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SML1469

Sigma-Aldrich

Ulipristal acetate

≥98% (HPLC)

Synonym(s):

(11β)-17-(Acetyloxy)-11-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione, CDB-2914

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About This Item

Empirical Formula (Hill Notation):
C30H37NO4
CAS Number:
126784-99-4
Molecular Weight:
475.62
MDL number:
MFCD00899035
UNSPSC Code:
51111800
PubChem Substance ID:
329825903
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +165 to +185°, c = 1 in dichloromethane

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

O=C(C)[C@@]1(OC(C)=O)CC[C@@]2([H])[C@]3([H])CCC4=CC(CCC4=C3[C@@H](C5=CC=C(N(C)C)C=C5)C[C@@]21C)=O

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

Gene Information

human ... PGR(5241)

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Biochem/physiol Actions

Ulipristal acetate is a selective progesterone receptor modulator (SPRM) with tissue-selective partial antagonist activity. It has clinical use both as an emergency contraceptive and as a treatment for uterine fibroids. Ulipristal acetate acts as a partial antagonist on the hypothalamic–pituitary–ovarian axis to inhibit or delay ovulation without affecting human embryo implantation. As a progesterone antagonist, Ulipristal acetate selectively suppresses neo-vascularization, cell proliferation, and survival in uterine fibroid cells, but not in normal myometrial cells.
Ulipristal acetate is known to reduce uncontrolled bleeding due to post uterine fibroid surgery.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361fd

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ulipristal acetate versus placebo for fibroid treatment before surgery.
Donnez J, et al.
The New England Journal of Medicine, 366(5), 409-420 (2012)

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