9047. Tamibarotene

Nomenclature

CAS number: 94497-51-5
4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino]carbonyl]benzoic acid; p-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthylcarbamoyl)benzoic acid; AM-80; Tamibaro (Toko).
C22H25NO3; mol wt 351.44.
C 75.19%, H 7.17%, N 3.99%, O 13.66%.

Description and references

Synthetic retinoic acid receptor-α/β-selective retinoid. Prepn: K. Shudo, EP 170105 (1986 to Sumitomo; Yoshitomi); idem, US 4703110 (1987); H. Kagechika et al., J. Med. Chem. 31, 2182 (1988). HPLC determn in plasma: M. Itoh, G. Kominami, J. Immunoassay Immunochem. 22, 213 (2001). Receptor binding studies in human leukemia cells: Y. Hashimoto et al., Jpn. J. Cancer Res. 79, 473 (1988). Series of articles on pharmacokinetics and reproductive and developmental toxicity: K. Mizojiri et al., Arzneim.-Forsch. 47, 59, 195, 201, 259, 270 (1997). Inhibition of myeloma cell-induced angiogeneis: T. Sanda et al., Leukemia 19, 901 (2005). Clinical evaluation in acute promyelocytic leukemia: K. Shinjo et al., Int. J. Hematol. 72, 470 (2000).

Chemical structure

Properties

Colorless prisms from ethyl acetate-n-hexane, mp 231-232°.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Retinoids and Analogs