08Y

bromoergocryptine

Created:	2011-10-31
Last modified:	2021-03-01

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Chemical Details
Formal Charge	0
Atom Count	83
Chiral Atom Count	6
Bond Count	89
Aromatic Bond Count	10

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Chemical Component Summary
Name	bromoergocryptine
Synonyms	bromocriptine
Systematic Name (OpenEye OEToolkits)	n/a
Formula	C₃₂ H₄₀ Br N₅ O₅
Molecular Weight	654.594
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	Brc7nc6cccc5C4=CC(C(=O)NC1(OC3(O)N(C1=O)C(C(=O)N2CCCC23)CC(C)C)C(C)C)CN(C)C4Cc7c56
SMILES	CACTVS	3.370	CC(C)C[CH]1N2C(=O)[C](NC(=O)[CH]3CN(C)[CH]4Cc5c(Br)[nH]c6cccc(C4=C3)c56)(O[C]2(O)[CH]7CCCN7C1=O)C(C)C
SMILES	OpenEye OEToolkits	1.7.2	CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5Cc6c7c(cccc7[nH]c6Br)C5=C4)C)O
Canonical SMILES	CACTVS	3.370	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
Canonical SMILES	OpenEye OEToolkits	1.7.2	CC(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
InChI	InChI	1.03	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	InChI	1.03	OZVBMTJYIDMWIL-AYFBDAFISA-N

Drug Info: DrugBank

DrugBank ID	DB01200
Name	Bromocriptine
Groups	withdrawn approved investigational
Description	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.[L43942,L43947] It continues to be used for the indications mentioned above.
Synonyms	Bromocriptine mesylate 2-Bromo-alpha-ergocryptine Bromocryptine 2-bromo-α-ergokryptine Bromocriptina Bromocriptine 2-bromo-α-ergocryptine 2-bromo-α-ergokryptin Bromocriptinum Bromoergocryptine 2-Bromo-alpha-ergokryptine 2-Bromo-alpha-ergokryptin Bromoergocriptine
Brand Names	Bromocriptine Nu-bromocriptine Syn-bromocriptine Tab 2.5mg Dom-bromocriptine Bromocriptine-2.5 - Tab 2.5mg Cycloset Co Bromocriptine Capsules 5mg Co Bromocriptine Tablets 2.5mg PMS-bromocriptine Parlodel Cap 5mg Parlodel Tab 2.5mg Bromocriptine Mesylate Syn-bromocriptine Cap 5mg Bromocriptine mesylate Bromocriptine-5 Parlodel
Indication	For 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 Adrenergic alpha-Antagonists Adrenergic Antagonists Agents producing tachycardia Agents that produce hypertension Alkaloids Anti-Dyskinesia Agents Anti-Parkinson Agents (Dopamine Agonist) Anti-Parkinson Drugs Antidepressive Agents Blood Glucose Lowering Agents Central Nervous System Agents Central Nervous System Depressants Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Dopamine Agents Dopamine Agonists Ergolines Ergot Alkaloids and Derivatives Ergot-derivative Dopamine Receptor Agonists Ergotamines Genito Urinary System and Sex Hormones Heterocyclic Compounds, Fused-Ring Hormone Antagonists Hormones, Hormone Substitutes, and Hormone Antagonists Hypotensive Agents Nervous System Neurotransmitter Agents P-glycoprotein inhibitors P-glycoprotein substrates Prolactine Inhibitors Serotonin 5-HT2 Receptor Agonists Serotonin Agents Serotonin Modulators Serotonin Receptor Agonists
ATC-Code	N04BC01 G02CB01
CAS number	25614-03-3

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Dopamine D2 receptor	MDPLNLSWYDDDLERQNWSRPFNGSDGKADRPHYNYYATLLTLLIAVIVF...	unknown	agonist
Dopamine D3 receptor	MASLSQLSSHLNYTCGAENSTGASQARPHAYYALSYCALILAIVFGNGLV...	unknown	agonist
5-hydroxytryptamine receptor 1D	MSPLNQSAEGLPQEASNRSLNATETSEAWDPRTLQALKISLAVVLSVITL...	unknown	agonist
Alpha-2A adrenergic receptor	MGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFG...	unknown	agonist
5-hydroxytryptamine receptor 1A	MDVLSPGQGNNTTSPPAPFETGGNTTGISDVTVSYQVITSLLLGTLIFCA...	unknown	agonist
Alpha-2C adrenergic receptor	MASPALAAALAVAAAAGPNASGAGERGSGGVANASGASWGPPRGQYSAGA...	unknown	agonist
Alpha-2B adrenergic receptor	MDHQDPYSVQATAAIAAAITFLILFTIFGNALVILAVLTSRSLRAPQNLF...	unknown	agonist
5-hydroxytryptamine receptor 2B	MALSYRVSELQSTIPEHILQSTFVHVISSNWSGLQTESIPEEMKQIVEEQ...	unknown	agonist
Dopamine D4 receptor	MGNRSTADADGLLAGRGPAAGASAGASAGLAGQGAAALVGGVLLIGAVLA...	unknown	antagonist
5-hydroxytryptamine receptor 2A	MDILCEENTSLSSTTNSLMQLNDDTRLYSNDFNSGEANTSDAFNWTVDSE...	unknown	agonist
5-hydroxytryptamine receptor 1B	MEEPGAQCAPPPPAGSETWVPQANLSSAPSQNCSAKDYIYQDSISLPWKV...	unknown	agonist
5-hydroxytryptamine receptor 2C	MVNLRNAVHSFLVHLIGLLVWQCDISVSPVAAIVTDIFNTSDGGRFKFPD...	unknown	agonist
Dopamine D5 receptor	MLPPGSNGTAYPGQFALYQQLAQGNAVGGSAGAPPLGPSQVVTACLLTLL...	unknown	agonist
Dopamine D1 receptor	MRTLNTSAMDGTGLVVERDFSVRILTACFLSLLILSTLLGNTLVCAAVIR...	unknown	agonist
Alpha-1A adrenergic receptor	MVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...	unknown	antagonist,agonist
Alpha-1B adrenergic receptor	MNPDLDTGHNTSAPAHWGELKNANFTGPNQTSSNSTLPQLDITRAISVGL...	unknown	antagonist,agonist
Alpha-1D adrenergic receptor	MTFRDLLSVSFEGPRPDSSAGGSSAGGGGGSAGGAAPSEGPAVGGVPGGA...	unknown	agonist
5-hydroxytryptamine receptor 7	MMDVNSSGRPDLYGHLRSFLLPEVGRGLPDLSPDGGADPVAGSWAPHLLS...	unknown	antagonist
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
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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