CAS Number81409-90-7
SynonymsCabergolinum [Latin]; Cabergolina [Spanish]; (8β)-6-Allyl-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)ergoline-8-carboxamide; Cabaseril; Dostinex; (8b)-N-[3-(Dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)ergoline-8-carboxamide; Cabaser; Dostinex(R); (8β)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-(prop-2-en-1-yl)ergoline-8-carboxamide; (8β)-N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-prop-2-en-1-ylergoline-8-carboxamide; Cabergolinum; 1-Ethyl-3-(3'-dimethylaminopropyl)-3-(6'-allylergoline-8'b-carbonyl)urea; cabergolide; (8β)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-prop-2-en-1-ylergoline-8-carboxamide; Cabergolina; MFCD00867887; Cabergoline; cabergolinum [INN_la]
Molecular FormulaC26H37N5O2
Molecular Weight451.60
Purity98%
Density1.2±0.1 g/cm3
Melting Point102-104°C
AppearanceWhite crystalline solid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 81409-90-7 |
| Catalog No. | 2A-9009523 |
| Chinese Name | 卡麦角林 |
| Synonyms | Cabergolinum [Latin]; Cabergolina [Spanish]; (8β)-6-Allyl-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)ergoline-8-carboxamide; Cabaseril; Dostinex; (8b)-N-[3-(Dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)ergoline-8-carboxamide; Cabaser; Dostinex(R); (8β)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-(prop-2-en-1-yl)ergoline-8-carboxamide; (8β)-N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-prop-2-en-1-ylergoline-8-carboxamide; Cabergolinum; 1-Ethyl-3-(3'-dimethylaminopropyl)-3-(6'-allylergoline-8'b-carbonyl)urea; cabergolide; (8β)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-prop-2-en-1-ylergoline-8-carboxamide; Cabergolina; MFCD00867887; Cabergoline; cabergolinum [INN_la] |
| Molecular Formula | C26H37N5O2 |
| Molecular Weight | 451.60 |
| Purity | 98 |
| Density | 1.2±0.1 g/cm3 |
| Melting Point | 102-104°C |
| Appearance | White crystalline solid |
| Storage Condition | Store at +4°C |
| Packaging | III |
| Application | Cabergoline is an ergot-derived dopamine D2 subclass receptor agonist with high affinity for D2, D3 and 5-HT2B receptors, with Ki of 0.7, 1.5 and 1.2 respectively. |
| MDL Number | MFCD00867887 |
| SMILES | CCNC(=O)N(CCCN(C)C)C(=O)[C@@H]1C[C@H]2[C@@H](Cc3c[nH]c4cccc2c34)N(CC=C)C1 |
| InChI | 1S/C26H37N5O2/c1-5-11-30-17-19(25(32)31(26(33)27-6-2)13-8-12-29(3)4)14-21-20-9-7-10-22-24(20)18(16-28-22)15-23(21)30/h5,7,9-10,16,19,21,23,28H,1,6,8,11-15,17H2,2-4H3,(H,27,33)/t19-,21-,23-/m1/s1 |
| InChI Key | KORNTPPJEAJQIU-KJXAQDMKSA-N |
| Hazard Symbols | 9 |
| MSDS | msds/9523_1_81409_90_7.pdf |
| Bioactivity | Cabergoline is an ergot derived-dopamine D2-like receptor agonist that has high affinity for D2, D3, and 5-HT2B receptors (Ki=0.7, 1.5, and 1.2, respectively). Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor Research Areas >> Endocrinology Target Ki: 0.7 (Dopamine D2 receptor), 1.5 (Dopamine D3 receptor), 1.2 (5-HT2B receptor)[1] In Vitro Cabergoline acts as a potent agonist of D2, D3 and 5-HT2B receptors. Pretreatment with Cabergoline inhibits H2O2-induced neuronal cell death in a dose-dependent manner. In the following experiments, 10 µM of Cabergoline is used to investigate its neuroprotective effects. MAP2 staining reveals that Cabergoline significantly suppresses the loss of neurons caused by H2O2 incubation. The detection of apoptotic nuclear condensation suggested that Cabergoline prevents apoptotic cell death following H2O2 exposure[1]. In Vivo Cabergoline has a longer elimination half-life (63 to 109 h) compared with other D2-like receptor agonists, both a long-lasting clinical effect following single-dose administration, and an improvement in the quality of life of patients with chronic diseases are expected[1]. The most significant reduction in rapid eye movement (REM) sleep bout number occurred during the light phase, in which Cabergoline-injected female handled mice has 67.3% less REM sleep bouts (F(1,11)=12.892, P=0.004) than Cabergoline-injected females that are restrained, although the greatest number in reduction of REM sleep bouts occurr during the dark phase (82.3% fewer REM sleep bouts; F(1,11)=3.667, P=0.082). In male mice, Cabergoline reduces baseline Prolactin (PRL) levels (98.5%; F(1,6)=13.192, P=0.011) from 5.8±1.3 to 0.08 ng/mL within 2 hours of injection. After a 7-day recovery period, PRL levels return to values that are not different from baseline (5.0±0.60 ng/mL; F(1,6)=0.715, P=0.43)[2]. Cell Assay Primary cortical neurons are prepared. Cabergoline (10 µM; except for experiments of dose-dependency) is applied to cortical cells at DIV 6-7. After 24-hour Cabergoline treatment (except for examination of pretreatment time-dependency of Cabergoline), H2O2 (50 µM; except for the dose-dependency of H2O2) is added. All inhibitors and antagonists, including spiperone, U0126, SB203580, SP600125, AP5, and nifedipine are applied 20 min before Cabergoline or H2O2 addition. L-glutamate is added at DIV 7-8 for cell death induction. Cell survival rate is measured by MTT assay. After the indicated treatment with drugs is completed, culture medium is replaced with 200 µL fresh medium containing 40 µl MTT solution (2.5 mg/mL, diluted in PBS) and cells are incubated at 37°C for 1.5-2.5 hours. Then, 200 µL lysis buffer containing isopropyl alcohol is applied to each well and mixed by pipetting. Each sample is moved to a 96-well plate and its absorbance at 570 nm is measured using an iMark Micro plate leader. Cell survival rate is quantitated by absorbance measurement, because MTT (yellow) is deoxidized to formazan (violet) in proportion to mitochondrial activity[1]. Animal Admin Mice[2] Female and male C57BL/6J mice are used.Cabergoline is dissolved in 100% pharmasolve and then diluted with 20% β-cyclodextrin in water to yield a final concentration of 0.15-0.5 mg/mL Cabergoline. Mice received a 0.3-mg/kg ip injection of Cabergoline or vehicle. All drugs are prepared within 48 hours of experiment and stored at 4°C. Solutions are allowed to reach at room temperature before injection. References [1]. Odaka H, et al. Cabergoline, dopamine D2 receptor agonist, prevents neuronal cell death under oxidative stress via reducing excitotoxicity. PLoS One. 2014 Jun 10;9(6):e99271. [2]. Jefferson F, et al. A dopamine receptor d2-type agonist attenuates the ability of stress to alter sleep in mice. Endocrinology. 2014 Nov;155(11):4411-21. Chemical & Physical Properties Density 1.2±0.1 g/cm3 Melting Point 102-104°C Molecular Formula C26H37N5O2 Molecular Weight 451.604 Exact Mass 451.294739 PSA 71.68000 LogP 2.43 Index of Refraction 1.594 InChIKey KORNTPPJEAJQIU-KJXAQDMKSA-N SMILES C=CCN1CC(C(=O)N(CCCN(C)C)C(=O)NCC)CC2c3cccc4[nH]cc(c34)CC21 Storage condition Store at +4°C |
| Use of | Cabergoline is an ergot derived-dopamine D2-like receptor agonist that has high affinity for D2, D3, and 5-HT2B receptors (Ki=0.7, 1.5, and 1.2, respectively). Properties Articles39 Name cabergoline Synonym More Synonyms Cabergoline Biological Activity Description Cabergoline is an ergot derived-dopamine D2-like receptor agonist that has high affinity for D2, D3, and 5-HT2B receptors (Ki=0.7, 1.5, and 1.2, respectively). Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor Research Areas >> Endocrinology Ki: 0.7 (Dopamine D2 receptor), 1.5 (Dopamine D3 receptor), 1.2 (5-HT2B receptor)[1] In Vitro Cabergoline acts as a potent agonist of D2, D3 and 5-HT2B receptors. Pretreatment with Cabergoline inhibits H2O2-induced neuronal cell death in a dose-dependent manner. In the following experiments, 10 µM of Cabergoline is used to investigate its neuroprotective effects. MAP2 staining reveals that Cabergoline significantly suppresses the loss of neurons caused by H2O2 incubation. The detection of apoptotic nuclear condensation suggested that Cabergoline prevents apoptotic cell death following H2O2 exposure[1]. References [1]. Odaka H, et al. Cabergoline, dopamine D2 receptor agonist, prevents neuronal cell death under oxidative stress via reducing excitotoxicity. PLoS One. 2014 Jun 10;9(6):e99271. [2]. Jefferson F, et al. A dopamine receptor d2-type agonist attenuates the ability of stress to alter sleep in mice. Endocrinology. 2014 Nov;155(11):4411-21. Chemical & Physical Properties Molecular Formula C26H37N5O2 Exact Mass 451.294739 PSA 71.68000 Index of Refraction 1.594 InChIKey KORNTPPJEAJQIU-KJXAQDMKSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available The above information is believed to be correct, but is not all-inclusive and should be used as a guide only. The information in this document is based on our current knowledge and is Correct safety instructions apply to this product. This information does not represent a warranty as to the properties of this product. See reverse side of invoice or packing slip. |
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