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ChemicalBook--->CAS DataBase List--->81409-90-7

81409-90-7

81409-90-7 Structure

81409-90-7 Structure
IdentificationMore
[Name]

Cabergoline
[CAS]

81409-90-7
[Synonyms]

6-allyl-n-[3-(dimethylamino)propyl]-n-(ethylcarbamoyl)ergoline-8-carboxamide
CABERGOLINE
(8-beta)-(2-propenyl)
n-(3-(dimethylamino)propyl)-n-((ethylamino)carbonyl)-6-ergoline-8-carboxamid
FCE-21336,Cabaser,Dostinex
(8b)-N-[3-(Dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propen-1-yl)-ergoline-8-carboxamide
Cabaser
Dostine
FCE-21336
C08187
Dostinex
Ergoline-8-carboxamide, N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)-, (8β)-
Galastop
Sogilen
((8 )-N-[3-(Dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propen-1-yl)-ergoline-8-carboxamide
(8β)-N-[3-(Dimethylamino)propyl]-N-[(ethylamino)earbonyl]-6-(2-propenyl)ergoline-8-carboxamide
(8R)-6-(2-Propenyl)-8-[[(ethylaminocarbonyl)[3-(dimethylamino)propyl]amino]carbonyl]ergoline
CG-101
N-(Ethylcarbamoyl)-N-[3-(dimethylamino)propyl]-6-allylergoline-8β-carboxamide
N-[3-(Dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)ergoline-8β-carboxamide
[EINECS(EC#)]

200-419-0
[Molecular Formula]

C26H37N5O2
[MDL Number]

MFCD00867887
[Molecular Weight]

451.6
[MOL File]

81409-90-7.mol
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Solid
[Melting point ]

102-104°C
[density ]

1.156±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

DMSO: ≥10mg/mL
[form ]

powder
[pka]

13.05±0.46(Predicted)
[color ]

White to Off-White
[optical activity]

[α]/D 61 to 68°, c = 0.5 in dichloromethane
[Usage]

A dopamine D2-receptor agonist.
[Stability:]

Hygroscopic
[InChIKey]

KORNTPPJEAJQIU-KJXAQDMKSA-N
[SMILES]

[C@]12([H])C[C@H](CN(CC=C)[C@]1([H])CC1=CNC3C=CC=C2C1=3)C(=O)N(CCCN(C)C)C(=O)NCC |&1:0,3,9,r|
[CAS DataBase Reference]

81409-90-7(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36/37
[WGK Germany ]

3
[RTECS ]

KE6167600
[HS Code ]

2939690000
[Toxicity]

Sol in ethyl alcohol, chloroform, DMF; slightly sol in 0.1 N HCl; very slightly sol in n-hexane. Insol in water. LD50 orally in male mice: >400 mg/kg (Brambilla)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Furan-->3-METHOXYPROPIONIC ACID-->Sodium hydroxide-->1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide-->Desethylcarbamoyl Cabergoline-->Des-N-allylcabergoline-->(82)-N-[[[3-(Dimethylamino)propyl]amino]carbonyl]-N-ethyl-6-(2-propen-1-yl)-ergoline-8-carboxamide-->6-Allyl-8beta-carboxyergoline-->Ethyl isocyanate-->1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
Hazard InformationBack Directory
[Description]

Cabergoline is a potent, selective, and long-lasting dopamine D2 receptor agonist launched in 1993 in Belgium as a prolactin inhibitor. A single 1 mg dose of cabergoline effectively prevents puerperal lactation for up to 14 days, remarkably superior to other drugs that require a daily regimen. It has a low rate of rebound breast activity and good tolerability. Cabergoline is also in clinical trials for Parkinson's disease, breast cancer, and hyperprolactinaemia.
[Chemical Properties]

White Crystalline Solid
[Originator]

Kabi Pharmacia (Sweden)
[Uses]

A dopamine D2-receptor agonist.
[Uses]

receptor stimulant
[Definition]

ChEBI: An N-acylurea that is (8R)-ergoline-8-carboxamide in which the hydrogen attached to the piperidine nitrogen (position 6) is substituted by an allyl group and the hydrogens attached to the carboxamide nitrogen are substit ted by a 3-(dimethylamino)propyl group and an N-ethylcarbamoyl group. A dopamine D2 receptor agonist, cabergoline is used in the management of Parkinson's disease and of disorders associated with hyperprolactinaemia.
[Manufacturing Process]

A mixture of 6-(2-propenyl)-8β-carboxy-ergoline and N-(3- dimethylaminopropyl)-N-ethyl carbodiimide in tetrahydrofuran were refluxed, with stirring and under nitrogen, for 24 h. The resultant solution was evaporated in vacuo to dryness and the residue taken up with chloroform and 5% sodium hydroxide solution. The organic phase was separated, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica (eluant chloroform with 1% methanol) to give the title compound N-(3-(dimethylamino)propyl)-N-((ethylamino)carbonyl)-8β- carboxamide-6-(2-propenyl)ergoline.
[Brand name]

Dostinex (Pharmacia & Upjohn).
[Therapeutic Function]

Prolactin inhibitor
[General Description]

Cabergoline, (6aR,9R,10aR)-7-allyl-N-(3-(dimethylamino)propyl)-N-(ethylcarbamoyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide (Dostinex), is a white powder soluble inalcohol, chloroform, and N,N-dimethylformamide; slightlysoluble in acidic solutions and in n-hexane; and insoluble inwater. Following oral administration, peak plasma concentrationsare reached within 2 to 3 hours. Cabergoline ismoderately bound to plasma proteins in a concentrationindependentmanner. The absolute bioavailability of cabergolineis unknown. Cabergoline is extensively metabolizedby the liver, predominantly via hydrolysis of the acylureabond of the urea moiety. CYP450 metabolism appears to beminimal. The major metabolites identified thus far do not contribute to the therapeutic effect of cabergoline. Lessthan 4% is excreted unchanged in the urine. Fecal excretionrepresents the main route of cabergoline elimination. Thereare no reports of interactions of cabergoline with other antiparkinsonianagents. Clarithromycin may elevate theplasma concentration of cabergoline by the inhibition ofboth CYP3A4 and P-glycoprotein.Cabergoline is a potentD2 receptor agonist and is indicated for the treatment ofhyperprolactinemic disorders, either idiopathic or causedby pituitary adenomas.
[Biological Activity]

Selective D 2 -like dopamine receptor agonist (K i values are 0.7, 1.5, 9.0 and 165 nM for D 2 , D 3 , D 4 and D 5 receptors respectively) that also displays high affinity for several serotonin receptor subtypes (K i = 1.2-20.0 nM for 5-HT 1A , 5-HT 1D , 5-HT 2A and 5-HT 2B ). Inhibits secretion of prolactin and growth hormone and reverses levodopa-induced dyskinesias in Parkinsonian monkeys.
[Biochem/physiol Actions]

Cabergoline, a lysergic acid amide derivative, is a potent dopamine D2 receptor agonist. It also acts on dopamine receptors in lactophilic hypothalamus cells to suppress prolactin production in the pituitary gland. It has been used for monotherapy of Parkinson′s disease in the early phase; combination therapy, together with levodopa and a decarboxylase inhibitor such as carbidopa, in progressive-phase Parkinson′s disease and adjunctive therapy of prolactin-producing pituitary gland tumors (microprolactinomas).
[Clinical Use]


Endocrine disorders

Adjunct to levodopa (with a decarboxylase inhibitor) in Parkinson’s disease

Inhibition / suppression of lactation
[Veterinary Drugs and Treatments]

For dogs, cabergoline may be useful for inducing estrus, treatment of primary or secondary anestrus, pseudopregnancy, and pregnancy termination in the second half of pregnancy. Cabergoline may be useful in treating some cases of pituitary-dependent hyperadrenocorticism (Cushing’s).
In cats, cabergoline, with or without a prostaglandin, may be useful for pregnancy termination, particularly earlier in pregnancy. Preliminary work has been done in psittacines (primarily Cockatiels) for adjunctive treatment of reproductive-related disorders, particularly persistent egg laying.
In humans, cabergoline is indicated for the treatment of disorders associated with hyperprolactenemia or the treatment of Parkinson’s disease.
[in vitro]

receptor binding studies have demonstrated that cabergoline has high in vitro selectivity and affinity for the subtype d2 of the dopamine receptor. in rat anterior pituitary cells, the concentration of cabergoline required to inhibit prl secretory activity by 50% were 0.1 nmol/l [1].
[in vivo]

in various animal models, cabergoline markedly reduced plasma prl levels in vivo after single or multiple doses, and the prl-lowering effects appeared 2 - 8 h after administration lasting for 72 h or longer. in addition, a single dose of cabergoline 0.6 mg/kg to rats, inhibited the serum levels of prl for 6 days significantly [1].
[Drug interactions]

Potentially hazardous interactions with other drugs
None known
[IC 50]

0.1 nm
[Metabolism]

Cabergoline is subject to first-pass metabolism and is extensively metabolised to several metabolites that do not appear to contribute to its pharmacological activityCabergoline is mainly eliminated via the faeces (72%); a small proportion is excreted in the urine (18%).
[storage]

Store at -20°C
[References]

[1] annamaria colao, gaetano lombardi & lucio annunziato. cabergoline. exp. opin. pharmacother. (2000) 1(3):555-574
Spectrum DetailBack Directory
[Spectrum Detail]

Cabergoline(81409-90-7)1HNMR
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