN-3',6',18-TRIONE, 9,10-DIHYDRO-12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(2-METHYLPROPYL)-, (5'.ALPHA.,10.ALPHA.)-, MONOMETHANESULFONATE (SALT)
Common Name English
DIHYDRO-.ALPHA.-ERGOCRYPTINE MESILATE
Common Name English
DIHYDROERGOCRYPTINE METHANESULFONATE
Common Name English
ERGOTAMAN-3',6',18-TRIONE, 9,10-DIHYDRO-12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(2-METHYLPROPYL)-, (5'.ALPHA.,10.ALPHA.)-, MONOMETHANESULPHONATE (SALT)
Common Name English
9,10.ALPHA.-DIHYDRO-12'-HYDROXY-5'.ALPHA.-ISOBUTYL-2'-ISOPROPYLERGOTAMAN-3',6',18-TRIONE MONOMETHANESULPHONATE
Common Name English
Dihydroergocryptine alfa-mesilate [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
Z4I7BU58DN
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
RXCUI
1426902
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
DAILYMED
Z4I7BU58DN
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
EPA CompTox
DTXSID20931605
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
CAS
14271-05-7
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
EVMPD
SUB13589MIG
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
NCI_THESAURUS
C75933
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
ECHA (EC/EINECS)
238-163-7
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
DRUG BANK
DBSALT002361
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
SMS_ID
100000079200
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
PUBCHEM
159729
Created by admin on Mon Mar 31 17:56:26 GMT 2025 , Edited by admin on Mon Mar 31 17:56:26 GMT 2025
PRIMARY
Related Record Type Details
Structure of DIHYDRO-.ALPHA.-ERGOCRYPTINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DIHYDRO-.ALPHA.-ERGOCRYPTINE
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