Identification

Summary

Epicriptine is a nootropic with an unknown mechanism of action indicated in individuals over sixty who manifest signs and symptoms of an idiopathic decline in mental capacity.

Generic Name
Epicriptine
DrugBank Accession Number
DB11275
Background

Epicriptine is also known as beta-dihydroergocryptine presents a molecular formula of 9,10 alpha-dihydro-13'-epi-b-ergocryptine. Together with the alpha-dihydroergocryptine, it represents one-third of the ergoloid mesylate mixture. Epicriptine differs from the alpha form on the position of one methyl group.1 To know more about the mixture please visit Ergoloid mesylate

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 577.726
Monoisotopic: 577.326419505
Chemical Formula
C32H43N5O5
Synonyms
  • dihydro-beta-ergocryptine
  • Epicriptina
  • Epicriptine
  • Epicriptinum
  • Epicryptine
External IDs
  • Dcn 203-922

Pharmacology

Indication

Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

Mechanism of action

Epicriptine effect is mainly due to the agonistic activity on dopamine receptor. This activity is categorized as part of the ergoline class which is defined as a producer of a vasoconstrictive effect.1 Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

TargetActionsOrganism
ADopamine receptor
agonist
Humans
Absorption

Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

Volume of distribution

Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

Protein binding

Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

Metabolism

Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

Route of elimination

Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

Half-life

Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

Clearance

Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

Adverse Effects
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Toxicity

Please refer to Ergoloid mesylate and to know more about the isomer please refer to Dihydro-alpha-ergocryptine.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetophenazineThe therapeutic efficacy of Epicriptine can be decreased when used in combination with Acetophenazine.
AmisulprideThe therapeutic efficacy of Epicriptine can be decreased when used in combination with Amisulpride.
AmoxapineThe therapeutic efficacy of Epicriptine can be decreased when used in combination with Amoxapine.
ApomorphineThe risk or severity of adverse effects can be decreased when Apomorphine is combined with Epicriptine.
AripiprazoleThe risk or severity of adverse effects can be decreased when Aripiprazole is combined with Epicriptine.
AsenapineThe therapeutic efficacy of Epicriptine can be decreased when used in combination with Asenapine.
BenperidolThe therapeutic efficacy of Epicriptine can be decreased when used in combination with Benperidol.
BrexpiprazoleThe risk or severity of adverse effects can be decreased when Brexpiprazole is combined with Epicriptine.
BromocriptineThe risk or severity of adverse effects can be decreased when Bromocriptine is combined with Epicriptine.
BuspironeThe therapeutic efficacy of Epicriptine can be decreased when used in combination with Buspirone.
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Epicriptine mesilate79Y4U49I2965914-79-6YKEUOHBRJUALFI-ILSKZLILSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ergoloid MesylatesEpicriptine mesilate (0.111 mg/1) + Dihydro-alpha-ergocryptine mesylate (0.222 mg/1) + Dihydroergocornine mesylate (0.333 mg/1) + Dihydroergocristine mesylate (0.333 mg/1)TabletOralAv Kare, Inc.2014-08-222015-09-15US flag
Ergoloid MesylatesEpicriptine mesilate (0.111 mg/1) + Dihydro-alpha-ergocryptine mesylate (0.222 mg/1) + Dihydroergocornine mesylate (0.333 mg/1) + Dihydroergocristine mesylate (0.333 mg/1)TabletOralSun Pharmaceutical Industries Limited1991-10-31Not applicableUS flag
Ergoloid MesylatesEpicriptine mesilate (0.111 mg/1) + Dihydro-alpha-ergocryptine mesylate (0.222 mg/1) + Dihydroergocornine mesylate (0.333 mg/1) + Dihydroergocristine mesylate (0.333 mg/1)TabletOralFrontida BioPharm, Inc.2017-06-01Not applicableUS flag
Ergoloid MesylatesEpicriptine mesilate (0.111 mg/1) + Dihydro-alpha-ergocryptine mesylate (0.222 mg/1) + Dihydroergocornine mesylate (0.333 mg/1) + Dihydroergocristine mesylate (0.333 mg/1)TabletOralPhysicians Total Care, Inc.1991-10-312012-10-08US flag
Ergoloid MesylatesEpicriptine mesilate (0.111 mg/1) + Dihydro-alpha-ergocryptine mesylate (0.222 mg/1) + Dihydroergocornine mesylate (0.333 mg/1) + Dihydroergocristine mesylate (0.333 mg/1)TabletOralCarilion Materials Management1991-10-31Not applicableUS flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
5M64643B5U
CAS number
88660-47-3
InChI Key
SBFXHXZNBNFPHV-PXXBSISHSA-N
InChI
InChI=1S/C32H43N5O5/c1-6-18(4)27-29(39)36-12-8-11-25(36)32(41)37(27)30(40)31(42-32,17(2)3)34-28(38)20-13-22-21-9-7-10-23-26(21)19(15-33-23)14-24(22)35(5)16-20/h7,9-10,15,17-18,20,22,24-25,27,33,41H,6,8,11-14,16H2,1-5H3,(H,34,38)/t18-,20-,22-,24-,25+,27+,31-,32+/m1/s1
IUPAC Name
(2R,4R,7R)-N-[(1S,2S,4R,7S)-7-[(2R)-butan-2-yl]-2-hydroxy-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(16),9,12,14-tetraene-4-carboxamide
SMILES
[H][C@@]12CCCN1C(=O)[C@]([H])([C@H](C)CC)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=CNC6=CC=CC(=C56)[C@@]4([H])C3)(O[C@@]21O)C(C)C

References

General References
  1. Steinhilber, D., Schubert M. and Roth H. (2005). Medizinische Chemie. Deutscher Apotheker Verlag. [ISBN:3-7692-3483-9]
ChemSpider
59102
RxNav
91171
ChEBI
135927
ChEMBL
CHEMBL2106411
ZINC
ZINC000004215812
Wikipedia
Epicriptine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)848 ºC at 760 mm Hg'MSDS'
Predicted Properties
PropertyValueSource
Water Solubility0.276 mg/mLALOGPS
logP3.39ALOGPS
logP3.5ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.71ChemAxon
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.21 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity157.26 m3·mol-1ChemAxon
Polarizability63.58 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.

Components:
References
  1. Steinhilber, D., Schubert M. and Roth H. (2005). Medizinische Chemie. Deutscher Apotheker Verlag. [ISBN:3-7692-3483-9]

Drug created at December 03, 2015 16:52 / Updated at February 21, 2021 18:53