Chemistry:Caroxazone
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Short description: Chemical compound
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| Routes of administration | Oral |
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| Formula | C10H10N2O3 |
| Molar mass | 206.201 g·mol−1 |
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Caroxazone (Surodil, Timostenil) is an antidepressant which was formerly used for the treatment of depression but is now no longer marketed.[1][2] It acts as a reversible monoamine oxidase inhibitor (RIMA) of both MAO-A and MAO-B subtypes, with five-fold preference for the latter.[3][4][5][6][7]
Synthesis
Synthesis starts by reductive amination of salicylaldehyde and glycinamide to give 3. The synthesis is completed by reaction with phosgene and NaHCO3.
See also
- Paraxazone, an isomer of Caroxazone
References
- ↑ Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8. https://books.google.com/books?id=zNZfxR-CsYcC&q=caroxazone&pg=PA1254.
- ↑ "A comparative double-blind trial of the new antidepressant caroxazone and amitriptyline". The Journal of International Medical Research 6 (5): 388–94. 1978. doi:10.1177/030006057800600507. PMID 359383.
- ↑ Monoamine oxidase inhibitors in neurological diseases. New York: M. Dekker. 1994. ISBN 0-8247-9082-0. https://books.google.com/books?id=kJP3f9YKSrUC&q=caroxazone%20%22MAO-A%22&pg=PA56.
- ↑ "Effect of caroxazone, a new antidepressant drug, on monoamine oxidases in healthy volunteers". British Journal of Clinical Pharmacology 11 (5): 511–5. May 1981. doi:10.1111/j.1365-2125.1981.tb01158.x. PMID 7272163.
- ↑ "Studies on the mechanism of action of caroxazone, a new antidepressant drug". Biochemical Pharmacology 30 (19): 2728–31. October 1981. doi:10.1016/0006-2952(81)90549-9. PMID 6170295.
- ↑ "Effects of caroxazone, a reversible monoamine oxidase inhibitor, on the pressor response to oral tyramine in man". British Journal of Clinical Pharmacology 11 (6): 611–5. June 1981. doi:10.1111/j.1365-2125.1981.tb01178.x. PMID 7272178.
- ↑ "Effects of caroxazone, a reversible monoamine oxidase inhibitor, on the pressor response to intravenous tyramine in man". British Journal of Clinical Pharmacology 11 (6): 605–10. June 1981. doi:10.1111/j.1365-2125.1981.tb01177.x. PMID 7272177.
- ↑ "Radioisotopic and synthetic studies related to caroxazone metabolism in man". Arzneimittel-Forschung 29 (9): 1412–6. 1979. PMID 583252.
- ↑ "Pharmacological properties of some derivatives of 1,3-benzoxazine". Experientia 24 (8): 774–5. August 1968. doi:10.1007/bf02144859. PMID 5683159.
- ↑ "Central depressant properties of 3,1-benzoxazine derivates". Experientia 25 (8): 787–8. August 1969. doi:10.1007/bf01897874. PMID 5348526.
- ↑ "Carboxamidoalkyl-1,3-benzoxazines" GB patent 1115759, published 1968-05-29, assigned to Societa Farmaceutici Italia
- ↑ L. Bernardi et al., U.S. Patent 3,427,313 (1969 to Soc. Farma. Italia).
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