.ALPHA.-ERGOCRYPTINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H41N5O5
Molecular Weight	575.6984
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N3C(=O)[C@](NC(=O)[C@H]4CN(C)[C@]5([H])CC6=CNC7=CC=CC(=C67)C5=C4)(O[C@@]23O)C(C)C

InChI

InChIKey=YDOTUXAWKBPQJW-NSLWYYNWSA-N

InChI=1S/C32H41N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,13,15,17-18,20,24-26,33,41H,7,10-12,14,16H2,1-5H3,(H,34,38)/t20-,24-,25+,26+,31-,32+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7665369 | https://www.ncbi.nlm.nih.gov/pubmed/11981648 | http://drugcentral.org/drugcard/885

Alpha-ergocryptine is a component of the ergotoxine complex; it is the main ergot alkaloid of Japanese & South American wid grasses. Alpha-ergocryptine is an agonist at the D2 dopamine receptor. Alpha-ergocryptine effectively decreases intraocular pressure in the alpha-chymotrypsin-induced model of ocular hypertension.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
guanylate cyclase activity 1 Target ID: GO:0004383 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6116597	Activator 1430
Serotonin 6 (5-HT6) receptor 45 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9798944	Antagonist 2778	49.0 nM [Ki]
Dopamine D2 receptor 297 Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7665369	Agonist 2678	28.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ocular hypertension 50 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17505840 https://www.ncbi.nlm.nih.gov/pubmed/11981648	Primary		Preclinical	Unknown Approved Use Unknown
Hyperprolactinemia 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6369001	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ergovaline binding and activation of D2 dopamine receptors in GH4ZR7 cells.	1995 May	7665369
Determination of plasma ziprasidone using liquid chromatography with fluorescence detection.	2004 Jan 25	14670738
Production and characterization of antibodies against fumigaclavine A.	2009 Oct	23605095

Patents

Sample Use Guides

In Vivo Use Guide

Rats were fed 0, 4, 20, 100 or 500 mg ergocryptine/kg diet for 28-32 days (equal to 0, 0.36, 1.7, 8.9 and 60 mg ergocryptine/kg body weight/day for females and 0, 0.34, 1.4, 6.6 and 44 mg ergocryptine/kg body weight/day for males). It is concluded that in rats fed ergocryptine for 28 days the dose-effect curve is rather steep and that the NOAEL is 4 mg/kg diet.

Route of Administration: Oral

In Vitro Use Guide

Bovine vascular smooth muscle cells (VSMC) from the dorsal metatarsal artery were grown in vitro and exposed to five concentrations (10(-6), 10(-8), 10(-9), 10(-11) and 0 M) of alpha-ergocryptine for 48 h. alpha-Ergocryptine stimulated (P < .01) growth at 10(-6) M concentration in growing cultures and at 10(-8) and 10(-9) M concentrations in quiescent cultures.

Name

Type

Language

.ALPHA.-ERGOCRYPTINE

Common Name

English

ERGOCRYPTINE

Common Name

English

NSC-407319

Code

English

NSC-169479

Code

English

ERGOTAMAN-3',6',18-TRIONE, 12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(2-METHYLPROPYL)-, (5'.ALPHA.)-

Common Name

English

ERGOKRYPTINE

Common Name

English

.ALPHA.-ERGOCRYPTINE [MI]

Common Name

English

Code System Code Type Description

MERCK INDEX

m4977