Ulipristal Acetate | CDB-2914 | CAS#126784-99-4 | SPRM

Ulipristal acetate
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319944

CAS#: 126784-99-4 (acetate)

Description: Ulipristal acetate, also known as CDB-2914, is a selective progesterone receptor modulator (SPRM) approved for contraception, and for uterine fibroid. As a SPRM, ulipristal acetate has partial agonistic as well as antagonistic effects on the progesterone receptor. It also binds to the glucocorticoid receptor, but is only a weak antiglucocorticoid relative to mifepristone, and has no relevant affinity to the estrogen, androgen and mineralocorticoid receptors.

Chemical Structure

Ulipristal acetate

CAS# 126784-99-4 (acetate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319944
Name: Ulipristal acetate
CAS#: 126784-99-4 (acetate)
Chemical Formula: C30H37NO4
Exact Mass: 475.27
Molecular Weight: 475.629
Elemental Analysis: C, 75.76; H, 7.84; N, 2.94; O, 13.46

Price and Availability

Size	Price	Availability
50mg	USD 150	Ready to ship
100mg	USD 220	Ready to ship
200mg	USD 350	Ready to ship
500mg	USD 550	Ready to ship
1g	USD 950	Ready to ship
2g	USD 1650	Ready to ship
5g	USD 3650	Ready to ship
10g	USD 6150	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 159811-51-5 126784-99-4 (acetate)

Synonym: CDB-2914, CDB 2914, CDB2914, HRP-2000, HRP 2000, HRP2000, VA2914, VA-2914, VA 2914, RTI 3021-012, RU 44675, Ulipristal acetate, EllaOne, Ella, Esmya

IUPAC/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

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

SMILES Code: CC([C@@]1(OC(C)=O)CC[C@@]2([H])[C@]3([H])CCC4=CC(CCC4=C3[C@@H](C5=CC=C(N(C)C)C=C5)C[C@]12C)=O)=O

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#A20T05K10

QC Data:

View QC data: current batch, Lot#A20T05K10

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Ulipristal acetate (CDB-2914, HRP 2000, RU 44675) is a selective SPRM for emergency contraception.
In vitro activity:	As shown in Figure 2A and 2B, normal myometrial cells were not significantly affected by 5 μM UPA (Ulipristal). On the contrary, in UPA-treated leiomyoma cells both the LC3-II level and the LC3-II:LC3-I ratio were significantly increased compared with untreated, control cells. The autophagic process occurring in leiomyoma cells was also confirmed by cotreating cells with CQ, which inhibits the fusion of autophagosomes with lysosomes, thus inhibiting the clearance of LC3-II. The resulting further accumulation of LC3-II indicates that an autophagic flux is actually taking place. As shown in Figure 2C, the cotreatment with CQ increased LC3-II protein level in leiomyoma cells, particularly in UPA-treated ones, suggesting that UPA actually stimulated the autophagic flux. Reference: Fertil Steril. 2019 Dec;112(6):1150-1159. https://pubmed.ncbi.nlm.nih.gov/31843092/
In vivo activity:	To define the physiological significance of ulipristal on glucocorticoid signaling in vivo, this study exposed female C57Bl/6 mice to 2 mg/kg ulipristal for 4 hours. Acute exposure to ulipristal resulted in tissue-specific effects on basal glucocorticoid signaling, including antagonist, agonist, and no effects. In the lung, ulipristal significantly reduced transcript levels of Per1 and Fkbp5 but not Gilz (Fig. 8A). Consistent with the findings in Hepg2 and UtLM cells, transcript levels of Per1, Fkbp5, and Gilz were significantly decreased by ulipristal in the liver and the uterus (Fig. 8A). However, no effect of ulipristal exposure was evident on the basal expression of the glucocorticoid-responsive genes Per1, Fkbp5, and Gilz in the spleen (Fig. 8B). Interestingly, exposure to ulipristal induced the expression of Fkbp5 and Gilz mRNA in the hippocampus and pituitary (Fig. 8C), suggesting that ulipristal may act as an agonist of glucocorticoid signaling in certain tissues. Reference: J Clin Endocrinol Metab. 2020 Mar; 105(3): 716–734. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7112983/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	56.5	118.79
	DMF	30.0	63.07
	Ethanol	22.0	46.25
	Ethanol:PBS (pH 7.2) (1:1)	0.2	0.42

Preparing Stock Solutions

The following data is based on the product molecular weight 475.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Del Bello B, Marcolongo P, Ciarmela P, Sorbi F, Petraglia F, Luisi S, Maellaro E. Autophagy up-regulation by ulipristal acetate as a novel target mechanism in the treatment of uterine leiomyoma: an in vitro study. Fertil Steril. 2019 Dec;112(6):1150-1159. doi: 10.1016/j.fertnstert.2019.08.007. PMID: 31843092. 2. Shin SJ, Kim J, Lee S, Baek J, Lee JE, Cho C, Ha E. Ulipristal acetate induces cell cycle delay and remodeling of extracellular matrix. Int J Mol Med. 2018 Oct;42(4):1857-1864. doi: 10.3892/ijmm.2018.3779. Epub 2018 Jul 17. PMID: 30015921; PMCID: PMC6108884. 3. Small B, Millard CEF, Kisanga EP, Burman A, Anam A, Flannery C, Al-Hendy A, Whirledge S. The Selective Progesterone Receptor Modulator Ulipristal Acetate Inhibits the Activity of the Glucocorticoid Receptor. J Clin Endocrinol Metab. 2020 Mar 1;105(3):716–34. doi: 10.1210/clinem/dgz139. PMID: 31665442; PMCID: PMC7112983. 4. Gómez-Elías MD, Munuce MJ, Bahamondes L, Cuasnicú PS, Cohen DJ. In vitro and in vivo effects of ulipristal acetate on fertilization and early embryo development in mice. Hum Reprod. 2016 Jan;31(1):53-9. doi: 10.1093/humrep/dev287. Epub 2015 Nov 17. PMID: 26582845.
In vitro protocol:	1. Del Bello B, Marcolongo P, Ciarmela P, Sorbi F, Petraglia F, Luisi S, Maellaro E. Autophagy up-regulation by ulipristal acetate as a novel target mechanism in the treatment of uterine leiomyoma: an in vitro study. Fertil Steril. 2019 Dec;112(6):1150-1159. doi: 10.1016/j.fertnstert.2019.08.007. PMID: 31843092. 2. Shin SJ, Kim J, Lee S, Baek J, Lee JE, Cho C, Ha E. Ulipristal acetate induces cell cycle delay and remodeling of extracellular matrix. Int J Mol Med. 2018 Oct;42(4):1857-1864. doi: 10.3892/ijmm.2018.3779. Epub 2018 Jul 17. PMID: 30015921; PMCID: PMC6108884.
In vivo protocol:	1. Small B, Millard CEF, Kisanga EP, Burman A, Anam A, Flannery C, Al-Hendy A, Whirledge S. The Selective Progesterone Receptor Modulator Ulipristal Acetate Inhibits the Activity of the Glucocorticoid Receptor. J Clin Endocrinol Metab. 2020 Mar 1;105(3):716–34. doi: 10.1210/clinem/dgz139. PMID: 31665442; PMCID: PMC7112983. 2. Gómez-Elías MD, Munuce MJ, Bahamondes L, Cuasnicú PS, Cohen DJ. In vitro and in vivo effects of ulipristal acetate on fertilization and early embryo development in mice. Hum Reprod. 2016 Jan;31(1):53-9. doi: 10.1093/humrep/dev287. Epub 2015 Nov 17. PMID: 26582845.

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1: Sancho JM, Delgado VS, Valero MJ, Soteras MG, Amate VP, Carrascosa AA. Hysteroscopic myomectomy outcomes after 3-month treatment with either Ulipristal Acetate or GnRH analogues: a retrospective comparative study. Eur J Obstet Gynecol Reprod Biol. 2016 Mar;198:127-30. doi: 10.1016/j.ejogrb.2016.01.014. Epub 2016 Jan 21. Review. PubMed PMID: 26871272.

2: 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. Review. PubMed PMID: 26793107; PubMed Central PMCID: PMC4709420.

3: Puchar A, Luton D, Koskas M. Ulipristal acetate for uterine fibroid-related symptoms. Drugs Today (Barc). 2015 Nov;51(11):661-7. doi: 10.1358/dot.2015.51.11.2413469. Review. PubMed PMID: 26744741.

4: Jatlaoui TC, Riley H, Curtis KM. Safety data for levonorgestrel, ulipristal acetate and Yuzpe regimens for emergency contraception. Contraception. 2016 Feb;93(2):93-112. doi: 10.1016/j.contraception.2015.11.001. Epub 2015 Nov 3. Review. PubMed PMID: 26546020.

5: Trefoux Bourdet A, Luton D, Koskas M. Clinical utility of ulipristal acetate for the treatment of uterine fibroids: current evidence. Int J Womens Health. 2015 Mar 26;7:321-30. doi: 10.2147/IJWH.S50016. eCollection 2015. Review. PubMed PMID: 25848323; PubMed Central PMCID: PMC4381886.

6: Tafi E, Scala C, Leone Roberti Maggiore U, Bizzarri N, Candiani M, Venturini PL, Ferrero S. Drug safety evaluation of ulipristal acetate in the treatment of uterine fibroids. Expert Opin Drug Saf. 2015 Jun;14(6):965-77. doi: 10.1517/14740338.2015.1021773. Epub 2015 Mar 14. Review. PubMed PMID: 25772793.

7: Galliano D. Ulipristal acetate in uterine fibroids. Fertil Steril. 2015 Feb;103(2):359-60. doi: 10.1016/j.fertnstert.2014.11.028. Epub 2014 Dec 30. Review. PubMed PMID: 25555419.

8: Pérez-López FR. Ulipristal acetate in the management of symptomatic uterine fibroids: facts and pending issues. Climacteric. 2015 Apr;18(2):177-81. doi: 10.3109/13697137.2014.981133. Epub 2014 Nov 12. Review. PubMed PMID: 25390187.

9: Pohl O, Zobrist RH, Gotteland JP. The clinical pharmacology and pharmacokinetics of ulipristal acetate for the treatment of uterine fibroids. Reprod Sci. 2015 Apr;22(4):476-83. doi: 10.1177/1933719114549850. Epub 2014 Sep 16. Review. PubMed PMID: 25228633; PubMed Central PMCID: PMC4812693.

10: Glasier A. The rationale for use of Ulipristal Acetate as first line in emergency contraception: biological and clinical evidence. Gynecol Endocrinol. 2014 Oct;30(10):688-90. doi: 10.3109/09513590.2014.950645. Epub 2014 Aug 18. Review. PubMed PMID: 25133564.

11: Goldstajn MS, Baldani DP, Skrgatić L, Radaković B, Vrbić H, Canić T. Ulipristal acetate in emergency contraception. Coll Antropol. 2014 Mar;38(1):379-84. Review. PubMed PMID: 24851646.

12: Ulipristal Acetate (Fibristal) (5 mg Tablets): Treatment of Moderate to Severe Signs and Symptoms of Uterine Fibroids in Adult Women of Reproductive Age Who are Eligible for Surgery. The Duration of Treatment is Limited to Three Months [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2013 Dec. Available from http://www.ncbi.nlm.nih.gov/books/NBK195457/ PubMed PMID: 24741734.

13: Delev DP. Ulipristal acetate--a review of the new therapeutic indications and future prospects. Folia Med (Plovdiv). 2013 Jul-Dec;55(3-4):5-10. Review. PubMed PMID: 24712276.

14: Biglia N, Carinelli S, Maiorana A, D'Alonzo M, Lo Monte G, Marci R. Ulipristal acetate: a novel pharmacological approach for the treatment of uterine fibroids. Drug Des Devel Ther. 2014 Feb 20;8:285-92. doi: 10.2147/DDDT.S54565. eCollection 2014. Review. PubMed PMID: 24591818; PubMed Central PMCID: PMC3934585.

15: Mozzanega B, Gizzo S, Di Gangi S, Cosmi E, Nardelli GB. Ulipristal acetate: critical review about endometrial and ovulatory effects in emergency contraception. Reprod Sci. 2014 Jun;21(6):678-85. doi: 10.1177/1933719113519178. Epub 2014 Jan 18. Review. PubMed PMID: 24440997.

16: Monleón Sancho J, Romaguera E, Romero A, Higueras G, Morcillo I, Fuster S. [Ulipristal acetate, 5mg: a new alternative]. Med Clin (Barc). 2013 Jul;141 Suppl 1:40-6. doi: 10.1016/S0025-7753(13)70052-6. Review. Spanish. PubMed PMID: 24314567.

17: Szamatowicz M, Kotarski J. [Selective progesterone receptor modulator (ulipristal acetate--a new option in the pharmacological treatment of uterine fibroids in women]. Ginekol Pol. 2013 Mar;84(3):219-22. Review. Polish. PubMed PMID: 23700851.

18: Talaulikar VS, Manyonda IT. Ulipristal acetate: a novel option for the medical management of symptomatic uterine fibroids. Adv Ther. 2012 Aug;29(8):655-63. doi: 10.1007/s12325-012-0042-8. Epub 2012 Aug 16. Review. PubMed PMID: 22903240.

19: Wilton JM. Ulipristal acetate: the newest emergency contraceptive. Nurs Womens Health. 2012 Aug-Sep;16(4):331-5. doi: 10.1111/j.1751-486X.2012.01752.x. Review. PubMed PMID: 22900810.

20: 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. Review. PubMed PMID: 22770536.

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