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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H35NO3
Molecular Weight 433.5834
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ULIPRISTAL

SMILES

CC(=O)[C@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CCC4=C3[C@]([H])(C[C@@]21C)c5ccc(cc5)N(C)C)O

InChI

InChIKey=HKDLNTKNLJPAIY-WKWWZUSTSA-N
InChI=1S/C28H35NO3/c1-17(30)28(32)14-13-25-23-11-7-19-15-21(31)10-12-22(19)26(23)24(16-27(25,28)2)18-5-8-20(9-6-18)29(3)4/h5-6,8-9,15,23-25,32H,7,10-14,16H2,1-4H3/t23-,24+,25-,27-,28-/m0/s1

HIDE SMILES / InChI
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ELLA

Approved Use

ella is a progesterone agonist/antagonist emergency contraceptive indicated for prevention of pregnancy following unprotected intercourse or a known or suspected contraceptive failure. ella is not intended for routine use as a contraceptive.

Launch Date

1.28165754E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
176 ng/mL
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ULIPRISTAL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
556 ng × h/mL
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ULIPRISTAL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
32 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ULIPRISTAL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ULIPRISTAL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
50 mg 1 times / day multiple, oral
Highest studied dose
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
healthy, 20–45
n = 8
Health Status: healthy
Age Group: 20–45
Sex: F
Population Size: 8
Sources:
30 mg single, oral
Recommended
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources: Page: p.33, 59
healthy, 24.5 ± 6.1
n = 1104
Health Status: healthy
Condition: Pregnancy prevention
Age Group: 24.5 ± 6.1
Sex: F
Population Size: 1104
Sources: Page: p.33, 59
Disc. AE: Vomiting...
AEs leading to
discontinuation/dose reduction:
Vomiting (0.09%)
Sources: Page: p.33, 59
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources: Page: p.8
healthy
Health Status: healthy
Condition: Pregnancy prevention
Sex: F
Sources: Page: p.8
30 mg single, oral
Recommended
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources: Page: p.2
healthy
Health Status: healthy
Condition: Pregnancy prevention
Sex: F
Sources: Page: p.2
Other AEs: Ectopic pregnancy...
AEs

AEs

AESignificanceDosePopulation
Vomiting 0.09%
Disc. AE
30 mg single, oral
Recommended
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources: Page: p.33, 59
healthy, 24.5 ± 6.1
n = 1104
Health Status: healthy
Condition: Pregnancy prevention
Age Group: 24.5 ± 6.1
Sex: F
Population Size: 1104
Sources: Page: p.33, 59
Ectopic pregnancy
30 mg single, oral
Recommended
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources: Page: p.2
healthy
Health Status: healthy
Condition: Pregnancy prevention
Sex: F
Sources: Page: p.2
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
yes [IC50 2.6 uM]
yes [IC50 4.7 uM]
yes
yes
yes
yes
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Emergency contraception: potential role of ulipristal acetate.
2010 Aug 9
Ulipristal acetate, a progesterone receptor modulator for emergency contraception.
2012 Apr
Ulipristal acetate as an emergency contraceptive agent.
2012 Sep
Patents

Patents

Sample Use Guides

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 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.
Name Type Language
ULIPRISTAL
EMA EPAR   INN   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
ULIPRISTAL ACETATE ULIPRISTAL [MI]
Common Name English
ULIPRISTAL [VANDF]
Common Name English
ULIPRISTAL [WHO-DD]
Common Name English
ULIPRISTAL [USAN]
Common Name English
11.BETA.-(4-(DIMETHYLAMINO)PHENYL)-17-HYDROXY-19-NORPREGNA-4,9-DIENE-3,20-DIONE
Common Name English
ULIPRISTAL [INN]
Common Name English
ULIPRISTAL [EMA EPAR]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1891
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
WHO-ATC G03XB02
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
WHO-VATC QG03XB02
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
WHO-ATC G03AD02
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
WHO-VATC QG03AD02
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
NDF-RT N0000191263
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
Code System Code Type Description
EVMPD
SUB30471
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY
DRUG CENTRAL
4166
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY
FDA UNII
6J5J15Q2X8
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY
DRUG BANK
DB08867
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY
CAS
159811-51-5
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY
MERCK INDEX
M11300
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C91056
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY
MESH
C094854
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY
RXCUI
1005921
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY RxNorm
PUBCHEM
13559281
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY
LACTMED
Ulipristal
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY
NDF-RT
N0000191262
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY Selective Progesterone Receptor Modulators [MoA]
ChEMBL
CHEMBL2103846
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY
INN
8367
Created by admin on Sat Jun 26 11:54:10 UTC 2021 , Edited by admin on Sat Jun 26 11:54:10 UTC 2021
PRIMARY