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<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability = 28% of oral dose absorbed and they absorb poopoo
| bioavailability = 28% of oral dose absorbed
| metabolism = ?
| metabolism = ?
| elimination_half-life = 12-14 hours
| elimination_half-life = 12-14 hours

Revision as of 22:11, 19 January 2012

Bromocriptine
Clinical data
Trade namesParlodel
AHFS/Drugs.comMonograph
MedlinePlusa682079
Routes of
administration		oral
ATC code
Legal status
Legal status
  • ?
Pharmacokinetic data
Bioavailability28% of oral dose absorbed
Metabolism?
Elimination half-life12-14 hours
Excretion85% bile (faeces)
Identifiers
  • (5′α)-2-bromo-12′-hydroxy-5′-(2-methylpropyl)-3′,6′,18-trioxo-2′-(propan-2-yl)ergotaman
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.042.829 Edit this at Wikidata
Chemical and physical data
FormulaC32H40BrN5O5
Molar mass654.595 g·mol−1
3D model (JSmol)
  • Brc2nc1cccc\3c1c2C[C@@H]7C/3=C/[C@@H](C(=O)N[C@@]4(O[C@]6(O)N(C4=O)[C@H](C(=O)N5CCC[C@H]56)CC(C)C)C(C)C)CN7C
  • InChI=1S/C32H40BrN5O5/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39)/t18-,23-,24+,25+,31-,32+/m1/s1 checkY
  • Key:OZVBMTJYIDMWIL-AYFBDAFISA-N checkY
  (verify)

Bromocriptine (INN; trade names Parlodel, Cycloset), an ergoline derivative, is a dopamine agonist that is used in the treatment of pituitary tumors, Parkinson's disease (PD), hyperprolactinaemia, neuroleptic malignant syndrome, and type 2 diabetes.

Indications

Amenorrhea, female infertility, galactorrhea, hypogonadism, and acromegaly may all be caused by pituitary problems, such as hyperprolactinaemia, and therefore, these problems may be treated by this drug. In 2009, bromocriptine mesylate was approved by the FDA for treatment of type 2 diabetes under the trade name Cycloset (VeroScience). It is currently unknown how this drug improves glycemic control, but it has been shown to reduce HbA1c by ~0.5 percentage points.[1]

Pharmacology

Bromocriptine is a potent agonist at dopamine D2 receptors[2] and various serotonin receptors. It also inhibits the release of glutamate, by reversing the glutamate GLT1 transporter. [3]

Side effects

Most frequent side effects are nausea, orthostatic hypotension, headaches and vomiting through stimulation of the brainstem vomiting centre.[4] Bromocriptine can cause worsening of liver problems. Vasospasms with serious consequences such as myocardial infarction and stroke have been reported in connection with the puerperium, appears to be extremely rare event. [5] Bromocriptine use has been anecdotically associated with causing or worsening psychotic symptoms (its mechanism is in opposition of most antipsychotics, whose mechanisms generally block dopamine).[6] Pulmonary fibrosis has been reported when bromocriptine was used in high doses for the treatment of Parkinson's disease. [7]

Chemistry

Like all ergopeptides, bromocriptine is a cyclol; two peptide groups of its tripeptide moiety are crosslinked, forming the >N-C(OH)< juncture between the two rings with the amide functionality.

Bromocriptine, 2-bromoergocriptine, 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.

  • E. Fluckiger, A. Hoffmann, U.S. patent 3,752,814 (1973).
  • A. Hofman, E. Flueckiger, DE 1926045  (1969).

See also

References

  1. ^ Pijl H, Ohashi S, Matsuda M; et al. (2000). "Bromocriptine: a novel approach to the treatment of type 2 diabetes". Diabetes Care. 23 (8): 1154–61. doi:10.2337/diacare.23.8.1154. PMID 10937514. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. ^ PMID 20138024
  3. ^ "ScienceDirect - European Journal of Pharmacology : Bromocriptine, an ergot alkaloid, inhibits excitatory amino acid release mediated by glutamate transporter reversal". Retrieved 2010-08-31. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)
  4. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 3516579, please use {{cite journal}} with |pmid=3516579 instead.
  5. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 8691994, please use {{cite journal}} with |pmid=8691994 instead.
  6. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 7701022 , please use {{cite journal}} with |pmid=7701022 instead.
  7. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 2129961, please use {{cite journal}} with |pmid=2129961 instead.
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