Cabergoline

Title: Cabergoline
CAS Registry Number: 81409-90-7
CAS Name: (8b)-N-[3-(Dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)ergoline-8-carboxamide
Additional Names: 1-ethyl-3-(3¢-dimethylaminopropyl)-3-(6¢-allylergoline-8¢b-carbonyl)urea; 1-[(6-allylergoline-8b-yl)carbonyl]-1-[3-(dimethylamino)propyl]-3-ethylurea
Manufacturers' Codes: FCE-21336
Trademarks: Dostinex (Pharmacia & Upjohn)
Molecular Formula: C26H37N5O2
Molecular Weight: 451.60
Percent Composition: C 69.15%, H 8.26%, N 15.51%, O 7.09%
Literature References: Dopamine D2-receptor agonist. Prepn: P. Salvati et al., BE 888243; eidem, US 4526892 (1981, 1985 both to Farmitalia Carlo Erba). Prepn and bioactivity: E. Brambilla et al., Eur. J. Med. Chem. 24, 421 (1989). Clinical pharmacology: C. Ferrari et al., J. Clin. Endocrinol. Metab. 63, 941 (1986). Veterinary trial as abortifacient in dogs: K. Post et al., Theriogenology 29, 1233 (1988). Clinical evaluation to prevent puerperal lactation: G. B. Melis et al., Obstet. Gynecol. 71, 311 (1988); in hyperprolactinemic disorders: C. Ferrari et al., J. Clin. Endocrinol. Metab. 68, 1201 (1989). Clinical trial in Parkinson's disease: J. T. Hutton et al., Neurology 46, 1062 (1996).
Properties: White crystals from diethyl ether, mp 102-104°. 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).
Melting point: mp 102-104°
Toxicity data: 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)
Derivative Type: Diphosphate
CAS Registry Number: 85329-89-1
Molecular Formula: C26H37N5O2.2H3PO4
Molecular Weight: 647.59
Percent Composition: C 48.22%, H 6.69%, N 10.81%, O 24.71%, P 9.57%
Properties: mp 153-155°.
Melting point: mp 153-155°
Therap-Cat: Prolactin inhibitor; antiparkinsonian.
Therap-Cat-Vet: Prolactin inhibitor.
Keywords: Antiparkinsonian; Dopamine Receptor Agonist; Prolactin Inhibitor.
Cacao Shell Cacodylic Acid Cacotheline Cactinomycin Cactus Grandiflorus

Cabergoline
Cabergoline.svg
Systematic (IUPAC) name
N-[3-(Dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)-8g-ergoline-8-carboxamide
or
1-[(6-Allylergolin-8β-yl)-carbonyl]-1-[3-(dimethylamino)propyl]-3-ethylurea
Clinical data
AHFS/Drugs.com monograph
Licence data US FDA:link
Pregnancy cat. B (US)
Legal status -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability First-pass effect seen; absolute bioavailability unknown
Protein binding Moderately bound (40% to 42%); concentration- independent
Metabolism Hepatic, predominately via hydrolysis of the acylurea bond or the urea moiety
Half-life 63-69 hours (estimated)
Excretion Urine (22%), feces (60%)
Identifiers
CAS number 81409-90-7 YesY
ATC code G02CB03 N04BC06
PubChem CID 54746
IUPHAR ligand 37
DrugBank DB00248
ChemSpider 49452 YesY
UNII LL60K9J05T YesY
KEGG D00987 YesY
ChEBI CHEBI:3286 YesY
ChEMBL CHEMBL1201087 N
Chemical data
Formula C26H37N5O2 
Mol. mass 451.604 g/mol
 N (what is this?)  (verify)

Cabergoline (brand names Dostinex and Cabaser), an ergot derivative, is a potent dopamine receptor agonist on D2 receptors. Rat studies show cabergoline has a direct inhibitory effect on pituitary lactotroph (prolactin) cells.[1] It is frequently used as a first-line agent in the management of prolactinomas due to higher affinity for D2 receptor sites, less severe side effects, and more convenient dosing schedule than the older bromocriptine.