Bromocriptine mesylateProduct ingredient for Bromocriptine
- Name
- Bromocriptine mesylate
- Drug Entry
- Bromocriptine
Bromocriptine 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.8,9 It continues to be used for the indications mentioned above.
- Accession Number
- DBSALT001209
- Structure
Structure for Bromocriptine mesylate (DBSALT001209)
- Synonyms
- Bromocriptine mesylate
- UNII
- FFP983J3OD
- CAS Number
- 22260-51-1
- Weight
- Average: 750.71
Monoisotopic: 749.209398 - Chemical Formula
- C33H44BrN5O8S
- InChI Key
- NOJMTMIRQRDZMT-GSPXQYRGSA-N
- InChI
- InChI=1S/C32H40BrN5O5.CH4O3S/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;1-5(2,3)4/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39);1H3,(H,2,3,4)/t18-,23-,24+,25+,31-,32+;/m1./s1
- IUPAC Name
- (4R,7R)-10-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide; methanesulfonic acid
- SMILES
- CS(O)(=O)=O.[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=C(Br)NC6=CC=CC(=C56)C4=C3)(O[C@@]21O)C(C)C
- External Links
- ChemSpider
- 28857
- ChEBI
- 3182
- ChEMBL
- CHEMBL1200503
- Wikipedia
- Bromocriptine
- Predicted Properties
Property Value Source Water Solubility 0.0858 mg/mL ALOGPS logP 3.2 ALOGPS logP 3.89 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 9.69 Chemaxon pKa (Strongest Basic) 6.71 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 118.21 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 165.51 m3·mol-1 Chemaxon Polarizability 65.97 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon