Caroxazone

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]

Caroxazone
Clinical data
Pregnancy
category
  •  ?
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • 2-(2-oxo-4H-1,3-benzoxazin-3-yl)acetamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.038.481
Chemical and physical data
FormulaC10H10N2O3
Molar mass206.201 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N)CN2C(=O)Oc1ccccc1C2

Synthesis
Caroxazone synthesis:[8][9][10][11][12]

Synthesis starts by reductive amination of salicylaldehyde and glycinamide to give 3. The synthesis is completed by reaction with phosgene and NaHCO3.

See also

References
  1. Dictionary of organic compounds. London: Chapman & Hall. 1996. ISBN 0-412-54090-8.
  2. Cecchini S, Petri P, Ardito R, Bareggi SR, 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. doi:10.1177/030006057800600507. PMID 359383. S2CID 40464443.
  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, et al. (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 FB, 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 FB, 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 GP, Gioia B, Minghetti A, et al. (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 GK (August 1968). "Pharmacological properties of some derivatives of 1,3-benzoxazine". Experientia. 24 (8): 774–5. doi:10.1007/bf02144859. PMID 5683159. S2CID 30917127.
  10. Bernardi L, Coda S, Bonsignori A, Pegrassi L, Suchowsky GK (August 1969). "Central depressant properties of 3,1-benzoxazine derivates". Experientia. 25 (8): 787–8. doi:10.1007/bf01897874. PMID 5348526. S2CID 5347811.
  11. GB 1115759, "Carboxamidoalkyl-1,3-benzoxazines", published 1968-05-29, assigned to Societa Farmaceutici Italia
  12. L. Bernardi et al., U.S. Patent 3,427,313 (1969 to Soc. Farma. Italia).
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