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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

[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N3C(=O)[C@](NC(=O)[C@H]4CN(C)[C@]5([H])CC6=CNC7=C6C(=CC=C7)[C@@]5([H])C4)(O[C@@]23O)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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.1 nM [Kd]
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
4.7 nM [Ki]
Target ID: P21728
Gene ID: 1812.0
Gene Symbol: DRD1
Target Organism: Homo sapiens (Human)
35.4 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HYDERGINE

Approved Use

For the treatment of senility and cerebrovascular insufficiency.

Launch Date

2.52288008E11
Primary
HYDERGINE

Approved Use

For the treatment of senility and cerebrovascular insufficiency.

Launch Date

2.52288008E11
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:
unhealthy, 47-70 years
n = 24
Health Status: unhealthy
Condition: Parkinson disease
Age Group: 47-70 years
Sex: M+F
Population Size: 24
Sources:
60 mg 1 times / day multiple, oral
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, 64 ±1.5 years
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
Sources:
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:
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:
unhealthy, 64 ±1.5 years
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
Sources:
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:
unhealthy, 64 ±1.5 years
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
Sources:
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:
unhealthy, 64 ±1.5 years
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
Sources:
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:
unhealthy, 64 ±1.5 years
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
Sources:
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:
unhealthy, 64 ±1.5 years
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
Sources:
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:
unhealthy, 64 ±1.5 years
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
Sources:
OverviewDrug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Studies on the hypotensive action of dihydroergokryptine (DHK) and epinephrine-reversal in the dog and cat.
1957 Sep
Identification of alpha-adrenergic receptors in uterine smooth muscle membranes by [3H]dihydroergocryptine binding.
1976 Nov 25
New detection of brain dopamine receptors with (3H)dihydroergocryptine.
1977 Sep
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
Binding of [3H]-prazosin and [3H]-dihydroergocryptine to rat cardiac alpha-adrenoceptors.
1981 May
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 Jun

Sample Use Guides

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 Fri Dec 15 15:28:24 UTC 2023
Edited
by admin
on Fri Dec 15 15:28:24 UTC 2023
Record UNII
202229IR8Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDRO-.ALPHA.-ERGOCRYPTINE
Common Name English
12'-HYDROXY-2'-(1-METHYLETHYL)-5'.ALPHA.-(2-METHYLPROPYL)-9,10.ALPHA.-DIHYDROERGOTAMAN-3',6',18-TRIONE
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
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Fri Dec 15 15:28:24 UTC 2023 , Edited by admin on Fri Dec 15 15:28:24 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID5048689
Created by admin on Fri Dec 15 15:28:24 UTC 2023 , Edited by admin on Fri Dec 15 15:28:24 UTC 2023
PRIMARY
FDA UNII
202229IR8Y
Created by admin on Fri Dec 15 15:28:24 UTC 2023 , Edited by admin on Fri Dec 15 15:28:24 UTC 2023
PRIMARY
CAS
25447-66-9
Created by admin on Fri Dec 15 15:28:24 UTC 2023 , Edited by admin on Fri Dec 15 15:28:24 UTC 2023
PRIMARY
NCI_THESAURUS
C75932
Created by admin on Fri Dec 15 15:28:24 UTC 2023 , Edited by admin on Fri Dec 15 15:28:24 UTC 2023
PRIMARY
DAILYMED
202229IR8Y
Created by admin on Fri Dec 15 15:28:24 UTC 2023 , Edited by admin on Fri Dec 15 15:28:24 UTC 2023
PRIMARY
ECHA (EC/EINECS)
246-993-6
Created by admin on Fri Dec 15 15:28:24 UTC 2023 , Edited by admin on Fri Dec 15 15:28:24 UTC 2023
PRIMARY
DRUG BANK
DB11274
Created by admin on Fri Dec 15 15:28:24 UTC 2023 , Edited by admin on Fri Dec 15 15:28:24 UTC 2023
PRIMARY
PUBCHEM
114948
Created by admin on Fri Dec 15 15:28:24 UTC 2023 , Edited by admin on Fri Dec 15 15:28:24 UTC 2023
PRIMARY
RXCUI
91170
Created by admin on Fri Dec 15 15:28:24 UTC 2023 , Edited by admin on Fri Dec 15 15:28:24 UTC 2023
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT