- Product Name:
- Bromocriptine mesylate
- (5'A)-2-BROMO-12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(2-METHYLPROPYL)ERGOTAMAN-3',6',18-TRIONE MESYLATE
- (+)-BROMOCRIPTINE MESYLATE
- BROMOCRIPTINE MESYLATE
- (+)-BROMOCRIPTINE METHANESULFONATE
- BROMOCRIPTINE METHANESULPHONATE
- BROMOCRYPTINE MESYLATE METHANESULFONATE SALT
- Product Categories:
- Intermediates & Fine Chemicals
- Dopamine receptor
- Mol File:
Bromocriptine mesylate Chemical Properties
- Melting point:
- 192-196° (dec)
- D20 +95° (c = 1 in methanol-methylene chloride)
- storage temp.
- H2O: 0.8 mg/mL
- 4.90(at 25℃)
- optical activity
- [α]20/D +95°, c = 1 in methanol: methylene chloride (1:1)(lit.)
- CAS DataBase Reference
- 22260-51-1(CAS DataBase Reference)
- Language:English Provider:SigmaAldrich
Bromocriptine mesylate Usage And Synthesis
Dopamine receptor agonist; derivative of the ergotoxin group of ergot alkaloids. Prolactin inhibitor; antiparkinsonian.
2-Bromo-α-Ergocryptine is a dopamine receptor agonist. 2-Bromo-α-Ergocryptine is a derivative of the ergotoxin group of ergot alkaloids. 2-Bromo-α-Ergocryptine is a prolactin inhibitor; antiparkinsoni an.
A solution of 3.4 grams of N-bromosuccinimide in 60 cc of absolute dioxane is
added drop wise in the dark, during the course of 5 minutes, to a stirred
solution, heated to 60°C, of 9.2 grams of ergocryptine in 180 cc of absolute
dioxane. The reaction mixture is stirred at this temperature for 70 minutes
and is concentrated to a syrup-like consistency in a rotary evaporator at a
bath temperature of 50°C. The reaction mixture is subsequently diluted with
300 cc of methylene chloride, is covered with a layer of about 200 cc of a 2 N
sodium carbonate solution in a separating funnel and is shaken thoroughly.
The aqueous phase is extracted thrice with 100 cc amounts of methylene
chloride. The combined organic phases are washed once with 50 cc of water,
are dried over sodium sulfate and the solvent is removed under a vacuum.
The resulting brown foam is chromatographed on a 50-fold quantity of aluminum oxide of activity II-III with 0.2% ethanol in methylene chloride as eluant, whereby the compound indicated in the heading is eluted immediately after a secondary fraction which migrates somewhat more rapidly than the fractions containing the heading compound. The last fractions to leave the aluminum oxide contain varying amounts of starting material together with the heading compound, and may be subjected directly, as mixed fractions, to an afterbromination in accordance with the method described above. The fractions containing the pure heading compound are combined and crystallized from methyl ethyl ketonehopropy1 ether. Melting point 215°-218°C (decomp.), [α]D 20-195° (c = 1 in methylene chloride).
Bromocriptine mesylate,(6aR,9R)-5-bromo-N-((2R,5S,10aS,10bS)-10b-hydroxy-5-isobutyl-2-isopropyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide methanesulfonate(Parlodel), is a white solid soluble in ethanol and slightly solublein water (pKa’s＝6.6 and 15). Bromocriptine is rapidlyabsorbed after oral administration and it has low systemicbioavailability because of its extensive first-pass metabolism.Bromocriptine enters the brain quickly with a half-lifefor uptake into the brain of approximately 0.3 hours; 8% ofthe drug crosses the BBB.The metabolites are excreted primarilyin the bile and feces. The high first-pass hepatic metabolismimplies an increased risk of drug interactions.Concomitant administration with the DA antagonists, metoclopramide,or domperidone may aggravate parkinsoniansymptoms and induce extrapyramidal side effects (EPS).Other drugs that may interact with bromocriptine are highlyplasma protein–bound drugs (e.g., warfarin, increased dyskinesiacaused by bromocriptine); macrolides antibacterials(enhanced dopaminergic effects); and caffeine (elevation inplasma bromocriptine concentrations). The combination oflevodopa/AADC inhibitors with bromocriptine permits a reductionof the dose of levodopa. Thus, the side effects oflevodopa are decreased, resulting in a more continuous stimulationof DA receptors.
Selective D 2 -like dopamine receptor agonist (K i values are ~ 8, ~ 5, ~ 290, ~ 440 and ~ 450 nM for D 2 , D 3 , D 4 , D 1 and D 5 receptors respectively).
Veterinary Drugs and Treatments
Bromocriptine may potentially be of benefit in treating acromegaly/ pituitary adenomas or pseudopregnancy in a variety of species. However, because of adverse effects, its potential value for treating hyperadrenocorticism in dogs is low. It has been used in dogs for pregnancy termination and pseudopregnancy.
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