Ulipristal Acetate

Ulipristal acetate (ULIPA) is a synthetic progesterone receptor modulator (SPRM) used in emergency hormonal contraceptives and for treatment of uterine fibroids.

Tags
Approvals
WHO Essential Medicine US FDA-Approved
ulipristal acetate
MOL SDF CML

Identifiers

Abbreviation

ULIPA

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References

Names

  • 17α-acetoxy-11β-(4-N,N-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20- dione
  • CDB(VA)-2914

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References

CASRN

126784-99-4

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References

PubChem CID

130904

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References

  1. PubChem: Ulipristal Acetate (View all citations for this reference)

IUPHAR/BPS

7460

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References

  1. IUPHAR/BPS: Ulipristal Acetate (View all citations for this reference)

DrugBank Accession Number

DB08867 (Ulipristal)

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References

  1. DrugBank: Ulipristal
    Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2017 Nov 8. doi: 10.1093/nar/gkx1037     (View all citations for this reference)

UNII

YF7V70N02B

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References

  1. UNII: Ulipristal Acetate (View all citations for this reference)

KEGG Entry Number

D09687

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References

  1. KEGG: Ulipristal Acetate (View all citations for this reference)

Wikipedia Entry Name

Ulipristal Acetate

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References

  1. Wikipedia: Ulipristal Acetate (View all citations for this reference)

ChEBI ID

CHEBI:71025

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References

  1. ChEBI: Ulipristal Acetate (View all citations for this reference)

ChEMBL ID

CHEMBL260538

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References

  1. ChEMBL: Ulipristal Acetate (View all citations for this reference)

ChemSpider ID

115762

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References

  1. ChemSpider: Ulipristal Acetate (View all citations for this reference)

ATC Code(s)

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References

  1. DrugBank: Ulipristal
    Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2017 Nov 8. doi: 10.1093/nar/gkx1037     (View all citations for this reference)

Physical & Chemical Properties

Molecular Formula

C30H37NO4

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References

Molecular Weight

475.62 g/mol

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References

Appearance

White to yellow crystalline powder

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References

  1. European Medicines Agency Evaluation of Medicines for Human Use. CHMP Assessment Report for Esmya (Ulipristal Acetate). 15 December 2011. (View all citations for this reference)

Solubility

Freely soluble in CHCl3, soluble in methanol, acetone, ethanol, and insoluble in water.

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References

  1. European Medicines Agency Evaluation of Medicines for Human Use. CHMP Assessment Report for Esmya (Ulipristal Acetate). 15 December 2011. (View all citations for this reference)

Polymorphism

Two found

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References

  1. European Medicines Agency Evaluation of Medicines for Human Use. CHMP Assessment Report for Esmya (Ulipristal Acetate). 15 December 2011. (View all citations for this reference)

Toxicology

Side Effects

Headache, abdominal pain, nausea, dysmenorrhea, fatigue, and dizziness.

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References

  1. Goodman & Gilman's: The Pharmacological Basis of Therapeutics, 12e, 2011 > Estrogens and Progestins. Laurence L. Brunton, Bruce A. Chabner, Björn C. Knollmann.
    2. (View all citations for this reference)
  2. Ulipristal acetate (ella) National Drug Monograph. October 2014. VA Pharmacy Benefits Management Services, Medical Advisory Panel, and VISN Pharmacist Executives. (View all citations for this reference)
  3. Side Effects Database, Ulipristal. (View all citations for this reference)

Genotoxicity

"No genotoxic potential was evident in any of the test systems when tested up to appropriate concentrations and dose levels according to guidelines."

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References

  1. European Medicines Agency Evaluation of Medicines for Human Use. CHMP Assessment Report for Esmya (Ulipristal Acetate). 15 December 2011. (View all citations for this reference)

LD50

< 1250 mg/kg (rat), >1250 mg/kg (rabbit)

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References

  1. European Medicines Agency Evaluation of Medicines for Human Use. CHMP Assessment Report for Esmya (Ulipristal Acetate). 15 December 2011. (View all citations for this reference)

Biochemistry & Pharmacology

Progesterone Receptor Activity

Partial agonist and antagonist

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References

  1. Goodman & Gilman's: The Pharmacological Basis of Therapeutics, 12e, 2011 > Estrogens and Progestins. Laurence L. Brunton, Bruce A. Chabner, Björn C. Knollmann.
    2. (View all citations for this reference)
  2. Zhao, Y.; Li, X.; Liu, H.; Yu, Y.; Hai, L.; Guo, L.; Wu, Y., First synthesis and characterization for the stereoisomers of Ulipristal acetate. Steroids 2015, 95, 7-16. (View all citations for this reference)

Androgen Receptor Activity

No activity

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References

  1. Attardi, B. J.; Burgenson, J.; Hild, S. A.; Reel, J. R., 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, 88 (3), 277-88. (View all citations for this reference)

Estrogen Receptor Activity

No activity

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References

  1. Attardi, B. J.; Burgenson, J.; Hild, S. A.; Reel, J. R., 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, 88 (3), 277-88. (View all citations for this reference)

Glucocorticoid Receptor Activity

Antagonist

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References

  1. Goodman & Gilman's: The Pharmacological Basis of Therapeutics, 12e, 2011 > Estrogens and Progestins. Laurence L. Brunton, Bruce A. Chabner, Björn C. Knollmann.
    2. (View all citations for this reference)
  2. Zhao, Y.; Li, X.; Liu, H.; Yu, Y.; Hai, L.; Guo, L.; Wu, Y., First synthesis and characterization for the stereoisomers of Ulipristal acetate. Steroids 2015, 95, 7-16. (View all citations for this reference)

Mineralocorticoid Receptor Activity

No activity

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References

  1. Attardi, B. J.; Burgenson, J.; Hild, S. A.; Reel, J. R., 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, 88 (3), 277-88. (View all citations for this reference)

Elimination Half-Life (t1/2)

32.4 +/- 6.3 h (from 30 mg oral dose)

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References

  1. 30 mg ulipristal acetate tablet for emergency contraception. Laboratoire HRA Pharma, Distributed by: Actavis Specialty Pharmaceuticals Co. January 22, 2015. (View all citations for this reference)
  2. DrugBank: Ulipristal
    Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2017 Nov 8. doi: 10.1093/nar/gkx1037     (View all citations for this reference)

Serum Protein Binding

>94% bound to plasma proteins, including high density lipoprotein, alpha-l-acid glycoprotein, and albumin

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References

  1. 30 mg ulipristal acetate tablet for emergency contraception. Laboratoire HRA Pharma, Distributed by: Actavis Specialty Pharmaceuticals Co. January 22, 2015. (View all citations for this reference)

Metabolism

Metabolized by CYP3A4 and to a lesser extent by CYP1A2

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References

  1. DrugBank: Ulipristal
    Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2017 Nov 8. doi: 10.1093/nar/gkx1037     (View all citations for this reference)

Excretion

Mostly eliminated in feces, <10% in urine. Small amounts excreted in breast milk.

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References

  1. 30 mg ulipristal acetate tablet for emergency contraception. Laboratoire HRA Pharma, Distributed by: Actavis Specialty Pharmaceuticals Co. January 22, 2015. (View all citations for this reference)
  2. Product Monograph: Fibristal, 5 mg ulipristal acetate tablet. Allergan Pharma Co. Nov. 23, 2016. (View all citations for this reference)

Cmax

176 +/- 89 ng/mL (healthy subjects, single oral dose)

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References

  1. DrugBank: Ulipristal
    Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2017 Nov 8. doi: 10.1093/nar/gkx1037     (View all citations for this reference)

Tmax

0.9 h

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References

  1. Ulipristal acetate (ella) National Drug Monograph. October 2014. VA Pharmacy Benefits Management Services, Medical Advisory Panel, and VISN Pharmacist Executives. (View all citations for this reference)

AUC

556 +/- 260 ng*h/mL (0-∞, healthy subjects, single oral dose)

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References

  1. DrugBank: Ulipristal
    Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2017 Nov 8. doi: 10.1093/nar/gkx1037     (View all citations for this reference)

Clearance

76.8 +/- 64.0 L/h (mean oral clearance, single oral dose, health subject)

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References

  1. DrugBank: Ulipristal
    Wishart DS, Feunang YD, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2017 Nov 8. doi: 10.1093/nar/gkx1037     (View all citations for this reference)

Permeability Glycoprotein (P-gp) Binding

Does not appear to be a P-gp substrate

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References

  1. European Medicines Agency Evaluation of Medicines for Human Use. CHMP Assessment Report for Esmya (Ulipristal Acetate). 15 December 2011. (View all citations for this reference)

Metabolites

Name
Structure
Notes
Di-N-demethylated Ulipristal Acetate
structure

Not pharmacologically active. Also referred to as PGL4004. Conversion from ulipristal acetate most likely mediated by CYP3A4.

Mono-N-demethylated Ulipristal Acetate
structure

Also known as metabolite PGL4002. Pharmacologically active. Binds to human plasma proteins extensively at 96.5%. Most likely mediated by CYP3A4.

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Impurities

Name
Structure
CASRN
Other Names & Identifiers
D-Ulipristal Acetate
structure

N-Desmethyl-Ulipristal Acetate
structure

11β,17β-Ulipristal Acetate
structure

11α,17β-Ulipristal Acetate
structure

11α,17α-Ulipristal Acetate
structure

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US FDA-Approved Products

Name
Formulation
Status
ANDA #
Logilia
ULIPRISTAL ACETATE: 30 mg Oral tablet

Prescription

207952

Ella
ULIPRISTAL ACETATE: 30 mg Oral tablet

Prescription

022474

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WHO Essential Medicines

Name
Formulation
Ulipristal Acetate Tablet
ULIPRISTAL ACETATE: 30 mg
Tablet
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