Clinical data
Trade namesAzafen, Azaphen
Routes of
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
  • 5-methyl-3-(4-methylpiperazin-1-yl)pyridazino[3,4-b][1,4]benzoxazine
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
Molar mass297.362 g·mol−1

Pipofezine, sold under the brand name Azafen or Azaphen, is a tricyclic antidepressant approved in Russia for the treatment of depression.[1][2][3][4] It was introduced in the late 1960s and is still used today.[5][6]

Pipofezine has been shown to act as a potent inhibitor of the reuptake of serotonin.[7][8] In addition to its antidepressant action, pipofezine has sedative effects as well, suggesting antihistamine activity.[9] Other properties such as anticholinergic or antiadrenergic actions are less clear but are likely.[citation needed]

See also


  1. ^ Aleeva GN, Molodavkin GM, Voronina TA (July 2009). "Comparison of antidepressant effects of azafan, tianeptine, and paroxetine". Bulletin of Experimental Biology and Medicine. 148 (1): 54–56. doi:10.1007/s10517-009-0638-4. PMID 19902096. S2CID 23923093.
  2. ^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 843. ISBN 3-88763-075-0.
  3. ^ Muller NF, Dessing RP (1998). European Drug Index, 4th Edition. Boca Raton: CRC Press. p. 126. ISBN 3-7692-2114-1.
  4. ^ Macor JE (2009). Annual Reports in Medicinal Chemistry, Volume V44. Boston: Academic Press. p. 16. ISBN 978-0-12-374766-2.
  5. ^ Mashkovskii MD, Polezhaeva AI, Avrutskii GI, Vertozgadova OP, Smulevich AB (1969). "[The pharmacologic properties and therapeutic effectiveness of the new antidepressant preparation Azaphen]". Zhurnal Nevropatologii I Psikhiatrii Imeni S.S. Korsakova (in Russian). 69 (8): 1234–1238. PMID 5392529.
  6. ^ Shinaev NN, Akzhigitov RG (2005). "[Azaphen: a return to clinical practice]". Zhurnal Nevrologii I Psikhiatrii Imeni S.S. Korsakova (in Russian). 105 (10): 55–56. PMID 16281382.
  7. ^ Avdulov NA, Maĭsov NI (November 1981). "[Atypical antidepressants: effect on synaptosomal uptake of serotonin and GABA]". Biulleten' Eksperimental'noi Biologii I Meditsiny (in Russian). 92 (11): 564–566. PMID 7198493.
  8. ^ Valdman AV, Avdulov NA, Rozganets VV, Rusacov DY (1983). "Behavioural and neurochemical studies of the action of atypical antidepressants". Acta Physiologica et Pharmacologica Bulgarica. 9 (3): 3–10. PMID 6142583.
  9. ^ Macor JE (2009). Annual Reports in Medicinal Chemistry, Volume V44. Boston: Academic Press. ISBN 978-0-12-374766-2.