Identification

Name
Ulipristal
Accession Number
DB08867  (DB05366)
Type
Small Molecule
Groups
Approved
Description

Ulipristal is a selective progesterone receptor modulator used for the purposes of emergency contraception (Ella) and for the treatment of uterine fibroids (Fibristal). It is a derivative of 19-norprogesterone and has both antagonistic and partial agonist activity at the progesterone receptor. It also binds to glucocorticoid receptor, however compared to mifepristone (a progesterone receptor antagonist), ulipristal is more tolerable and has lower glucocorticoid activity and better binding affinity.

Ulipristal is currently recommended as first line therapy for emergency contraception, due to improved efficacy and similar side effect profile as compared to the traditional use of levonorgestrel or the Yuzpe regimen. The exact mechanism of action for ulipristal is still currently debated, though there is evidence that it functions by inhibiting ovulation. A recent systematic review proclaimed that the majority of available evidence demonstrates an inhibitory effect on ovulation rather than a post-fertilization effect on the endometrium, which has been heavily debated due to ethical concerns related to abortion (Rosato et al, 2016).

Structure
Thumb
Synonyms
Not Available
External IDs
CDB 2914 / CDB-2914 / CDB2914
Product Ingredients
IngredientUNIICASInChI Key
Ulipristal AcetateYF7V70N02B126784-99-4OOLLAFOLCSJHRE-ZHAKMVSLSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EllaTablet30 mg/1OralA S Medication Solutions2010-08-132017-06-20Us
EllaTablet30 mgOralLaboratoire HRA Pharma2015-09-01Not applicableCanada
EllaTablet30 mg/1OralAfaxys Pharma Llc2010-08-13Not applicableUs
EllaoneTablet30 mgOralLaboratoire HRA Pharma2009-05-15Not applicableEu
EsmyaTablet5 mgOralGedeon Richter Ltd.2012-02-23Not applicableEu
EsmyaTablet5 mgOralGedeon Richter Ltd.2012-02-23Not applicableEu
EsmyaTablet5 mgOralGedeon Richter Ltd.2012-02-23Not applicableEu
EsmyaTablet5 mgOralGedeon Richter Ltd.2012-02-23Not applicableEu
EsmyaTablet5 mgOralGedeon Richter Ltd.2012-02-23Not applicableEu
FibristalTablet5 mgOralAllergan Pharma Co.2013-07-04Not applicableCanada
International/Other Brands
EllaOne (HRA Pharma ) / Esmya (Preglen UK )
Categories
UNII
6J5J15Q2X8
CAS number
159811-51-5
Weight
Average: 433.592
Monoisotopic: 433.261693991
Chemical Formula
C28H35NO3
InChI Key
HKDLNTKNLJPAIY-WKWWZUSTSA-N
InChI
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
IUPAC Name
(10S,11S,14R,15S,17R)-14-acetyl-17-[4-(dimethylamino)phenyl]-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6-dien-5-one
SMILES
CN(C)C1=CC=C(C=C1)[[email protected]]1C[[email protected]@]2(C)[[email protected]@H](CC[[email protected]]2(O)C(C)=O)[[email protected]@H]2CCC3=CC(=O)CCC3=C12

Pharmacology

Indication

As the product Ella (available in Canada and the US), ulipristal is indicated for use as emergency contraception after unprotected intercourse or possible contraceptive failure when administered within 120 hours (5 days) after unprotected intercourse or a known or suspected contraceptive failure. As the product Fibristal (available in Canada), ulipristal is indicated for treatment of the signs and symptoms of uterine fibroids in adult women.

Structured Indications
Pharmacodynamics

Ulipristal is a selective, reversible progestin receptor modulator and its tissue targets include the uterus, cervix, ovaries, and hypothalamus. Ulipristal may act as an agonist or antagonist in the presence or absence of progesterone based on the tissue target. If given mid-follicular phase, development of the follicle growth is delayed and estradiol concentrations decrease. If given at the time when luteinizing hormone peaks, follicular rapture is delayed by several days. If given early-luteal phase, a decrease in endometrial thickness can be observed.

Mechanism of action

The exact mechanism of action has been heavily debated, although recent evidence suggests that ulipristal functions primarily through inhibition of ovulation, via prevention of progestin binding to the progesterone receptor. In the treatment of fibroids, ulipristal exerts a direct action on fibroids reducing their size through inhibition of cell proliferation and induction of apoptosis.

TargetActionsOrganism
AProgesterone receptor
modulator
Human
AGlucocorticoid receptor
antagonist
Human
UAndrogen receptorNot AvailableHuman
Absorption

Tmax, healthy subjects, single oral dose = 60-90 minutes; Cmax, healthy subjects, single oral dose = 176 ± 89 ng/mL; AUC(0-∞), healthy subjects, single oral dose = 556 ± 260 ng·h/mL;

Volume of distribution
Not Available
Protein binding

>94% bound to plasma proteins such as albumin, alpha1-acid glycoprotein, lipoproteins (VLDL, LDL, and HDL- due to its lipophillic nature)

Metabolism

Ulipristal is metabolized by CYP3A4 and to a lesser extent by CYP1A2 into mono-demethylated (active) and di-methylated (inactive) metabolites.

Route of elimination
Not Available
Half life

Mean elimination half-life, single oral dose, healthy subject = 32.4 ± 6.3 hours

Clearance

Mean oral clearance, single oral dose, healthy subject (CL/F) = 76.8 ± 64.0L/h

Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Ulipristal can be increased when it is combined with Abiraterone.Approved
AllylestrenolThe therapeutic efficacy of Allylestrenol can be decreased when used in combination with Ulipristal.Approved
AltrenogestThe therapeutic efficacy of Altrenogest can be decreased when used in combination with Ulipristal.Vet Approved
AmiodaroneThe serum concentration of Ulipristal can be increased when it is combined with Amiodarone.Approved, Investigational
AmobarbitalThe serum concentration of Ulipristal can be decreased when it is combined with Amobarbital.Approved, Illicit
AprepitantThe serum concentration of Ulipristal can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe serum concentration of Ulipristal can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe serum concentration of Ulipristal can be increased when it is combined with Atomoxetine.Approved
AzithromycinThe metabolism of Ulipristal can be decreased when combined with Azithromycin.Approved
BarbexacloneThe serum concentration of Ulipristal can be decreased when it is combined with Barbexaclone.Experimental
BarbitalThe serum concentration of Ulipristal can be decreased when it is combined with Barbital.Illicit
BoceprevirThe serum concentration of Ulipristal can be increased when it is combined with Boceprevir.Approved, Withdrawn
BortezomibThe serum concentration of Ulipristal can be increased when it is combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Ulipristal can be decreased when it is combined with Bosentan.Approved, Investigational
CaffeineThe metabolism of Ulipristal can be decreased when combined with Caffeine.Approved
CarbamazepineThe serum concentration of Ulipristal can be decreased when it is combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Ulipristal can be increased when it is combined with Ceritinib.Approved
CitalopramThe metabolism of Ulipristal can be decreased when combined with Citalopram.Approved
ClarithromycinThe serum concentration of Ulipristal can be increased when it is combined with Clarithromycin.Approved
ClemastineThe serum concentration of Ulipristal can be increased when it is combined with Clemastine.Approved
ClotrimazoleThe serum concentration of Ulipristal can be increased when it is combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Ulipristal can be increased when it is combined with Cobicistat.Approved
ConivaptanThe serum concentration of Ulipristal can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe serum concentration of Ulipristal can be increased when it is combined with Crizotinib.Approved
CyclosporineThe serum concentration of Ulipristal can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Ulipristal can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Ulipristal can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe serum concentration of Ulipristal can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Ulipristal can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Ulipristal can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe serum concentration of Ulipristal can be increased when it is combined with Delavirdine.Approved
DemegestoneThe therapeutic efficacy of Demegestone can be decreased when used in combination with Ulipristal.Experimental
DesogestrelThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Ulipristal.Approved
DienogestThe therapeutic efficacy of Dienogest can be decreased when used in combination with Ulipristal.Approved
DihydroergotamineThe serum concentration of Ulipristal can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Ulipristal can be increased when it is combined with Diltiazem.Approved
DosulepinThe metabolism of Ulipristal can be decreased when combined with Dosulepin.Approved
DoxycyclineThe serum concentration of Ulipristal can be increased when it is combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe serum concentration of Ulipristal can be increased when it is combined with Dronedarone.Approved
DydrogesteroneThe therapeutic efficacy of Dydrogesterone can be decreased when used in combination with Ulipristal.Approved, Investigational, Withdrawn
EfavirenzThe serum concentration of Ulipristal can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Ulipristal can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe serum concentration of Ulipristal can be increased when it is combined with Erythromycin.Approved, Vet Approved
EthynodiolThe therapeutic efficacy of Ethynodiol can be decreased when used in combination with Ulipristal.Experimental
EtonogestrelThe therapeutic efficacy of Etonogestrel can be decreased when used in combination with Ulipristal.Approved, Investigational
FelbamateThe serum concentration of Ulipristal can be decreased when it is combined with Felbamate.Approved
FluconazoleThe serum concentration of Ulipristal can be increased when it is combined with Fluconazole.Approved
FluvoxamineThe serum concentration of Ulipristal can be increased when it is combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe serum concentration of Ulipristal can be increased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Ulipristal can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Ulipristal can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Ulipristal can be increased when it is combined with Fusidic Acid.Approved
GestodeneThe therapeutic efficacy of Gestodene can be decreased when used in combination with Ulipristal.Approved, Investigational
GestonoroneThe therapeutic efficacy of Gestonorone can be decreased when used in combination with Ulipristal.Experimental
GestrinoneThe therapeutic efficacy of Gestrinone can be decreased when used in combination with Ulipristal.Approved
GriseofulvinThe serum concentration of Ulipristal can be decreased when it is combined with Griseofulvin.Approved, Vet Approved
HexobarbitalThe serum concentration of Ulipristal can be decreased when it is combined with Hexobarbital.Approved
Hydroxyprogesterone caproateThe therapeutic efficacy of Hydroxyprogesterone caproate can be decreased when used in combination with Ulipristal.Approved
IdelalisibThe serum concentration of Ulipristal can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of Ulipristal can be increased when it is combined with Imatinib.Approved
IndinavirThe serum concentration of Ulipristal can be increased when it is combined with Indinavir.Approved
IsavuconazoniumThe serum concentration of Ulipristal can be increased when it is combined with Isavuconazonium.Approved, Investigational
IsradipineThe serum concentration of Ulipristal can be increased when it is combined with Isradipine.Approved
ItraconazoleThe serum concentration of Ulipristal can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Ulipristal can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe serum concentration of Ulipristal can be increased when it is combined with Ketoconazole.Approved, Investigational
LevonorgestrelThe therapeutic efficacy of Levonorgestrel can be decreased when used in combination with Ulipristal.Approved, Investigational
LidocaineThe metabolism of Ulipristal can be decreased when combined with Lidocaine.Approved, Vet Approved
LobeglitazoneThe metabolism of Ulipristal can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe serum concentration of Ulipristal can be increased when it is combined with Lopinavir.Approved
LovastatinThe serum concentration of Ulipristal can be increased when it is combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Ulipristal can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Ulipristal can be decreased when it is combined with Lumacaftor.Approved
MedrogestoneThe therapeutic efficacy of Medrogestone can be decreased when used in combination with Ulipristal.Approved
Medroxyprogesterone acetateThe therapeutic efficacy of Medroxyprogesterone acetate can be decreased when used in combination with Ulipristal.Approved, Investigational
Megestrol acetateThe therapeutic efficacy of Megestrol acetate can be decreased when used in combination with Ulipristal.Approved, Vet Approved
MethohexitalThe serum concentration of Ulipristal can be decreased when it is combined with Methohexital.Approved
MethylestrenoloneThe therapeutic efficacy of Methylestrenolone can be decreased when used in combination with Ulipristal.Experimental
MethylphenobarbitalThe serum concentration of Ulipristal can be decreased when it is combined with Methylphenobarbital.Approved
MexiletineThe metabolism of Ulipristal can be decreased when combined with Mexiletine.Approved
MidostaurinThe metabolism of Ulipristal can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Ulipristal can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Ulipristal can be decreased when it is combined with Mitotane.Approved
NefazodoneThe serum concentration of Ulipristal can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Ulipristal can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Ulipristal can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Ulipristal can be decreased when it is combined with Nevirapine.Approved
NilotinibThe serum concentration of Ulipristal can be increased when it is combined with Nilotinib.Approved, Investigational
NomegestrolThe therapeutic efficacy of Nomegestrol can be decreased when used in combination with Ulipristal.Approved
NorethisteroneThe therapeutic efficacy of Norethisterone can be decreased when used in combination with Ulipristal.Approved
NorgestrienoneThe therapeutic efficacy of Norgestrienone can be decreased when used in combination with Ulipristal.Experimental
OlaparibThe serum concentration of Ulipristal can be increased when it is combined with Olaparib.Approved
OsimertinibThe serum concentration of Ulipristal can be increased when it is combined with Osimertinib.Approved
OxcarbazepineThe serum concentration of Ulipristal can be decreased when it is combined with Oxcarbazepine.Approved
PalbociclibThe serum concentration of Ulipristal can be increased when it is combined with Palbociclib.Approved
Peginterferon alfa-2bThe serum concentration of Ulipristal can be increased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe serum concentration of Ulipristal can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe serum concentration of Ulipristal can be decreased when it is combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Ulipristal can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PosaconazoleThe serum concentration of Ulipristal can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe serum concentration of Ulipristal can be decreased when it is combined with Primidone.Approved, Vet Approved
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Ulipristal.Approved, Vet Approved
PromegestoneThe therapeutic efficacy of Promegestone can be decreased when used in combination with Ulipristal.Experimental
RanolazineThe serum concentration of Ulipristal can be increased when it is combined with Ranolazine.Approved, Investigational
RifabutinThe serum concentration of Ulipristal can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Ulipristal can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Ulipristal can be decreased when it is combined with Rifapentine.Approved
RopiniroleThe metabolism of Ulipristal can be decreased when combined with Ropinirole.Approved, Investigational
SaquinavirThe serum concentration of Ulipristal can be increased when it is combined with Saquinavir.Approved, Investigational
SecobarbitalThe serum concentration of Ulipristal can be decreased when it is combined with Secobarbital.Approved, Vet Approved
SildenafilThe serum concentration of Ulipristal can be increased when it is combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Ulipristal can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Ulipristal can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Ulipristal can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Ulipristal can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe serum concentration of Ulipristal can be increased when it is combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe serum concentration of Ulipristal can be increased when it is combined with Telaprevir.Approved, Withdrawn
TelithromycinThe serum concentration of Ulipristal can be increased when it is combined with Telithromycin.Approved
Tenofovir disoproxilThe metabolism of Ulipristal can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TeriflunomideThe serum concentration of Ulipristal can be decreased when it is combined with Teriflunomide.Approved
TheophyllineThe metabolism of Ulipristal can be decreased when combined with Theophylline.Approved
ThiamylalThe serum concentration of Ulipristal can be decreased when it is combined with Thiamylal.Approved, Vet Approved
ThiopentalThe serum concentration of Ulipristal can be decreased when it is combined with Thiopental.Approved, Vet Approved
TiclopidineThe serum concentration of Ulipristal can be increased when it is combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Ulipristal can be decreased when it is combined with Tocilizumab.Approved
TopiramateThe serum concentration of Ulipristal can be decreased when it is combined with Topiramate.Approved
VenlafaxineThe serum concentration of Ulipristal can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Ulipristal can be increased when it is combined with Verapamil.Approved
VoriconazoleThe serum concentration of Ulipristal can be increased when it is combined with Voriconazole.Approved, Investigational
ZiprasidoneThe serum concentration of Ulipristal can be increased when it is combined with Ziprasidone.Approved
ZucapsaicinThe metabolism of Ulipristal can be decreased when combined with Zucapsaicin.Approved
Food Interactions
  • A high fat meal may lower mean Cmax and increase mean AUC(0-∞) but these changes are not clinically significant. Take without regards to meals.

References

General References
  1. Pohl O, Osterloh I, Gotteland JP: Ulipristal acetate - safety and pharmacokinetics following multiple doses of 10-50 mg per day. J Clin Pharm Ther. 2013 Aug;38(4):314-20. doi: 10.1111/jcpt.12065. Epub 2013 Apr 3. [PubMed:23550906]
  2. Melis GB, Piras B, Marotto MF, Orru' MM, Maricosu G, Pilloni M, Guerriero S, Angiolucci M, Lello S, Paoletti AM: Pharmacokinetic evaluation of ulipristal acetate for uterine leiomyoma treatment. Expert Opin Drug Metab Toxicol. 2012 Jul;8(7):901-8. doi: 10.1517/17425255.2012.695775. Epub 2012 Jun 10. [PubMed:22681335]
  3. Gemzell-Danielsson K, Rabe T, Cheng L: Emergency contraception. Gynecol Endocrinol. 2013 Mar;29 Suppl 1:1-14. doi: 10.3109/09513590.2013.774591. [PubMed:23437846]
  4. Martinez AM, Thomas MA: Ulipristal acetate as an emergency contraceptive agent. Expert Opin Pharmacother. 2012 Sep;13(13):1937-42. doi: 10.1517/14656566.2012.705832. Epub 2012 Jul 7. [PubMed:22770536]
  5. Maruo T, Ohara N, Matsuo H, Xu Q, Chen W, Sitruk-Ware R, Johansson ED: Effects of levonorgestrel-releasing IUS and progesterone receptor modulator PRM CDB-2914 on uterine leiomyomas. Contraception. 2007 Jun;75(6 Suppl):S99-103. Epub 2007 Mar 21. [PubMed:17531625]
  6. Creinin MD, Schlaff W, Archer DF, Wan L, Frezieres R, Thomas M, Rosenberg M, Higgins J: Progesterone receptor modulator for emergency contraception: a randomized controlled trial. Obstet Gynecol. 2006 Nov;108(5):1089-97. [PubMed:17077229]
  7. Blithe DL, Nieman LK, Blye RP, Stratton P, Passaro M: Development of the selective progesterone receptor modulator CDB-2914 for clinical indications. Steroids. 2003 Nov;68(10-13):1013-7. [PubMed:14667994]
  8. Attardi BJ, Burgenson J, Hild SA, Reel JR: In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone. J Steroid Biochem Mol Biol. 2004 Mar;88(3):277-88. [PubMed:15120421]
  9. Rosato E, Farris M, Bastianelli C: Mechanism of Action of Ulipristal Acetate for Emergency Contraception: A Systematic Review. Front Pharmacol. 2016 Jan 12;6:315. doi: 10.3389/fphar.2015.00315. eCollection 2015. [PubMed:26793107]
External Links
KEGG Drug
D09567
PubChem Compound
13559281
PubChem Substance
310264902
ChemSpider
19349271
ChEBI
71025
ChEMBL
CHEMBL2103846
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ulipristal_acetate
ATC Codes
G03AD02 — UlipristalG03XB02 — Ulipristal
AHFS Codes
  • 68:12.00 — Contraceptives
FDA label
Download (309 KB)
MSDS
Download (479 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0WithdrawnTreatmentUrogenital Abnormalities1
1CompletedTreatmentHealthy Volunteers1
1Not Yet RecruitingOtherLeiomyomas1
1Not Yet RecruitingTreatmentHeavy Menstrual Bleeding1
1RecruitingBasic ScienceRenal Function1
1RecruitingPreventionContraception1
1, 2RecruitingTreatmentOvulation Inhibition1
2CompletedNot AvailableContraception1
2CompletedPreventionFocus: Estrogen-free Oral Contraception1
2CompletedTreatmentContraception1
2CompletedTreatmentLeiomyomas3
2CompletedTreatmentOne to five years postmenopausal1
2Not Yet RecruitingOtherContraception / Healthy Female1
2Not Yet RecruitingPreventionCancer, Breast1
2RecruitingTreatmentCMT1A1
2RecruitingTreatmentEndometriosis of Uterus1
2TerminatedTreatmentDepression / PMDD / Premenstrual Dysphoric Disorder / Premenstrual Syndrome1
2, 3CompletedTreatmentPost coital contraception1
3CompletedTreatmentContraception1
3CompletedTreatmentIntramural Fibroids / Uterine Leiomyomas1
3CompletedTreatmentPost coital contraception1
3CompletedTreatmentUterine Bleeding in Women With Leiomyomas2
3CompletedTreatmentUterine Leiomyomas6
3RecruitingOtherPost coital contraception1
3RecruitingTreatmentContraception / Haemorrhage1
3RecruitingTreatmentUterine Leiomyomas1
3WithdrawnTreatmentLeiomyomas1
4Active Not RecruitingBasic ScienceContraception1
4Active Not RecruitingTreatmentEndometriosis1
4Not Yet RecruitingTreatmentDysmenorrhea / Endometriosis of Uterus / Heavy Uterine Bleeding1
4Not Yet RecruitingTreatmentUterine Leiomyomas1
4Not Yet RecruitingTreatmentWomen With Leiomyoma After at Least One Unsuccessful IVF Treatment1
4RecruitingBasic ScienceContraception1
4RecruitingTreatmentAbnormal Bleeding / Heavy Menstrual Bleeding1
4RecruitingTreatmentBMI >30 kg/m2 / Contraception1
4RecruitingTreatmentInfertilities1
4RecruitingTreatmentLeiomyomas5
Not AvailableCompletedNot AvailableContraception2
Not AvailableRecruitingNot AvailablePost coital contraception1
Not AvailableRecruitingPreventionPregnancy; Accident / Unplanned Pregnancy1
Not AvailableUnknown StatusNot AvailableInfertilities1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral30 mg
TabletOral30 mg/1
TabletOral5 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8426392No2010-06-122030-06-12Us
US8962603No2010-06-122030-06-12Us
US9283233No2010-04-132030-04-13Us
US8735380No2009-02-202029-02-20Us
US8512745No2010-06-022030-06-02Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00943 mg/mLALOGPS
logP4.45ALOGPS
logP4.18ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)12.7ChemAxon
pKa (Strongest Basic)4.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity129.29 m3·mol-1ChemAxon
Polarizability49.66 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9964
Blood Brain Barrier+0.6396
Caco-2 permeable+0.577
P-glycoprotein substrateSubstrate0.6286
P-glycoprotein inhibitor IInhibitor0.9708
P-glycoprotein inhibitor IIInhibitor0.9321
Renal organic cation transporterNon-inhibitor0.799
CYP450 2C9 substrateNon-substrate0.8337
CYP450 2D6 substrateNon-substrate0.8848
CYP450 3A4 substrateSubstrate0.8312
CYP450 1A2 substrateNon-inhibitor0.5677
CYP450 2C9 inhibitorNon-inhibitor0.7078
CYP450 2D6 inhibitorNon-inhibitor0.7827
CYP450 2C19 inhibitorNon-inhibitor0.6021
CYP450 3A4 inhibitorInhibitor0.7866
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6633
Ames testNon AMES toxic0.8603
CarcinogenicityNon-carcinogens0.7916
BiodegradationNot ready biodegradable0.9933
Rat acute toxicity2.6728 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9538
hERG inhibition (predictor II)Non-inhibitor0.686
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Oxosteroids
Direct Parent
20-oxosteroids
Alternative Parents
3-oxosteroids / 17-hydroxysteroids / Dialkylarylamines / Aniline and substituted anilines / Cyclohexenones / Tertiary alcohols / Alpha-hydroxy ketones / Cyclic alcohols and derivatives / Organopnictogen compounds / Organic oxides
show 1 more
Substituents
20-oxosteroid / 3-oxosteroid / Hydroxysteroid / 17-hydroxysteroid / Tertiary aliphatic/aromatic amine / Aniline or substituted anilines / Dialkylarylamine / Cyclohexenone / Monocyclic benzene moiety / Benzenoid
show 17 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Progesterone receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Modulator
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Gemzell-Danielsson K, Rabe T, Cheng L: Emergency contraception. Gynecol Endocrinol. 2013 Mar;29 Suppl 1:1-14. doi: 10.3109/09513590.2013.774591. [PubMed:23437846]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Gemzell-Danielsson K, Rabe T, Cheng L: Emergency contraception. Gynecol Endocrinol. 2013 Mar;29 Suppl 1:1-14. doi: 10.3109/09513590.2013.774591. [PubMed:23437846]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Gemzell-Danielsson K, Rabe T, Cheng L: Emergency contraception. Gynecol Endocrinol. 2013 Mar;29 Suppl 1:1-14. doi: 10.3109/09513590.2013.774591. [PubMed:23437846]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Gemzell-Danielsson K, Rabe T, Cheng L: Emergency contraception. Gynecol Endocrinol. 2013 Mar;29 Suppl 1:1-14. doi: 10.3109/09513590.2013.774591. [PubMed:23437846]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Martinez AM, Thomas MA: Ulipristal acetate as an emergency contraceptive agent. Expert Opin Pharmacother. 2012 Sep;13(13):1937-42. doi: 10.1517/14656566.2012.705832. Epub 2012 Jul 7. [PubMed:22770536]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da

Drug created on April 26, 2013 23:33 / Updated on November 22, 2017 12:37