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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
  • [(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
FormulaC31H43Cl2NO3
Molar mass548.59 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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=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 edit

References edit

  1. ^ a b c 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. ^ a b c 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.

testifenon, also, known, testiphenon, testiphenone, chlorphenacyl, dihydrotestosterone, ester, dihydrotestosterone, 17β, chloroethyl, amino, phenyl, acetate, synthetic, anabolic, androgenic, steroid, cytostatic, antineoplastic, agent, chemotherapeutic, that, n. Testifenon also known as testiphenon testiphenone chlorphenacyl dihydrotestosterone ester or dihydrotestosterone 17b 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 TestifenonClinical dataOther namesTestiphenon Testiphenone Chlorphenacyl dihydrotestosterone ester Dihydrotestosterone 17b 4 bis 2 chloroethyl amino phenyl acetate LS 19378IdentifiersIUPAC 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 acetateCAS Number104730 58 7 YPubChem CID128659ChemSpider114020UNII3U50JYF0B9CompTox Dashboard EPA DTXSID10909156Chemical and physical dataFormulaC 31H 43Cl 2N O 3Molar mass548 59 g mol 13D model JSmol Interactive imageSMILES 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 CInChI 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 s1Key JWLXQUMDRGJLMS SJQIPMMSSA NSee also editList of hormonal cytostatic antineoplastic agents List of androgen esters Dihydrotestosterone estersReferences edit a b c 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 a b c 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 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 nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte nbsp This antineoplastic or immunomodulatory drug article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Testifenon amp oldid 1184634359, wikipedia, wiki, book, books, library,

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