Structure via PubChem · Public domain (PubChem)
izonsteride
Sign in to saveIzonsteride (developmental code name LY-320,236) is a selective inhibitor of the 5α-reductase, with dual effects on both the type I and type II isoforms of the enzyme. It was under development by Eli Lilly and Company and Fujisawa for the treatment of benign prostatic hyperplasia but was never marketed. Izonsteride may also be useful in the treatment of androgenic alopecia.
Chemical data
- Formula
- C24H26N2OS2
- Molecular weight
- 422.6 g/mol
- IUPAC name
- (4aR,10bR)-8-[(4-ethyl-1,3-benzothiazol-2-yl)sulfanyl]-4,10b-dimethyl-2,4a,5,6-tetrahydro-1H-benzo[f]quinolin-3-one
- SMILES
- CCC1=C2C(=CC=C1)SC(=N2)SC3=CC4=C(C=C3)[C@]5(CCC(=O)N([C@@H]5CC4)C)C
- InChIKey
- VMGWGDPZHXPFTC-HYBUGGRVSA-N
- XLogP
- 6.2
- Polar surface area
- 86.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 422.149
Show 5 more facts
- chemical formula
- C₂₄H₂₆N₂OS₂
- canonical SMILES
- CCC1=C2C(=CC=C1)SC(=N2)SC3=CC4=C(C=C3)C5(CCC(=O)N(C5CC4)C)C
- isomeric SMILES
- CCC1=C2C(=CC=C1)SC(=N2)SC3=CC4=C(C=C3)[C@]5(CCC(=O)N([C@@H]5CC4)C)C
- Commons category
- Izonsteride
- subject has role
- 5-alpha-reductase inhibitors
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Chemistry
- Synthesis
- See also
- References
Izonsteride (developmental code name LY-320,236) is a selective inhibitor of the 5α-reductase, with dual effects on both the type I and type II isoforms of the enzyme. It was under development by Eli Lilly and Company and Fujisawa for the treatment of benign prostatic hyperplasia but was never marketed. Izonsteride may also be useful in the treatment of androgenic alopecia.
==Chemistry== ===Synthesis=== The scheme used to produce a somewhat more complex 5-a-reductase inhibitor relies on a chiral auxiliary to yield the final product as a single enantiomer. The first step starts with the reaction of bromotetralone with R-α-phenethylamine to afford the enamine. Reaction with methyl iodide adds the methyl group at what will be a steroid-like AB ring junction.
Excerpted from Wikipedia’s “izonsteride” article, available under the CC BY-SA 4.0 licence.