Clomiphene

Base Information

• Chemical Name: Clomiphene
• CAS No.: 911-45-5
• Deprecated CAS: 96189-16-1
• Molecular Formula: C26H28ClNO
• Molecular Weight: 405.967
• European Community (EC) Number: 213-008-6
• UNII: R6D2UI4FLS
• DSSTox Substance ID: DTXSID201318048
• Wikipedia: Clomifene,Enclomifene
• Wikidata: Q28208734
• NCI Thesaurus Code: C28211
• RXCUI: 2596
• Pharos Ligand ID: JCJQH2T9V16W,JCJR52WLRN2J
• Metabolomics Workbench ID: 43157,149942
• ChEMBL ID: CHEMBL954
• Mol file: 911-45-5.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

Chemical Property:

• Vapor Pressure: 1.77E-10mmHg at 25°C
• Melting Point: 117.25°C
• Refractive Index: 1.588
• Boiling Point: 509 °C at 760 mmHg
• PKA: 9.54±0.25(Predicted)
• Flash Point: 261.634 °C
• PSA: 12.47000
• Density: 1.104 g/cm³
• LogP: 6.56260
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 405.1859422
• Heavy Atom Count: 29
• Complexity: 481

Purity/Quality:

99%, ^*data from raw suppliers

Clomiphene 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Infertility Agents
• Canonical SMILES: CCN(CC)CCOC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3
• Isomeric SMILES: CCN(CC)CCOC1=CC=C(C=C1)/C(=C(\C2=CC=CC=C2)/Cl)/C3=CC=CC=C3
• Recent ClinicalTrials: Use of Clomiphene Citrate as an Inhibitor of Ovulation in an Oocyte Cryopreservation Cycle
• 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)
• Description: Clomiphene is an antiestrogen thought to increase sperm parameters in males attempting to conceive. The objective of this review was to evaluate the efficacy and safety of Clomiphene citrate in the treatment of male patients with infertility. It is an oral agent used to treat infertility in women desiring pregnancy. Clomiphene has been linked to a low rate of transient serum aminotransferase elevations during therapy and to rare instances of clinically apparent liver injury, which can be severe and even fatal.A triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue.
• Uses: Clomifene is used for infertility in order to increase reproductive properties of oligoovulatory women who have three or four ovulatory cycles per year, leading to normal monthly ovulation. Antiestrogen.
• Indications: Clomifene acts by enhancing follicular growth caused by ovulation. The primary indication for using clomifene is induction of ovulation in non-ovulating women who still have some estrogen production.

Technology Process of Clomiphene

There total 48 articles about Clomiphene 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: 81.0%

zuclomiphene binaphthyl hydrogen phosphate → Zuclomiphene (911-45-5,15690-55-8,15690-57-0)

Guidance literature:

With potassium carbonate; In water; ethyl acetate; at 20 ℃; for 5h;

Reference yield: 55.0%

cis-1-Chloro-2-(4-hydroxyphenyl)-1,2-diphenylethylene (72474-40-9) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → Zuclomiphene (911-45-5,15690-55-8,15690-57-0)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 70 ℃;

Reference yield:

2-{4-[(Z)-1,2-diphenylvinyl]phenoxy}-N,N-diethylethanaminium hydrogen sulfate → clomiphene (911-45-5)

Guidance literature:

2-{4-[(Z)-1,2-diphenylvinyl]phenoxy}-N,N-diethylethanaminium hydrogen sulfate; With N-chloro-succinimide; In dichloromethane; at 20 ℃; for 32h;

With sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃; for 0.5h; pH=8 - 9;

upstream raw materials:

N,N-diethyl-2-[4-(1,2-diphenylvinyl)phenoxy]ethylamine hydrochloride

4-<2-(diethylamino)ethoxy>iodobenzene

(E)-bis(trimethylstannyl)stilbene

p-Iodophenol

Downstream raw materials:

clomiphene citrate

clomifene citrate

(Z)-1-<4-(2-diethylaminoethoxy)phenyl>-1,2-diphenyl-1-penten-5-ol

cis-clomiphene citrate

Refernces

• 1、 -. "Processes for the Preparation of Zuclomiphene and Intermediates Thereof". Paragraph 0147-0149. . Retrieved 2021/05/21.
• 2、 Blazecka, Peter,Chung, Andrew,Emmett, Michael,Green, Stuart,Karadeolian, Avedis,Le Sueur, Richard,Patel, Dineshkumar,Rey, Allan,Souza, Fabio,Zhao, Yajun. "Stereoselective Nickel(II)-Catalyzed Addition of Aryl Grignards to Diphenylacetylene in the Synthesis of Zuclomiphene". . . Retrieved 2022/03/16.