Clinical data
Trade names Azafen, Azaphen
Routes of
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
CAS Number
PubChem CID
Chemical and physical data
Formula C16H19N5O
Molar mass 297.36 g/mol

Pipofezine, sold under the brand name Azafen or Azaphen, is a tricyclic antidepressant (TCA) 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.[4] Other properties such as anticholinergic or antiadrenergic actions are less clear but are likely.

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): 54–6. doi:10.1007/s10517-009-0638-4. PMID 19902096.
  2. Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
  3. European Drug Index, 4th Edition. Boca Raton: CRC Press. 1998. ISBN 3-7692-2114-1.
  4. 1 2 John E. Macor (2009). Annual Reports in Medicinal Chemistry, Volume V44. Boston: Academic Press. ISBN 0-12-374766-X.
  5. Mashkovskii MD; Polezhaeva AI; Avrutskii GIa; 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 (Moscow, Russia : 1952) (in Russian). 69 (8): 1234–8. PMID 5392529.
  6. Shinaev NN, Akzhigitov RG (2005). "[Azaphen: a return to clinical practice]". Zhurnal Nevrologii I Psikhiatrii Imeni S.S. Korsakova / Ministerstvo Zdravookhraneniia I Meditsinskoĭ Promyshlennosti Rossiĭskoĭ Federatsii, Vserossiĭskoe Obshchestvo Nevrologov [I] Vserossiĭskoe Obshchestvo Psikhiatrov (in Russian). 105 (10): 55–6. PMID 16281382.
  7. Avdulov NA, Maĭsov NI (November 1981). "[Atypical antidepressants: effect on synaptosomal uptake of serotonin and GABA]". Biulleten' Eksperimental'noĭ Biologii I Meditsiny (in Russian). 92 (11): 564–6. 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.

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