Available from stock

Ulipristal acetate

SKU: U0027

Category: Steroids

Synonyms: (11beta)-17-(Acetyloxy)-11-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione , CDB-2914 , HRP 2000 , RU 44675; 126784-99-4
CAS-Number: C₃₀H₃₇NO₄
Molecular Formula: 475.62
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Appearance: White to light yellow crystalline powder
Identity: 1H-NMR

Properties

Solvents: DMSO (30mg/ml), ethanol (30mg/ml), DMF (30mg/ml).
Melting Point: 185-188°C
Optical Activity: [α]/D +165 to +185°, c=1 in dichloromethane

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.

Hazard statements: H361fd
Precautionary statements: P280
GHS Symbol: GHS08
Signal word: Warning
Transportation: Packing Group III

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 7.7nM, respectively), rabbit uterine PR (EC50=13.6nM), and rabbit thymic glucocorticoid receptor (GR, EC50=15.4nM). It is selective for human progesterone receptors over the human estrogen receptor (ER, EC50>10,000nM). It inhibits growth of IGROV-1 and SKOV3 human ovarian cancer cells (IC50s=15.5 and 31.5?M, respectively) even after resistance to combined cisplatin and paclitaxel treatment has developed. Ulipristal acetate reverses the proliferative effect of progesterone on patient-derived germline mutant BRCA1 breast tissue xenografts in ovariectomized athymic mice. Formulations containing ulipristal acetate have been used as emergency contraceptives and to treat uterine fibroids.
Smiles: O=C1CCC2=C3[C@@]([C@@](CC[C@]4(OC(C)=O)C(C)=O)([H])[C@]4(C)C[C@]3([H])C5=CC=C(N(C)C)C=C5)([H])CCC2=C1
InChi Key: OOLLAFOLCSJHRE-ZHAKMVSLSA-N
References: (1) B.J. Attardi, et al., J. Steroid Biochem. Mol. Biol. 88, 277 (2004) , (2) P.A. Orihuela, Curr. Opin. Investig. Drugs 8, 859 (2007) (Review) , (3) K. McKeage & J.D. Croxtall, Drugs 71, 935 (2011) (Review) , (4) B. Mozzanega, et al., Trends Pharmacol. Sci. 34, 195 (2013) , (5) S. Nallasamy, et al., Reprod. Sci. 20, 371 (2013) , (6) C.D. Gamarra-Luques, et al., J. Ovarian Res. 7, 45 (2014) , (7) N. Esber, et al., PLoS One 10, e0140795 (2015) , (8) L. Communcal, et al., Oncotarget 7, 45317 (2016)

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 7.7nM, respectively), rabbit uterine PR (EC50=13.6nM), and rabbit thymic glucocorticoid receptor (GR, EC50=15.4nM). It is selective for human progesterone receptors over the human estrogen receptor (ER, EC50>10,000nM). It inhibits growth of IGROV-1 and SKOV3 human ovarian cancer cells (IC50s=15.5 and 31.5?M, respectively) even after resistance to combined cisplatin and paclitaxel treatment has developed. Ulipristal acetate reverses the proliferative effect of progesterone on patient-derived germline mutant BRCA1 breast tissue xenografts in ovariectomized athymic mice. Formulations containing ulipristal acetate have been used as emergency contraceptives and to treat uterine fibroids.

SKU: U0027 Category: Steroids

Additional information

Additional information

Synonyms	(11beta)-17-(Acetyloxy)-11-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione, CDB-2914, HRP 2000, RU 44675
Purity	≥98% (HPLC)
Appearance	White to light yellow crystalline powder
CAS-Number	126784-99-4
Molecular Formula	C30H37NO4
Molecular Weight	475.62
Identity	1H-NMR
Solvents	DMSO (30mg/ml), ethanol (30mg/ml), DMF (30mg/ml).
Melting Point	185-188°C
Optical Activity	[α]/D +165 to +185°, c=1 in dichloromethane
Smiles	O=C1CCC2=C3[C@@]([C@@](CC[C@]4(OC(C)=O)C(C)=O)([H])[C@]4(C)C[C@]3([H])C5=CC=C(N(C)C)C=C5)([H])CCC2=C1
InChi Key	OOLLAFOLCSJHRE-ZHAKMVSLSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Hazard statements	H361fd
Precautionary statements	P280
GHS Symbol	GHS08
Signal word	Warning
Transportation	Packing Group III
References	(1) B.J. Attardi, et al., J. Steroid Biochem. Mol. Biol. 88, 277 (2004), (2) P.A. Orihuela, Curr. Opin. Investig. Drugs 8, 859 (2007) (Review), (3) K. McKeage & J.D. Croxtall, Drugs 71, 935 (2011) (Review), (4) B. Mozzanega, et al., Trends Pharmacol. Sci. 34, 195 (2013), (5) S. Nallasamy, et al., Reprod. Sci. 20, 371 (2013), (6) C.D. Gamarra-Luques, et al., J. Ovarian Res. 7, 45 (2014), (7) N. Esber, et al., PLoS One 10, e0140795 (2015), (8) L. Communcal, et al., Oncotarget 7, 45317 (2016)
Quantity	50 mg, 100 mg, Bulk