911-45-5 Usage
Description
Clomifene, also known as Clomiphene citrate, is a triphenyl ethylene stilbene derivative that acts as an estrogen agonist or antagonist depending on the target tissue. It is an oral agent used to treat infertility in both men and women, with the aim of increasing sperm parameters in males and promoting normal monthly ovulation in oligoovulatory women.
Uses
Used in Infertility Treatment:
Clomifene is used as an antiestrogen for the treatment of infertility in men attempting to conceive. It is believed to increase sperm parameters, thereby improving the chances of conception.
Used in Women's Infertility Treatment:
Clomifene is used as an oral agent for the treatment of infertility in women who desire pregnancy. It is particularly effective for women with oligoovulatory cycles, helping to increase their reproductive properties and promote normal monthly ovulation.
Used in Liver Function Monitoring:
While Clomifene is generally considered safe, it has been linked to a low rate of transient serum aminotransferase elevations during therapy. In rare instances, it can also cause clinically apparent liver injury, which can be severe and even fatal. Therefore, monitoring liver function is an important aspect of Clomifene usage.
Hormonal modulation
CLOMIPHENE exerts its effects centrally with a
result of increased LH and FSH secretion and increased testicular
testosterone production. Many studies have described significant
increases in serum testosterone, LH, and FSH with CLOMIPHENE treatment.
Studies have revealed comparable increases in serum testosterone levels
in hypogonadal men treated with CLOMIPHENE compared with TRT. CLOMIPHENE
has also been compared with aromatase inhibitors, such as anastrozole,
and CLOMIPHENE has proven to be more effective in increasing
testosterone levels.
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.
Synthesis
Clomifene, 2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]triethylamine
(28.2.4), is synthesized from 4-hydroxybenzophenone by reacting it with 2-diethylaminoethylchloride
in the presence of an alkali, which gives 4-(2-diethylaminoethoxy)benzophenone
(28.2.1). This is reacted with benzylmagnesium chloride in a Grignard reaction,
forming as a result the corresponding carbinol (28.2.2). Dehydrating this with hydrogen chloride gives 2-[p-(1,2-diphenylvinyl) phenoxy]triethylamine (28.2.4), the vinylic hydrogen
atom of which is replaced with a chlorine atom using N-chlorosuccinimide, giving clomifene
(28.2.4) .
Check Digit Verification of cas no
The CAS Registry Mumber 911-45-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,1 and 1 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 911-45:
(5*9)+(4*1)+(3*1)+(2*4)+(1*5)=65
65 % 10 = 5
So 911-45-5 is a valid CAS Registry Number.
InChI:InChI=1/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3/b26-25-
911-45-5Relevant articles and documents
Stereoselective Nickel(II)-Catalyzed Addition of Aryl Grignards to Diphenylacetylene in the Synthesis of Zuclomiphene
Blazecka, Peter,Chung, Andrew,Emmett, Michael,Green, Stuart,Karadeolian, Avedis,Le Sueur, Richard,Patel, Dineshkumar,Rey, Allan,Souza, Fabio,Zhao, Yajun
, (2022/03/16)
Stereoselective synthesis of zuclomiphene was developed using nickel-catalyzed addition of 4-fluorophenylmagnesium bromide to 1,2-diphenylacetylene, followed by quenching with a chlorinating reagent. Since the aryl fluoride addition and chlorination reactions occur consecutively in one pot, the cis orientation of the two phenyl groups of 1,2-diphenylacetylene is conserved, leading to the highly selective synthesis of zuclomiphene. The use of the Grignard reagent resulted in the presence of bromide ions in the reaction mixture, which led to the formation of the bromo-analog of zuclomiphene. Alternative routes were then explored to overcome this issue to yield high-purity zuclomiphene.
TEMPO-Regulated Regio- and Stereoselective Cross-Dihalogenation with Dual Electrophilic X+ Reagents
Kong, Yi,Cao, Tongxiang,Zhu, Shifa
, p. 3004 - 3010 (2021/08/23)
A TEMPO catalyzed cross-dihalogenation reaction was established via redox-regulation of the otherwise complex system of dual electrophilic X+ reagents. Formally, the ICl, BrCl, I2 and Br2 were generated in-situ, which enabled high regio- or stereoselective access to a myriad of iodochlorination, bromochlorination and homo-dihalogenation products with a wide spectrum of functionalities. With its mild conditions and operational simplicity, this method could enable wide applications in organic synthesis, which was exemplified by divergent synthesis of two pharmaceuticals. Detailed mechanistic investigations via radical clock reaction, pinacol ring expansion and Hammett experiments were conducted, which confirmed the intermediacy of halonium ion. In addition, a dynamic catalytic model based on the versatile catalytic role of TEMPO was proposed to explain the selective outcomes.
COMPOSITION FOR CROSS TALK BETWEEN ESTROGEN RECEPTORS AND CANNABIONOID RECEPTORS
-
Paragraph 0068; 0074-0076, (2020/03/28)
A composition for cross talk between estrogen receptors and cannabinoid receptors including a chelator and a receptor ligand is provided. A method of synthesizing the composition is also provided, and the composition may be further prepared in pharmaceutical formulations or kits for therapy or molecular imaging.
