ChemicalBook > CAS DataBase List > Cabergoline

Cabergoline

Product Name
Cabergoline
CAS No.
81409-90-7
Chemical Name
Cabergoline
Synonyms
Dostinex;CG-101;cabergoline powder;Caber;C08187;Dostine;Cabaser;Sogilen;Galastop;FCE-21336
CBNumber
CB0282495
Molecular Formula
C26H37N5O2
Formula Weight
451.6
MOL File
81409-90-7.mol
More
Less

Cabergoline Property

Melting point:
102-104°C
Density 
1.156±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: ≥10mg/mL
pka
13.05±0.46(Predicted)
form 
powder
color 
White to Off-White
optical activity
[α]/D 61 to 68°, c = 0.5 in dichloromethane
Stability:
Hygroscopic
InChI
InChI=1/C26H37N5O2/c1-5-11-30-17-19(25(32)31(26(33)27-6-2)13-8-12-29(3)4)14-21-20-9-7-10-22-24(20)18(16-28-22)15-23(21)30/h5,7,9-10,16,19,21,23,28H,1,6,8,11-15,17H2,2-4H3,(H,27,33)/t19-,21-,23-/s3
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)
More
Less

Safety

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)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C0246
Product name
Cabergoline
Purity
≥98% (HPLC)
Packaging
10mg
Price
$247
Updated
2024/03/01
Sigma-Aldrich
Product number
1084306
Product name
Cabergoline
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
125mg
Price
$3660
Updated
2024/03/01
Cayman Chemical
Product number
23934
Product name
Cabergoline
Purity
≥98%
Packaging
1mg
Price
$44
Updated
2024/03/01
Cayman Chemical
Product number
23934
Product name
Cabergoline
Purity
≥98%
Packaging
5mg
Price
$87
Updated
2024/03/01
Sigma-Aldrich
Product number
Y0000472
Product name
Cabergoline
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0000472
Price
$153
Updated
2024/03/01
More
Less

Cabergoline Chemical Properties,Usage,Production

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

Uses

Cabergoline is an ergot derivative and a dopamine D2-receptor agonist (1,2,3). It inhibits the secretion of prolactin and growth hormone.

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].

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 +4°C

References

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

Cabergoline Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Cabergoline Suppliers

Wellman Pharmaceutical Group Limited
Tel
027-83778875 15807197853
Fax
027-83991220
Email
15807197853@163.com
Country
China
ProdList
4024
Advantage
58
Shanghai Zhibang Biological Medicine Co., LTD
Tel
021-54285032 18116461626
Fax
021-54285032
Email
25493162@qq.com
Country
China
ProdList
142
Advantage
58
Wuhan Senwayer Century Chemical Co.,Ltd
Tel
027-86652399 13627115097;
Fax
86-27-59707018
Email
sales@senwayer.com
Country
China
ProdList
267
Advantage
55
Hunan Fengdu Biotechnology Co., Ltd
Tel
13533334465
Email
396587392@qq.com
Country
China
ProdList
28
Advantage
58
Wuhan Dingxintong Pharmaceutical Co. , Ltd.
Tel
027-52344656 15871722230
Fax
2796190295
Email
15871722230@163.com
Country
China
ProdList
4898
Advantage
58
ADKS Technology(Hebei)., Ltd.
Tel
13032624271
Email
liuchunguang@adksmedical.com.cn
Country
China
ProdList
12
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chemvon Biotechnology Co., Ltd
Tel
021-50790412
Fax
+86-21-50790419
Email
info@chemvon.com
Country
China
ProdList
371
Advantage
57
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
More
Less

View Lastest Price from Cabergoline manufacturers

Shandong Huizhihan Supply Chain Co., Ltd
Product
Cabergoline Tablets 81409-90-7
Price
US $0.00-0.00/BOX
Min. Order
1BOX
Purity
99%
Supply Ability
1000
Release date
2024-11-04
Shandong Huizhihan Supply Chain Co., Ltd
Product
Cabergoline 81409-90-7
Price
US $0.00-0.00/BOX
Min. Order
1BOX
Purity
99%
Supply Ability
1000
Release date
2024-11-11
Shandong Huizhihan Supply Chain Co., Ltd
Product
Cabergoline 81409-90-7
Price
US $0.00-0.00/BOX
Min. Order
1BOX
Purity
99%
Supply Ability
1000
Release date
2024-11-11

81409-90-7, CabergolineRelated Search:


  • 6-allyl-n-[3-(dimethylamino)propyl]-n-(ethylcarbamoyl)ergoline-8-carboxamide
  • CABERGOLINE
  • (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
  • (8-beta)-(2-propenyl)
  • n-(3-(dimethylamino)propyl)-n-((ethylamino)carbonyl)-6-ergoline-8-carboxamid
  • FCE-21336,Cabaser,Dostinex
  • (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
  • Cabergoline (125 mg)
  • 1-[(6-Allylergoline-8β-yl)carbonyl]-1-[3-(dimethylamino)-propyl]-3-ethylurea
  • 1-Ethyl-3-(3′-dimethylaminopropyl)-3-(6′-allylergoline-8′β-carbonyl)urea
  • Cabergoline Impurity
  • Ergoline-8-carboxamide, N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propen-1-yl)-, (8β)-
  • cabergoline powder
  • cabergoline powder E:candyli(at)speedgainpharma(dot)com
  • Cabergoline CRS
  • Maccagorin
  • (8β)-N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propen-1-yl)-Ergoline-8-carboxamide
  • CABERGILINE
  • Cabergoline (Crude)
  • CabergolineQ: What is Cabergoline Q: What is the CAS Number of Cabergoline Q: What is the storage condition of Cabergoline Q: What are the applications of Cabergoline
  • Cabergoline (1084306)
  • Cefetamet HCl
  • Caber
  • (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
  • Carmergoline
  • Cabergoline IP/BP/USP
  • Cabergoline 0.25mg Tablets
  • Cabergoline Tablets
  • 81409-90-7
  • C26H37N5O2
  • API
  • Neurochemicals
  • Pharmaceuticals
  • Intermediates & Fine Chemicals
  • PP
  • 81409-90-7