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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H37NO4
Molecular Weight 475.6191
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ULIPRISTAL ACETATE

SMILES

CN(C)C1=CC=C(C=C1)[C@H]2C[C@@]3(C)[C@@H](CC[C@]3(OC(C)=O)C(C)=O)[C@@H]4CCC5=CC(=O)CCC5=C24

InChI

InChIKey=OOLLAFOLCSJHRE-ZHAKMVSLSA-N
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

HIDE SMILES / InChI

Molecular Formula C30H37NO4
Molecular Weight 475.6191
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ulipristal acetate (also known as CDB-2914 and PGL4001 and trade name Ella in the U.S) is a novel oral emergency contraceptive designed and developed by HRA Pharma. It is a selective progesterone receptor modulator, which reversibly blocks the progesterone receptors in target tissues it was approved in May 2009 by the European Commission and in August 2010 by the FDA as safe and effective in preventing unintended pregnancy for up to 120 hours – or five days – post- unprotected intercourse or contraceptive failure. Ella is not intended for routine use as a contraceptive. When taken immediately before ovulation is to occur, ella postpones follicular rupture. The likely primary mechanism of action of ulipristal acetate for emergency contraception is therefore inhibition or delay of ovulation; however, alterations to the endometrium that may affect implantation may also contribute to efficacy. The most common side effects are: headache, nausea, stomach (abdominal) pain, menstrual pain. Some women taking ella may have their next period earlier or later than expected. If your period is more than a week late, you should get a pregnancy test.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ELLA

Cmax

ValueDoseCo-administeredAnalytePopulation
176 ng/mL
30 mg single, oral
ULIPRISTAL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
556 ng × h/mL
30 mg single, oral
ULIPRISTAL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
32 h
30 mg single, oral
ULIPRISTAL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
30 mg single, oral
ULIPRISTAL plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Instruct patients to take one tablet orally as soon as possible within 120 hours (5 days) after unprotected intercourse or a known or suspected contraceptive failure. The tablet can be taken with or without food. If vomiting occurs within 3 hours of ella (ulipristal acetate) intake, consideration should be given to repeating the dose. ella can be taken at any time during the menstrual cycle.
Route of Administration: Oral
In Vitro Use Guide
In vitro studies revealed that the presence of ulipristal acetate (UPA) during capacitation and/or gamete co-incubation does not affect fertilization. For in vitro fertilization experiments, mouse epididymal spermatozoa capacitated in the presence of different concentrations of UPA (0-1000 ng/ml) were used to inseminate cumulus-intact or cumulus-free eggs in the presence or absence of UPA during gamete co-incubation, and the percentage of fertilized eggs was determined.
Substance Class Chemical
Record UNII
YF7V70N02B
Record Status Validated (UNII)
Record Version