Bromocriptine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Bromocriptine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Bromocriptine?

The molecule Bromocriptine presents a molecular formula of C32H40BrN5O5 and its IUPAC name is (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.

Bromocriptine is a dopamine agonist that is used to treat a variety of conditions, including Parkinson's disease, pituitary adenomas, and type 2 diabetes. It is also used as an adjunct therapy for the treatment of prolactin-secreting adenomas. Bromocriptine has a high affinity for the dopamine D2 receptor and a moderate affinity for the dopamine D1 receptor. The exact mechanism of action of bromocriptine is not known, but it is thought to work by stimulating the release of dopamine from the brain..

Bromocriptine exists as a tablet, capsule, and solution for oral administration. It can be found as an injection. Bromocriptine should be taken with food. The usual starting dose is 2.5 mg two times a day. The dose may be increased by 2.5 mg every two to three days until the desired response is achieved. The usual maintenance dose is 10 mg to 30 mg two times a day. Bromocriptine should be tapered gradually when discontinuing treatment..

Common side effects of bromocriptine include nausea, vomiting, constipation, diarrhea, headache, dizziness, lightheadedness, and drowsiness. Bromocriptine can also cause hypotension and hallucinations. This medication can cause a serious condition called neuroleptic malignant syndrome. Symptoms of neuroleptic malignant syndrome include fever, muscle rigidity, irregular heartbeat, and changes in mental status. Bromocriptine should be used with caution in patients with a history of mental illness or substance abuse..

Bromocriptine is a pregnancy category C medication. This means that it is not known if bromocriptine will harm an unborn baby. Bromocriptine should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus. This medication passes into breast milk and may harm a nursing infant. Bromocriptine should not be used by women who are breastfeeding..

Bromocriptine is a prescription medication that is used to treat a variety of conditions. It is important to take this medication exactly as prescribed by your healthcare provider. Bromocriptine can cause serious side effects. If you experience any of the following symptoms, call your doctor immediately: fever, muscle rigidity, irregular heartbeat, changes in mental status, or nausea and vomiting..

3D structure

Cartesian coordinates

Geometry of Bromocriptine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Bromocriptine OZVBMTJYIDMWIL-AYFBDAFISA-N chemical compound 2D structure molecule svg
Bromocriptine

 

Molecule descriptors

 
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 codeInChI=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
SMILESCC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C=C4c5cccc6[nH]c(Br)c(c56)C[C@H]4N(C)C3)(C(C)C)C(=O)N12

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-Bromocriptine
  • (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
  • (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
  • (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
  • (5alpha,5'beta)-2-bromo-12'-hydroxy-5'-(2-methylpropyl)-3',6',18-trioxo-2'-(propan-2-yl)ergotaman
  • (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
  • (6aR,9R)-5-bromo-N-((2R,5S,10aS,10bS)-
  • (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
  • 08Y
  • 10b-hydroxy-5-isobutyl-2-isopropyl-3,6-
  • 2-Bromo-.alpha.-ergocryptine
  • 2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-alpha-(2-methylpropyl)ergotamin-3',6',18-trione
  • 2-Bromo-alpha-ergocryptine
  • 2-Bromo-alpha-ergokryptin
  • 2-Bromo-alpha-ergokryptine
  • 2-Bromoergocryptine
  • 22260-51-1
  • 25614-03-3
  • 3A64E3G5ZO
  • AC-13601
  • BDBM81993
  • BIDD:GT0464
  • BPBio1_001131
  • Bagren
  • Biomol-NT_000005
  • Bromergocryptine
  • Bromergon
  • Bromocriptin
  • Bromocriptina
  • Bromocriptine
  • Bromocriptine (USAN/INN)
  • Bromocriptine (mesylate)
  • Bromocriptine+ (GTP-)
  • Bromocriptinum
  • Bromocryptine
  • Bromoergocriptine
  • Bromoergocryptine
  • C06856
  • CB 154
  • CB-154
  • CCG-204266
  • CCRIS 3244
  • Carboprost Methylate,(S)
  • D03165
  • DB01200
  • DSSTox_CID_2687
  • DSSTox_GSID_22687
  • DSSTox_RID_76692
  • Ergocryptine, 2-bromo-
  • Ergoset
  • Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'.alpha.)-
  • Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)-
  • GTPL35
  • J-016067
  • Lopac0_000171
  • 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
  • NCGC00024584-03
  • NCGC00024584-04
  • NCGC00024584-05
  • NCGC00024584-07
  • NCGC00024584-09
  • NCI60_001365
  • NSC169774
  • PDSP2_001500
  • Prestwick0_000121
  • Prestwick1_000121
  • Prestwick2_000121
  • Q413581
  • SANDOZ 15-754
  • SDCCGSBI-0050159.P003
  • SR-01000075356
  • SR-01000075356-5
  • [2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-
  • bromocriptine
  • dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo
  • hexahydroindolo[4,3-fg]quinoline-9-carboxamide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC53683151
  • CAS-25614-03-3
  • UNII-3A64E3G5ZO
  • AKOS015961273
  • BRD-K14496212-001-01-1
  • BRD-K14496212-066-04-8
  • DTXSID1022687
  • CHEMBL493
  • CHEBI:3181
  • Tox21_110907
  • EINECS 247-128-5
  • SPBio_002101
  • SCHEMBL25297

Physico-Chemical properties

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
Molecular formulaC32H40BrN5O5
Molecular weight654.595
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity177.59
LogP3.4
Topological polar surface area118.2

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.