13-Hydroxylergotrile
| Clinical data | |
|---|---|
| Other names | 2-Chloro-6-methyl-13-hydroxyergoline-8β-acetonitrile |
| Drug class | Dopamine receptor agonist |
| ATC code |
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| Chemical and physical data | |
| Formula | C17H17ClN3O |
| Molar mass | 314.79 g·mol−1 |
| 3D model (JSmol) | |
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13-Hydroxylergotrile, also known as 2-chloro-6-methyl-13-hydroxyergoline-8β-acetonitrile, is a dopamine receptor agonist of the ergoline family.[1][2] It is an active metabolite of the never-marketed antiparkinsonian agent lergotrile (LY-79907).[1][2] The drug has been found to be 100-fold more potent as a dopamine receptor agonist than lergotrile itself in vitro.[1][2] 13-Hydroxylergotrile was first described in the scientific literature by 1978.[1]
See also
References
- ^ a b c d Parli CJ, Schmidt B, Shaar CJ (May 1978). "Metabolism of lergotrile to 13-hydroxy lergotrile, a potent inhibitor of prolactin release in vitro". Biochemical Pharmacology. 27 (9): 1405–1408. doi:10.1016/0006-2952(78)90131-4. PMID 29651.
- ^ a b c Cannon JG, Lee T, Ilhan M, Koons J, Long JP (March 1984). "6-Hydroxy-4-[2-(di-n-propylamino)ethyl]indole: synthesis and dopaminergic actions". Journal of Medicinal Chemistry. 27 (3): 386–389. doi:10.1021/jm00369a026. PMID 6699883.
Prior communications have described prominent dopaminergic agonist actions of a simple indole derivative, 1, designed as a fragment of the dopaminergic ergoline derivative lergotrile (2). The slow (30–40 min) onset of pharmacological effects following intravenous administration of 1 in intact animals, coupled with its dopaminergic inactivity in an in vitro assay using isolated cat atrium and its very weak binding activity in calf caudate tissue,2 led to the proposal that 1 may be metabolically activated in vivo. Wong and Bymaster4 reported that 13-hydroxylergotrile (3)) a metabolite of lergotrile, had greater affinity than lergotrile in a dopamine agonist receptor binding assay. Parli et al.5 reported that 13-hydroxylergotrile is 100 times more active than lergotrile in vitro in inhibiting prolactin release from the anterior pituitary.