Testifenon

Testifenon, also known as testiphenon, testiphenone, chlorphenacyl dihydrotestosterone ester, or dihydrotestosterone 17β-(4-(bis(2-chloroethyl)amino)phenyl)acetate, is a synthetic anabolic–androgenic steroid (AAS) and a cytostatic antineoplastic agent (i.e., chemotherapeutic) that was never marketed.[1][2][3] It is an androgen ester – specifically, a chlorphenacyl nitrogen mustard ester of dihydrotestosterone (DHT) – and acts as a prodrug of these two components in the body.[1][2] The drug was developed in Russia as a tissue-selective cytostatic drug for the treatment of various cancers occurring in androgen receptor-expressing tissues that would have reduced side effects and toxicity relative to other chemotherapy drugs.[1][2]

Testifenon
Clinical data
Other namesTestiphenon; Testiphenone; Chlorphenacyl dihydrotestosterone ester; Dihydrotestosterone 17β-(4-(bis(2-chloroethyl)amino)phenyl)acetate; LS-19378
Identifiers
IUPAC name
  • [(5S,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] 2-[4-[bis(2-chloroethyl)amino]phenyl]acetate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC31H43Cl2NO3
Molar mass548.59 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4OC(=O)CC5=CC=C(C=C5)N(CCCl)CCCl)C
InChI
  • InChI=1S/C31H43Cl2NO3/c1-30-13-11-24(35)20-22(30)5-8-25-26-9-10-28(31(26,2)14-12-27(25)30)37-29(36)19-21-3-6-23(7-4-21)34(17-15-32)18-16-33/h3-4,6-7,22,25-28H,5,8-20H2,1-2H3/t22-,25-,26-,27-,28-,30-,31-/m0/s1
  • Key:JWLXQUMDRGJLMS-SJQIPMMSSA-N

See also

References
  1. Lagova ND, Sof'ina ZP, Shkodinskaia EN, Kurdiumova KN, Valueva IM (1988). "[The antineoplastic activity of testiphenon]". Vopr Onkol (in Russian). 34 (11): 1363–8. PMID 3201773.
  2. Demidova, N. V.; Serebryakova, E. A.; Gasan-Guseinova, Z. G.; Zimakova, N. I.; Arzamastsev, A. P. (1995). "Comparative pharmacokinetics of3H-testiphenone and3H-chlorophenacyl in peroral administration to mice". Pharmaceutical Chemistry Journal. 29 (11): 737–739. doi:10.1007/BF02331848. ISSN 0091-150X. S2CID 31434647.
  3. Oborotova NA, Smirnova ZS, Polozkova ZS, Baryshnikov AI (2002). "[Pharmacological aspects in the development of liposomal medicinal preparations for the internal injection of hydrophobic cytostatics]". Vestn. Akad. Med. Nauk SSSR (in Russian) (1): 42–5. PMID 11882971.



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