| Identification | More | [Name]
Pergolide mesylate salt | [CAS]
66104-23-2 | [Synonyms]
8BETA-[(METHYLTHIO)METHYL]-6-PROPYLERGOLINE MESYLATE SALT
8-BETA-[(METHYLTHIO)METHYL]-6-PROPYLERGOLINE MONOMETHANE SULFONATE
MPE
PERGOLIDE MESYLATE
PERGOLIDE MESYLATE SALT
8-beta-((methylthio)methyl)-6-propylergolinemethanesulfonate
8-beta-((methylthio)methyl)-6-propyl-ergolinmethanesulfonate(1:1)
ly127809
Pergolide mesylate EPIV
Pergolidemetylsulfonate
(8b)-8-[(Methylthio)methyl]-6-propylergoline Mesylate
Celance
Nopar
Permax
8-alpha-Methylthiomethyl-6-pro
8β-[(methylthio)methyl]-6-propylergoline methanesulfonate salt
Ergoline, 8-[(methylthio)methyl]-6-propyl-, (8b)-, monomethanesulfonate (9CI)
NSC 319773
Pergolide methanesulfonate
8beta-[(Methylthio)methyl]-6-propylergoline methanesulfonate salt | [Molecular Formula]
C20H30N2O3S2 | [MDL Number]
MFCD00153859 | [Molecular Weight]
410.59 | [MOL File]
66104-23-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White to Off-White Solid | [Melting point ]
252-254°C | [alpha ]
aD20 between -18.0° and -23.0° (c = 10 mg/ml in DMF) | [storage temp. ]
−20°C | [solubility ]
ethanol: soluble2mg/mL | [form ]
solid | [pka]
pKa (66% DMF) 7.8(at 25℃) | [color ]
white | [optical activity]
[α]20/D 35°, c = 0.2 in pyridine(lit.) | [Usage]
A dopaminergic agonist that also decrease plasma prolactin concentrations. An antiparkinsonian agent | [CAS DataBase Reference]
66104-23-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T+ | [Risk Statements ]
R28:Very Toxic if swallowed. | [Safety Statements ]
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 1544 | [WGK Germany ]
3 | [RTECS ]
KE6345000 | [HS Code ]
2939690000 |
| Hazard Information | Back Directory | [Description]
Pergolide mesylate is a potent, long-acting dopamine agonist useful in the treatment of
Parkinson’s disease and hyperprolactinemia, Compared with lergotrile, pergolide mesylate
has shown less toxicity and lower propensity for inducing psychosis. | [Chemical Properties]
White to Off-White Solid | [Originator]
Lilly (USA) | [Uses]
A dopaminergic agonist that also decrease plasma prolactin concentrations. An antiparkinsonian agent | [Uses]
dopamine receptor agonist, anti-Parkinson's agent | [Uses]
glucocorticoid, antiinflammatory | [Definition]
ChEBI: A methanesulfonate salt obtained from pergolide by mixing eqimolar amount of pergolide and methanesulfonic acid. A dopamine D2 receptor agonist which also has D1 and D2 agonist properties, it i
used in the management of Parkinson's disease, although it was withdrawn from the U.S. and Canadian markets in 2007 due to an increased risk of cardiac valve dysfunction. | [Manufacturing Process]
Dimethyl disulfide (73.6 ml, 0.79 mol) and tri-n-butylphosphine (79.6 ml, 0.32 mol) were added to a solution of 9,10-dihydrolysergol in (8.1 g, 0.032 mol) in the 150 ml of anhydrous DMF and were stirred at room temperature for 6 hours under a nitrogen atmosphere. Dimethyl disulfide of the reaction mixture was removed under vacuo. A solution of the residue in ethyl acetate was extracted with 3.7% HCl (aq.). The aqueous layer was basified with ammonium hydroxide to a pH of 10 and then extracted with ethyl acetate. Removal of ethyl acetate followed by a silica gel column purification eluting with 10% MeOH/CH2Cl2 gave5.5.g of D-6-methyl-8β(methylthiomethyl)ergoline (60%).
A solution of D-6-methyl-8β-(methylthiomethyl)ergoline (0.4 g, 0.0014 mol) and NaI (0.63 g, 0.0042 mol) in 10 ml of propionic anhydride was refluxed for 40 hours. The reaction mixture was guenched with a 10% Na2CO3 solution and extracted by ethyl acetate. The combined organic layers were washed with a saturated brine solution, dried with magnesium sulfate and concentrated to produce oil. The oil was purified by silica gel column, eluting with 10% MeOH/CH2Cl2 to give 0.33 g of D-1,6-dipropionyl-8β(methylthiomethyl)ergoline.
LiAlH4 (0.6 g, 0.0156 mol) was slowly added to a solution of D-1,6dipropionyl-8β-(methylthiomethyl)ergoline in the 20 ml anhydrous THF at 0°C under nitrogene atmosphere. The mixture was stirred at 0°C for 30 min and then at room temperature for 4 hours. The reaction was cooled to 0°C and 0.6 ml of water was slowly added. The mixture was stirred at 0°C for 10 min and 1.8 ml of 15% NaOH (aq.) and 2.5 ml of water were added respectively. The mixture was stirred for 30 min at room temperature and then filtered. Excess of the solvent was removed under reduced pressure to give 150 mg of 8β-((methylthio)methyl)-6-propyl-ergoline or pergolide (yield: 68%). Ergoline,8-((methylthio)methyl)-6-propyl-, monomethanesulfonate, (8β)- may be prepared by mixing of components in solution. | [Brand name]
Permax (Valeant). | [Therapeutic Function]
Dopamine agonist | [Biochem/physiol Actions]
Dopaminergic agonist; suppresses pituitary secretion of prolactin; anti-Parkinsonian agent. |
|
|