Bromocriptine

Details

• Internal ID: 36e866de-a898-47e3-ac42-edd792c370f1
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Lysergamides
• IUPAC Name: (6aR,9R)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• 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
• InChI Key: OZVBMTJYIDMWIL-AYFBDAFISA-N
• Popularity: 16,557 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₀BrN₅O₅
• Molecular Weight: 654.60 g/mol
• Exact Mass: 653.22128 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• Bromocryptine
• 25614-03-3
• Bromocriptin
• Bromoergocryptine
• Bromergocryptine
• Bromoergocriptine
• 2-Bromo-alpha-ergocryptine
• Bromocriptina
• Bromocriptinum
• 2-Bromo-alpha-ergokryptine
• Ergoset
• 2-Bromo-alpha-ergokryptin
• Ergocryptine, 2-bromo-
• Bromocriptinum [INN-Latin]
• Bromocriptina [INN-Spanish]
• 2-Bromoergocryptine
• CB-154
• CCRIS 3244
• EINECS 247-128-5
• UNII-3A64E3G5ZO
• 3A64E3G5ZO
• CHEBI:3181
• DTXSID1022687
• SANDOZ 15-754
• Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)-
• 2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-alpha-(2-methylpropyl)ergotamin-3',6',18-trione
• Bromocriptine (mesylate)
• DTXCID602687
• Bromocryptin
• (5'alpha)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-3',6',18-trioxoergotaman
• (5'alpha)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione
• 2-Bromoergokryptine
• (+)-Bromocriptine
• CB 154
• Bromocriptinum (INN-Latin)
• (5'alpha)-2-bromo-12'-hydroxy-5'-(2-methylpropyl)-2'-(propan-2-yl)-3',6',18-trioxoergotaman
• (5'alpha)-2-bromo-12'-hydroxy-5'-isobutyl-2'-isopropyl-3',6',18-trioxoergotaman
• Bromocriptina (INN-Spanish)
• Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'.alpha.)-
• 2-Bromo-.alpha.-ergocryptine
• (6aR,9R)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• 2 Bromoergocryptine
• 2 Bromoergokryptine
• NSC169774
• 2 Bromo alpha ergocryptine
• 2 Bromo alpha ergokryptine
• Bromocriptine (USAN/INN)
• Bromokryptine
• SR-01000075356
• Bromocriptine [USAN:INN:BAN]
• NCGC00024584-03
• 08Y
• Bromocriptine+ (GTP-)
• Prestwick0_000121
• Prestwick1_000121
• Prestwick2_000121
• Carboprost Methylate,(S)
• BROMOCRIPTINE [MI]
• Biomol-NT_000005
• CHEMBL493
• GTPL35
• BROMOCRIPTINE [INN]
• BROMOCRIPTINE [USAN]
• Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'alpha-(2-methylpropyl)-
• Lopac0_000171
• SCHEMBL25297
• BROMOCRIPTINE [VANDF]
• BIDD:GT0464
• SPBio_002101
• BROMOCRIPTINE [WHO-DD]
• BPBio1_001131
• BDBM81993
• G02CB01
• N04BC01
• OZVBMTJYIDMWIL-AYFBDAFISA-N
• Tox21_110907
• PDSP2_001500
• AKOS015961273
• CCG-204266
• DB01200
• SDCCGSBI-0050159.P003
• dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo
• NCGC00024584-04
• NCGC00024584-05
• NCGC00024584-07
• NCGC00024584-09
• (6aR,9R)-5-Bromo-N-((2R,5S,10aS,10bS)-10b-hydroxy-5-isobutyl-2-isopropyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
• AC-13601
• NCI60_001365
• 10b-hydroxy-5-isobutyl-2-isopropyl-3,6-
• CAS-25614-03-3
• C06856
• D03165
• hexahydroindolo[4,3-fg]quinoline-9-carboxamide
• EN300-19768234
• Q413581
• J-016067
• SR-01000075356-5
• (6aR,9R)-5-bromo-N-((2R,5S,10aS,10bS)-
• [2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-
• BRD-K14496212-001-01-1
• BRD-K14496212-066-04-8
• SAN 15-754; Sandoz 15-754; -Bromocryptine; -Bromoergocryptine; -Ergolactin
• (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(15),2,9,12(16),13-pentaene-4-carboxamide
• (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
• (5alpha,5'beta)-2-bromo-12'-hydroxy-5'-(2-methylpropyl)-3',6',18-trioxo-2'-(propan-2-yl)ergotaman
• N-[(2R,5S,10aS,10bS)-10b-hydroxy-5-isobutyl-2-isopropyl-3,6-dioxo-8,9,10,10a-tetrahydro-5H-oxazolo[[?]]pyrrolo[[?]]pyrazin-2-yl]-bromo-methyl-[?]carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9799	97.99%
Caco-2	-	0.8072	80.72%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.9429	94.29%
Subcellular localzation	Nucleus	0.3672	36.72%
OATP2B1 inhibitior	-	0.5655	56.55%
OATP1B1 inhibitior	+	0.9334	93.34%
OATP1B3 inhibitior	+	0.9238	92.38%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9220	92.20%
P-glycoprotein inhibitior	+	0.9512	95.12%
P-glycoprotein substrate	-	0.6784	67.84%
CYP3A4 substrate	+	0.7980	79.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7787	77.87%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	+	0.8326	83.26%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9031	90.31%
CYP2C8 inhibition	+	0.6294	62.94%
CYP inhibitory promiscuity	+	0.5149	51.49%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4952	49.52%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.7461	74.61%
Skin corrosion	-	0.9224	92.24%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6489	64.89%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	+	0.5117	51.17%
skin sensitisation	-	0.8525	85.25%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.6029	60.29%
Acute Oral Toxicity (c)	III	0.6285	62.85%
Estrogen receptor binding	+	0.8905	89.05%
Androgen receptor binding	+	0.7989	79.89%
Thyroid receptor binding	+	0.5730	57.30%
Glucocorticoid receptor binding	+	0.7661	76.61%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	+	0.8709	87.09%
Honey bee toxicity	-	0.7671	76.71%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	0.9959	99.59%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL217	P14416	Dopamine D2 receptor	0.5012 nM	EC50	via Super-PRED
CHEMBL234	P35462	Dopamine D3 receptor	87 nM	Ki	via Super-PRED
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	24 nM	Ki	via Super-PRED
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	1.778 nM	EC50	via Super-PRED
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	50 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.81%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.46%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.45%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	96.48%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.23%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.45%	82.69%
CHEMBL5103	Q969S8	Histone deacetylase 10	95.16%	90.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.96%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.43%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.29%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	92.80%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.03%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.87%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.65%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	90.62%	93.03%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	90.12%	95.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.74%	97.50%
CHEMBL3310	Q96DB2	Histone deacetylase 11	87.55%	88.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.52%	85.14%
CHEMBL4073	P09237	Matrix metalloproteinase 7	86.73%	97.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.26%	96.47%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.46%	94.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	85.28%	98.05%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.97%	86.33%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	84.53%	98.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.44%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.32%	91.24%
CHEMBL4208	P20618	Proteasome component C5	84.05%	90.00%
CHEMBL2535	P11166	Glucose transporter	83.18%	98.75%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.04%	89.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.56%	90.71%
CHEMBL4805	Q99572	P2X purinoceptor 7	81.17%	97.50%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	80.44%	85.83%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.05%	85.11%

Plants that contains it

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Cross-Links

• PubChem: 31101
• LOTUS: LTS0062623
• wikiData: Q413581