Alpha-dihydroergocryptine

Dihydroergocryptine

Clinical data
Trade names	Almirid, Cripar
Pregnancy category	Contraindicated
Routes of administration	Oral
ATC code	N04BC03 (WHO) (alpha/beta)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Biological half-life	12–16 hours
Identifiers
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
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
CAS Number	25447-66-9 Y
PubChem CID	114948
ChemSpider	102887 Y
UNII	67V3FSL2GL
ChEBI	CHEBI:59919 Y
ChEMBL	CHEMBL1743263
ECHA InfoCard	100.042.706
Chemical and physical data
Formula	C32H43N5O5
Molar mass	577.715 g/mol
3D model (Jmol)	Interactive image
SMILES O=C3N1CCC[C@H]1[C@]2(O)O[C@](C(=O)N2[C@H]3CC(C)C)(NC(=O)[C@@H]6C[C@@H]7c4cccc5c4c(cn5)C[C@H]7N(C)C6)C(C)C
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 Y Key:PBUNVLRHZGSROC-VTIMJTGVSA-N Y

Dihydroergocryptine (DHEC, trade names Almirid, Cripar) is a dopamine agonist of the ergoline chemical class that is used as an antiparkinson agent. Dihydroergocryptine has been shown to be particularly effective as monotherapy in the early stages of Parkinson's disease. Initial monotherapy with a dopamine agonist (other examples include pergolide, pramipexole, and ropinirole) is associated with reduced risk for motor complications in Parkinson patients relative to levodopa. DHEC, like other dopamine agonists, aims to mimic the endogenous neurotransmitter and exert an antiparkinsonian effect. Recent evidence also supports that dopamine receptor agonists, instead of L-DOPA may slow or prevent the progression of Parkinson's disease.

Dihydroergocryptine can also be used in migraine prophylaxis, as well as for the treatment of low blood pressure in elderly patients and peripheral vascular disorder. More commonly, it is used in combination with two similar compounds, dihydroergocornine and dihydroergocristine. This mixture is called ergoloid or codergocrine.

Dihydroergocryptine is a mixture of two very similar compounds, alpha- and beta-dihydroergocryptine (epicriptine) at a ratio of 2:1. 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.