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Bromocriptine mesylate

Product Name
Bromocriptine mesylate
CAS No.
22260-51-1
Chemical Name
Bromocriptine mesylate
Synonyms
BCT;BRC;Bromocryptine mesylate;Bromocriptine-13C-d3 Mesylate;Bromocriptine Mesylate (150 mg);Bagren;cb-154;Pravidel;Serono-Bagren;CB-154 mesylate
CBNumber
CB4335584
Molecular Formula
C33H44BrN5O8S
Formula Weight
750.7
MOL File
22260-51-1.mol
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Bromocriptine mesylate Property

Melting point:
192-196° (dec)
alpha 
D20 +95° (c = 1 in methanol-methylene chloride)
storage temp. 
2-8°C
solubility 
H2O: 0.8 mg/mL
form 
solid
pka
4.90(at 25℃)
color 
white
optical activity
[α]20/D +95°, c = 1 in methanol: methylene chloride (1:1)(lit.)
Merck 
13,1400
BRN 
4115238
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months
InChIKey
NOJMTMIRQRDZMT-JGYCFGIMSA-N
CAS DataBase Reference
22260-51-1(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
22-24/25-36
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
RTECS 
KE1595000
F 
3-10
HS Code 
29396900
Toxicity
LD50 in mice, rats, rabbits (mg/kg): 190, 72, 12.5 i.v. (Parkes)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
B2134
Product name
2-Bromo-α-ergocryptine methanesulfonate salt
Purity
solid
Packaging
25mg
Price
$95.3
Updated
2024/03/01
Sigma-Aldrich
Product number
1076501
Product name
Bromocriptine mesylate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
150mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
BP050
Product name
Bromocriptine mesilate
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$274
Updated
2023/06/20
Alfa Aesar
Product number
H37854
Product name
Bromocriptine mesylate
Packaging
250mg
Price
$0
Updated
2021/12/16
Alfa Aesar
Product number
H37854
Product name
Bromocriptine mesylate
Packaging
1g
Price
$0
Updated
2021/12/16
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Bromocriptine mesylate Chemical Properties,Usage,Production

Description

Bromocriptine is a dopamine receptor agonist (Kis = 1,659, 12.2, 12.2, 59.7, and 1,691 nM for dopamine D1, D2, D3, D4, and D5 receptors, respectively). It also binds to the serotonin (5-HT) receptor subtypes 5-HT1A and 5-HT1D (Kis = 12.9 and 10.7 nM, respectively), as well as α1-adrenergic receptors (Kis = 1.12-4.17 nM). Bromocriptine (5 mg/kg) restores locomotor activity, without inducing dyskinesia, in a macaque model of Parkinson’s disease induced by MPTP. Formulations containing bromocriptine have been used in the treatment of Parkinson''s disease, hyperprolactinemia-associated dysfunctions, and acromegaly.

Chemical Properties

Solid

Originator

Parlodel,Sandoz,UK,1975

Uses

Dopamine receptor agonist; derivative of the ergotoxin group of ergot alkaloids. Prolactin inhibitor; antiparkinsonian.

Uses

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.

Uses

2-Bromo-α-ergocryptine methanesulfonate salt has been used:

  • as D2 agonist in bird zebra finches
  • for Prl secretion inhibitor in mice
  • for the inhibition of motility in planaria worm

Definition

ChEBI: Bromocriptine methanesulfonate is a methanesulfonate salt. It has a role as an antiparkinson drug. It contains a bromocriptine.

Manufacturing Process

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).

brand name

Parlodel (Novartis).

Therapeutic Function

Prolactin inhibitor

General Description

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.

Biological Activity

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).

Biochem/physiol Actions

Bromocriptine is an ergot alkaloid and a dopamine D2 receptor agonist. It is prescribed for Parkinson′s disorder, hyperprolactinemia and galactorrhoea. It modulates β cells of the pancreas from insulin hypersecretion and improves the metabolic profile in type 2 diabetes patients with obesity. It also modulates glutamate release by glutamate transporter,GLT-1.

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.

storage

Room temperature

References

1) Nilsson and Hokfelt (1978), Effect of the dopamine agonist bromocriptine on blood pressure, catecholamines and renin activity in acromegalics at rest, following exercise, and during insulin induced hypoglycemia; Acta Endocrinol., Supp. 216 83 2) Seeman and Van Tol (1994), Dopamine receptor pharmacology; Trends Pharmacol. Sci., 15 264 3) Carvalho et al. (2015), Maternal prolactin inhibition causes changes in leptin at 22- and 30-day old pups; Horm. Metab. Res., 47 528 4) Hubner and Koob (1990), Bromocriptine produces decreases in cocaine self-administration in the rat; Neuropsychopharmacol., 3 101

Bromocriptine mesylate Preparation Products And Raw materials

Raw materials

Preparation Products

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Bromocriptine mesylate Suppliers

Belgium 2 Brazil 1 Canada 2 China 191 Czech 1 Czech Republic 1 Europe 1 France 2 Germany 2 India 15 Israel 2 Italy 3 Japan 2 Malaysia 1 Mexico 1 Poland 1 Russia 1 Slovenia 1 Switzerland 3 The Netherlands 1 United Kingdom 11 United States 30 Uruguay 1 Global 276
Nanjing Sunlida Biological Technology Co., Ltd.
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View Lastest Price from Bromocriptine mesylate manufacturers

Hebei Mojin Biotechnology Co., Ltd
Product
Bromocriptine mesylate 22260-51-1
Price
US $0.00/KG
Min. Order
1KG
Purity
99.1%
Supply Ability
50000KG/month
Release date
2024-11-01
Hebei Yanxi Chemical Co., Ltd.
Product
bromocriptine methanesulfonate 22260-51-1
Price
US $40.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-09-26
Career Henan Chemica Co
Product
Bromocriptine mesylate 22260-51-1
Price
US $2.20/KG
Min. Order
1KG
Purity
98%
Supply Ability
1KG/10KG/100KG
Release date
2020-10-29

22260-51-1, Bromocriptine mesylateRelated Search:

CHLOROPHOSPHONAZO III Pazufloxacin mesilate Imatinib Methanesulfonic acid Pefloxacin mesylate Bromocriptine Trifluoromethanesulfonic acid ALPHA-ERGOCRYPTINE BroMocriptine IMpurity E Ergoline-8-carboxylic acid, 2-bromo-9,10-didehydro-6-methyl-, (8β)- BroMocriptine IMpurity F BroMocriptine-13C-d3 BroMocriptine IMpurity G Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (2'β,5'α,8α)- (9CI) 5'alpha(S)-sec-butyl-12'-hydroxy-2'-isopropylergotaman-3',6',18-trione (8S)-2-BroMo α-Ergocryptine Bromocriptine Impurity A (Mixture of Diastereomers) Bromocriptine Impurity 2

  • (5'A)-2-BROMO-12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(2-METHYLPROPYL)ERGOTAMAN-3',6',18-TRIONE MESYLATE
  • BCT
  • BRC
  • (+)-BROMOCRIPTINE MESYLATE
  • BROMOCRIPTINE MESYLATE
  • (+)-BROMOCRIPTINE METHANESULFONATE
  • BROMOCRIPTINE METHANESULPHONATE
  • BROMOCRYPTINE MESYLATE METHANESULFONATE SALT
  • (+)-2-BROMO-12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(2-METHYLPROPYL)-ERGOTAMAN-3',6',18-TRIONE METHANESULFONATE
  • (+)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6'-18-trione methanesulfonate salt
  • 2-BROMO-12'-HYDROXY-2'-(1-METHYLETHYL)-5'-(2-METHYL-PROPYL)ERGOTAMAN-3',6',18-TRIONE-METHANESULFONATE
  • 2-BROMOERGOCRYPTINE MONOMETHANESULFONATE SALT
  • 2-BROMO-ALPHA-ERGOCRYPTINE METHANESULFONATE
  • 2-BROMO-ALPHA-ERGOCRYPTINE METHANESULFONATE SALT
  • (+)-Bromocriptine methanesulfonate salt, Bromocriptine mesylate salt, (+)-2-Bromo-12μ-hydroxy-2μ-(1-methylethyl)-5μ-(2-methylpropyl)ergotaman-3μ,6μ-18-trione methanesulfonate salt
  • Ergotaman-3,6,18-trione, 2-bromo-12-hydroxy-2-(1-methylethyl)-5-(2-methylpropyl)-, (5.alpha.)-, monomethanesulfonate (salt)
  • 2-bromo-α-ergocryptine methanesulfonate salt
  • BROMOCRIPTINEMESYLATE,USP
  • Bagren
  • Bromocryptine mesylate
  • Ergocryptine, 2-bromo-, monomethanesulfonate (salt) (8CI)
  • Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'α)-, monomethanesulfonate (salt) (9CI)
  • Pravidel
  • 2-Bromo-α-ergocryptine methanesulfonate salt,(+)-2-Bromo-12′-hydroxy-2′-(1-methylethyl)-5′-(2-methylpropyl)ergotaman-3′,6′-18-trione methanesulfonate salt, (+)-Bromocriptine methanesulfonate salt, Bro
  • Bromocriptine Mesylate (150 mg)
  • 2-BroMo α-Ergocryptine Mesylate
  • (5'alpha)-2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6', 18-trione mesylate
  • Serono-Bagren
  • (5'α)-2-BroMo-12'-hydroxy-2'-(1-Methylethyl)-5'-(2-Methylpropyl)ergotaMan-3',6',18-trione Methanesulfonate
  • (6aR,9R)-5-broMo-N-((2R,5S,10aS,10bS)-10b-hydroxy-5-isobutyl-2-isopropyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-Methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxaMide Methanesulfonate
  • (+)-Bromocriptine methanesulfonate salt
  • Bromocriptine mesylate salt
  • Bromocriptin mesylate
  • 2-bromo-alpha-ergocryptinemesylate
  • 2-bromo-alpha-ergocryptinmethanesulfonate
  • 2-bromo-alpha-ergokryptine-mesilate
  • bromocriptinemesilate
  • bromocryptinemethanesulfonate
  • cb-154
  • 2-bromo-A-ergocryptine methanesulfonate salt
  • 2-bromo-12'-hydroxy-5'alpha-isobutyl-2'-isopropylergotaman-3',6',18-trione monomethanesulphonate
  • Bromocriptine mesylate EP
  • Bromocriptine-13C-d3 Mesylate
  • Bromocriptine mesilate CRS
  • Bromocriptine mesilate for system suitability CRS
  • CB-154 mesylate
  • Bromocriptine mesylate USP/EP/BP
  • Bromocriptine mesyla
  • High Quality Bromocriptine Mesylate Powder CAS?22260-51-1
  • Bromocriptine Mesylate (CB-154)
  • TIANFU-CHEM CAS NO.22260-51-1 Bromocriptine mesylate
  • Bromocriptine Mesylate (1076501)
  • 2-Bromo α-Ergocryptine Mesylate
  • 22260-51-1
  • C32H40BrN5O5CH4O3S
  • C33H44BrN5O8S
  • C32H40BrN5O5CH3SO3H
  • C32H40N5O5BRCH4SO3