10336. Ulipristal Acetate

Nomenclature

CAS number: 126784-99-4
(11β)-17-(Acetyloxy)-11-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione; 17α-acetoxy-11β-(4-dimethylaminophenyl)-19-norpregna-4,9-dien-3,20-dione; CDB-2914; PGL-4001; RTI-3021-012; VA-2914; Ella (HRA Pharma).
C30H37NO4; mol wt 475.62.
C 75.76%, H 7.84%, N 2.94%, O 13.46%.

Description and references

Selective progesterone receptor modulator (SPRM); synthetic 19-norprogesterone derivative. Prepn: C. E. Cook et al., WO 8912448; eidem, US 4954490 (1989, 1990 both to Research Triangle Inst.). Large scale synthesis: P. N. Rao et al., Steroids 65, 395 (2000) DOI PubMed. Pharmacology: E. E. Gainer, A. Ulmann, ibid. 68, 1005 (2003) DOI PubMed; D. L. Blithe et al., ibid., 1013 DOI PubMed. Clinical evaluation as ovulation inhibitor: N. Chabbert-Buffet et al., J. Clin. Endocrinol. Metab. 92, 3582 (2007) DOI PubMed; in treatment of uterine fibroids: E. D. Levens et al., Obstet. Gynecol. 111, 1129 (2008) DOI PubMed. Review: P. A. Orihuela, Curr. Opin. Investig. Drugs 8, 859-866 (2007) PubMed.

Chemical structure

Properties

Crystals from aq ethanol, mp 183-185° (Rao); also reported as crystals from methanol + water, mp 118-121° (Cook). uv max (methanol): 261 nm.

Derivative

Ulipristal.

Nomenclature

CAS number: 159811-51-5
(11β)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-19-norpregna-4,9-diene-3,20-dione.
C28H35NO3; mol wt 433.58.
C 77.56%, H 8.14%, N 3.23%, O 11.07%.

Properties

Crystals from ether, mp 125-128°.

Therapeutic Category

In treatment of uterine fibroids.

Keywords

Selective Progesterone Receptor Modulator (SPRM)