Bromocriptine

Bromocriptine
Clinical data
Trade names	Originally Parlodel, subsequently many
Other names	2-Bromoergocriptine; CB-154
AHFS/Drugs.com	Monograph, International Drug Names
MedlinePlus	a682079
Pregnancy; category	AU: A; ;
Routes of; administration	By mouth, vaginal, intravenous
ATC code	G02CB01 (WHO) N04BC01 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	28% of oral dose absorbed
Metabolism	Extensively liver-mediated
Elimination half-life	12–14 hours
Excretion	85% bile (feces), 2.5–5.5% urine
Identifiers
	IUPAC name (5′α)-2-Bromo-12′-hydroxy-5′-(2-methylpropyl)-3′,6′,18-trioxo-2′-(propan-2-yl)ergotaman;
CAS Number	25614-03-3 ;
PubChem CID	31101;
IUPHAR/BPS	35;
DrugBank	DB01200 ;
ChemSpider	28858 ;
UNII	3A64E3G5ZO;
KEGG	D03165 ;
ChEBI	CHEBI:3181 ;
ChEMBL	ChEMBL493 ;
CompTox Dashboard (EPA)	DTXSID1022687 ;
ECHA InfoCard	100.042.829
Chemical and physical data
Formula	C32H40BrN5O5
Molar mass	654.606 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES BrC1=C(C[C@H]2N(C)C3)C4=C(C=CC=C4C2=C[C@H]3C(N[C@]5(C(C)C)O[C@@]6(N([C@@H](CC(C)C)C(N7CCC[C@H]76)=O)C5=O)O)=O)N1;
	InChI 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 ; Key:OZVBMTJYIDMWIL-AYFBDAFISA-N ;
	(verify)

Bromocriptine, originally marketed as Parlodel and subsequently under many brand names,^[1] is an ergoline derivative and dopamine agonist that is used in the treatment of pituitary tumors, Parkinson's disease, hyperprolactinaemia, neuroleptic malignant syndrome, and, as an adjunct, type 2 diabetes.

It was patented in 1968 and approved for medical use in 1975.^[2]

^ ^a ^b Cite error: The named reference brands was invoked but never defined (see the help page).
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 533. ISBN 9783527607495.

Clinical data

Trade names	Originally Parlodel, subsequently many^[1]
Other names	2-Bromoergocriptine; CB-154
AHFS/Drugs.com	Monograph, International Drug Names
MedlinePlus	a682079
Pregnancy category	AU: A
Routes of administration	By mouth, vaginal, intravenous
ATC code	G02CB01 (WHO) N04BC01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	28% of oral dose absorbed
Metabolism	Extensively liver-mediated
Elimination half-life	12–14 hours
Excretion	85% bile (feces), 2.5–5.5% urine
Identifiers
IUPAC name (5′α)-2-Bromo-12′-hydroxy-5′-(2-methylpropyl)-3′,6′,18-trioxo-2′-(propan-2-yl)ergotaman
CAS Number	25614-03-3^Y
PubChem CID	31101
IUPHAR/BPS	35
DrugBank	DB01200^Y
ChemSpider	28858^Y
UNII	3A64E3G5ZO
KEGG	D03165^Y
ChEBI	CHEBI:3181^Y
ChEMBL	ChEMBL493^Y
CompTox Dashboard (EPA)	DTXSID1022687
ECHA InfoCard	100.042.829
Chemical and physical data
Formula	C₃₂H₄₀BrN₅O₅
Molar mass	654.606 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES BrC1=C(C[C@H]2N(C)C3)C4=C(C=CC=C4C2=C[C@H]3C(N[C@]5(C(C)C)O[C@@]6(N([C@@H](CC(C)C)C(N7CCC[C@H]76)=O)C5=O)O)=O)N1
InChI 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^Y Key:OZVBMTJYIDMWIL-AYFBDAFISA-N^Y
(verify)