U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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
104
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 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
2678
 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
290
 35.4 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
HYDERGINE

Approved Use

For the treatment of senility and cerebrovascular insufficiency.

Launch Date

1977
Primary
Approved
8429
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
n = 24
Health Status: unhealthy
Condition: Parkinson disease
Age Group: 47-70 years
Sex: M+F
Population Size: 24
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
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
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
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
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
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
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
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
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
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
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
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
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
n = 32
Health Status: unhealthy
Condition: idiopathic Parkinson’s disease
Age Group: 64 ±1.5 years
Sex: M+F
Population Size: 32
Sources:
https://pubmed.ncbi.nlm.nih.gov/9925236
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

substrate
1737

inducer
781
substrate
1037
substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
K+ channels
70
CYP1A1
349

CYP1A2
1054

CYP1B1
92

CYP2A6
543

CYP2C8
693

CYP2C18
138

CYP2C19
991

CYP2E1
667
CYP2E1
128
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2E1
970
 likely
CYP3A4
1925
 likely
K+ channels
70
 unlikely
CYP3A4
1925
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A1
349
 no
CYP1A2
1054
 no
CYP1B1
92
 no
CYP2A6
543
 no
CYP2C18
138
 no
CYP2C19
991
 no
CYP2C8
693
 no
CYP2C9
1037
 no
CYP2D6
1217
 no
CYP2E1
667
 no
CYP3A4
1737
 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
Identification of alpha-adrenergic receptors in uterine smooth muscle membranes by [3H]dihydroergocryptine binding.
1976 Nov 25
Preparation and characterization of conjugates of recombinant CD4 and deglycosylated ricin A chain using different cross-linkers.
1990 Jan-Feb

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.
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 GMT 2023 , Edited by admin on Fri Dec 15 15:28:24 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID5048689
Created by admin on Fri Dec 15 15:28:24 GMT 2023 , Edited by admin on Fri Dec 15 15:28:24 GMT 2023
PRIMARY
FDA UNII
202229IR8Y
Created by admin on Fri Dec 15 15:28:24 GMT 2023 , Edited by admin on Fri Dec 15 15:28:24 GMT 2023
PRIMARY
CAS
25447-66-9
Created by admin on Fri Dec 15 15:28:24 GMT 2023 , Edited by admin on Fri Dec 15 15:28:24 GMT 2023
PRIMARY
NCI_THESAURUS
C75932
Created by admin on Fri Dec 15 15:28:24 GMT 2023 , Edited by admin on Fri Dec 15 15:28:24 GMT 2023
PRIMARY
DAILYMED
202229IR8Y
Created by admin on Fri Dec 15 15:28:24 GMT 2023 , Edited by admin on Fri Dec 15 15:28:24 GMT 2023
PRIMARY
ECHA (EC/EINECS)
246-993-6
Created by admin on Fri Dec 15 15:28:24 GMT 2023 , Edited by admin on Fri Dec 15 15:28:24 GMT 2023
PRIMARY
DRUG BANK
DB11274
Created by admin on Fri Dec 15 15:28:24 GMT 2023 , Edited by admin on Fri Dec 15 15:28:24 GMT 2023
PRIMARY
PUBCHEM
114948
Created by admin on Fri Dec 15 15:28:24 GMT 2023 , Edited by admin on Fri Dec 15 15:28:24 GMT 2023
PRIMARY
RXCUI
91170
Created by admin on Fri Dec 15 15:28:24 GMT 2023 , Edited by admin on Fri Dec 15 15:28:24 GMT 2023
PRIMARY RxNorm
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966