ULIPRISTAL ACETATE

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 Search

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

Molecular Formula	C30H37NO4
Molecular Weight	475.6191
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022474s000lbl.pdf

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 Target	Pharmacology	Condition	Potency
Progesterone receptor 61 Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29999714	Modulator 828
Progesterone receptor 61 Target ID: CHEMBL208 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022474s000lbl.pdf	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pregnancy 65 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022474s000lbl.pdf	Preventing		Approved 8429	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 2010

C_max

Value	Dose	Co-administered	Analyte	Population
176 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022474s010lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022474s010lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
32 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022474s010lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
6% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022474s010lbl.pdf	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: https://pubmed.ncbi.nlm.nih.gov/23550906	healthy, 20–45 n = 8 Health Status: healthy Age Group: 20–45 Sex: F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/23550906	Sources: https://pubmed.ncbi.nlm.nih.gov/23550906
30 mg single, oral Recommended Dose: 30 mg Route: oral Route: single Dose: 30 mg Sources: https://www.fda.gov/media/83203/download 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: https://www.fda.gov/media/83203/download Page: p.33, 59	Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (0.09%) Sources: https://www.fda.gov/media/83203/download Page: p.33, 59
200 mg single, oral Overdose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://www.ema.europa.eu/en/documents/product-information/ellaone-epar-product-information_en.pdf Page: p.8	healthy Health Status: healthy Condition: Pregnancy prevention Sex: F Sources: https://www.ema.europa.eu/en/documents/product-information/ellaone-epar-product-information_en.pdf Page: p.8	Sources: https://www.ema.europa.eu/en/documents/product-information/ellaone-epar-product-information_en.pdf Page: p.8
30 mg single, oral Recommended Dose: 30 mg Route: oral Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022474s000lbl.pdf Page: p.2	healthy Health Status: healthy Condition: Pregnancy prevention Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022474s000lbl.pdf Page: p.2	Other AEs: Ectopic pregnancy... Other AEs: Ectopic pregnancy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022474s000lbl.pdf 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: https://www.fda.gov/media/83203/download 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: https://www.fda.gov/media/83203/download Page: p.33, 59
Ectopic pregnancy		30 mg single, oral Recommended Dose: 30 mg Route: oral Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022474s000lbl.pdf Page: p.2	healthy Health Status: healthy Condition: Pregnancy prevention Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022474s000lbl.pdf Page: p.2

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587 inducer 781	substrate 1037 inhibitor 1767	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1478 CYP1A2 1524 CYP2E1 882 CYP2A6 707 CYP2B6 810 CYP2C8 911	CYP2E1 667 CYP1A2 1054 CYP2A6 543 CYP2C19 991	CYP1A2 701

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=63 Page: 63-65	no
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=63 Page: 63-65	no	CDB-3877 2
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=60 Page: 60.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=61 Page: 61-63	no	CDB-3877 2
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=61 Page: 61-63	no	CDB-3877 2
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=60 Page: 60.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=61 Page: 61-63	no	CDB-3877 2
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=61 Page: 61-63	no	CDB-3877 2
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=60 Page: 60.0	no
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=63 Page: 63-65	no
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=63 Page: 63-65	no	CDB-3877 2
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=61 Page: 61-63	no	CDB-3877 2
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=61 Page: 61-63	yes [IC50 2.6 uM]	CDB-3877 2
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=61 Page: 61-63	yes [IC50 4.7 uM]	CDB-3877 2
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=61 Page: 61-63	yes	CDB-3877 2
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=60 Page: 34, 58-60	yes
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=60 Page: 34, 58-60	yes
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=61 Page: 61-63	yes	CDB-3877 2
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=60 Page: 15, 34, 58-60	yes

Drug as victim

Target	Modality	Activity
CYP2E1 667	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=58 Page: 34, 58	major
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=58 Page: 15, 34, 58	major
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=58 Page: 58.0	minor
CYP2A6 543	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=58 Page: 58.0	minor
CYP2C19 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=58 Page: 58.0	weak
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=58 Page: 58.0	weak
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=58 Page: 58.0	weak

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022474s000PharmR.pdf#page=30 Page: 23, 30-31

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY528300	https://www.001chemical.com/chem/159811-51-5
AK Scientific, Inc. (AKSCI)	2779AH	http://www.aksci.com/item_detail.php?cat=2779AH
Aaron Chemicals	AR001S3N	http://www.aaronchem.com/159811-51-5
Acadechem	ACDS-078140	http://acadechemical.com/product/229125
Achemtek	0102-013523	http://www.achemtek.com/159811-51-5
Acorn PharmaTech	ACN-053816	http://www.acornpharmatech.com/
Alsachim	3794	http://www.alsachim.com/product-C5098-glo.bal-view.html
Angel Pharmatech	AG257506	http://www.angelpharmatech.com/159811-51-5.html
Angene	AGN-PC-00N2AG	http://www.angenechemical.com/productshow/AGN-PC-00N2AG.html
ApexBio Technology	B2134	http://www.apexbt.com/ulipristal.html
BioChemPartner	BCP12665	http://www.biochempartner.com/159811-51-5-BCP12665
BioCrick	BCC4944	http://www.biocrick.com/Ulipristal-BCC4944.html
BioSynth	J-009646	https://www.biosynth.com/en/products/all-products/products/J-009646.html
Chem Scene	CS-0003658	http://www.chemscene.com/159811-51-5.html
Chemspace	CSSB00015189861	https://chem-space.com/CSSB00015189861
Chemspace	CSSB00020669023	https://chem-space.com/CSSB00020669023
Finetech	FT-0675730	http://www.finetechnology-ind.com/prod/detail/pub/159811-51-5.html
Hairui	HR145039	http://www.hairuichem.com/en/product/159811-51-5.html
Lab Network	LN01293266	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01293266
Matrix Scientific	146132	https://www.matrixscientific.com/146132.html
MedChem Express	HY-14959	https://www.medchemexpress.com/ulipristal.html
MolPort	MolPort-044-193-855	https://www.molport.com/shop/molecule-link/MolPort-044-193-855
Molcore	MC528300	https://www.molcore.com/product/159811-51-5
MuseChem	A000611	https://www.musechem.com/product/A000611.html
Smolecule	S546316	http://www.smolecule.com/products/s546316
Smolecule	S646139	https://www.smolecule.com/products/s646139
THE BioTek	bt-284865	https://www.thebiotek.com/product/inhibitors/bt-284865
eNovation Chemicals	D320179	http://www.enovationchem.com/productDetails.asp?productID=D320179
iChemical	EBD146589	http://www.ichemical.com/products/159811-51-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Emergency contraception: potential role of ulipristal acetate.	2010 Aug 9	21072297
Ulipristal acetate, a progesterone receptor modulator for emergency contraception.	2012 Apr	22629083
Ulipristal acetate as an emergency contraceptive agent.	2012 Sep	22770536

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 Created by `admin` on `Fri Dec 15 15:45:34 GMT 2023` Edited by `admin` on `Fri Dec 15 15:45:34 GMT 2023`
Record UNII	YF7V70N02B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ULIPRISTAL ACETATE

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)