Cabergoline
[CAS# 81409-90-7]

Identification

• Classification: Analytical chemistry >> Standard >> Pharmacopoeia standards and magazine standards
• Name: Cabergoline
• Synonyms: 6-Allyl-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)ergoline-8-carboxamide
• Molecular Formula: C₂₆H₃₇N₅O₂
• Molecular Weight: 451.60
• CAS Registry Number: 81409-90-7
• EC Number: 627-031-8
• SMILES: CCNC(=O)N(CCCN(C)C)C(=O)[C@@H]1C[C@H]2[C@@H](CC3=CNC4=CC=CC2=C34)N(C1)CC=C

Properties

• Solubility: =10 mg/mL (DMSO)
• alpha: -63 to -74 ° (c=0.5 dichloromethane)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Reproductive toxicity	Lact.	-	H362
Acute toxicity	Acute Tox.	4	H312
Reproductive toxicity	Repr.	2	H361
Reproductive toxicity	Repr.	1B	H360
Respiratory sensitization	Resp. Sens.	1B	H334
Skin sensitization	Skin Sens.	1B	H317

Discovery and Applications

Cabergoline was developed by the Italian pharmaceutical company Farmitalia Carlo Erba. Its discovery involved modifying the chemical structure of ergot alkaloids to enhance their dopamine agonist properties while reducing side effects. The researchers’ quest for a drug with a longer half-life and better tolerability than existing treatments led to the synthesis of cabergoline.

Cabergoline is a potent agonist of D2 dopamine receptors, which are ubiquitous in the pituitary gland. By stimulating these receptors, it inhibits the secretion of prolactin, which is particularly useful in the treatment of hyperprolactinemia – a condition characterized by excessive prolactin levels that can lead to infertility, galactorrhea, and menstrual disorders.

The main use of cabergoline is in the treatment of hyperprolactinemia. It effectively reduces prolactin levels, normalizes reproductive function, and relieves symptoms such as galactorrhea (inappropriate milk secretion) and amenorrhea (absence of menstruation).

Cabergoline also plays a role in treating Parkinson's disease, a neurological disorder characterized by a dopamine deficiency. By stimulating dopamine receptors, cabergoline helps relieve motor symptoms such as tremor, rigidity, and bradykinesia (slow movement).

Cabergoline is used to treat prolactin-secreting pituitary adenomas. It can reduce tumor size and prolactin secretion, improve symptoms, and often eliminate the need for surgery.

Cabergoline has several advantages over older treatments. Its longer half-life allows for less frequent dosing, typically just once or twice a week. Patients generally experience fewer side effects and a better quality of life than with other dopamine agonists.

However, cabergoline must be used with caution. Potential side effects include nausea, dizziness, and, in rare cases, valvular heart disease (a condition in which the heart valves are abnormal). Regular monitoring and appropriate dose adjustments are essential to minimize the risk.

References

1990. Osteocalcin levels in patients with microprolactinoma before and during medical treatment. Journal of Endocrinological Investigation, 13(5).
DOI: 10.1007/bf03350694

1998. Cabergoline treatment rapidly improves gonadal function in hyperprolactinemic males: a comparison with bromocriptine. European Journal of Endocrinology, 138(3).
DOI: 10.1530/eje.0.1380286

2024. Pituitary Adenomas. Neurosurgical Treatment of Central Nervous System Tumors.
DOI: 10.1007/978-3-031-68578-1_13