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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H41N5O5.CH4O3S
Molecular Weight 659.793
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROERGOCORNINE MESYLATE

SMILES

CS(O)(=O)=O.[H][C@@]12CCCN1C(=O)[C@H](C(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=UOOWRCRLTSXSAV-GSZJWLEYSA-N
InChI=1S/C31H41N5O5.CH4O3S/c1-16(2)26-28(38)35-11-7-10-24(35)31(40)36(26)29(39)30(41-31,17(3)4)33-27(37)19-12-21-20-8-6-9-22-25(20)18(14-32-22)13-23(21)34(5)15-19;1-5(2,3)4/h6,8-9,14,16-17,19,21,23-24,26,32,40H,7,10-13,15H2,1-5H3,(H,33,37);1H3,(H,2,3,4)/t19-,21-,23-,24+,26+,30-,31+;/m1./s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2869188 | https://www.ncbi.nlm.nih.gov/pubmed/4205319 | https://www.ncbi.nlm.nih.gov/pubmed/14350151 | https://www.ncbi.nlm.nih.gov/pubmed/17941060

Dihydroergocornine is an ergot alkaloid, one of the three components of ergoloid (trade name Hydergine). Dihydroergocornine (as the component of Ergoloid mesylates) has been used to treat dementia and age-related cognitive impairment (such as in Alzheimer disease), as well as to aid in recovery after stroke. There is no specific evidence which clearly establishes the mechanism by which Hydergine® (ergoloid mesylates) preparations produce mental effects, nor is there conclusive evidence that the drug particularly affects cerebral arteriosclerosis or cerebrovascular insufficiency. Hydergine may stimulates dopaminergic and serotonergic receptors and blocks alpha-adrenoreceptors.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Hydergine

Approved Use

Unknown

Launch Date

1977
Primary
Hydergine

Approved Use

Unknown

Launch Date

1977
Primary
Hydergine

Approved Use

Unknown

Launch Date

1977
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.04 μg/L
27 mg single, oral
dose: 27 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIHYDROERGOCRISTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.04 μg/L
27 mg single, oral
dose: 27 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIHYDROERGOCRYPTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.04 μg/L
27 mg single, oral
dose: 27 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIHYDROERGOCORNINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.98 μg/L
27 mg single, oral
dose: 27 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXY-DIHYDROERGOCORNIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.53 μg/L
27 mg single, oral
dose: 27 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXY-DIHYDROERGOCRYPTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.3 μg/L
27 mg single, oral
dose: 27 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDROXY-DIHYDROERGOCRISTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
The treatment of minocycline-induced brainstem vertigo by the combined administration of piracetam and ergotoxin.
1989
Bioavailability and pharmacokinetic profile of dihydroergotoxine from a tablet and from an oral solution formulation.
2001 Jan
Placebo adverse events in headache trials: headache as an adverse event of placebo.
2003 Sep
Contractile responses to ergotamine and dihydroergotamine in the perfused middle cerebral artery of rat.
2007 Apr
Identification and human pharmacokinetics of dihydroergotoxine metabolites in man: preliminary results.
2008 Jan
Patents

Patents

Sample Use Guides

In Vivo Use Guide
1 mg of ergoloid mesylates three times daily. 1 mg of ergoloid mesylates contains: dihydroergocornine mesylate 0.333 mg, dihydroergocristine mesylate 0.333 mg, and dihydroergocryptine (dihydro-alpha-ergocryptine and dihydro-beta-ergocryptine in the proportion of 2:1) mesylate 0.333 mg,
Route of Administration: Oral
Biotransformation assays were performed in incubates of rat liver microsomes. Dihydroergotoxine alkaloids in CH3CN–H2O (1:1, v/v) were individually added (30 mm, final concentration) to cold Sorensen buffer 0.1 m pH 7.4 containing the liver enzyme preparation (5mgprot/ml), MgCl2 (10mm), glucose 6-phosphate (10mm), NADP (0.5mm) and glucose 6-phosphate dehydrogenase (1 U/ml) in a total volume of 500 ml. Blank and control incubates were performed similarly, except by adding the buffer solution instead of the drug and NADPH regenerating system, respectively. After incubation at 378C for 30 min, the reactions were terminated by the addition of 50 ml NaOH 0.1m, and vortex-mixing (30 s) with 4ml of diethyl ether. After 15 min at -80C, the upper organic layers were separated and concentrated under a gentle N2 stream.
Name Type Language
DIHYDROERGOCORNINE MESYLATE
VANDF  
Common Name English
DIHYDROERGOCORNINE MESYLATE [VANDF]
Common Name English
DIHYDROERGOCORNINE METHANESULFONATE
Common Name English
DIHYDROERGOCORNINE MESILATE
WHO-DD  
Common Name English
DIHYDROERGOCORNINE METHANESULPHONATE
Common Name English
Dihydroergocornine mesilate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
NCI_THESAURUS C66884
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
Code System Code Type Description
CAS
29261-94-7
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY
SMS_ID
100000079764
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY
DRUG BANK
DBSALT001569
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY
PUBCHEM
168870
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY
DAILYMED
42RX8KPW29
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY
EVMPD
SUB13585MIG
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY
NCI_THESAURUS
C75937
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY
RXCUI
42644
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY RxNorm
CHEBI
34502
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY
FDA UNII
42RX8KPW29
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY
ECHA (EC/EINECS)
249-539-5
Created by admin on Fri Dec 15 15:46:29 GMT 2023 , Edited by admin on Fri Dec 15 15:46:29 GMT 2023
PRIMARY