Caroxazone

Caroxazone

Systematic (IUPAC) name
2-(2-oxo-4H-1,3-benzoxazin-3-yl)acetamide
Clinical data
Pregnancy category	?
Routes of administration	Oral
Legal status	℞ (Prescription only)
Identifiers
CAS Number	18464-39-6
ATC code	none
PubChem	CID 29083
ChemSpider	27057
UNII	807N226MNL
ChEMBL	CHEMBL2104164
Chemical data
Formula	C10H10N2O3
Molar mass	206.20 g/mol
SMILES O=C(N)CN2C(=O)Oc1ccccc1C2

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

Caroxazone synthesis:^{[8][9][10][11]}

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

References

1. Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.
2. Cecchini, S; Petri, P; Ardito, R; Bareggi, S. R.; Torriti, A (1978). "A comparative double-blind trial of the new antidepressant caroxazone and amitriptyline". The Journal of International Medical Research 6 (5): 388–94. PMID 359383.
3. Monoamine oxidase inhibitors in neurological diseases. New York: M. Dekker. 1994. ISBN 0-8247-9082-0.
4. Moretti, A; Caccia, C; Martini, A; Bonollo, L; Amico, A; Sega, R; Nicolella, V; Nicolis, F. B. (May 1981). "Effect of caroxazone, a new antidepressant drug, on monoamine oxidases in healthy volunteers". British Journal of Clinical Pharmacology 11 (5): 511–5. doi:10.1111/j.1365-2125.1981.tb01158.x. PMC 1401585. PMID 7272163.
5. Moretti, A; Caccia, C; Calderini, G; Menozzi, M; Amico, A (October 1981). "Studies on the mechanism of action of caroxazone, a new antidepressant drug". Biochemical Pharmacology 30 (19): 2728–31. doi:10.1016/0006-2952(81)90549-9. PMID 6170295.
6. Martini, A; Bonollo, L; Nicolis, F. B.; Sega, R; Palermo, A (June 1981). "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. doi:10.1111/j.1365-2125.1981.tb01178.x. PMC 1402186. PMID 7272178.
7. Martini, A; Bonollo, L; Nicolis, F. B.; Sega, R; Palermo, A; Braibanti, E (June 1981). "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. doi:10.1111/j.1365-2125.1981.tb01177.x. PMC 1402193. PMID 7272177.
8. Bernardi, L; Coda, S; Nicolella, V; Vicario, G. P.; Gioia, B; Minghetti, A; Vigevani, A; Arcamone, F (1979). "Radioisotopic and synthetic studies related to caroxazone metabolism in man". Arzneimittel-Forschung 29 (9): 1412–6. PMID 583252.
9. Bernardi, L; Coda, S; Pegrassi, L; Suchowsky, G. K. (1968). "Pharmacological properties of some derivatives of 1,3-benzoxazine". Experientia 24 (8): 774–5. PMID 5683159.
10. Bernardi, L; Coda, S; Bonsignori, A; Pegrassi, L; Suchowsky, G. K. (1969). "Central depressant properties of 3,1-benzoxazine derivates". Experientia 25 (8): 787–8. PMID 5348526.
11. GB 1115759 ; L. Bernardi et al., U.S. Patent 3,427,313 (1965, 1969 both to Soc. Farma. Italia).