Spiclomazine
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| Synonyms | Clospirazine, APY-606, Disepron. |
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| CAS Number | |
| PubChem CID | |
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| ChEBI | |
| ChEMBL | |
| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}} |
| Chemical and physical data | |
| Formula | C22H24ClN3OS2 |
| Molar mass | 446.02 g·mol−1 |
| 3D model (JSmol) | |
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| |
| |
| Clinical data | |
|---|---|
| Synonyms | Clospirazine, APY-606, Disepron. |
| Identifiers | |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}} |
| Chemical and physical data | |
| Formula | C22H24ClN3OS2 |
| Molar mass | 446.02 g·mol−1 |
| 3D model (JSmol) | |
| |
Neuroleptic Tranquilliser (used in treatment of schizophrenia).
Pharmacol:[1][2] Antineoplastic:[3]
Synthesis
A chemical synthesis is proposed:[4][5][6]
The reaction between the hydrochloride of 4-piperidone [41661-47-6] HCl H2O [40064-34-4] (1), ammonium carbonate [506-87-6] (2) and thioglycolic acid [68-11-1] (3) gives 1-thia-4,8-diazaspiro[4.5]decan-3-one, PC10419642 (4). The alkylation of the last with 2-chloro-10-(3-chloropropyl)phenothiazine [2765-59-5] (5) completed the synthesis of Spiclomazine (6)
References
- ↑ Nakanishi M, Okada T, Tsumagari T (July 1970). "[Studies on psychotropic drugs. V. Pharmacological effects of 8-(3-(2-chloro-10-phenothiazinyl)propyl)-1-thia-4,8-diazaspiro(4,5) decan-3-one hydrochloride (APY-606)]". Yakugaku Zasshi : Journal of the Pharmaceutical Society of Japan (in Japanese). 90 (7): 800–7. doi:10.1248/yakushi1947.90.7_800. PMID 5465390.CS1 maint: Unrecognized language (link)
- ↑ Nakanishi M, Okada T, Kato Y (July 1970). "[Studies on psychotropic drugs. VI. Metabolic fate of APY-606. (1). Excretion and metabolism in rats]". Yakugaku Zasshi : Journal of the Pharmaceutical Society of Japan (in Japanese). 90 (7): 808–12. doi:10.1248/yakushi1947.90.7_808. PMID 5465391.CS1 maint: Unrecognized language (link)
- ↑ Zhao W, Li D, Liu Z, Zheng X, Wang J, Wang E (2013). "Spiclomazine induces apoptosis associated with the suppression of cell viability, migration and invasion in pancreatic carcinoma cells". PLOS ONE. 8 (6): e66362. Bibcode:2013PLoSO...866362Z. doi:10.1371/journal.pone.0066362. PMC 3688794. PMID 23840452.
- ↑ Michio Nakanishi, Katsuo Arimura, Tatsumi Tsumagari Masa Shiroki, US3574204 (1971 to Yoshitomi Pharmaceutical).
- ↑ Katsuo Arimura, Michio Nakanishi, Tadao Okada, US3661902 (1972 to Yoshitomi Pharmaceutical).
- ↑ Michio Nakanishi, et al. US3651052 (1972 to Welfide Corp).
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