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
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
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 |
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095203 |
2.4 nM [Ki] | ||
Target ID: CHEMBL2096905 Sources: https://www.tocris.com/pdfs/dopreview.pdf |
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Target ID: CHEMBL2096904 Sources: https://www.tocris.com/pdfs/dopreview.pdf |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | HYDERGINE Approved UseThe treatment of senility and cerebrovascular insufficiency. Launch Date1977 |
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Primary | HYDERGINE Approved UseThe treatment of senility and cerebrovascular insufficiency. Launch Date1977 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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: |
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: |
Other AEs: Gastric pain... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
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: |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Bioavailability and pharmacokinetic profile of dihydroergotoxine from a tablet and from an oral solution formulation. | 2001 Jan |
|
Effects of topical natural ergot alkaloids on intraocular pressure and aqueous humor dynamics in ocular normotensive rabbits. | 2002 Feb |
|
Spinal gabapentin and antinociception: mechanisms of action. | 2003 Apr |
|
Pharmacokinetics of dihydroergocristine and its major metabolite 8'-hydroxy-dihydroergocristine in human plasma. | 2005 Dec |
|
[Milestones of cardiovascular therapy. IV. Reserpine]. | 2007 |
|
Identification and human pharmacokinetics of dihydroergotoxine metabolites in man: preliminary results. | 2008 Jan |
|
Inappropriate medication use and risk of falls--a prospective study in a large community-dwelling elderly cohort. | 2009 Jul 23 |
|
High-performance liquid chromatographic determination of dihydroergocristine in a pharmaceutical formulation with fluorescence detection. | 2010 Jan-Feb |
|
Roles of adenosine and serotonin receptors on the antinociception of sildenafil in the spinal cord of rats. | 2010 Nov |
Patents
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
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
Edited
Fri Dec 15 15:30:46 GMT 2023
by
admin
on
Fri Dec 15 15:30:46 GMT 2023
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Record UNII |
DS7CL18UAM
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29713
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NCI_THESAURUS |
C66884
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SUB13587MIG
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DTXSID20872322
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m4980
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C75939
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100000091063
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |