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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H41N5O5.CH4O3S
Molecular Weight 707.836
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROERGOCRISTINE MESYLATE

SMILES

CS(O)(=O)=O.[H][C@@]12CCCN1C(=O)[C@H](CC3=CC=CC=C3)N4C(=O)[C@](NC(=O)[C@H]5CN(C)[C@]6([H])CC7=CNC8=C7C(=CC=C8)[C@@]6([H])C5)(O[C@@]24O)C(C)C

InChI

InChIKey=SPXACGZWWVIDGR-SPZWACKZSA-N
InChI=1S/C35H41N5O5.CH4O3S/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34;1-5(2,3)4/h4-7,9-12,18,20,23,25,27-29,36,44H,8,13-17,19H2,1-3H3,(H,37,41);1H3,(H,2,3,4)/t23-,25-,27-,28+,29+,34-,35+;/m1./s1

HIDE SMILES / InChI
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
Molecular Formula C35H41N5O5
Molecular Weight 611.7305
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Dihydroergocristine is an ergot alkaloid that has an partial agonist activity on dopaminergic and alpha-adrenergic receptors and antagonist activity on serotonin receptors. The drug was approved by FDA in combination with other alkaloids (dihydroergocornine, dihydro-alpha-ergocryptine and dihydro-beta-ergocryptine mesylate salts) under the name Hydergine for the treatment of dimentia and cerebrovascular insufficiency.

CNS Activity

Approval Year

1951
104
Targets

Targets

Primary TargetPharmacologyConditionPotency
Partial Agonist
290
 2.4 nM [Ki]
Partial Agonist
290
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
HYDERGINE

Approved Use

The treatment of senility and cerebrovascular insufficiency.

Launch Date

1977
Primary
Approved
8429
HYDERGINE

Approved Use

The treatment of senility and cerebrovascular insufficiency.

Launch Date

1977
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.28 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16379666/
18 mg single, oral
dose: 18 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIHYDROERGOCRISTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
5.63 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16379666/
18 mg single, oral
dose: 18 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
8'-HYDROXY-DIHYDROERGOCRISTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.46 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16379666/
18 mg single, oral
dose: 18 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIHYDROERGOCRISTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
13.36 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16379666/
18 mg single, oral
dose: 18 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
8'-HYDROXY-DIHYDROERGOCRISTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16379666/
18 mg single, oral
dose: 18 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIHYDROERGOCRISTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
3.9 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16379666/
18 mg single, oral
dose: 18 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
8'-HYDROXY-DIHYDROERGOCRISTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
20 mg 1 times / day steady, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: steady
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7589764/
unhealthy, 55 - 80 years
n = 20
Health Status: unhealthy
Condition: chronic cerebro-vascular disease
Age Group: 55 - 80 years
Sex: M+F
Population Size: 20
Sources:
https://pubmed.ncbi.nlm.nih.gov/7589764/
Other AEs: Gastric pain...
Other AEs:
Gastric pain (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7589764/
AEs

AEs

AESignificanceDosePopulation
Gastric pain 1 patient
20 mg 1 times / day steady, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: steady
Dose: 20 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7589764/
unhealthy, 55 - 80 years
n = 20
Health Status: unhealthy
Condition: chronic cerebro-vascular disease
Age Group: 55 - 80 years
Sex: M+F
Population Size: 20
Sources:
https://pubmed.ncbi.nlm.nih.gov/7589764/
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:59912
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59912
ZINC
ZINC000003995616
http://zinc15.docking.org/substances/ZINC000003995616
PubMed

PubMed

TitleDatePubMed
Effects of phentolamine, dihydroergocristine and isoxsuprine on the blood pressure and heart rate in normotensive, hypotensive and hypertensive rats.
1975
The treatment of minocycline-induced brainstem vertigo by the combined administration of piracetam and ergotoxin.
1989
Effects of topical natural ergot alkaloids on intraocular pressure and aqueous humor dynamics in ocular normotensive rabbits.
2002 Feb
Pharmacokinetics of dihydroergocristine and its major metabolite 8'-hydroxy-dihydroergocristine in human plasma.
2005 Dec
Inappropriate medication use and risk of falls--a prospective study in a large community-dwelling elderly cohort.
2009 Jul 23
Roles of adenosine and serotonin receptors on the antinociception of sildenafil in the spinal cord of rats.
2010 Nov
Patents

Patents

EP0202365 A2
2
EP0411494 A2
2

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
Sources: www.ncbi.nlm.nih.gov/pubmed/6438125
C-1300 neuroblastoma cells were incubated with dihydroergocristine at concentration of 2 uM. In another experiment dihydroergocristine was added to the perfusion medium of the isolated rat brain in a concentration of 5 uM. In both experiments the drug caused changes in the concentrations of the high-energy phosphates.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:30:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:30:46 GMT 2023
Record UNII
DS7CL18UAM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDROERGOCRISTINE MESYLATE
VANDF  
Common Name English
DIHYDROERGOCRISTINE METHANESULFONATE
MI  
Common Name English
ERGOTAMAN-3',6',18-TRIONE, 9,10-DIHYDRO-12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(PHENYLMETHYL)-, (5'.ALPHA.,10.ALPHA.)-, MONOMETHANESULFONATE (SALT)
Common Name English
9,10-DIHYDROERGOCRISTINE METHANESULPHONATE
Common Name English
DIHYDROERGOCRISTINE MESYLATE [VANDF]
Common Name English
5'.ALPHA.-BENZYL-9,10.ALPHA.-DIHYDRO-12'-HYDROXY-2'-ISOPROPYLERGOTAMAN-3',6',18-TRIONE MONOMETHANESULPHONATE
Common Name English
9,10-DIHYDROERGOCRISTINE METHANESULFONATE
Common Name English
ERGOTAMAN-3',6',18-TRIONE, 9,10-DIHYDRO-12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(PHENYLMETHYL)-, (5'.ALPHA.,10.ALPHA.)-, MONOMETHANESULPHONATE (SALT)
Common Name English
DIHYDROERGOCRISTINE MESILATE [EP MONOGRAPH]
Common Name English
Dihydroergocristine mesilate [WHO-DD]
Common Name English
DIHYDROERGOCRISTINE METHANESULFONATE [MI]
Common Name English
DIHYDROERGOCRISTINE MONOMESYLATE
Common Name English
DIHYDROERGOCRISTINE MESILATE [MART.]
Common Name English
DIHYDROERGOCRISTINE MESILATE
EP   MART.   WHO-DD  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
NCI_THESAURUS C66884
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
Code System Code Type Description
EVMPD
SUB13587MIG
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID20872322
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
MERCK INDEX
m4980
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C75939
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
SMS_ID
100000091063
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
DRUG BANK
DBSALT002618
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
CAS
24730-10-7
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
RXCUI
42645
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY RxNorm
PUBCHEM
444034
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
CHEBI
31490
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
ECHA (EC/EINECS)
246-434-6
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
DAILYMED
DS7CL18UAM
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
FDA UNII
DS7CL18UAM
Created by admin on Fri Dec 15 15:30:46 GMT 2023 , Edited by admin on Fri Dec 15 15:30:46 GMT 2023
PRIMARY
Related Record Type Details
Structure of DIHYDROERGOCRISTINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DIHYDROERGOCRISTINE
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