Adapalene-d3

Adapalene-d3 is intended for use as an internal standard for the quantification of adapalene (Cay-13655) by GC- or LC-MS. Adapalene is a synthetic retinoid and an agonist of retinoic acid receptors (RARs, Kds = 1,100, 34, and 130 nM for RARalpha, RARbeta, and RARgamma, respectively). It inhibits growth and differentiation of sebocytes in a concentration-dependent manner in primary rat preputial cell culture. Adapalene (10 µM) completely inhibits the activity of soybean 15-lipoxygenase (15-LOX) in an enzyme assay and inhibits the 5- and 15-LOX pathways in human blood polymorphonuclear leukocytes (PMNs). It reduces the protein levels of toll-like receptor 2 (TLR2) and IL-10 in skin explants isolated from patients with acne and healthy controls in a concentration-dependent manner but increases the expression of the antigen-presenting protein CD1d in acne skin explants while decreasing it in control explants. It inhibits inflammation in rodent models of ear edema induced by arachidonic acid and carrageenan-induced paw edema. Adapalene (100 µM) also induces apoptosis and inhibits proliferation of CC-531, HT-29, and LoVo colon cancer cells and reduces tumor growth in a DLD-1 colon cancer nude mouse xenograft model in a dose-dependent manner. Formulations containing adapalene have been used in the treatment of acne vulgaris.Formal Name: 6-(3-((3R,5R,7R)-adamantan-1-yl)-4-(methoxy-d3)phenyl)-2-naphthoic acid. CAS Number: 1276433-89-6. Molecular Formula: C28H25D3O3. Formula Weight: 415.5. Purity: >99% deuterated forms (d1-d3). Formulation: (Request formulation change), A solid. Solubility: DMF: 5 mg/ml, DMSO: 5 mg/ml. SMILES: [2H]C([2H])([2H])OC1=C(C2(C[C@H](C3)C4)C[C@H]4C[C@H]3C2)C=C(C=C1)C(C=C5)=CC6=C5C=C(C(O)=O)C=C6. InChi Code: InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)/t17-,18+,19-,28?/i1D3. InChi Key: LZCDAPDGXCYOEH-FRKLENEQSA-N.