Ulipristal acetate

Base Information

• Chemical Name: Ulipristal acetate
• CAS No.: 126784-99-4
• Deprecated CAS: 199015-61-7,136960-00-4
• Molecular Formula: C30H37NO4
• Molecular Weight: 475.628
• European Community (EC) Number: 682-170-1
• UNII: YF7V70N02B
• DSSTox Substance ID: DTXSID30155294
• Nikkaji Number: J533.262A
• Wikipedia: Ulipristal_acetate
• Wikidata: Q975059
• NCI Thesaurus Code: C91057
• RXCUI: 1005920
• Pharos Ligand ID: SQMHQGH31URQ
• Metabolomics Workbench ID: 65405
• ChEMBL ID: CHEMBL260538
• Mol file: 126784-99-4.mol

Synonyms:(11beta)-17-(acetyloxy)-11-(4-(dimethylamino)phenyl)-19-norpregna-4,9-diene-3,20-dione;Ella norpregnadiene;Esmya;ulipristal acetate

Chemical Property of Ulipristal acetate

Chemical Property:

• Vapor Pressure: 2.77E-16mmHg at 25°C
• Melting Point: 183-185 °C
• Refractive Index: 1.593
• Boiling Point: 640.1 °C at 760mmHg
• PKA: 5.49±0.24(Predicted)
• Flash Point: 340.9 °C
• PSA: 63.68000
• Density: 1.19 g/cm³
• LogP: 5.54300
• Storage Temp.: -20°C
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 475.27225866
• Heavy Atom Count: 35
• Complexity: 984

Purity/Quality:

99%min ^*data from raw suppliers

Ulipristal Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CCC2C1(CC(C3=C4CCC(=O)C=C4CCC23)C5=CC=C(C=C5)N(C)C)C)OC(=O)C
• Isomeric 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)OC(=O)C
• Recent ClinicalTrials: Esmya Versus Surgery Before IVF/ICSI
• Recent EU Clinical Trials: A prospective, randomized, parallel-group study to assess the effects on ovarian activity of ellaOne (ulipristal acetate 30 mg single dose) taken after three consecutive days of missed combined oral contraceptive pills
• Description: Ulipristal acetate (UPA) is a selective progesterone receptor modulator. Attributing to its higher efficacy and a similar rate of side effects compared to levonorgestrel emergency contraception, it is now recommended as first line treatment for emergency contraception. Emergency contraception is defined as the use of drug or device after unprotected or under-protected intercourse to prevent an unwanted pregnancy. Ulipristal acetate can be used up to 5 days (120 h) after unprotected sexual intercourse. As progesterone promotes the growth of uterine fibroids, the blocking characteristic of ulipristal acetate can thereby be used to reduce the size of uterine fibroids. Ulipristal acetate has also shown efficacy with a significant reduction in uterine bleeding caused by uterine fibroids. The treatment of fibroids by ulipristal acetate should begin in the first week of a menstrual period. Drugs or herbal products that induce enzymes, including CYP3A4, such as carbamazepine, phenytoin, rifampin, St. John's Wort, etc., may decrease the plasma concentrations of ulipristal acetate, and may decrease its effectiveness while CYP3A4 inhibitors such as itraconazole, ketoconazole, etc., may increase plasma concentrations of ulipristal acetate. The half-life after oral intake is 32 h; it binds to plasma proteins for 97–99%, and it is metabolized by the citochrome P450. Ulipristal acetate is a synthetic steroid derived from 19-nor-progesterone that exerts potent progesterone receptor (PR) antagonist activity at the transcriptional level. It is an orally administered drug indicated for emergency contraception (i.e., postcoital contraception) up to 120 h following unprotected intercourse. Ulipristal acetate is the second oral progestogen marketed for this indication behind levonorgestrel. As PR antagonists, both drugs are believed to act via delay of ovulation and inhibition of follicular development. Levonorgestrel 1.5 mg is approved for contraception up to 72 h following unprotected intercourse and is widely accessible via prescription, and directly from clinics and community pharmacies. Prior to ulipristal acetate, the only approved postcoital contraceptive option between 72 and 120 h was the insertion of an intrauterine device (IUD). The recommended dose of ulipristal acetate is one 30-mg tablet taken as soon as possible and no more than 120 h following intercourse. The vast majority of PR antagonists belonging to the mifepristone (RU486) family also bind to the glucocorticoid receptor (GR) with high affinity and thereby exert antiglucocorticoid activity. The most common adverse effects with ulipristal acetate were headache, dysmenorrhea, nausea, abdominal pain, dizziness, fatigue, and upper abdominal pain.
• Uses: Α selective labelled progesterone receptor modulator Ulipristal acetate is a selective progesterone receptor modulator Labelled Ulipristal
• Clinical Use: Ulipristal acetate, a selective progesterone receptor modulator (SPRM), was developed at the Research Triangle Institute. In 2009, HRA Pharma received FDA approval for emergency contraception within 120 h (5 days) of unprotected sexual intercourse or contraceptive failure. Ulipristal acetate is a well-known steroid that possesses antiprogestational and antiglucocorticoid activity. It is the first SPRM that was specifically designed as an oral emergency contraceptive. Unlike earlier levonorgestrel-based emergency contraceptives, this SPRM drug maintains efficacy for 5 days after unprotected intercourse while having safety profile comparable to levonorgestrel.

Technology Process of Ulipristal acetate

There total 41 articles about Ulipristal acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

trifluoroacetic anhydride (96-63-9) + CDB-3236 (159811-51-5) → ulipristal acetate (126784-99-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1016/S0039-128X(00)00100-8

Reference yield:

acetic anhydride (108-24-7) + 3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene (126690-41-3) → ulipristal acetate (126784-99-4)

Guidance literature:

With perchloric acid; acetic acid; In dichloromethane; at -10 - 0 ℃; for 0.5h; Cooling with ice;

Reference yield:

acetic acid (64-19-7,77671-22-8) + CDB-3236 (159811-51-5) → ulipristal acetate (126784-99-4)

Guidance literature:

With perchloric acid; In acetic anhydride; at -10 - 0 ℃; for 0.5h;

upstream raw materials:

trifluoroacetic anhydride

CDB-3236

5α,10α-epoxy-17α-hydroxy-19-norpregn-9(11)-ene-3,20-dione 3,20-bis(ethylene acetal)

3,3-ethylenedioxy-17β-cyano-17α-chloromethyl(dimethyl)siloxy estren-5(10),9(11)diene

Downstream raw materials:

CDB-3877

Refernces

• 1、 -. "Synthesis method of ulipristal acetate". Paragraph 0054; 0055. . Retrieved 2018/04/02.
• 2、 -. "Ulipristal acetate impurities and preparation and detection method thereof". Paragraph 0036; 0037; 0118. . Retrieved 2016/10/31.