Dimethylcurcumin - Misplaced Pages

Chemical compound Pharmaceutical compound

Dimethylcurcumin
Clinical data

Other names	ASC-J9; GO-Y025
Routes of administration	Topical
Drug class	Nonsteroidal 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	52328-98-0
PubChem CID	6477182
ChemSpider	4978553
UNII	D60XLY608D
CompTox Dashboard (EPA)	DTXSID101316356 DTXSID10200352, DTXSID101316356
Chemical and physical data
Formula	C₂₃H₂₄O₆
Molar mass	396.439 g·mol
3D model (JSmol)	Interactive image
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 (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. 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. There has been interest in the drug for the potential treatment of prostate cancer as well. As of 2017, it is in phase II clinical trials for acne vulgaris.

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. 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.

References

^ "ASC-J9 (dimethylcurcumin)". AdisInsight.
^ 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.
^ 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.

ARTooltip Androgen receptor

Agonists

17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone
5α-Dihydronormethandrone

5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
5α-Dihydronorethisterone

SARMsTooltip Selective androgen receptor modulator

Antagonists

Agonists	Cations (incl. aluminium, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone

See also: Receptor/signaling modulators; Androgens and antiandrogens; Estrogen receptor modulators; Progesterone receptor modulators; List of androgens and anabolic steroids

v t e Curcuminoids
1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one Bisdemethoxycurcumin Curcumin Desmethoxycurcumin Dimethylcurcumin
Curcuminoid dyes	Rosocyanine Rubrocurcumin

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