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Substance Name: Bromocriptine [USAN:INN:BAN]
RN: 25614-03-3
UNII: 3A64E3G5ZO
InChIKey: OZVBMTJYIDMWIL-AYFBDAFISA-N

Note

  • A semisynthetic ergotamine alkaloid that is a dopamine D2 agonist. It suppresses prolactin secretion.

Molecular Formula

  • C32-H40-Br-N5-O5

Molecular Weight

  • 654.602
 

Classification Codes

  • Anti-Dyskinesia Agents
  • Antiparkinson Agents
  • Central Nervous System Agents
  • Dopamine Agents
  • Dopamine Agonists
  • Drug / Therapeutic Agent
  • Enzyme Inhibitor (Prolactin)
  • Hormone Antagonists
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Reproductive Effect
  • Tumor Data

Names and Synonyms

Name of Substance

  • Bromocriptine
  • Bromocriptine [USAN:INN:BAN]

MeSH Heading

  • Bromocriptine

Synonyms

  • 2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-alpha-(2-methylpropyl)ergotamin-3',6',18-trione
  • 2-Bromo-alpha-ergocryptine
  • 2-Bromo-alpha-ergokryptin
  • 2-Bromo-alpha-ergokryptine
  • Bromergocryptine
  • Bromocriptin
  • Bromocriptina
  • Bromocriptina [INN-Spanish]
  • Bromocriptine
  • Bromocriptinum
  • Bromocriptinum [INN-Latin]
  • Bromocryptine
  • Bromoergocriptine
  • Bromoergocryptine
  • CB-154
  • CCRIS 3244
  • EINECS 247-128-5
  • Ergoset
  • UNII-3A64E3G5ZO

Systematic Names

  • 2-Bromo-alpha-ergocryptine
  • Bromocriptine
  • Ergocryptine, 2-bromo- (8CI)
  • Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)-

Registry Numbers

CAS Registry Number

  • 25614-03-3

FDA UNII

  • 3A64E3G5ZO

Related Registry Number

  • 22260-51-1 (mesylate (salt))

System Generated Number

  • 0025614033

Structure Descriptors

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

InChIKey

OZVBMTJYIDMWIL-AYFBDAFISA-N

Smiles

N12[C@@]([C@H]3N(CCC3)C([C@@H]2CC(C)C)=O)(O[C@@](C1=O)(NC([C@@H]1C=C2c3c4c(c(Br)[nH]c4ccc3)C[C@H]2[N@@](C1)C)=O)C(C)C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 313mg/kg/2Y-I (313mg/kg) CARDIAC: PERICARDITIS

LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Annals of Pharmacotherpy. Vol. 33, Pg. 1050, 1999.
mouse LD50 oral > 800mg/kg (800mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 24, Pg. 421, 1989.
mouse LD50 unreported 200mg/kg (200mg/kg)   Biomedica Biochimica Acta. Vol. 43, Pg. 1305, 1984.
rabbit LD50 intravenous 12mg/kg (12mg/kg)   United States Patent Document. Vol. #3752814,
rabbit LD50 oral > 1gm/kg (1000mg/kg)   United States Patent Document. Vol. #3752814,
rat LD50 intravenous 72mg/kg (72mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 17, Pg. 313, 1979.
women TDLo oral 6mg/kg/60D-I (6mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION New England Journal of Medicine. Vol. 306, Pg. 178, 1982.