Dimethylcurcumin

Dimethylcurcumin (development code ASC-J9) is a nonsteroidal antiandrogen and a synthetic curcuminoid which is under development by AndroScience Corporation as a topical medication for the treatment of acne vulgaris.[1][2] It has also been under investigation for the treatment of male pattern hair loss, spinal muscular atrophy, and wounds, but no development has been reported for these indications.[1] There has been interest in the drug for the potential treatment of prostate cancer as well.[2][3] As of 2017, it is in phase II clinical trials for acne vulgaris.[1]

Dimethylcurcumin
Clinical data
Other namesASC-J9; GO-Y025
Routes of
administration		Topical
Drug classNonsteroidal antiandrogen; Selective androgen receptor degrader
Identifiers
IUPAC name
  • (1E,4Z,6E)-1,7-Bis(3,4-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H24O6
Molar mass396.439 g·mol−1
3D model (JSmol)
SMILES
  • COC1=C(C=C(C=C1)/C=C/C(=C/C(=O)/C=C/C2=CC(=C(C=C2)OC)OC)/O)OC
InChI
  • InChI=1S/C23H24O6/c1-26-20-11-7-16(13-22(20)28-3)5-9-18(24)15-19(25)10-6-17-8-12-21(27-2)23(14-17)29-4/h5-15,24H,1-4H3/b9-5+,10-6+,18-15-
  • Key:ZMGUKFHHNQMKJI-CIOHCNBKSA-N

Dimethylcurcumin is an androgen receptor (AR) inhibitor and shows strong and specific antiandrogenic activity in vitro (e.g., against LNCaP cell growth) at sufficiently high concentrations.[3] However, its mechanism of action and effects differ from those of conventional antiandrogens; it is not an antagonist of the AR and instead appears to act as a selective degradation enhancer (SARD) of certain subpopulations of the AR, for instance those present in the prostate gland.[1][3][2]

See also

References
  1. "ASC-J9 (dimethylcurcumin)". AdisInsight.
  2. Shi Q, Shih CC, Lee KH (2009). "Novel anti-prostate cancer curcumin analogues that enhance androgen receptor degradation activity". Anticancer Agents Med Chem. 9 (8): 904–12. doi:10.2174/187152009789124655. PMID 19663790.
  3. Lai KP, Huang CK, Chang YJ, Chung CY, Yamashita S, Li L, Lee SO, Yeh S, Chang C (2013). "New therapeutic approach to suppress castration-resistant prostate cancer using ASC-J9 via targeting androgen receptor in selective prostate cells". Am. J. Pathol. 182 (2): 460–73. doi:10.1016/j.ajpath.2012.10.029. PMC 3562731. PMID 23219429.


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