A selective progesterone receptor modulator
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Labeled Version(s)
26446Ulipristal Acetate-d6
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Ulipristal Acetate

Item No. 23657

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
17-(acetyloxy)-11β-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione
CAS Number
126784-99-4
Synonyms
  • CDB 2914
  • HRP 2000
  • RU 44675
Molecular Formula
C30H37NO4
Formula Weight
475.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.2 mg/ml
λmax
265, 304 nm
SMILES
CN(C)C(C=C1)=CC=C1[C@H]2C[C@@]3(C)[C@](CC[C@]3(OC(C)=O)C(C)=O)([H])[C@]4([H])CCC5=CC(CCC5=C42)=O
InChi Code
InChI=1S/C30H37NO4/c1-18(32)30(35-19(2)33)15-14-27-25-12-8-21-16-23(34)11-13-24(21)28(25)26(17-29(27,30)3)20-6-9-22(10-7-20)31(4)5/h6-7,9-10,16,25-27H,8,11-15,17H2,1-5H3/t25-,26+,27-,29-,30-/m0/s1
InChi Key
OOLLAFOLCSJHRE-ZHAKMVSLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    50 mg

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    Cayman Chemical
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    Product Description

    Ulipristal acetate is a selective progesterone receptor modulator (SPRM) that binds to the human progesterone receptors PR-A and PR-B (EC50s = 8.5 and 7.7 nM, respectively), rabbit uterine PR (EC50 = 13.6 nM), and rabbit thymic glucocorticoid receptor (GR; EC50 = 15.4 nM).1 It is selective for human progesterone receptors over the human estrogen receptor (ER; EC50 = >10,000 nM). It inhibits growth of IGROV-1 and SKOV3 human ovarian cancer cells (IC50s = 15.5 and 31.5 μM, respectively) even after resistance to combined cisplatin (Item No. 13119) and paclitaxel (Item No. 10461) treatment has developed.2 Ulipristal acetate reverses the proliferative effect of progesterone on patient-derived germline mutant BRCA1 breast tissue xenografts in ovariectomized athymic mice.3 Ulipristal acetate (40 mg/kg, i.p.) administered to female mice within 6 hours of human chorionic gonadotropin (hCG) treatment inhibits ovulation.4 Formulations containing ulipristal acetate have been used as emergency contraceptives and to treat uterine fibroids.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Attardi, B.J., Burgenson, J., Hild, S.A., et al. In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone. J. Steroid Biochem. Mol. Biol. 88(3), 277-288 (2004).

    2. Gamarra-Luques, C.D., Hapon, M.B., Goyeneche, A., et al. Resistance to cisplatin and paclitaxel does not affect the sensitivity of human ovarian cancer cells to antiprogestin-induced cytotoxicity. J. Ovarian Res. 7:45, (2014).

    3. Communcal, L., Vilasco, M., Hugon-Rodin, J., et al. Proliferation and ovarian hormone signaling are impaired in normal breast tissues from women with BRCA1 mutations: Benefit of a progesterone receptor modulator treatment as a breast cancer preventive strategy in women with inherited BRCA1 mutations. Oncotarget 7(29), 45317-45330 (2016).

    4. Nallasamy, S., Kim, J., Sitruk-Ware, R., et al. Ulipristal blocks ovulation by inhibiting progesterone receptor-dependent pathways intrinsic to the ovary. Reprod. Sci. 20(4), 371-381 (2013).