Ulipristal acetateProduct ingredient for Ulipristal

Name
Ulipristal acetate
Drug Entry
Ulipristal

Ulipristal is a selective progesterone receptor modulator used for the purposes of emergency contraception (Ella) and for the treatment of uterine fibroids (Fibristal). It is a derivative of 19-norprogesterone and has both antagonistic and partial agonist activity at the progesterone receptor. It also binds to glucocorticoid receptor, however compared to mifepristone (a progesterone receptor antagonist), ulipristal is more tolerable and has lower glucocorticoid activity and better binding affinity.

Ulipristal is currently recommended as first line therapy for emergency contraception, due to improved efficacy and similar side effect profile as compared to the traditional use of levonorgestrel or the Yuzpe regimen. The exact mechanism of action for ulipristal is still currently debated, though there is evidence that it functions by inhibiting ovulation. A recent systematic review proclaimed that the majority of available evidence demonstrates an inhibitory effect on ovulation rather than a post-fertilization effect on the endometrium, which has been heavily debated due to ethical concerns related to abortion (Rosato et al, 2016). Nevertheless, current and ongoing research into the agent's mechanism of action as an emergency contraceptive continue to provide potentially plausible evidence that ulipristal may, in fact, elicit activity on the endometrium that prevents embryo implantation 10,11,12.

Accession Number
DBSALT000184
Structure
Synonyms
Not Available
UNII
YF7V70N02B
CAS Number
126784-99-4
Weight
Average: 475.6191
Monoisotopic: 475.272258677
Chemical Formula
C30H37NO4
InChI Key
OOLLAFOLCSJHRE-ZHAKMVSLSA-N
InChI
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
IUPAC Name
(1R,3aS,3bS,10R,11aS)-1-acetyl-10-[4-(dimethylamino)phenyl]-11a-methyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl acetate
SMILES
[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)C[C@H](C1=CC=C(C=C1)N(C)C)C1=C3CCC(=O)C=C3CC[C@@]21[H]
PubChem Compound
130904
ChemSpider
115762
BindingDB
50375424
ChEBI
71025
ChEMBL
CHEMBL260538
ZINC
ZINC000003920657
PDBe Ligand
2S0
Wikipedia
Ulipristal_acetate
Predicted Properties
PropertyValueSource
Water Solubility0.00341 mg/mLALOGPS
logP5.11ALOGPS
logP4.62Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)17.74Chemaxon
pKa (Strongest Basic)4.89Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area63.68 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity138.44 m3·mol-1Chemaxon
Polarizability53.91 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon