Page last updated: 2024-11-07

dihydroergocryptine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Dihydroergocryptine is a semisynthetic ergot alkaloid derivative. It is a potent vasoconstrictor and has been used in the treatment of migraine headaches. It is thought to work by constricting blood vessels in the brain. Dihydroergocryptine has also been studied for its potential to improve cognitive function in patients with Alzheimer's disease. However, its use has been limited due to its potential side effects, such as nausea, vomiting, and dizziness. Dihydroergocryptine is no longer widely used in medicine, but research continues to explore its potential therapeutic applications.'

dihydro-alpha-ergocryptine : alpha-Ergocryptine in which a single bond replaces the double bond between positions 9 and 10. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Dihydroergocryptine: A 9,10alpha-dihydro derivative of ERGOTAMINE that contains an isopropyl sidechain at the 2' position and an alpha-isobutyl sidechain at 5'alpha position of the molecule. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID114948
CHEMBL ID1743263
CHEBI ID59919
SCHEMBL ID233373
MeSH IDM0006405
PubMed CID12899069
MeSH IDM0006405

Synonyms (35)

Synonym
alpha-dihydroergocryptine
PDSP2_001088
ergotaman-3',6',18-trione, 9,10-dihydro-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha,10alpha)-
12'-hydroxy-2'-(1-methylethyl)-5'alpha-(2-methylpropyl)-9,10alpha-dihydroergotaman-3',6',18-trione
einecs 246-993-6
(10alphah)-12'-hydroxy-5'alpha-(2-methylpropyl)-3',6',18-trioxo-2'-(propan-2-yl)-9,10-dihydroergotaman
CHEBI:59919 ,
9,10-dihydro-alpha-ergocryptine
dihydro-alpha-ergocryptine
D07835
25447-66-9
CHEMBL1743263 ,
alpha-dihydroergocriptine
nsc_159729
cas_159729
bdbm81453
tox21_113078
dtxsid5048689 ,
cas-25447-66-9
dihydroergocriptine
dtxcid5028615
bdbm50390994
unii-202229ir8y
202229ir8y ,
dihydro-.alpha.-ergocryptine
ergotaman-3',6',18-trione, 9,10-dihydro-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'.alpha.,10.alpha.)-
12'-hydroxy-2'-(1-methylethyl)-5'.alpha.-(2-methylpropyl)-9,10.alpha.-dihydroergotaman-3',6',18-trione
SCHEMBL233373
DB11274
Q905717
(6ar,9r,10ar)-n-[(1s,2s,4r,7s)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide
(6ar,9r,10ar)-n-[(1s,2r,4r,7s)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide
(2r,4r,7r)-n-[(1s,2s,4r,7s)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(15),9,12(16),13-tetraene-4-carboxamide
EN300-27019944
dihydroergocryptine

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" This effect was small but statistically significant for the area under the plasma concentration-time curve, whereas tmax (time of maximum plasma concentration) and peak-to-trough fluctuation were not affected."( Influence of the dopamine agonist alpha-dihydroergocryptine on the pharmacokinetics of levodopa in patients with Parkinson's disease.
Althaus, M; de Mey, C; Falup-Pecurariu, C; Minea, D; Retzow, A; Varga, I,
)
0.13
"This study was carried out to evaluate the pharmacokinetic profile of alpha-dihydroergocryptine (CAS 14271-05-7, DHEC, Almirid) in plasma and urine in patients with moderately to severely impaired renal function (creatinine clearance < 30 ml."( Single dose pharmacokinetics of alpha-dihydroergocryptine in patients with moderate to severe renal insufficiency.
Althaus, M; de Mey, C; Ezan, E; Retzow, A; Stompór, T; Sułowicz, W, 2003
)
0.32

Bioavailability

ExcerptReferenceRelevance
"P-glycoprotein (P-gp) is an efflux transporter involved in limiting the oral bioavailability and tissue penetration of a variety of structurally divergent molecules."( Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein.
Dantzig, AH; Ekins, S; Kim, RB; Lan, LB; Leake, BF; Schuetz, EG; Schuetz, JD; Shepard, RL; Wikel, JH; Winter, MA; Wrighton, SA; Yasuda, K, 2002
)
0.31
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
ergot alkaloid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (9)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency17.80030.000811.382244.6684AID686978; AID686979
AR proteinHomo sapiens (human)Potency26.83250.000221.22318,912.5098AID743035
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency11.98560.000214.376460.0339AID720691
estrogen nuclear receptor alphaHomo sapiens (human)Potency18.99590.000229.305416,493.5996AID743075
aryl hydrocarbon receptorHomo sapiens (human)Potency9.43920.000723.06741,258.9301AID743085
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency29.28740.000323.4451159.6830AID743065; AID743067
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
ATP-dependent translocase ABCB1Mus musculus (house mouse)Ki159.90003.50005.60676.9300AID681138
ATP-dependent translocase ABCB1Homo sapiens (human)Ki190.16000.02002.35948.5900AID681142; AID681143
ATP-dependent translocase ABCB1Mus musculus (house mouse)Ki333.40002.10004.31507.4800AID681137
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
G2/M transition of mitotic cell cycleATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic metabolic processATP-dependent translocase ABCB1Homo sapiens (human)
response to xenobiotic stimulusATP-dependent translocase ABCB1Homo sapiens (human)
phospholipid translocationATP-dependent translocase ABCB1Homo sapiens (human)
terpenoid transportATP-dependent translocase ABCB1Homo sapiens (human)
regulation of response to osmotic stressATP-dependent translocase ABCB1Homo sapiens (human)
transmembrane transportATP-dependent translocase ABCB1Homo sapiens (human)
transepithelial transportATP-dependent translocase ABCB1Homo sapiens (human)
stem cell proliferationATP-dependent translocase ABCB1Homo sapiens (human)
ceramide translocationATP-dependent translocase ABCB1Homo sapiens (human)
export across plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
transport across blood-brain barrierATP-dependent translocase ABCB1Homo sapiens (human)
positive regulation of anion channel activityATP-dependent translocase ABCB1Homo sapiens (human)
carboxylic acid transmembrane transportATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic detoxification by transmembrane export across the plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic transport across blood-brain barrierATP-dependent translocase ABCB1Homo sapiens (human)
regulation of chloride transportATP-dependent translocase ABCB1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
protein bindingATP-dependent translocase ABCB1Homo sapiens (human)
ATP bindingATP-dependent translocase ABCB1Homo sapiens (human)
ABC-type xenobiotic transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
efflux transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
ATP hydrolysis activityATP-dependent translocase ABCB1Homo sapiens (human)
transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
ubiquitin protein ligase bindingATP-dependent translocase ABCB1Homo sapiens (human)
ATPase-coupled transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
carboxylic acid transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
phosphatidylcholine floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
phosphatidylethanolamine flippase activityATP-dependent translocase ABCB1Homo sapiens (human)
ceramide floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
ATPase-coupled transmembrane transporter activityATP-dependent translocase ABCB1Mus musculus (house mouse)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
cytoplasmATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
cell surfaceATP-dependent translocase ABCB1Homo sapiens (human)
membraneATP-dependent translocase ABCB1Homo sapiens (human)
apical plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
extracellular exosomeATP-dependent translocase ABCB1Homo sapiens (human)
external side of apical plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Mus musculus (house mouse)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID680104TP_TRANSPORTER: increase in kidney concentration in mdr1a(-/-) mouse2002The Journal of pharmacology and experimental therapeutics, Oct, Volume: 303, Issue:1
Interaction of cytochrome P450 3A inhibitors with P-glycoprotein.
AID681143TP_TRANSPORTER: increase in Calcein-AM intracellular accumulation in MDR1-expressing LLC-PK1 cells2002Molecular pharmacology, May, Volume: 61, Issue:5
Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein.
AID681138TP_TRANSPORTER: increase in Calcein-AM intracellular accumulation in mdr1b-expressing LLC-PK1 cells2002The Journal of pharmacology and experimental therapeutics, Oct, Volume: 303, Issue:1
Interaction of cytochrome P450 3A inhibitors with P-glycoprotein.
AID681137TP_TRANSPORTER: increase in Calcein-AM intracellular accumulation in mdr1a-expressing LLC-PK1 cells2002The Journal of pharmacology and experimental therapeutics, Oct, Volume: 303, Issue:1
Interaction of cytochrome P450 3A inhibitors with P-glycoprotein.
AID681142TP_TRANSPORTER: increase in Vinblastine intracellular accumulation in MDR1-expressing LLC-PK1 cells2002Molecular pharmacology, May, Volume: 61, Issue:5
Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein.
AID679339TP_TRANSPORTER: transepithelial transport (basal to apical) in mdr1a-expressing LLC-PK1 cell2002The Journal of pharmacology and experimental therapeutics, Oct, Volume: 303, Issue:1
Interaction of cytochrome P450 3A inhibitors with P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (8.33)18.7374
1990's0 (0.00)18.2507
2000's16 (66.67)29.6817
2010's4 (16.67)24.3611
2020's2 (8.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.52

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.52 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index25.99 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.52)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials8 (38.10%)5.53%
Reviews0 (0.00%)6.00%
Reviews3 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies1 (4.76%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
Other9 (42.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]