Editing Bromocriptine

{{Short description|Dopamine agonist medication}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 459983915
| IUPAC_name = (5{{prime}}α)-2-Bromo-12{{prime}}-hydroxy-5{{prime}}-(2-methylpropyl)-3{{prime}},6{{prime}},18-trioxo-2{{prime}}-(propan-2-yl)ergotaman
| image = Bromocriptine.svg
| width =

<!--Clinical data-->
| tradename = Originally Parlodel, subsequently many<ref name=brands/>
| Drugs.com = {{drugs.com|monograph|parlodel}}, {{drugs.com|international|brotin}}
| MedlinePlus = a682079
| pregnancy_AU = A
| legal_AU = S4
| legal_CA = Rx-only
| legal_US = Rx-only
| legal_UK = POM
| routes_of_administration = [[Oral administration|By mouth]], [[vaginal administration|vaginal]], [[intravenous administration|intravenous]]

<!--Pharmacokinetic data-->
| bioavailability = 28% of oral dose absorbed
| protein_bound = 
| metabolism = Extensively [[liver]]-mediated
| elimination_half-life = 12–14 hours
| excretion = 85% [[bile]] ([[feces]]), 2.5–5.5% [[urine]]

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 25614-03-3
| ATC_prefix = G02
| ATC_suffix = CB01
| ATC_supplemental = {{ATC|N04|BC01}}
| PubChem = 31101
| IUPHAR_ligand = 35
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01200
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 28858
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3A64E3G5ZO
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03165
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3181
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 493
| synonyms = 2-Bromoergocriptine; CB-154

<!--Chemical data-->
| C=32 | H=40 | Br=1 | N=5 | O=5
| SMILES = BrC1=C(C[C@H]2N(C)C3)C4=C(C=CC=C4C2=C[C@H]3C(N[C@]5(C(C)C)O[C@@]6(N([C@@H](CC(C)C)C(N7CCC[C@H]76)=O)C5=O)O)=O)N1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C32H40BrN5O5/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39)/t18-,23-,24+,25+,31-,32+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OZVBMTJYIDMWIL-AYFBDAFISA-N
}}
<!-- Definition and medical uses -->
'''Bromocriptine''', originally marketed as '''Parlodel''' and subsequently under many brand names,<ref name=brands/> is an [[ergoline]] derivative and [[dopamine agonist]] that is used in the treatment of [[pituitary]] [[tumors]], [[Parkinson's disease]], [[hyperprolactinaemia]], [[neuroleptic malignant syndrome]], and, as an adjunct, [[Diabetes mellitus type 2|type 2 diabetes]].

<!-- Society and culture -->
It was patented in 1968 and approved for medical use in 1975.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR | title = Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=533 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA533 |language=en}}</ref>

==Medical uses==
Bromocriptine is used to treat [[acromegaly]] and conditions associated with [[hyperprolactinemia]] like [[amenorrhea]], infertility, [[hypogonadism]], and prolactin-secreting [[adenomas]]. It is also used to prevent [[ovarian hyperstimulation syndrome]]<ref name=OlderLabel>{{cite web|title=Bromocriptine mesylate tablets -- original uses|url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/017962s065s068lbl.pdf|publisher=FDA|date=January 2012|url-status=live|archive-url=https://web.archive.org/web/20170228152534/http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/017962s065s068lbl.pdf|archive-date=2017-02-28}} For label updates see [https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=017962 FDA index page for NDA 017962] {{webarchive|url=https://web.archive.org/web/20170629041043/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=017962 |date=2017-06-29 }}</ref><ref>{{cite journal | vauthors = Molitch ME | title = Diagnosis and Treatment of Pituitary Adenomas: A Review | journal = JAMA | volume = 317 | issue = 5 | pages = 516–524 | date = February 2017 | pmid = 28170483 | doi = 10.1001/jama.2016.19699 | s2cid = 205077946 }}</ref><ref>{{cite journal|vauthors=Tang H, Mourad SM, Wang A, Zhai SD, Hart RJ|date=14 Apr 2021|title=Dopamine agonists for preventing ovarian hyperstimulation syndrome|journal=The Cochrane Database of Systematic Reviews|volume=2021 |issue=4 |pages=CD008605 |doi=10.1002/14651858.CD008605.pub4 | pmc=8092425 |pmid=33851429}}</ref> and to treat [[Parkinson's disease]].<ref name=OlderLabel/>

Since the late 1980s it has been used, off-label, to reduce the symptoms of [[cocaine]] withdrawal but the evidence for this use is poor.<ref>{{cite journal | vauthors = Minozzi S, Amato L, Pani PP, Solimini R, Vecchi S, De Crescenzo F, Zuccaro P, Davoli M | title = Dopamine agonists for the treatment of cocaine dependence | journal = The Cochrane Database of Systematic Reviews | issue = 5 | pages = CD003352 | date = May 2015 | volume = 2015 | pmid = 26014366 | pmc = 6999795 | doi = 10.1002/14651858.CD003352.pub4 }}</ref> Bromocriptine has been successfully used in cases of galactorrhea precipitated by dopamine antagonists like [[risperidone]].

A quick-release formulation of bromocriptine, Cycloset, is also used to treat [[type 2 diabetes]].<ref name=DiabetesLabel>{{cite web|title=Bromocriptine mesylate tablet label|url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020866s006s007lbl.pdf|publisher=FDA|date=February 2017|url-status=live|archive-url=https://web.archive.org/web/20180513230418/https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020866s006s007lbl.pdf|archive-date=2018-05-13}}. For label updates see [https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=020866 FDA index page for NDA 020866] {{webarchive|url=https://web.archive.org/web/20170628072832/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=020866 |date=2017-06-28 }}</ref><ref>{{cite journal | vauthors = Garber AJ, Blonde L, Bloomgarden ZT, Handelsman Y, Dagogo-Jack S | title = The role of bromocriptine-QR in the management of type 2 diabetes expert panel recommendations | journal = Endocrine Practice | volume = 19 | issue = 1 | pages = 100–6 | date = 2013 | pmid = 23337160 | doi = 10.4158/EP12325.OR }}</ref><ref>{{cite journal | vauthors = Liang W, Gao L, Li N, Wang B, Wang L, Wang Y, Yang H, You L, Hou J, Chen S, Zhu H, Jiang Y, Pan H | title = Efficacy and Safety of Bromocriptine-QR in Type 2 Diabetes: A Systematic Review and Meta-Analysis | journal = Hormone and Metabolic Research | volume = 47 | issue = 11 | pages = 805–12 | date = October 2015 | pmid = 26332757 | doi = 10.1055/s-0035-1559684 | s2cid = 423132 }}</ref> When administered within 2 hours of awakening, it increases hypothalamic dopamine level.  That results to a significant weight loss as well as decreases in blood glucose levels, hepatic glucose production, and insulin resistance.<ref name=":0">{{cite journal | vauthors = Birhan MT, Ayele TM, Abebe FW, Dgnew FN | title = Effect of bromocriptine on glycemic control, risk of cardiovascular diseases and weight in patients with type 2 diabetes: a systematic review | journal = Diabetology & Metabolic Syndrome | volume = 15 | issue = 1 | pages = 151 | date = July 2023 | pmid = 37415177 | pmc = 10324265 | doi = 10.1186/s13098-023-01073-2 | doi-access = free }}</ref> It therefore acts as an adjunct to diet and exercise to improve glycemic control and cardiovascular risk.<ref name=":0" /><ref>{{cite journal | vauthors = Defronzo RA | title = Bromocriptine: a sympatholytic, d2-dopamine agonist for the treatment of type 2 diabetes | journal = Diabetes Care | volume = 34 | issue = 4 | pages = 789–94 | date = April 2011 | pmid = 21447659 | pmc = 3064029 | doi = 10.2337/dc11-0064 }}</ref>

==Side effects==
Most frequent side effects are nausea, [[orthostatic hypotension]], headaches, and vomiting through stimulation of the brainstem vomiting centre.<ref>{{cite journal | vauthors = Weil C | title = The safety of bromocriptine in long-term use: a review of the literature | journal = Current Medical Research and Opinion | volume = 10 | issue = 1 | pages = 25–51 | year = 1986 | pmid = 3516579 | doi = 10.1185/03007998609111089 }}</ref> Vasospasms with serious consequences such as myocardial infarction and stroke that have been reported in  connection with the [[puerperium]], appear to be extremely rare events.<ref>{{cite journal | vauthors = Iffy L, McArdle JJ, Ganesh V, Hopp L | title = Bromocriptine related atypical vascular accidents postpartum identified through medicolegal reviews | journal = Medicine and Law | volume = 15 | issue = 1 | pages = 127–34 | year = 1996 | pmid = 8691994 }}</ref>  Peripheral vasospasm (of the fingers or toes) can cause [[Raynaud's phenomenon]].

Bromocriptine use has been anecdotally associated with causing or worsening [[psychosis|psychotic]] symptoms (its mechanism is in opposition of most antipsychotics, whose mechanisms generally block dopamine receptors).<ref>{{cite journal | vauthors = Boyd A | title = Bromocriptine and psychosis: a literature review | journal = The Psychiatric Quarterly | volume = 66 | issue = 1 | pages = 87–95 | year = 1995 | pmid = 7701022 | doi = 10.1007/BF02238717 | s2cid = 29539691 }}</ref> It should be understood, however, that the greater affinity bromocriptine and many similar antiparkinson's drugs have for the D<sub>2S</sub> receptor form (considered to be mostly present at inhibitory D<sub>2</sub> autoreceptor locatations)<ref>{{cite journal | vauthors = Ford CP | title = The role of D2-autoreceptors in regulating dopamine neuron activity and transmission | journal = Neuroscience | volume = 282 | pages = 13–22 | date = December 2014 | pmid = 24463000 | pmc = 4108583 | doi = 10.1016/j.neuroscience.2014.01.025 }}</ref> relative to the D<sub>2L</sub> form, sufficiently low partial agonist activity (ie where a molecule binding to a receptor induces limited effects while preventing a stronger [[ligand]] like dopamine from binding), and, possibly, the [[functional selectivity]] of a particular drug may generate antidopaminergic effects that are more similar than oppositional in nature to antipsychotics.

[[Pulmonary fibrosis]] has been reported when bromocriptine was used in high doses for the treatment of Parkinson's disease.<ref>{{cite journal | vauthors = Todman DH, Oliver WA, Edwards RL | title = Pleuropulmonary fibrosis due to bromocriptine treatment for Parkinson's disease | journal = Clinical and Experimental Neurology | volume = 27 | pages = 79–82 | year = 1990 | pmid = 2129961 }}</ref>

Use to suppress milk production after childbirth was reviewed in 2014 and it was concluded that in this context a causal association with serious cardiovascular, neurological or psychiatric events could not be excluded with an overall incidence estimated to range between 0.005% and 0.04%. Additional safety precautions and stricter prescribing rules were suggested based on the data.<ref>{{cite web|url=http://www.ema.europa.eu/ema/index.jsp?curl=pages/news_and_events/news/2014/08/news_detail_002157.jsp&mid=WC0b01ac058004d5c1|title=European Medicines Agency - News and Events - CMDh endorses restricted use of bromocriptine for stopping breast milk production|date=2018-09-17|website=www.ema.europa.eu|url-status=live|archive-url=https://web.archive.org/web/20140828112730/http://www.ema.europa.eu/ema/index.jsp?curl=pages%2Fnews_and_events%2Fnews%2F2014%2F08%2Fnews_detail_002157.jsp&mid=WC0b01ac058004d5c1|archive-date=2014-08-28}}</ref><ref>{{cite web |url=http://m.aerzteblatt.de/news/59857.htm |title=EMA rät vom Abstillmittel Bromocriptin ab |access-date=2014-08-26 |url-status=live |archive-url=https://web.archive.org/web/20150609025916/http://m.aerzteblatt.de/news/59857.htm |archive-date=2015-06-09 |date=2014-08-25 }} "EMA rät vom Abstillmittel Bromocriptin ab", article in Ärzteblatt</ref>  It is a bile salt export pump inhibitor.<ref>{{cite journal | vauthors = Montanari F, Pinto M, Khunweeraphong N, Wlcek K, Sohail MI, Noeske T, Boyer S, Chiba P, Stieger B, Kuchler K, Ecker GF | title = Flagging Drugs That Inhibit the Bile Salt Export Pump | journal = Molecular Pharmaceutics | volume = 13 | issue = 1 | pages = 163–71 | date = January 2016 | pmid = 26642869 | doi = 10.1021/acs.molpharmaceut.5b00594 | s2cid = 46496531 | url = http://www.zora.uzh.ch/id/eprint/118806/1/acs.molpharmaceut.pdf }}</ref>

After long-term use of [[dopamine agonist]]s, a [[withdrawal syndrome]] may occur during dose reduction or discontinuation with the following possible side effects:  anxiety, panic attacks, [[dysphoria]], depression, agitation, irritability, suicidal ideation, fatigue, [[orthostatic hypotension]], nausea, vomiting, [[diaphoresis]], generalized pain, and drug cravings. For some individuals, these withdrawal symptoms are short-lived and they make a full recovery, for others a [[protracted withdrawal syndrome]] may occur with withdrawal symptoms persisting for months or years.<ref name="pmid23686524">{{cite journal | vauthors = Nirenberg MJ | title = Dopamine agonist withdrawal syndrome: implications for patient care | journal = Drugs & Aging | volume = 30 | issue = 8 | pages = 587–92 | date = August 2013 | pmid = 23686524 | doi = 10.1007/s40266-013-0090-z | s2cid = 207489653 }}</ref>

==Pharmacology==

===Pharmacodynamics===
[[File:Bromocriptin.png|thumb|Bromocriptine in a dopamine receptor bound conformation.]]

Bromocriptine is a [[partial agonist]] of the [[dopamine]] [[D2 receptor|D<sub>2</sub> receptor]].<ref name="pmid12388666" /><ref name="pmid12388667" /><ref name="pmid20138024">{{cite journal | vauthors = de Leeuw van Weenen JE, Parlevliet ET, Maechler P, Havekes LM, Romijn JA, Ouwens DM, Pijl H, Guigas B | title = The dopamine receptor D2 agonist bromocriptine inhibits glucose-stimulated insulin secretion by direct activation of the alpha2-adrenergic receptors in beta cells | journal = Biochemical Pharmacology | volume = 79 | issue = 12 | pages = 1827–36 | date = June 2010 | pmid = 20138024 | doi = 10.1016/j.bcp.2010.01.029 }}</ref> It also interacts with other [[dopamine receptor]]s and with various [[serotonin receptor|serotonin]] and [[adrenergic receptor]]s.<ref name="pmid12388666" /><ref name="pmid12388667" /><ref name="pmid12388668" /> Bromocriptine has additionally been found to inhibit the [[neurotransmitter release|release]] of [[glutamate]] by [[transporter reversal|reversing]] the [[GLT1]] [[glutamate transporter]].<ref>{{cite journal | vauthors = Shirasaki Y, Sugimura M, Sato T | title = Bromocriptine, an ergot alkaloid, inhibits excitatory amino acid release mediated by glutamate transporter reversal | journal = European Journal of Pharmacology | volume = 643 | issue = 1 | pages = 48–57 | date = September 2010 | pmid = 20599932 | doi = 10.1016/j.ejphar.2010.06.007 }}</ref>

Despite acting as a [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]] [[agonist]], bromocriptine is described as non-[[hallucinogen]]ic.<ref name="GumpperRoth2024">{{cite journal | vauthors = Gumpper RH, Roth BL | title = Psychedelics: preclinical insights provide directions for future research | journal = Neuropsychopharmacology | volume = 49 | issue = 1 | pages = 119–127 | date = January 2024 | pmid = 36932180 | doi = 10.1038/s41386-023-01567-7 | url = | pmc = 10700551 }}</ref>

As a [[silent antagonist]] of the serotonin [[5-HT2B receptor|5-HT<sub>2B</sub> receptor]],<ref name="pmid12388668" /> bromocriptine has been said not to pose a risk of [[cardiac valvulopathy]].<ref name="pmid24361689">{{cite journal | vauthors = Cavero I, Guillon JM | title = Safety Pharmacology assessment of drugs with biased 5-HT(2B) receptor agonism mediating cardiac valvulopathy | journal = J Pharmacol Toxicol Methods | volume = 69 | issue = 2 | pages = 150–61 | date = 2014 | pmid = 24361689 | doi = 10.1016/j.vascn.2013.12.004 | url = }}</ref> This is in contrast to other ergolines acting instead as 5-HT<sub>2B</sub> receptor agonists such as [[cabergoline]] and [[pergolide]] but is similar to [[lisuride]] which likewise acts as a 5-HT<sub>2B</sub> receptor antagonist.<ref name="pmid24361689" /> However, in other research, bromocriptine has subsequently been found to be a [[partial agonist]] of the serotonin 5-HT<sub>2B</sub> receptor and has been associated with cardiac valvulopathy and related complications.<ref name="SamsonEzzat2014">{{cite journal | vauthors = Samson SL, Ezzat S | title = AACE/ACE Disease State Clinical Review: Dopamine Agonists for Hyperprolactinemia and the Risk of Cardiac Valve Disease | journal = Endocr Pract | volume = 20 | issue = 6 | pages = 608–616 | date = June 2014 | pmid = 24969114 | doi = 10.4158/EP14148.RA | url = | quote = Bromocriptine was first described as a 5HT-2BR antagonist (22) but was subsequently found to have partial agonist properties (23,24). [...] Regarding bromocriptine, there was no increased incidence of valve regurgitation in PD patients on bromocriptine in the population-based study of Schade et al (33), despite the significant findings for cabergoline and pergolide. However, there is a case report implicating high doses of bromocriptine as the cause of triple valve disease in a PD patient (37), and 1 study reported a significant correlation between cumulative dose of bromocriptine and the risk of valve regurgitation in a PD cohort (38). Other publications have reported fibrotic events, including retroperitoneal, pericardial and pleural fibrosis, in PD patients on high-dose bromocriptine (39-43). [...] Although there seems to be a lower risk of valvulopathy with bromocriptine, as a partial 5HT-2BR agonist, there still appears to be some risk with high-dose bromocriptine in PD patients.}}</ref><ref name="ElenkovaShabaniKalinov2012">{{cite journal | vauthors = Elenkova A, Shabani R, Kalinov K, Zacharieva S | title = Increased prevalence of subclinical cardiac valve fibrosis in patients with prolactinomas on long-term bromocriptine and cabergoline treatment | journal = Eur J Endocrinol | volume = 167 | issue = 1 | pages = 17–25 | date = July 2012 | pmid = 22511808 | doi = 10.1530/EJE-12-0121 | url = }}</ref><ref name="BoguszewskidosSantosSakamoto2012">{{cite journal | vauthors = Boguszewski CL, dos Santos CM, Sakamoto KS, Marini LC, de Souza AM, Azevedo M | title = A comparison of cabergoline and bromocriptine on the risk of valvular heart disease in patients with prolactinomas | journal = Pituitary | volume = 15 | issue = 1 | pages = 44–49 | date = March 2012 | pmid = 21847572 | doi = 10.1007/s11102-011-0339-7 | url = }}</ref><ref name="TanNgAu2009">{{cite journal | vauthors = Tan LC, Ng KK, Au WL, Lee RK, Chan YH, Tan NC | title = Bromocriptine use and the risk of valvular heart disease | journal = Mov Disord | volume = 24 | issue = 3 | pages = 344–349 | date = February 2009 | pmid = 18989898 | doi = 10.1002/mds.22228 | url = }}</ref> In any case, bromocriptine seems to have lower risk than certain other drugs.<ref name="SamsonEzzat2014" />

{| class="wikitable"
|+ {{Nowrap|Activities of bromocriptine at various sites<ref name="pmid12388666">{{cite journal | vauthors = Millan MJ, Maiofiss L, Cussac D, Audinot V, Boutin JA, Newman-Tancredi A | title = Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. I. A multivariate analysis of the binding profiles of 14 drugs at 21 native and cloned human receptor subtypes | journal = J Pharmacol Exp Ther | volume = 303 | issue = 2 | pages = 791–804 | date = November 2002 | pmid = 12388666 | doi = 10.1124/jpet.102.039867 | s2cid = 6200455 | url = }}</ref><ref name="pmid12388667">{{cite journal | vauthors = Newman-Tancredi A, Cussac D, Audinot V, Nicolas JP, De Ceuninck F, Boutin JA, Millan MJ | title = Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. II. Agonist and antagonist properties at subtypes of dopamine D(2)-like receptor and alpha(1)/alpha(2)-adrenoceptor | journal = J Pharmacol Exp Ther | volume = 303 | issue = 2 | pages = 805–14 | date = November 2002 | pmid = 12388667 | doi = 10.1124/jpet.102.039875 | s2cid = 35238120 | url = }}</ref><ref name="pmid12388668">{{cite journal | vauthors = Newman-Tancredi A, Cussac D, Quentric Y, Touzard M, Verrièle L, Carpentier N, Millan MJ | title = Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. III. Agonist and antagonist properties at serotonin, 5-HT(1) and 5-HT(2), receptor subtypes | journal = J Pharmacol Exp Ther | volume = 303 | issue = 2 | pages = 815–22 | date = November 2002 | pmid = 12388668 | doi = 10.1124/jpet.102.039883 | s2cid = 19260572 | url = }}</ref><ref name="PDSPKiDatabase">National Institute of Mental Health. PDSP Ki&nbsp;Database (Internet). ChapelHill (NC): University of North Carolina. Available from:&nbsp;{{cite web|url=http://pdsp.med.unc.edu/pdsp.php |title=PDSP Database - UNC |access-date=2021-04-12 |url-status=dead |archive-url=https://web.archive.org/web/20210413022746/https://pdsp.unc.edu/databases/pdsp.php?testFreeRadio=testFreeRadio&testLigand=Bromocriptine&doQuery=Submit+Query|archive-date=2021-04-13}}</ref>}}
! Site
! Affinity (K<sub>i</sub> [nM])
! Efficacy (E<sub>max</sub> [%])
! Action
|-
| [[D1 receptor|D<sub>1</sub>]]
| 692
| ?
| ?
|-
| [[D2S receptor|D<sub>2S</sub>]]
| 5.0
| 41
| Partial agonist
|-
| [[D2L receptor|D<sub>2L</sub>]]
| 15
| 28
| Partial agonist
|-
| [[D3 receptor|D<sub>3</sub>]]
| 6.8
| 68
| Partial agonist
|-
| [[D4 receptor|D<sub>4</sub>]]
| 372
| 0
| Silent antagonist
|-
| [[D5 receptor|D<sub>5</sub>]]
| 537
| ?
| ?
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]]
| 13
| 72
| Partial agonist
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]]
| 355
| 66
| Partial agonist
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]]
| 11
| 86
| Partial agonist
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]]
| 107
| 69
| Partial agonist
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]]
| 56
| ?
| Partial agonist
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]]
| 741
| 79
| Partial agonist
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]]
| 33
| ?
| ?
|-
| [[5-HT7 receptor|5-HT<sub>7</sub>]]
| 11–126
| ?
| ?
|-
| [[α1A-Adrenergic receptor|α<sub>1A</sub>]]
| 4.2
| 0
| Silent antagonist
|-
| [[α1B-Adrenergic receptor|α<sub>1B</sub>]]
| 1.4
| ?
| ?
|-
| [[α1D-Adrenergic receptor|α<sub>1D</sub>]]
| 1.1
| ?
| ?
|-
| [[α2A-Adrenergic receptor|α<sub>2A</sub>]]
| 11
| 0
| Silent antagonist
|-
| [[α2B-Adrenergic receptor|α<sub>2B</sub>]]
| 35
| 0
| Silent antagonist
|-
| [[α2C-Adrenergic receptor|α<sub>2C</sub>]]
| 28
| 0
| Silent antagonist
|-
| [[α2D-Adrenergic receptor|α<sub>2D</sub>]]
| 68
| ?
| ?
|-
| [[β1-Adrenergic receptor|β<sub>1</sub>]]
| 589
| ?
| ?
|-
| [[β2-Adrenergic receptor|β<sub>2</sub>]]
| 741
| ?
| ?
|-
| [[H1 receptor|H<sub>1</sub>]]
| >10,000
| –
| –
|-
| [[Muscarinic acetylcholine receptor M1|M<sub>1</sub>]]
| >10,000
| –
| –
|- class="sortbottom"
| colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' All receptors are human except α<sub>2D</sub>-adrenergic, which is rat (no human counterpart), and 5-HT<sub>7</sub>, which is rat/mouse.<ref name="pmid12388666" /><ref name="PDSPKiDatabase" />
|}

==Chemistry==
Like all [[ergoline|ergopeptides]], bromocriptine is a [[cyclol]]; two peptide groups of its tri[[peptide]] moiety are crosslinked, forming the >N-C(OH)< juncture between the two rings with the [[amide]] [[functional group|functionality]].

Bromocriptine is a [[semisynthetic]] derivative of a natural [[ergot]] [[alkaloid]], [[ergocryptine]] (a derivative of [[lysergic acid]]), which is synthesized by bromination of ergocryptine using [[N-Bromosuccinimide|''N''-bromosuccinimide]].<ref>{{cite patent | country = US | number = 3752814 | title = 2-Bromo-alpha-ergocryptine | inventor = Fluckiger E, Hofmann A | url = https://patents.google.com/patent/US3752814A/en | assign = Sandoz AG | gdate = 14 August 1973 }}</ref><ref>{{cite patent|country=DE|number=1926045A1|title=Verfahren zur Herstellung einer neuen heterocyclischen Verbindung [Process for the preparation of a new heterocyclic compound] |inventor = Hofmann A, Flueckiger E, Troxler F | assign = Sandoz AG |gdate = 21 September }}</ref>

[[File:Bromocriptine synthesis.png|400px]]

==History==
Bromocriptine was discovered by scientists at [[Sandoz]] in 1965 and was first published in 1968; it was first marketed under the brand name Parlodel.<ref>{{cite book| vauthors = Sneader W, Corey EJ |title=Drug Discovery: A History|date=2005|publisher=John Wiley & Sons|isbn=9780471899792|page=352|url=https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA352|language=en}}</ref><ref>{{cite journal| vauthors = Beekman AM, Barrow RA |title=Fungal Metabolites as Pharmaceuticals|journal=Australian Journal of Chemistry|date=2014|volume=67|issue=6|pages=827|doi=10.1071/CH13639}}</ref>

A quick-release formulation of bromocriptine was approved by the FDA in 2009.<ref>{{cite journal | vauthors = Holt RI, Barnett AH, Bailey CJ | title = Bromocriptine: old drug, new formulation and new indication | journal = Diabetes, Obesity & Metabolism | volume = 12 | issue = 12 | pages = 1048–57 | date = December 2010 | pmid = 20977575 | doi = 10.1111/j.1463-1326.2010.01304.x | s2cid = 22908831 }}</ref>

==Society and culture==

===Brand names===
As of July 2017, bromocriptine was marketed under many brand names worldwide, including Abergin, Barlolin, Brameston, Brocriptin, Brom, Broma-Del, Bromergocryptine, Bromergon, Bromicon, Bromocorn, Bromocriptin, Bromocriptina, Bromocriptine, Bromocriptine mesilate, Bromocriptine mesylate, Bromocriptine methanesulfonate, Bromocriptini mesilas, Bromocriptinmesilat, Bromodel, Bromokriptin, Bromolac, Bromotine, Bromtine, Brotin, Butin, Corpadel, Cripsa, Criptine, Criten, Cycloset, Degala, Demil, Deparo, Deprolac, Diacriptin, Dopagon, Erenant, Grifocriptina, Gynodel, kirim, Kriptonal, Lactodel, Medocriptine, Melen, Padoparine, Palolactin, Parlodel, Pravidel, Proctinal, Ronalin, Semi-Brom, Serocriptin, Serocryptin, Suplac, Syntocriptine, Umprel, Unew, Updopa, Upnol B, and Volbro.<ref name=brands>{{cite web|title=Bromocriptine international brand names|url=https://www.drugs.com/international/bromocriptine.html|publisher=Drugs.com|access-date=13 July 2017|url-status=live|archive-url=https://web.archive.org/web/20170806023201/https://www.drugs.com/international/bromocriptine.html|archive-date=6 August 2017}}</ref>

As of July 2017 it was also marketed as a [[combination drug]] with [[metformin]] as Diacriptin-M, and as a veterinary drug under the brand Pseudogravin.<ref name=brands/>

==References==
{{Reflist}}

==External links==
* {{MedlinePlusDrugInfo|medmaster|a682079}}

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[[Category:5-HT2B agonists]]
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