Dihydroergocryptine

alpha-Dihydroergocryptine
Systematic (IUPAC) name
	(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 [7.3.0.02,6]dodecan-4-yl]- 6-methyl- 6,11-diazatetracyclo [7.6.1.02,7.012,16] hexadeca- 1(16),9,12,14-tetraene- 4-carboxamide
Clinical data
Trade names	Almirid, Cripar
Pregnancy cat.	Contraindicated
Legal status	℞ Prescription only
Routes	Oral
Identifiers
CAS number	25447-66-9
ATC code	N04BC03 (alpha/beta)
PubChem	CID 114948
ChemSpider	102887
UNII	67V3FSL2GL
ChEBI	CHEBI:59919
Synonyms	12'-Hydroxy- 2'-(1-methylethyl)- 5'α-(2-methylpropyl)- 9,10α-dihydroergotaman- 3',6',18-trione;; OR; (5'α,10α)-9,10-dihydro- 12'-hydroxy-2'- (1-methylethyl)- 5'-(2-methylpropyl)- ergotaman- 3',6',18-trione
Chemical data
Formula	C32H43N5O5
Mol. mass	577.715 g/mol
SMILES	eMolecules & PubChem
	InChI InChI=1S/C32H43N5O5/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/h6,8-9,15,17-18,20,22,24-26,33,41H,7,10-14,16H2,1-5H3,(H,34,38)/t20-,22-,24-,25+,26+,31-,32+/m1/s1 ; Key:PBUNVLRHZGSROC-VTIMJTGVSA-N ;
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Dihydroergocryptine (trade names Almirid, Cripar) is a dopamine agonist of the ergoline chemical class that is used as an antiparkinson agent^[1] and in migraine prophylaxis,^[2] as well as for the treatment of low blood pressure in elderly patients and peripheral vascular disorder.^[3] More commonly, it is used in combination with two similar compounds, dihydroergocornine and dihydroergocristine. This mixture is called ergoloid or codergocrine.^[4]

[edit] Chemistry

Dihydroergocryptine is a mixture of two very similar compounds, alpha- and beta-dihydroergocryptine (epicriptine) at a ratio of 2:1.^[3] The beta differs from the alpha form only in the position of a single methyl group, which is a consequence of the biosynthesis of the parent compound ergocryptine, in which the proteinogenic amino acid leucine is replaced by isoleucine.^[5]

^ Battistin, L.; Bardin, P. G.; Ferro-Milone, F.; Ravenna, C.; Toso, V.; Reboldi, G. (1999). "Alpha-dihydroergocryptine in Parkinson's disease: A multicentre randomized double blind parallel group study". Acta neurologica Scandinavica 99 (1): 36–42. PMID 9925236. edit
^ Micieli, G.; Cavallini, A.; Marcheselli, S.; Mailland, F.; Ambrosoli, L.; Nappi, G. (2001). "Alpha-dihydroergocryptine and predictive factors in migraine prophylaxis". International journal of clinical pharmacology and therapeutics 39 (4): 144–151. PMID 11332869. edit
^ ^a ^b Haberfeld, H, ed (2007) (in German). Austria-Codex (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-183-8.
^ Drugs.com: Ergoloid Mesylates
^ Steinhilber, D; Schubert-Zsilavecz, M; Roth, HJ (2005) (in German). Medizinische Chemie. Stuttgart: Deutscher Apotheker Verlag. p. 142. ISBN 3-7692-3483-9.

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