Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H35NO3 |
Molecular Weight | 433.5824 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[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=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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29999714 |
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Target ID: CHEMBL208 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | ELLA Approved Useella 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 Date2010 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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: |
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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... Other AEs: Ectopic pregnancy Sources: Page: p.2 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 63-65 |
no | |||
Page: 63-65 |
no | |||
Page: 60.0 |
no | |||
Page: 61-63 |
no | |||
Page: 61-63 |
no | |||
Page: 60.0 |
no | |||
Page: 61-63 |
no | |||
Page: 61-63 |
no | |||
Page: 60.0 |
no | |||
Page: 63-65 |
no | |||
Page: 63-65 |
no | |||
Page: 61-63 |
no | |||
Page: 61-63 |
yes [IC50 2.6 uM] | |||
Page: 61-63 |
yes [IC50 4.7 uM] | |||
Page: 61-63 |
yes | |||
Page: 34, 58-60 |
yes | |||
Page: 34, 58-60 |
yes | |||
Page: 61-63 |
yes | |||
Page: 15, 34, 58-60 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 34, 58 |
major | |||
Page: 15, 34, 58 |
major | |||
Page: 58.0 |
minor | |||
Page: 58.0 |
minor | |||
Page: 58.0 |
weak | |||
Page: 58.0 |
weak | |||
Page: 58.0 |
weak |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 23, 30-31 |
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 Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26582845
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.
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NCI_THESAURUS |
C1891
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WHO-ATC |
G03XB02
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WHO-VATC |
QG03XB02
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WHO-ATC |
G03AD02
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WHO-VATC |
QG03AD02
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NDF-RT |
N0000191263
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m11300
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C91056
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C094854
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1005921
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13559281
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Ulipristal
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N0000191262
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PRIMARY | Selective Progesterone Receptor Modulators [MoA] | ||
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CHEMBL2103846
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ACTIVE MOIETY