Clomiphene citrate

Base Information

• Chemical Name: Clomiphene citrate
• CAS No.: 7619-53-6
• Deprecated CAS: 207563-42-6
• Molecular Formula: C32H36ClNO8
• Molecular Weight: 598.093
• European Community (EC) Number: 200-035-3,690-644-4
• NSC Number: 756698,151466,35770
• UNII: UY5X264QZV
• Wikidata: Q27291328
• NCI Thesaurus Code: C28322
• RXCUI: 142431
• ChEMBL ID: CHEMBL1213137
• Mol file: 7619-53-6.mol

Synonyms:Chloramiphene;Citrate, Clomiphene;Clomid;Clomide;Clomifen;Clomifene;Clomiphene;Clomiphene Citrate;Clomiphene Hydrochloride;Clostilbegit;Dyneric;Gravosan;Hydrochloride, Clomiphene;Klostilbegit;Serophene

Chemical Property of Clomiphene citrate

Chemical Property:

• Melting Point: 139 - 141°C
• PSA: 144.60000
• LogP: 5.31410
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 14
• Exact Mass: 597.2129448
• Heavy Atom Count: 42
• Complexity: 708

Purity/Quality:

99% ^*data from raw suppliers

cis-ClomipheneCitrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CCOC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Isomeric SMILES: CCN(CC)CCOC1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\Cl)/C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Recent ClinicalTrials: Effect of Oral Sildenafil Citrate on Improvement of Endometrial Thickness
• Recent EU Clinical Trials: Letrozole or Clomifene, with or without metformin, for ovulation induction in women with polycystic ovary syndrome: a 2x2 factorial design randomised trial (The LOCI trial)
• Recent NIPH Clinical Trials: Orlistat as a clomiphene citrate adjuvant in overweight and obese patients with polycystic ovary syndrome.
• Uses: cis-Clomiphene Citrate is the cis isomer of Clomiphene (C587025). Found to be antiestrogenic and a more potent inhibitor of LH secretion than the trans isomer.

Technology Process of Clomiphene citrate

There total 13 articles about Clomiphene citrate 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: 96.0%

Zuclomiphene (911-45-5,15690-55-8,15690-57-0) + citric acid (77-92-9,906507-37-7) → cis-clomiphene citrate (7619-53-6)

Guidance literature:

In methanol; tert-butyl methyl ether; at 50 ℃; for 1h; Temperature; Solvent;

Reference yield: 81.2%

zuclomiphene binaphthyl hydrogen phosphate + citric acid (77-92-9,906507-37-7) → cis-clomiphene citrate (7619-53-6)

Guidance literature:

zuclomiphene binaphthyl hydrogen phosphate; With potassium carbonate; In water; ethyl acetate; at 20 ℃; for 32h;

citric acid; In methanol; at 0 - 60 ℃; for 6h;

Reference yield:

clomifene citrate (50-41-9) → cis-clomiphene citrate (7619-53-6)

Guidance literature:

clomifene citrate; With 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; In methanol; at 45 - 50 ℃; for 4h;

With citric acid; In ethanol; tert-butyl methyl ether; at 20 ℃; for 5h;

upstream raw materials:

4-fluoro-1-iodobenzene

1-bromo-4-methoxy-benzene

4-methoxyphenyl magnesium bromide

(Z)-(1-chloro-2-(4-methoxyphenyl)ethene-1,2-diyl)dibenzene

Refernces

• 1、 -. "Processes for the Preparation of Zuclomiphene and Intermediates Thereof". . . Retrieved 2021/05/21.
• 2、 -. "Zuclomiphene Salts and Crystalline Forms Thereof". Paragraph 0144. . Retrieved 2021/05/21.