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11332869, 5414, cpp39144, 144, international, therapeutics, clarke, guttman, november, 9347, 25118777, 12480442, 11668, 1767, 360, olanow, 1992, suppl, 1349262, 1017, s0317167100041469, 108, canadian, neurological, sciences, rationale, primary, ramaker, marinus, stiggelbout, van, hilten, september, systematic, evaluation, scales, impairment, disability, 2562332, 12360535, 10248, 867, martignoni, pacchetti, sibilla, bruggi, pedevilla, 1991, six, months, trial, 1903079, 1097, 00002826, 199102000, 00006, neuropharmacology, bergamasco, frattola, muratorio, piccoli, parnetti, june, novo, parkinsonian, placebo, controlled, 9859381, 10877152, 90295a, 372, albanese, colosimo, 18094044, 12713527, 02049, 349, 107, comparison, 11926889, 1001, transporter, imaging, assess, gerlach, arzberger, leblhuber, tatschner, riederer, comparative, binding, profiles, defined, human, striatum, 10073899, 14523624, 1007, s00702, 0027, 1119, 110, neural, transmission, antonini, tolosa, mizuno, 2009, reassessment, 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toggle the table of contents dihydroergocryptine 5 languages العربية deutsch español srpskohrvatski српскохрватски српски srpski edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical compound pharmaceutical compound dihydroergocryptine clinical data trade names almirid cripar other names dihydroergocriptine dhec 12 hydroxy 2 1 methylethyl 5 α 2 methylpropyl 9 10α dihydroergotaman 3 6 18 trione 5 α 10α 9 10 dihydro 12 hydroxy 2 1 methylethyl 5 2 methylpropyl ergotaman 3 6 18 trione pregnancy category contraindicated routes of administration oral atc code n04bc03 who alpha beta legal status legal status in general prescription only pharmacokinetic data elimination half life 12 16 hours identifiers iupac name 2 r 4 r 7 r n 1 s 2 s 4 r 7 s 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 16 9 12 14 tetraene 4 carboxamide cas number 25447 66 9 y pubchem cid 114948 chemspider 102887 y unii 67v3fsl2gl chebi chebi 59919 y chembl chembl1743263 comptox dashboard epa dtxsid5048689 echa infocard 100 042 706 chemical and physical data formula c 32 h 43 n 5 o 5 molar mass 577 726 g mol 1 3d model jsmol 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 c nh 5 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 verify dihydroergocryptine dhec sold under the brand names almirid and cripar among others is a dopamine agonist of the ergoline group that is used as an antiparkinson agent in the treatment of parkinson s disease 1 it is taken by mouth citation needed medical uses edit parkinson s disease edit 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 2 dhec like other dopamine agonists aims to mimic the endogenous neurotransmitter and exert an antiparkinsonian effect 3 recent evidence also supports that dopamine receptor agonists instead of levodopa may slow or prevent the progression of parkinson s disease 4 the relatively long half life and lack of dietary influence of dihydroergocriptine is considered to contribute to the compound s effectiveness in parkinson s disease particularly since it allows for more continuous stimulation of brain dopaminergic receptors than short acting drugs such as levodopa 5 dhec is also proven to be a safe and effective in improving symptoms in parkinson s patients 6 motor improvements in parkinson s patients are usually observed in patients who take at least a mean daily dose of approximately 40 mg 7 patients on dhec demonstrate a better score than if they were on levodopa on the webster scale a standardized rating scale of parkinson s disease symptoms such as gait parameters and dyskinesia 5 8 another clinical study has shown that dhec had superior efficacy in reducing the clinical and motorcomplications associated with long term levodopa use as well as in reducing the incidence and severity of adverse effects 1 activation of presynaptic dopamine autoreceptors by dihydroergocriptine leads to reduced dopamine receptor turnover and indirect antioxidant effects in particular further activation of intracellular kinase systems due to dopamine agonists are hypothesized to lead to antiapoptotic effects that also help in halting and slowing the disease progression 2 this may also contribute to prevention of development of motor fluctuations though more research is needed 9 modern agonists like dihydroergocryptine typically cost two to three times more than levodopa therapy more health economics assessments may be needed to determine whether the initial increased costs of the agonists are offset by less patients needing surgery in later stages of the disease 10 other uses edit dihydroergocryptine can also be used in migraine prophylaxis 11 as well as for the treatment of low blood pressure in elderly patients and peripheral vascular disorder 12 more commonly it is used in combination with two similar compounds dihydroergocornine and dihydroergocristine this mixture is called ergoloid or codergocrine 13 side effects edit dihydroergocryptine has been suggested to produce fewer side effects and have similar efficacy to a classical dopamine agonist due to its biochemical profile 5 there is also no interference with levodopa metabolism 10 although dhec may come with some acute side effects described further below dhec has overall good tolerability with little to no withdrawal or changes in its scheduling 7 acute side effects usually accompany the beginning of treatment but tend to decrease as the patient develops increased tolerance to the drug 14 in randomized double blinded trials individuals on different dopamine agonists including dihydroergocryptine did not differ in discontinuation rate associated with adverse events 15 16 however there do seem to be a higher incidence of dopaminergic related side effects such as hallucinations and gastrointestinal complaints tend to be more frequent 6 nausea vomiting anxiety cardiac arrhythmias postural hypotension somnolence hallucinations impulse control disorders peripheral oedema pharmacology edit pharmacodynamics edit several in vitro and in vivo studies have demonstrated that dihydroergocriptine is an effective anti parkinson drug most likely exerting its effects as a potent agonist of d 2 receptors the k d of dhec is found to be around 5 8 nm at d2 receptors less certain is the contribution of its partial d 1 receptor and d 3 receptor agonist activity dhec has a lower affinity for d 1 and d 3 receptors k d is around 30 nm for both than for d 2 receptors 3 it is widely believed that dopamine receptor agonists demonstrate their antiparkinsonian effects by stimulating d2 receptors primarily but other dopamine receptors such as d1 and d3 may be involved 3 remarkably dhec is said to not significantly interact with serotonergic and adrenergic receptors 5 pharmacokinetics edit dihydroergocriptine has two main pharmacokinetic advantages over levodopa the first pharmacokinetic advantage is its half life of 12 to 16 hours this relatively long half life is considered to contribute to the compound s effectiveness in parkinson s disease particularly since it allows for more continuous stimulation of brain dopaminergic receptors than short acting drugs such as levodopa though the exact reason is not known continuous stimulation is considered to reduce risk for motor complications 2 the second pharmacokinetic advantage is the lack of dietary influence on drug absorption this characteristic also allows for more sustained dopamine receptor stimulation 5 dhec can be taken with a single oral dose and is rapidly absorbed peak plasma concentrations occur between 30 and 120 minutes after administration the strong first pass hepatic metabolism results in poor bioavailability less than 5 of the original dosage reaches the circulation 5 chemistry edit dihydroergocryptine is a mixture of two very similar compounds alpha and beta dihydroergocryptine epicriptine at a ratio of 2 1 12 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 17 dihydroergocryptine is a hydrogenated ergot derivative that is also structurally very similar to bromocriptine another drug that has anti parkinson effects dhec differs in that it is hydrogenated in c9 c10 and lacks bromine in c2 in fact all ergot derivatives are uniquely or mainly d 2 like receptor agonists 5 references edit 1 2 battistin l bardin pg ferro milone f ravenna c toso v reboldi g january 1999 alpha dihydroergocryptine in parkinson s disease a multicentre randomized double blind parallel group study acta neurologica scandinavica 99 1 36 42 doi 10 1111 j 1600 0404 1999 tb00655 x pmid 9925236 s2cid 45192184 1 2 3 antonini a tolosa e mizuno y yamamoto m poewe wh october 2009 a reassessment of risks and benefits of dopamine agonists in parkinson s disease the lancet neurology 8 10 929 37 doi 10 1016 s1474 4422 09 70225 x pmid 19709931 s2cid 33649811 1 2 3 gerlach m double k arzberger t leblhuber f tatschner t riederer p october 2003 dopamine receptor agonists in current clinical use comparative dopamine receptor binding profiles defined in the human striatum journal of neural transmission 110 10 1119 27 doi 10 1007 s00702 003 0027 5 pmid 14523624 s2cid 10073899 parkinson study group april 2002 dopamine transporter brain imaging to assess the effects of pramipexole vs levodopa on parkinson disease progression jama 287 13 1653 61 doi 10 1001 jama 287 13 1653 pmid 11926889 1 2 3 4 5 6 7 albanese a colosimo c may 2003 dihydroergocriptine in parkinson s disease clinical efficacy and comparison with other dopamine agonists acta neurologica scandinavica 107 5 349 55 doi 10 1034 j 1600 0404 2003 02049 x pmid 12713527 s2cid 18094044 1 2 bergamasco b frattola l muratorio a piccoli f mailland f parnetti l june 2000 alpha dihydroergocryptine in the treatment of de novo parkinsonian patients results of a multicentre randomized double blind placebo controlled study acta neurologica scandinavica 101 6 372 80 doi 10 1034 j 1600 0404 2000 90295a x pmid 10877152 s2cid 9859381 1 2 martignoni e pacchetti c sibilla l bruggi p pedevilla m nappi g february 1991 dihydroergocryptine in the treatment of parkinson s disease a six months double blind clinical trial clinical neuropharmacology 14 1 78 83 doi 10 1097 00002826 199102000 00006 pmid 1903079 ramaker c marinus j stiggelbout am van hilten bj september 2002 systematic evaluation of rating scales for impairment and disability in parkinson s disease movement disorders 17 5 867 76 doi 10 1002 mds 10248 pmid 12360535 s2cid 2562332 olanow cw february 1992 a rationale for dopamine agonists as primary therapy for parkinson s disease the canadian journal of neurological sciences 19 1 suppl 108 12 doi 10 1017 s0317167100041469 pmid 1349262 1 2 clarke ce guttman m november 2002 dopamine agonist monotherapy in parkinson s disease lancet 360 9347 1767 9 doi 10 1016 s0140 6736 02 11668 0 pmid 12480442 s2cid 25118777 micieli g cavallini a marcheselli s mailland f ambrosoli l nappi g april 2001 alpha dihydroergocryptine and predictive factors in migraine prophylaxis international journal of clinical pharmacology and therapeutics 39 4 144 51 doi 10 5414 cpp39144 pmid 11332869 1 2 haberfeld h ed 2007 austria codex in german 2007 2008 ed vienna österreichischer apothekerverlag isbn 978 3 85200 183 8 drugs com ergoloid mesylates yamamoto m schapira ah april 2008 dopamine agonists in parkinson s disease expert review of neurotherapeutics 8 4 671 7 doi 10 1586 14737175 8 4 671 pmid 18416667 s2cid 207194957 rascol o goetz c koller w poewe w sampaio c may 2002 treatment interventions for parkinson s disease an evidence based assessment lancet 359 9317 1589 98 doi 10 1016 s0140 6736 02 08520 3 pmid 12047983 s2cid 24426198 goetz cg poewe w rascol o sampaio c may 2005 evidence based medical review update pharmacological and surgical treatments of parkinson s disease 2001 to 2004 movement disorders 20 5 523 39 doi 10 1002 mds 20464 pmid 15818599 s2cid 16260982 steinhilber d schubert zsilavecz m roth hj 2005 medizinische chemie in german stuttgart deutscher apotheker verlag p 142 isbn 978 3 7692 3483 1 v t e antiparkinson agents n04 dopaminergics da precursors levodopa benserazide carbidopa carbidopa entacapone foslevodopa foscarbodipa melevodopa carbidopa da receptor agonists ergoline bromocriptine cabergoline dihydroergocryptine lisuride pergolide non ergoline apomorphine piribedil pramipexole ropinirole rotigotine talipexole d 1 like agonists tavapadon mao b inhibitors rasagiline safinamide selegiline comt inhibitors entacapone opicapone tolcapone aaad inhibitors benserazide levodopa carbidopa carbidopa melevodopa carbidopa entacapone foscarbidopa foslevodopa anticholinergics benzatropine biperiden bornaprine chlorphenoxamine cycrimine dexetimide diphenhydramine etanautine etybenzatropine mazaticol metixene orphenadrine phenglutarimide piroheptine procyclidine profenamine tigloidine trihexyphenidyl tropatepine others adamantanes e g amantadine memantine rimantadine adenosine receptor antagonists e g caffeine istradefylline budipine who em withdrawn from market clinical trials phase iii never to phase iii v t e antimigraine preparations n02c analgesic abortive serotonergics ergolines dihydroergocryptine dihydroergotamine ergotamine caffeine chlorcyclizine caffeine lisuride methylergometrine methysergide 5 ht 1 agonists triptans almotriptan avitriptan donitriptan eletriptan frovatriptan naratriptan rizatriptan meloxicam sumatriptan zolmitriptan ditans alniditan lasmiditan others dimetotiazine dotarizine iprazochrome oxetorone pizotifen cgrp r antagonists rimegepant ubrogepant zavegepant others paracetamol amidrine prophylactic calcium channel blockers dotarizine lomerizine verapamil flunarizine progestogens flumedroxone acetate sympatholytics beta blockers propranolol timolol clonidine tricyclic antidepressants amitriptyline nortriptyline imipramine anticonvulsants carbamazepine oxcarbazepine topiramate valproate anti cgrp cgrp r mabs eptinezumab erenumab fremanezumab galcanezumab cgrp r antagonists atogepant rimegepant who em withdrawn from market clinical trials phase iii never to phase iii v t e dopamine receptor modulators d 1 like agonists benzazepines 6 br apb fenoldopam skf 38 393 skf 77 434 skf 81 297 skf 82 958 skf 83 959 trepipam zelandopam ergolines cabergoline cy 208 243 dihydroergocryptine lek 8829 lisuride pergolide terguride dihydrexidine derivatives a 77636 a 86929 adrogolide abt 431 das 431 dihydrexidine dinapsoline dinoxyline doxanthrine phenethylamines bco 001 deoxyepinephrine n methyldopamine epinine dipropyldopamine dpda dopamine dopexamine etilevodopa ibopamine l dopa levodopa lu ae04621 melevodopa l phenylalanine l tyrosine xp21279 others a 68930 apomorphine isocorypalmine lu af28996 nuciferine pf 2334 pf 06412562 pf 6649751 pf 6669571 propylnorapomorphine rotigotine ru 29717 skf 89 145 s...