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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:57 UTC
HMDB IDHMDB0015331
Secondary Accession Numbers
  • HMDB15331
Metabolite Identification
Common NameBromocriptine
DescriptionBromocriptine, also known as parlodel, belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids. Bromocriptine is a drug which is used 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. Bromocriptine is a very strong basic compound (based on its pKa). Bromocriptine use has been anecdotally associated with causing or worsening psychotic symptoms (its mechanism is in opposition of most antipsychotics, whose mechanisms generally block dopamine receptors). Bromocriptine is a potentially toxic compound. Bromocriptine is a semisynthetic derivative of a natural ergot alkaloid, ergocryptine (a derivative of lysergic acid), which is synthesized by bromination of ergocryptine using N-bromosuccinimide. Since the late 1980s it has been used, off-label, to reduce the symptoms of cocaine withdrawal but the evidence for this use is poor. It is a bile salt export pump inhibitor. As of July 2017, bromocriptine was marketed under many brand names worldwide, including Abergin, Barlolin, Brameston, Brocriptin, Brom, Broma-Del, Bromergocryptine, Bromergon, Bromicon, Bromocorn, Bromocriptin, Bromocriptina, Bromocriptine, Bromocriptine mesilate, Bromocriptine mesylate, Bromocriptine methanesulfonate, Bromocriptini mesilas, Bromocriptinmesilat, Bromodel, Bromokriptin, Bromolac, Bromotine, Bromtine, Brotin, Butin, Corpadel, Cripsa, Criptine, Criten, Cycloset, Degala, Demil, Deparo, Deprolac, Diacriptin, Dopagon, Erenant, Grifocriptina, Gynodel, kirim, Kriptonal, Lactodel, Medocriptine, Melen, Padoparine, Palolactin, Parlodel, Pravidel, Proctinal, Ronalin, Semi-Brom, Serocriptin, Serocryptin, Suplac, Syntocriptine, Umprel, Unew, Updopa, Upnol B, and Volbro. Bromocriptine is a potent agonist at dopamine D2 receptors and various serotonin receptors. Bromocriptine (originally marketed as Parlodel, subsequently under many names) is an ergoline derivative and dopamine agonist that is used in the treatment of pituitary tumors, Parkinson's disease (PD), hyperprolactinaemia, neuroleptic malignant syndrome, and type 2 diabetes. Most frequent side effects are nausea, orthostatic hypotension, headaches, and vomiting through stimulation of the brainstem vomiting centre.
Structure
Data?1582753285
Synonyms
ValueSource
(5'alpha)-2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-3',6',18-trioxoergotamanChEBI
(5'alpha)-2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trioneChEBI
(5'alpha)-2-Bromo-12'-hydroxy-5'-isobutyl-2'-isopropyl-3',6',18-trioxoergotamanChEBI
2-Bromo-alpha-ergocryptineChEBI
2-Bromo-alpha-ergokryptinChEBI
2-Bromo-alpha-ergokryptineChEBI
BromocriptinumChEBI
BromocryptineChEBI
BromoergocriptineChEBI
(5'a)-2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-3',6',18-trioxoergotamanGenerator
(5'Α)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-3',6',18-trioxoergotamanGenerator
(5'a)-2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trioneGenerator
(5'Α)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trioneGenerator
(5'a)-2-Bromo-12'-hydroxy-5'-isobutyl-2'-isopropyl-3',6',18-trioxoergotamanGenerator
(5'Α)-2-bromo-12'-hydroxy-5'-isobutyl-2'-isopropyl-3',6',18-trioxoergotamanGenerator
2-Bromo-a-ergocryptineGenerator
2-Bromo-α-ergocryptineGenerator
2-Bromo-a-ergokryptinGenerator
2-Bromo-α-ergokryptinGenerator
2-Bromo-a-ergokryptineGenerator
2-Bromo-α-ergokryptineGenerator
BromergocryptineHMDB
BromocriptinHMDB
Bromocriptine methanesulfonateHMDB
BromoergocryptineHMDB
2 Bromo alpha ergocryptineHMDB
2 Bromoergocryptine mesylateHMDB
2 BromoergokryptineHMDB
2-Bromoergocryptine mesylateHMDB
Mesylate, bromocriptineHMDB
Methanesulfonate, 2-bromoergocryptineHMDB
ParlodelHMDB
2 BromoergocryptineHMDB
2 Bromoergocryptine methanesulfonateHMDB
2-BromoergocryptineHMDB
2-Bromoergocryptine methanesulfonateHMDB
2-BromoergokryptineHMDB
Mesylate, 2-bromoergocryptineHMDB
2 Bromo alpha ergokryptineHMDB
Bromocriptine mesylateHMDB
BromocryptinHMDB
Chemical FormulaC32H40BrN5O5
Average Molecular Weight654.595
Monoisotopic Molecular Weight653.221282062
IUPAC Name(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[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
Traditional Namebromocriptine
CAS Registry Number25614-03-3
SMILES
[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=C(Br)NC6=CC=CC(=C56)C4=C3)(O[C@@]21O)C(C)C
InChI Identifier
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 KeyOZVBMTJYIDMWIL-AYFBDAFISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentLysergamides
Alternative Parents
Substituents
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • N-acyl-alpha amino acid or derivatives
  • Pyrroloquinoline
  • Alpha-amino acid or derivatives
  • Quinoline
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Aralkylamine
  • N-alkylpiperazine
  • Aryl bromide
  • Aryl halide
  • 1,4-diazinane
  • Oxazolidinone
  • Piperazine
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrolidine
  • Pyrrole
  • Tertiary carboxylic acid amide
  • Oxazolidine
  • Carboxamide group
  • Lactam
  • Tertiary amine
  • Tertiary aliphatic amine
  • Orthocarboxylic acid derivative
  • Amino acid or derivatives
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Alkanolamine
  • Carboximidic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organobromide
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.086 g/LNot Available
LogP3.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available244.447http://allccs.zhulab.cn/database/detail?ID=AllCCS00001359
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP3.2ALOGPS
logP3.89ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.68ChemAxon
pKa (Strongest Basic)6.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.21 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity165.51 m³·mol⁻¹ChemAxon
Polarizability66.44 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-271.22430932474
DeepCCS[M+Na]+244.99830932474
AllCCS[M+H]+238.632859911
AllCCS[M+H-H2O]+237.932859911
AllCCS[M+NH4]+239.132859911
AllCCS[M+Na]+239.332859911
AllCCS[M-H]-227.332859911
AllCCS[M+Na-2H]-230.032859911
AllCCS[M+HCOO]-233.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Bromocriptine[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=C(Br)NC6=CC=CC(=C56)C4=C3)(O[C@@]21O)C(C)C5898.6Standard polar33892256
Bromocriptine[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=C(Br)NC6=CC=CC(=C56)C4=C3)(O[C@@]21O)C(C)C4251.5Standard non polar33892256
Bromocriptine[H][C@@]12CCCN1C(=O)[C@H](CC(C)C)N1C(=O)[C@](NC(=O)[C@H]3CN(C)[C@]4([H])CC5=C(Br)NC6=CC=CC(=C56)C4=C3)(O[C@@]21O)C(C)C5139.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bromocriptine,1TMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)(C(C)C)C(=O)N124653.5Semi standard non polar33892256
Bromocriptine,1TMS,isomer #2CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N124505.9Semi standard non polar33892256
Bromocriptine,1TMS,isomer #3CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N124659.1Semi standard non polar33892256
Bromocriptine,2TMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N124511.3Semi standard non polar33892256
Bromocriptine,2TMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N124733.3Standard non polar33892256
Bromocriptine,2TMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N126106.8Standard polar33892256
Bromocriptine,2TMS,isomer #2CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N124610.7Semi standard non polar33892256
Bromocriptine,2TMS,isomer #2CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N124699.1Standard non polar33892256
Bromocriptine,2TMS,isomer #2CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N126116.4Standard polar33892256
Bromocriptine,2TMS,isomer #3CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N124536.0Semi standard non polar33892256
Bromocriptine,2TMS,isomer #3CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N124747.1Standard non polar33892256
Bromocriptine,2TMS,isomer #3CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N126059.1Standard polar33892256
Bromocriptine,3TMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N124543.0Semi standard non polar33892256
Bromocriptine,3TMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N124756.7Standard non polar33892256
Bromocriptine,3TMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C)C(=O)N125770.4Standard polar33892256
Bromocriptine,1TBDMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)(C(C)C)C(=O)N124845.6Semi standard non polar33892256
Bromocriptine,1TBDMS,isomer #2CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N124721.5Semi standard non polar33892256
Bromocriptine,1TBDMS,isomer #3CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N124814.6Semi standard non polar33892256
Bromocriptine,2TBDMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N124896.0Semi standard non polar33892256
Bromocriptine,2TBDMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N125168.4Standard non polar33892256
Bromocriptine,2TBDMS,isomer #1CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)[NH]6)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N126104.9Standard polar33892256
Bromocriptine,2TBDMS,isomer #2CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N124966.5Semi standard non polar33892256
Bromocriptine,2TBDMS,isomer #2CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N125142.2Standard non polar33892256
Bromocriptine,2TBDMS,isomer #2CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O[Si](C)(C)C(C)(C)C)O[C@](NC(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)(C(C)C)C(=O)N126115.0Standard polar33892256
Bromocriptine,2TBDMS,isomer #3CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N124890.8Semi standard non polar33892256
Bromocriptine,2TBDMS,isomer #3CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N125183.5Standard non polar33892256
Bromocriptine,2TBDMS,isomer #3CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(C)C)(N(C(=O)[C@@H]3C=C4C5=CC=CC6=C5C(=C(Br)N6[Si](C)(C)C(C)(C)C)C[C@H]4N(C)C3)[Si](C)(C)C(C)(C)C)C(=O)N126059.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bromocriptine GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-9321002000-4a6a862f3d310c4b1ddc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bromocriptine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bromocriptine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bromocriptine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bromocriptine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bromocriptine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bromocriptine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bromocriptine GC-MS ("Bromocriptine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 10V, Positive-QTOFsplash10-0udi-0002009000-d51e2392ddc2f88f3e4e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 20V, Positive-QTOFsplash10-0fi0-1019002000-5ec9b007ab29026f0c682016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 40V, Positive-QTOFsplash10-0udi-6029000000-f3b760903bf99f727a1f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 10V, Negative-QTOFsplash10-0udl-0003907000-9135b64a6bbc11172f2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 20V, Negative-QTOFsplash10-0ika-8139817000-f971791e9c2caf9b01752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 40V, Negative-QTOFsplash10-01ba-9301000000-344064b476a2087757142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 10V, Positive-QTOFsplash10-0udi-0000009000-a432702c23226daf972f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 20V, Positive-QTOFsplash10-0udi-0045019000-a5eeda23fd43d58794692021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 40V, Positive-QTOFsplash10-0udi-2049004000-149f9f3768b43e24b56f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 10V, Negative-QTOFsplash10-0udi-0000009000-e2c1692967aaeab3212f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 20V, Negative-QTOFsplash10-0udi-1031319000-12704c05dc3bfba9eb192021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromocriptine 40V, Negative-QTOFsplash10-00vi-9143001000-068ff47eb0d7789a1ad22021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01200 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01200 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01200
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28858
KEGG Compound IDC06856
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBromocriptine
METLIN IDNot Available
PubChem Compound31101
PDB IDNot Available
ChEBI ID3181
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
  2. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]
  3. Malgaroli A, Vallar L, Elahi FR, Pozzan T, Spada A, Meldolesi J: Dopamine inhibits cytosolic Ca2+ increases in rat lactotroph cells. Evidence of a dual mechanism of action. J Biol Chem. 1987 Oct 15;262(29):13920-7. [PubMed:2443499 ]
  4. Vallar L, Meldolesi J: Mechanisms of signal transduction at the dopamine D2 receptor. Trends Pharmacol Sci. 1989 Feb;10(2):74-7. [PubMed:2655242 ]
  5. Vallar L, Vicentini LM, Meldolesi J: Inhibition of inositol phosphate production is a late, Ca2+-dependent effect of D2 dopaminergic receptor activation in rat lactotroph cells. J Biol Chem. 1988 Jul 25;263(21):10127-34. [PubMed:2839476 ]
  6. Banihashemi B, Albert PR: Dopamine-D2S receptor inhibition of calcium influx, adenylyl cyclase, and mitogen-activated protein kinase in pituitary cells: distinct Galpha and Gbetagamma requirements. Mol Endocrinol. 2002 Oct;16(10):2393-404. [PubMed:12351703 ]
  7. Nishina Y, Takano K, Yasufuku-Takano J, Teramoto A, Fujita T: Mechanism of D(2) agonist-induced inhibition of GH secretion from human GH-secreting adenoma cells. Endocr J. 2005 Dec;52(6):775-9. [PubMed:16410672 ]

Only showing the first 10 proteins. There are 21 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Fernando H, Halpert JR, Davydov DR: Resolution of multiple substrate binding sites in cytochrome P450 3A4: the stoichiometry of the enzyme-substrate complexes probed by FRET and Job's titration. Biochemistry. 2006 Apr 4;45(13):4199-209. [PubMed:16566594 ]
  2. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
  3. Nath A, Grinkova YV, Sligar SG, Atkins WM: Ligand binding to cytochrome P450 3A4 in phospholipid bilayer nanodiscs: the effect of model membranes. J Biol Chem. 2007 Sep 28;282(39):28309-20. Epub 2007 Jun 15. [PubMed:17573349 ]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. de Leeuw van Weenen JE, Parlevliet ET, Maechler P, Havekes LM, Romijn JA, Ouwens DM, Pijl H, Guigas B: The dopamine receptor D2 agonist bromocriptine inhibits glucose-stimulated insulin secretion by direct activation of the alpha2-adrenergic receptors in beta cells. Biochem Pharmacol. 2010 Jun 15;79(12):1827-36. doi: 10.1016/j.bcp.2010.01.029. Epub 2010 Feb 4. [PubMed:20138024 ]
  2. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
  3. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
References
  1. de Leeuw van Weenen JE, Parlevliet ET, Maechler P, Havekes LM, Romijn JA, Ouwens DM, Pijl H, Guigas B: The dopamine receptor D2 agonist bromocriptine inhibits glucose-stimulated insulin secretion by direct activation of the alpha2-adrenergic receptors in beta cells. Biochem Pharmacol. 2010 Jun 15;79(12):1827-36. doi: 10.1016/j.bcp.2010.01.029. Epub 2010 Feb 4. [PubMed:20138024 ]
  2. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
  3. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Cavallotti C, Nuti F, Bruzzone P, Mancone M: Age-related changes in dopamine D2 receptors in rat heart and coronary vessels. Clin Exp Pharmacol Physiol. 2002 May-Jun;29(5-6):412-8. [PubMed:12010185 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
  4. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]
  5. Lahlou S: Cardiovascular responses to intrathecal dopamine receptor agonists in conscious DOCA-salt hypertensive rats. Fundam Clin Pharmacol. 1999;13(6):624-34. [PubMed:10626749 ]
  6. Lahlou S, Araujo Lima PF, Interaminense LF, Duarte GP: Blunted central bromocriptine-induced tachycardia in conscious, malnourished rats. Pharmacol Toxicol. 2003 Apr;92(4):189-94. [PubMed:12753422 ]
  7. Lahlou S, Lima GC, Leao-Filho CS, Duarte GP: Effects of long-term pretreatment with isoproterenol on bromocriptine-induced tachycardia in conscious rats. Can J Physiol Pharmacol. 2000 Mar;78(3):260-5. [PubMed:10721819 ]
  8. Stefaneanu L, Kovacs K, Horvath E, Buchfelder M, Fahlbusch R, Lancranjan L: Dopamine D2 receptor gene expression in human adenohypophysial adenomas. Endocrine. 2001 Apr;14(3):329-36. [PubMed:11444429 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:
HTR7
Uniprot ID:
P34969
Molecular weight:
53554.4
References
  1. Knight JA, Smith C, Toohey N, Klein MT, Teitler M: Pharmacological analysis of the novel, rapid, and potent inactivation of the human 5-Hydroxytryptamine7 receptor by risperidone, 9-OH-Risperidone, and other inactivating antagonists. Mol Pharmacol. 2009 Feb;75(2):374-80. doi: 10.1124/mol.108.052084. Epub 2008 Nov 7. [PubMed:18996971 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular weight:
54297.4
References
  1. Cussac D, Boutet-Robinet E, Ailhaud MC, Newman-Tancredi A, Martel JC, Danty N, Rauly-Lestienne I: Agonist-directed trafficking of signalling at serotonin 5-HT2A, 5-HT2B and 5-HT2C-VSV receptors mediated Gq/11 activation and calcium mobilisation in CHO cells. Eur J Pharmacol. 2008 Oct 10;594(1-3):32-8. doi: 10.1016/j.ejphar.2008.07.040. Epub 2008 Jul 30. [PubMed:18703043 ]
  2. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
  3. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
References
  1. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
  2. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD4
Uniprot ID:
P21917
Molecular weight:
48359.9
References
  1. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
References
  1. Kvernmo T, Houben J, Sylte I: Receptor-binding and pharmacokinetic properties of dopaminergic agonists. Curr Top Med Chem. 2008;8(12):1049-67. [PubMed:18691132 ]
  2. Lam YW: Clinical pharmacology of dopamine agonists. Pharmacotherapy. 2000 Jan;20(1 Pt 2):17S-25S. [PubMed:10641988 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [PubMed:11961113 ]
  2. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267 ]
  3. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]
  4. Renaud JP, Davydov DR, Heirwegh KP, Mansuy D, Hui Bon Hoa GH: Thermodynamic studies of substrate binding and spin transitions in human cytochrome P-450 3A4 expressed in yeast microsomes. Biochem J. 1996 Nov 1;319 ( Pt 3):675-81. [PubMed:8920966 ]

Only showing the first 10 proteins. There are 21 proteins in total.