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Substance Name: Bromocriptine mesylate [USAN:USP]
RN: 22260-51-1
UNII: FFP983J3OD
InChIKey: NOJMTMIRQRDZMT-GSPXQYRGSA-N

Note

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

Molecular Formulas

  • C32-H40-Br-N5-O5.C-H4-O3-S
  • C32-H40-Br-N5-O5.C-H4-S-O3
  • C32-H4O-Br-N5-O5.C-H4-O3-S

Molecular Weight

  • 750.7076
 

Classification Codes

  • Drug / Therapeutic Agent
  • Enzyme Inhibitor (Prolactin)
  • Human Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Bromocriptine mesylate [USAN:USP]

Synonyms

  • 2-Bromine-alpha-ergocryptine methanesulfonate
  • 2-Bromo-alpha-ergocryptine mesylate
  • 2-Bromo-alpha-ergocryptine methanesulfonate
  • 2-Bromo-alpha-ergokryptine-mesilate
  • 2-Bromo-alpha-ergokryptine-mesilate [German]
  • 2-Bromoergocryptine monomethanesulfonate (salt)
  • Bagren
  • Bromergon
  • Bromocriptine mesilate
  • Bromocriptine mesylate
  • Bromocryptine mesylate
  • Bromocryptine methanesulfonate
  • CB 154
  • CB-154
  • CB-154 mesylate
  • Cycloset
  • EINECS 244-881-1
  • Parlodel
  • Pravidel
  • UNII-FFP983J3OD

Systematic Names

  • 2-Bromo-12'-hydroxy-5'alpha-isobutyl-2'-isopropylergotaman-3',6',18-trione monomethanesulphonate
  • alpha-Ergocryptine, 2-bromo-, methanesulfonate
  • Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, monomethanesulfonate (salt), (5'alpha)-

Registry Numbers

CAS Registry Number

  • 22260-51-1

FDA UNII

  • FFP983J3OD

Related Registry Number

  • 25614-03-3 (Parent)

System Generated Number

  • 0022260511

Molecular Formulas

Molecular Formulas

  • C32-H40-Br-N5-O5.C-H4-O3-S
  • C32-H40-Br-N5-O5.C-H4-S-O3
  • C32-H4O-Br-N5-O5.C-H4-O3-S

Molecular Formula Fragments

  • C-H4-O3-S
  • C-H4-S-O3
  • C32-H40-Br-N5-O5
  • C32-H4O-Br-N5-O5
  • COMPONENT

Structure Descriptors

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

InChIKey

NOJMTMIRQRDZMT-GSPXQYRGSA-N

Smiles

CC(C)C[C@@H]1N2C(=O)[C@](NC(=O)[C@H]3CN(C)[C@@H]4Cc5c(Br)[nH]c6cccc(C4=C3)c56)(O[C@@]2(O)[C@@H]7CCCN7C1=O)C(C)C.CS(=O)(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 375ug/kg (0.375mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Pediatrics. Vol. 105, Pg. 838, 1984.
man TDLo oral 52mg/kg/35W-I (52mg/kg) BRAIN AND COVERINGS: CHANGES IN CEREBRAL SPINAL FLUID Neurology. Vol. 35, Pg. 1193, 1985.
mouse LD50 intravenous 189mg/kg (189mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 809, 1979.
mouse LD50 oral 2502mg/kg (2502mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 809, 1979.
rabbit LD50 intravenous 8200ug/kg (8.2mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 10, Pg. 232, 1979.
rabbit LD50 oral > 1gm/kg (1000mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 809, 1979.
rat LD50 intravenous 10500ug/kg (10.5mg/kg)   Yakkyoku. Pharmacy. Vol. 29, Pg. 1231, 1978.
rat LD50 oral > 2gm/kg (2000mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 809, 1979.
rat LD50 subcutaneous > 1gm/kg (1000mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 809, 1979.
women TDLo oral 50ug/kg (0.05mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE Lancet. Vol. 340, Pg. 1410, 1992.
women TDLo oral 650ug/kg/9D-I (0.65mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

BEHAVIORAL: HEADACHE

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Annals of Internal Medicine. Vol. 118, Pg. 199, 1993.
women TDLo oral 1mg/kg/20D-I (1mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS American Journal of Psychiatry. Vol. 143, Pg. 935, 1985.