Ciclazindol
From Wikipedia, the free encyclopedia
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| Systematic (IUPAC) name | |
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10-(3-chlorophenyl)-3,4-dihydro-2H-pyrimido[1,2-a]indol-10-ol
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| Clinical data | |
| Legal status |
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| Routes of administration |
Oral |
| Pharmacokinetic data | |
| Metabolism | Renal[1] |
| Biological half-life | ~32 hours[1] |
| Excretion | Urine, feces[1] |
| Identifiers | |
| CAS Number | 37751-39-6 |
| ATC code | None |
| PubChem | CID 37825 |
| ChemSpider | 34683 |
| UNII | Y3I9520J7P  |
| KEGG | D03486 |
| ChEMBL | CHEMBL1192491 |
| Chemical data | |
| Formula | C17H15ClN2O |
| Molar mass | 298.77 g/mol |
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Ciclazindol (WY-23,409) is an antidepressant and anorectic drug of the tetracyclic chemical class that was developed in the mid to late 1970s, but was never marketed.[2][3] It acts as a norepinephrine reuptake inhibitor, and to a lesser extent as a dopamine reuptake inhibitor.[2][4] Ciclazindol has no effects on the SERT, 5-HT receptors, mACh receptors, or α-adrenergic receptors, and has only weak affinity for the H1 receptor.[4][5][6] As suggested by its local anesthetic properties,[5] ciclazindol may also inhibit sodium channels. It is known to block potassium channels as well.[7][8]
Synthesis[edit]
Ciclazindol can be synthesized from isitin (1). Reaction with 2-chlorophenylmagnesium bromide thus gives 2. Conjugate addition of the anion of that product to acrylonitrile affords the propionitrile 3. The cyano group is then reduced to the primary amine by means of lithium aluminum hydride. Internal imine formation leads to cyclization to form ciclazindol.
See also[edit]
References[edit]
- ^ a b c Swaisland AJ, Franklin RA, Southgate PJ, Coleman AJ (February 1977). "The pharmacokinetics of ciclazindol (Wy 23409) in human volunteers". British Journal of Clinical Pharmacology 4 (1): 61–5. doi:10.1111/j.1365-2125.1977.tb00668.x. PMC 1428987. PMID 843425.
- ^ a b Ghose K, Rama Rao VA, Bailey J, Coppen A (April 1978). "Antidepressant activity and pharmacological interactions of ciclazindol". Psychopharmacology 57 (1): 109–14. doi:10.1007/BF00426966. PMID 96461.
- ^ Levine S (1979). "A controlled comparative trial of a new antidepressant, ciclazindol". The Journal of International Medical Research 7 (1): 1–6. PMID 369921.
- ^ a b Oh VM, Ehsanullah RS, Leighton M, Kirby MJ (January 1979). "Influence of ciclazindol on monoamine uptake and CNS function in normal subjects". Psychopharmacology 60 (2): 177–81. doi:10.1007/BF00432290. PMID 106428.
- ^ a b Waterfall JF, Smith MA, Gaston WH, Maher J, Warburton G (July 1979). "Cardiovascular and autonomic actions of ciclazindol and tricyclic antidepressants". Archives Internationales De Pharmacodynamie Et De Thérapie 240 (1): 116–36. PMID 507990.
- ^ Gardner CR, Wilford AE (January 1980). "The effects of mianserine, amitriptyline, ciclazindol and viloxazine on presynaptic alpha-receptors in isolated rat atria [proceedings]". British Journal of Pharmacology 68 (1): 184P–185P. doi:10.1111/j.1476-5381.1980.tb10705.x. PMC 2044122. PMID 6244029.
- ^ Noack T, Edwards G, Deitmer P; et al. (May 1992). "The involvement of potassium channels in the action of ciclazindol in rat portal vein". British Journal of Pharmacology 106 (1): 17–24. doi:10.1111/j.1476-5381.1992.tb14286.x. PMC 1907450. PMID 1504725.
- ^ Lee K, Khan RN, Rowe IC; et al. (April 1996). "Ciclazindol inhibits ATP-sensitive K+ channels and stimulates insulin secretion in CR1-G1 insulin-secreting cells". Molecular Pharmacology 49 (4): 715–20. PMID 8609901.
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