U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)C[C@H](C3=CC=C(C=C3)N(C)C)C4=C5CCC(=O)C=C5CC[C@@]24[H]

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
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 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 ACETATE
DASH   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
ULIPRISTAL ACETATE [MI]
Common Name English
Ulipristal acetate [WHO-DD]
Common Name English
VA-2914
Code English
ULIPRISTAL ACETATE [MART.]
Common Name English
CDB-2914
Code English
17.ALPHA.-ACETOXY-11.BETA.-(4-DIMETHYLAMINOPHENYL)-19-NORPREGNA-4,9-DIEN-3,20-DIONE
Common Name English
ELLAONE
Brand Name English
ULIPRISTAL ACETATE [JAN]
Common Name English
ULIPRISTAL ACETATE [USAN]
Common Name English
(11.BETA.)-17-(ACETYLOXY)-11-(4-(DIMETHYLAMINO)PHENYL)-19-NORPREGNA-4,9-DIENE-3,20-DIONE
Common Name English
ULIPRISTAL ACETATE [VANDF]
Common Name English
VA2914
Code English
ULIPRISTAL ACETATE [ORANGE BOOK]
Common Name English
ELLA
Brand Name English
RTI-3021-012
Code English
PGL-4001
Code English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS ELLAONE (AUTHORIZED: CONTRACEPTION, POSTCOITAL)
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
NCI_THESAURUS C1891
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
EMA ASSESSMENT REPORTS ESMYA (AUTHORIZED: LEIOMYOMA)
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
Code System Code Type Description
FDA UNII
YF7V70N02B
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
USAN
WW-144
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
RS_ITEM_NUM
1705367
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
DRUG BANK
DBSALT000184
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
NCI_THESAURUS
C91057
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
IUPHAR
7460
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
MESH
C555622
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
SMS_ID
100000093411
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
EVMPD
SUB30470
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
CAS
126784-99-4
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
DAILYMED
YF7V70N02B
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
RXCUI
1005920
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID30155294
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
WIKIPEDIA
ULIPRISTAL ACETATE
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
MERCK INDEX
m11300
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY Merck Index
CHEBI
71025
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
PUBCHEM
130904
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL260538
Created by admin on Fri Dec 15 15:45:34 UTC 2023 , Edited by admin on Fri Dec 15 15:45:34 UTC 2023
PRIMARY