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 names	Testiphenon; 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	104730-58-7 Y
PubChem CID	128659
ChemSpider	114020
UNII	3U50JYF0B9
CompTox Dashboard (EPA)	DTXSID10909156
Chemical and physical data
Formula	C31H43Cl2NO3
Molar mass	548.59 g·mol−1
3D model (JSmol)	Interactive image
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

• List of hormonal cytostatic antineoplastic agents
• List of androgen esters § Dihydrotestosterone esters
• List of Russian drugs

References

1. Lagova ND, Sof'ina ZP, Shkodinskaia EN, Kurdiumova KN, Valueva IM (1988). "[The antineoplastic activity of testiphenon]". Voprosy Onkologii (in Russian). 34 (11): 1363–1368. PMID 3201773.
2. Demidova NV, Serebryakova EA, Gasan-Guseinova ZG, Zimakova NI, Arzamastsev AP (November 1995). "Comparative pharmacokinetics of 3H-testiphenone and 3H-chlorophenacyl in peroral administration to mice". Pharmaceutical Chemistry Journal. 29 (11): 737–739. doi:10.1007/BF02331848. 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]". Vestnik Rossiiskoi Akademii Meditsinskikh Nauk (in Russian) (1): 42–45. PMID 11882971.