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81409-90-7 molecular structure
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1-[3-(dimethylamino)propyl]-3-ethyl-1-[(2R,4R,7R)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene-4-carbonyl]urea

ChemBase ID: 133
Molecular Formular: C26H37N5O2
Molecular Mass: 451.60428
Monoisotopic Mass: 451.29472545
SMILES and InChIs

SMILES:
O=C(N(CCCN(C)C)C(=O)NCC)[C@@H]1C[C@H]2[C@H](N(C1)CC=C)Cc1c3c2cccc3[nH]c1
Canonical SMILES:
C=CCN1C[C@@H](C[C@H]2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)N(C(=O)NCC)CCCN(C)C
InChI:
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
InChIKey:
KORNTPPJEAJQIU-KJXAQDMKSA-N

Cite this record

CBID:133 http://www.chembase.cn/molecule-133.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-[3-(dimethylamino)propyl]-3-ethyl-1-[(2R,4R,7R)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene-4-carbonyl]urea
1-[3-(dimethylamino)propyl]-3-ethyl-1-[(2R,4R,7R)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene-4-carbonyl]urea
IUPAC Traditional name
1-[3-(dimethylamino)propyl]-3-ethyl-1-[(2R,4R,7R)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene-4-carbonyl]urea
cabergoline
Brand Name
Cabaser
Dostinex
Synonyms
Cabergolina [Spanish]
Cabergolinum [Latin]
Cabergoline
1-[(6-Allylergoline-8β-yl)carbonyl]-1-[3-(dimethylamino)-propyl]-3-ethylurea
1-Ethyl-3-(3′-dimethylaminopropyl)-3-(6′-allylergoline-8′β-carbonyl)urea
Cabaser
Dostinex
FCE-21336
(8β)-N-[3-(Dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propen-1-yl)-ergoline-8-carboxamide
Cabergoline
CAS Number
81409-90-7
MDL Number
MFCD00867887
PubChem SID
46508571
160963596
PubChem CID
54746

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 15.248916  H Acceptors
H Donor LogD (pH = 5.5) -3.24733 
LogD (pH = 7.4) -0.04766144  Log P 2.5785162 
Molar Refractivity 133.5029 cm3 Polarizability 52.385506 Å3
Polar Surface Area 71.68 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.97  LOG S -3.85 
Solubility (Water) 6.40e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO: ≥10 mg/mL expand Show data source
Ether expand Show data source
Insoluble expand Show data source
Methanol expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
102-104°C expand Show data source
Hydrophobicity(logP)
2.6 expand Show data source
Storage Condition
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
KE6167600 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36/37 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C26H37N5O2 expand Show data source

DETAILS

DETAILS

TRC TRC DrugBank DrugBank Sigma Aldrich Sigma Aldrich
Toronto Research Chemicals - C050000 external link
A dopamine D2-receptor agonist.
DrugBank - DB00248 external link
Item Information
Drug Groups approved
Description Cabergoline, an ergot derivative, is a long-acting dopamine agonist and prolactin inhibitor. It is used to treat hyperprolactinemic disorders and Parkinsonian Syndrome. Cabergoline possesses potent agonist activity on dopamine D2 receptors.
Indication For the treatment of hyperprolactinemic disorders, either idiopathic or due to prolactinoma (prolactin-secreting adenomas). May also be used to manage symptoms of Parkinsonian Syndrome as monotherapy during initial symptomatic management or as an adjunct to levodopa therapy during advanced stages of disease.
Pharmacology Cabergoline stimulates centrally-located dopaminergic receptors resulting in a number of pharmacologic effects. Five dopamine receptor types from two dopaminergic subfamilies have been identified. The dopaminergic D1 receptor subfamily consists of D1 and D5 subreceptors, which are associated with dyskinesias. The dopaminergic D2 receptor subfamily consists of D2, D3 and D4 subreceptors, which are associated with improvement of symptoms of movement disorders. Thus, agonist activity specific for D2 subfamily receptors, primarily D2 and D3 receptor subtypes, are the primary targets of dopaminergic antiparkinsonian agents. It is thought that postsynaptic D2 stimulation is primarily responsible for the antiparkinsonian effect of dopamine agonists, while presynaptic D2 stimulation confers neuroprotective effects. This semisynthetic ergot derivative exhibits potent agonist activity on dopamine D2- and D3-receptors. It also exhibits: agonist activity (in order of decreasing binding affinities) on 5-hydroxytryptamine (5-HT)2B, 5-HT2A, 5-HT1D, dopamine D4, 5-HT1A, dopamine D1, 5-HT1B and 5-HT2C receptors and antagonist activity on α2B, α2A, and α2C receptors. Parkinsonian Syndrome manifests when approximately 80% of dopaminergic activity in the nigrostriatal pathway of the brain is lost. As this striatum is involved in modulating the intensity of coordinated muscle activity (e.g. movement, balance, walking), loss of activity may result in dystonia (acute muscle contraction), Parkinsonism (including symptoms of bradykinesia, tremor, rigidity, and flattened affect), akathesia (inner restlessness), tardive dyskinesia (involuntary muscle movements usually associated with long-term loss of dopaminergic activity), and neuroleptic malignant syndrome, which manifests when complete blockage of nigrostriatal dopamine occurs. High dopaminergic activity in the mesolimbic pathway of the brain causes hallucinations and delusions; these side effects of dopamine agonists are manifestations seen in patients with schizophrenia who have overractivity in this area of the brain. The hallucinogenic side effects of dopamine agonists may also be due to 5-HT2A agonism. The tuberoinfundibular pathway of the brain originates in the hypothalamus and terminates in the pituitary gland. In this pathway, dopamine inhibits lactotrophs in anterior pituitary from secreting prolactin. Increased dopaminergic activity in the tuberoinfundibular pathway inhibits prolactin secretion.
Toxicity Overdosage might be expected to produce nasal congestion, syncope, or hallucinations.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Cabergoline is extensively metabolized, predominately via hydrolysis of the acylurea bond of the urea moiety. Cytochrome P-450 mediated metabolism appears to be minimal. The main metabolite identified in urine is 6-allyl-8b-carboxy-ergoline (4-6% of dose). Three other metabolites were identified urine (less than 3% of dose).
Absorption First-pass effect is seen, however the absolute bioavailability is unknown.
Half Life The elimination half-life is estimated from urinary data of 12 healthy subjects to range between 63 to 69 hours.
Protein Binding Moderately bound (40% to 42%) to human plasma proteins in a concentration-independent manner.
Elimination After oral dosing of radioactive cabergoline to five healthy volunteers, approximately 22% and 60% of the dose was excreted within 20 days in the urine and feces, respectively. Less than 4% of the dose was excreted unchanged in the urine.
Clearance * renal cl=0,008 L/min
* nonrenal cl=3.2 L/min
References
Pastor P, Tolosa E: [Cabergoline in the treatment of Parkinson's disease] Neurologia. 2003 May;18(4):202-9. [Pubmed]
Curran MP, Perry CM: Cabergoline : a review of its use in the treatment of Parkinson's disease. Drugs. 2004;64(18):2125-41. [Pubmed]
Bracco F, Battaglia A, Chouza C, Dupont E, Gershanik O, Marti Masso JF, Montastruc JL: The long-acting dopamine receptor agonist cabergoline in early Parkinson's disease: final results of a 5-year, double-blind, levodopa-controlled study. CNS Drugs. 2004;18(11):733-46. [Pubmed]
Miyagi M, Arai N, Taya F, Itoh F, Komatsu Y, Kojima M, Isaji M: Effect of cabergoline, a long-acting dopamine D2 agonist, on reserpine-treated rodents. Biol Pharm Bull. 1996 Nov;19(11):1499-502. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - C0246 external link
Biochem/physiol Actions
Cabergoline, a lysergic acid amide derivative, is a potent dopamine D2 receptor agonist. It also acts on dopamine receptors in lactophilic hypothalamus cells to suppress prolactin production in the pituitary gland. It has been used for monotherapy of Parkinson′s disease in the early phase; combination therapy, together with levodopa and a decarboxylase inhibitor such as carbidopa, in progressive-phase Parkinson′s disease and adjunctive therapy of prolactin-producing pituitary gland tumors (microprolactinomas).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Brambilla, E., et al.: Eur. J. Med. Chem., 24, 421 (1989)
  • • Ferrari, C., et al.: J. Clin. Endocrinol. Metab., 68, 1201 (1989)
  • • Hutton, J.T., et al.: Neurology, 46, 1062 (1996)
  • • Pastor P, Tolosa E: [Cabergoline in the treatment of Parkinson's disease] Neurologia. 2003 May;18(4):202-9. Pubmed
  • • Curran MP, Perry CM: Cabergoline : a review of its use in the treatment of Parkinson's disease. Drugs. 2004;64(18):2125-41. Pubmed
  • • Bracco F, Battaglia A, Chouza C, Dupont E, Gershanik O, Marti Masso JF, Montastruc JL: The long-acting dopamine receptor agonist cabergoline in early Parkinson's disease: final results of a 5-year, double-blind, levodopa-controlled study. CNS Drugs. 2004;18(11):733-46. Pubmed
  • • Miyagi M, Arai N, Taya F, Itoh F, Komatsu Y, Kojima M, Isaji M: Effect of cabergoline, a long-acting dopamine D2 agonist, on reserpine-treated rodents. Biol Pharm Bull. 1996 Nov;19(11):1499-502. Pubmed
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