08Y

bromoergocryptine


Toggle HydrogenToggle Labels

Chemical Component Summary

Namebromoergocryptine
Synonymsbromocriptine
Identifiersn/a
FormulaC32 H40 Br N5 O5
Molecular Weight654.594
TypeNON-POLYMER
Isomeric SMILESCC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@H]4CN([C@@H]5Cc6c7c(cccc7[nH]c6Br)C5=C4)C)O
InChIInChI=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
InChIKeyOZVBMTJYIDMWIL-AYFBDAFISA-N

Chemical Details

Formal Charge0
Atom Count83
Chiral Atom Count6
Bond Count89
Aromatic Bond Count10

Drug Info: DrugBank

DrugBank IDDB01200 
NameBromocriptine
Groups
  • approved
  • investigational
  • withdrawn
DescriptionBromocriptine mesylate is a semisynthetic ergot alkaloid derivative with potent dopaminergic activity. It inhibits prolactin secretion and may be used to treat dysfunctions associated with hyperprolactinemia. Bromocriptine is also indicated for the management of signs and symptoms of Parkinsonian Syndrome, as well as the treatment of acromegaly. Bromocriptine has been associated with pulmonary fibrosis, and can also cause sustained suppression of somatotropin (growth hormone) secretion in some patients with acromegaly. In 1995, the FDA withdrew the approval of bromocriptine mesylate for the prevention of physiological lactation after finding that bromocriptine was not shown to be safe for use.[L43942,L43947] It continues to be used for the indications mentioned above.
Synonyms
  • Bromoergocriptine
  • Bromocryptine
  • 2-bromo-α-ergokryptine
  • 2-bromo-α-ergocryptine
  • 2-Bromo-alpha-ergokryptin
Brand Names
  • Bromocriptine mesylate
  • Cycloset
  • Co Bromocriptine Tablets 2.5mg
  • Co Bromocriptine Capsules 5mg
  • Dom-bromocriptine
IndicationFor the treatment of galactorrhea due to hyperprolactinemia, prolactin-dependent menstrual disorders and infertility, prolactin-secreting adenomas, prolactin-dependent male hypogonadism, as adjunct therapy to surgery or radiotherapy for acromegaly or as monotherapy is special cases, as monotherapy in early Parksinsonian Syndrome or as an adjunct with levodopa in advanced cases with motor complications. Bromocriptine has also been used off-label to treat restless legs syndrome and neuroleptic malignant syndrome.
Categories
  • Adrenergic Agonists
  • Adrenergic alpha-1 Receptor Agonists
  • Adrenergic alpha-1 Receptor Antagonists
  • Adrenergic alpha-2 Receptor Agonists
  • Adrenergic alpha-Agonists
ATC-Code
  • N04BC01
  • G02CB01
CAS number25614-03-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Dopamine D2 receptorMDPLNLSWYDDDLERQNWSRPFNGSDGKADRPHYNYYATLLTLLIAVIVF...unknownagonist
Dopamine D3 receptorMASLSQLSSHLNYTCGAENSTGASQARPHAYYALSYCALILAIVFGNGLV...unknownagonist
5-hydroxytryptamine receptor 1DMSPLNQSAEGLPQEASNRSLNATETSEAWDPRTLQALKISLAVVLSVITL...unknownagonist
Alpha-2A adrenergic receptorMGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFG...unknownagonist
5-hydroxytryptamine receptor 1AMDVLSPGQGNNTTSPPAPFETGGNTTGISDVTVSYQVITSLLLGTLIFCA...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL493
PubChem 31101
ChEMBL CHEMBL493
ChEBI CHEBI:3181