25614-03-3 Usage
Description
Bromocriptine is a semisynthetic ergotamine alkaloid derivative and a powerful dopamine D2 agonist. It is known for its antiparkinsonian activity and its ability to inhibit prolactin secretion and release from the pituitary gland, as well as its potential to retard tumor growth. Bromocriptine is available under various brand names, including Parlodel (Novartis), Bromed, Lactismine, Parilac, and Umprel.
Uses
Used in Pharmaceutical Industry:
Bromocriptine is used as a dopaminomimetic agent for treating all phases of idiopathic and postencephalic Parkinsonism. It exhibits antiparkinsonian activity by acting as a dopamine D2 receptor agonist, which helps alleviate the symptoms of Parkinson's disease.
Used in Endocrinology:
As an enzyme inhibitor, specifically for prolactin, Bromocriptine is used to inhibit prolactin secretion and release from the pituitary gland. This application is particularly relevant for conditions where excessive prolactin levels are present, such as hyperprolactinemia.
Used in Oncology:
Bromocriptine is also used in the field of oncology for its potential to retard tumor growth. Although the exact mechanisms are not fully understood, it is believed that its action as a dopamine D2 agonist may contribute to this effect.
Used in Drug Delivery Systems:
While not explicitly mentioned in the provided materials, Bromocriptine could potentially be incorporated into drug delivery systems to improve its bioavailability, targeting, and therapeutic outcomes in various medical applications.
World Health Organization (WHO)
Bromocriptine, a semisynthetic ergot alkaloid derivative and
prolactin inhibitor was introduced into medicine in 1976. It is used in the
prevention of lactation, but because of the risk of rebound effect and since only
10% of women benefit therapeutically from such intervention, the United States
Food and Drug Administration has requested manufacturers to no longer indicate
preparations containing bromocriptine for this purpose. The World Health
Organization is not aware of similar action having been taken elsewhere.
Hazard
Poison; teratogen; developmental abnor-
malities of the respiratory system,musculoskeletal
system, rogenital system, craniofacial area, and
body wall; teratogen; mutagen; questionable car-
cinogen; tumorigen; causes nausea, vomiting,
orthostatic hypotension; constipation, dyskinesias,
psychoses, digital spasm, erythromelalgia.
Mechanism of action
Bromocriptine is
absorbed after oral administration, but approximately 90% of a dose undergoes extensive
first-pass hepatic metabolism, with the remainder hydrolyzed in the liver to inactive metabolites
that are eliminated mostly in the bile. The half-life is relatively short (~3 hours).
Clinical Use
Bromocriptine is an ergot peptide derivative that is a partial agonist at D1-type and a
full agonist at D2-type postsynaptic dopamine receptors, usually given in combination with levodopa therapy. It was the first direct dopamine receptor
agonist used in treatment of Parkinson's disease after its development as an inhibitor of prolactin
release (via activation of anterior pituitary D2 receptors). At low doses (typically 1–5 mg/day),
bromocriptine is an effective prolactin inhibitor, and at higher doses (typically 10–20 mg/day), the
antiparkinsonism and mood-elevating effects of bromocriptine become apparent.
Side effects
Bromocriptine has a number of undesirable side effects, even causing mental disturbances in long-term use.
Synthesis
Bromocriptine, 2-bromoergocriptine (10.1.13), is a semisynthetic derivative of a natural ergot alkaloid, ergocriptin (a derivative of lysergic acid), which is synthesized by bromination of ergocriptin using N-bromosuccinimide [18,19].
Drug interactions
Potentially hazardous interactions with other drugs
Increased risk of toxicity with bromocriptine and
isometheptene.
Metabolism
Bromocriptine is extensively metabolised. It undergoes
extensive first-pass biotransformation in the liver,
reflected by complex metabolite profiles and by almost
complete absence of parent drug in urine and faeces.
In plasma the elimination half life is 3-4 hours for the
parent drug and 50 hours for the inactive metabolites.The parent drug and its metabolites are also completely
excreted via the liver with only 6% being eliminated via
the kidney.
Check Digit Verification of cas no
The CAS Registry Mumber 25614-03-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,6,1 and 4 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 25614-03:
(7*2)+(6*5)+(5*6)+(4*1)+(3*4)+(2*0)+(1*3)=93
93 % 10 = 3
So 25614-03-3 is a valid CAS Registry Number.
25614-03-3Relevant articles and documents
SIDE REACTIONS IN BROMINATION OF α-ERGOCRYPTINE
Cvak, Ladislav,Stuchlik, Josef,Schreiberova, Magdalena,Sedmera, Petr,Flieger, Miroslav
, p. 565 - 572 (2007/10/02)
2,3-Dihydro-2-oxo-α-ergocryptine (III) and 2,3-dihydro-2-oxo-3-hydroxy-α-ergocryptine (IV) were found as the side reaction products in bromination of α-ergocryptine (I) with bromine in the presence of water. 2,3-Dihydro-2-oxo-3-ethoxy-α-ergocryptine (V) was formed in the presence of ethanol.
HALOGENATION OF INDOLE ALKALOIDS WITH HALODIMETHYLSULFONIUM HALOGENIDS AND HALODIMETHYLSULFOXONIUM HALOGENIDS
Megyeri, Gabor,Keve, Tibor
, p. 3415 - 3430 (2007/10/02)
A new field of application of halodimethylsulfonium halogenids and halodimethylsulfoxonium halogenids had been studied.The formers were used for the halogenation of indole alkaloids, compounds of ergoline or aspidospermidine structure, and vincamine.
Process for the preparation of 2-halogenated ergoline derivatives
-
, (2008/06/13)
The invention relates to a novel process for the halogenation in 2-position of ergot alkaloids. The process is characterized by that as a halogenating agent a system consisting of dimethylsulfoxide, a trialkylhalosilane or triaryl-halosilane and optionally a hydrogen halide is used.