Ulipristal (CDB-2914; HRP2000, VA2914, RTI 3021-012, RU 44675, EllaOne, Ella, Esmya) is a potent and selective SPRM (selective progesterone receptor modulator) used for emergency contraception after an unprotected intercourse or contraceptive failure. Ulipristal acetate has partial agonistic as well as antagonistic effects on the progesterone receptor. It also binds to the glucocorticoid receptor, but has no relevant affinity to the estrogen, androgen and mineralocorticoid receptors. Ulipristal acetate dose dependently suppressed progesterone-induced acrosome reaction and hyperactivation in human spermatozoa.

Physicochemical Properties

Molecular Formula	C28H35NO3
Molecular Weight	433.58
Exact Mass	433.261
CAS #	159811-51-5
Related CAS #	Ulipristal acetate;126784-99-4
PubChem CID	13559281
Appearance	Light yellow to yellow solid powder
Density	1.2±0.1 g/cm3
Boiling Point	638.5±55.0 °C at 760 mmHg
Melting Point	183.5-184.5ºC /Losartan/
Flash Point	340.0±31.5 °C
Vapour Pressure	0.0±2.0 mmHg at 25°C
Index of Refraction	1.613
LogP	3.86
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Heavy Atom Count	32
Complexity	877
Defined Atom Stereocenter Count	5
SMILES	CC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H](C3=C4CCC(=O)C=C4CC[C@@H]23)C5=CC=C(C=C5)N(C)C)C)O
InChi Key	OOLLAFOLCSJHRE-ZHAKMVSLSA-N
InChi Code	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
Chemical Name	(8S,11R,13S,14S,17R)-17-acetyl-11-(4-(dimethylamino)phenyl)-13-methyl-3-oxo-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
Synonyms	CDB-2914; HRP2000, VA2914,RTI 3021-012, RU 44675,CDB2914, HRP 2000, VA-2914, CDB 2914, CDB-2914, CDB 2914,CDB2914,HRP-2000, VA 2914, Ulipristal acetate, EllaOne, Ella, Esmya
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	In vitro activity: Ulipristal acetate has partial agonistic as well as antagonistic effects on the progesterone receptor. It also binds to theglucocorticoid receptor, but has no relevant affinity to the estrogen, androgen and mineralocorticoid receptors.
ln Vivo	Uterine leiomyomatosis may be inhibited in growth by ulipristal (CDB 3236). Ulibrtal can be used as an emergency contraceptive since it affects endometrial tissue and inhibits or delays ovulation[1].
Animal Protocol
ADME/Pharmacokinetics	Absorption, Distribution and Excretion 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; Mean oral clearance, single oral dose, healthy subject (CL/F) = 76.8 ± 64.0L/h Metabolism / Metabolites Ulipristal is metabolized by CYP3A4 and to a lesser extent by CYP1A2 into mono-demethylated (active) and di-methylated (inactive) metabolites. Biological Half-Life Mean elimination half-life, single oral dose, healthy subject = 32.4 ± 6.3 hours
Toxicity/Toxicokinetics	Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Ulipristal is a selective progesterone receptor modulator used in a single dose as an emergency postcoital contraceptive. No information is available on the clinical use of ulipristal during breastfeeding; however, amounts in milk are low. If ulipristal is required by the mother, it is not a reason to discontinue breastfeeding. Some older sources recommend withholding breastfeeding for 24 hours after a dose, but this is no longer a requirement according to current FDA-approved labeling. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. Protein Binding >94% bound to plasma proteins such as albumin, alpha1-acid glycoprotein, lipoproteins (VLDL, LDL, and HDL- due to its lipophillic nature)
References	[1]. Is Ulipristal Acetate a Liver Toxic Biomolecule? Toxicity assessment of ulipristal acetate. REV.CHIM.(Bucharest).
Additional Infomation	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.

Solubility Data

Solubility (In Vitro)

DMSO:83 mg/mL (191.4 mM) Water:<1 mg/mL Ethanol:14 mg/mL (32.3 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 6.25 mg/mL (14.41 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 62.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 6.25 mg/mL (14.41 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 62.5 mg/mL clear DMSO stock solution to 900 μL corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.3064 mL	11.5319 mL	23.0638 mL
	5 mM	0.4613 mL	2.3064 mL	4.6128 mL
	10 mM	0.2306 mL	1.1532 mL	2.3064 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.