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Alarelin acetate is an organic compound with CAS 79561-22-1, chemical formula C23H34O5, and molecular weight of 386.53. It is a white or almost white powder, almost odorless, with no special odor, but has a certain degree of toxicity. Its molecular structure contains multiple functional groups, such as carboxyl and ketone groups, which have a significant impact on its chemical properties and biological activity.
Stable under natural light and has a certain degree of thermal stability, but degradation may occur under high temperature and light conditions. The solubility in water is low, but it has good solubility in organic solvents such as methanol and ethanol. In addition, its solubility increases under acidic conditions.
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Alarelin\Alarelin acetate COA
It is an organic compound that can be used to synthesize other compounds or as a pharmaceutical raw material. The specific steps of the laboratory synthesis method for alarelin acetate are as follows:
Acetic anhydride protection of phenylacetylene:
C6H5C2H3+CH3COOH → C6H5CH2COOCH3
(1) Add phenylacetylene and acetic anhydride to a dry round bottom flask and stir evenly.
(2) Heat the mixture to reflux temperature (approximately 100-120 ℃) and continue stirring until there is no unreacted phenylacetylene.
(3) Cool to room temperature, pour the reaction mixture into cold water, and stir with a glass rod until the solid precipitates.
(4) Filter and collect solids, wash with a small amount of cold water, and then dry at room temperature. Obtain the product phenylethyl acetate.
Hydrolysis deprotection of phenylethyl acetate:
C6H5CH2COOCH3+NH3 → C6H5C2H3+CH3COONH4
(1) Add ethyl acetate and pyridine to a dry round bottomed flask and stir evenly.
(2) Heat the mixture to reflux temperature (approximately 100-120 ℃) and continue stirring until there is no unreacted phenylethyl acetate.
(3) Cool to room temperature, pour the reaction mixture into cold water, and stir with a glass rod until the solid precipitates.
(4) Filter and collect solids, wash with a small amount of cold water, and then dry at room temperature. Obtain the product phenylacetylene.
Acetylation reaction of phenylacetylene:
C6H5C2H3+CH3COOH+ZnCl2 → C6H5CH2COOCH3+HCl
(1) Add phenylacetylene, acetic anhydride, and anhydrous zinc chloride to a dry round bottom flask and stir evenly.
(2) Heat the mixture to reflux temperature (approximately 100-120 ℃) and continue stirring until there is no unreacted phenylacetylene.
(3) Cool to room temperature, pour the reaction mixture into cold water, and stir with a glass rod until the solid precipitates.
(4) Filter and collect solids, wash with a small amount of cold water, and then dry at room temperature. Obtain the product phenylacetylene acetate.
Oxidation reaction of phenylacetylene acetate:
C6H5CH2COOCH3 → C10H11NO2
(1) Add phenylacetylene acetate and an appropriate amount of ethyl acetate to a dry round bottom flask and stir evenly.
(2) Heat the mixture to reflux temperature (approximately 100-120 ℃) and continue stirring.
(3) When the reaction mixture turns reddish brown, stop heating and cool naturally to room temperature.
(4) Add an appropriate amount of potassium carbonate and water, stir well.
(5) Filter the mixture and collect the filtrate. Pour the filtrate into ice water and stir with a glass rod until the solid precipitates.
(6) Filter and collect solids, wash with a small amount of cold water, and then dry at room temperature. Obtain the product 3-oxo-N-phenylbutyramide.
Reduction reaction of 3-oxo-N-phenylbutyramide:
C6H5CH2COOCH3+NaOH+H2 → C6H5CH2CH2CONH2+CH3OH+H2O
(1) Add 3-oxo-N-phenylbutyramide and an appropriate amount of ethyl acetate to a dry round bottomed flask and stir evenly.
(2) Heat the mixture to reflux temperature (approximately 100-120 ℃) and continue stirring.
(3) When the reaction mixture turns dark red, stop heating and cool naturally to room temperature.
(4) Add an appropriate amount of sodium hydroxide and water, stir well. Then use hydrogen gas to catalyze the reduction reaction for reduction. Reducing agents such as formaldehyde or sodium borohydride can be used. The specific reduction conditions can be adjusted according to experimental needs. Optimize the dosage of reducing agent and reaction time as needed. Obtain the product N-phenylbutylamine.
Acetylation reaction of N-phenylbutylamine:
C6H5CH2CH2CONH2+CH3COOH+ZnCl2 → C6H5CH2CH2COOCH3+ZnCl2+NH4Cl
(1) Add N-phenylbutylamine, acetic anhydride, and anhydrous zinc chloride to a dry round bottom flask and stir evenly.
(2) Heat the mixture to reflux temperature (approximately 100-120 ℃) and continue stirring until there is no unreacted N-phenylbutylamine.
(3) Cool to room temperature, pour the reaction mixture into cold water, and stir with a glass rod until the solid precipitates.
(4) Filter and collect solids, wash with a small amount of cold water, and then dry at room temperature. Obtain the product N-phenylbutylamine acetate.
Deprotection and rearrangement of N-phenylbutylamine acetate:
C6H5CH2CH2COOCH3+H2O → C17H17NO3+CH3COOH
(1) In (7) deprotection and rearrangement of N-phenylbutylamine acetate:
(2) Add N-phenylbutylamine acetate, ethyl acetate, and a small amount of pyridine to a dry round bottom flask and stir evenly.
(3) Heat the mixture to reflux temperature (approximately 100-120 ℃) and continue stirring.
(4) When the reaction mixture turns reddish brown, stop heating and cool naturally to room temperature.
(5) Add an appropriate amount of water and stir well. Then dry with magnesium sulfate.
(6) Filter the mixture and collect the filtrate. Pour the filtrate into ice water and stir with a glass rod until the solid precipitates.
(7) Filter and collect solids, wash with a small amount of cold water, and then dry at room temperature. Obtain the product Alarelin.
Clinical Applications in Human Gynecology
(I) Infertility (Ovulatory Disorders)
Ovulatory disorders are one of the leading causes of female infertility, accounting for approximately 30%–40% of infertility cases. They are commonly associated with conditions such as polycystic ovary syndrome, hypothalamic dysfunction, and ovarian insufficiency. The core manifestations include delayed ovulation, anovulation, or menstrual cycle irregularities, which prevent the normal fertilization of sperm and egg. By mimicking the action of natural GnRH, alarelin acetate precisely regulates the secretion of pituitary gonadotropins (LH and FSH), thereby achieving the therapeutic goals of ovulation induction and restoration of regular menstruation.
(II) Adjuvant Therapy for Hysteroscopy/Laparoscopy
Hysteroscopy and laparoscopy are minimally invasive surgical procedures commonly used in gynecology, widely applied in the treatment of uterine fibroids, endometrial polyps, intrauterine adhesions, endometriosis, and other gynecological diseases. They offer advantages such as minimal trauma, rapid recovery, and a low incidence of complications. However, surgical outcomes are closely related to preoperative uterine conditions. Particularly in patients with an excessively large uterus, thickened endometrium, or extensive lesions, inadequate preoperative preparation may lead to excessive intraoperative bleeding, poor surgical visualization, and increased surgical difficulty and complication risks. As a preoperative pretreatment agent, the product effectively addresses these issues and ensures the smooth progress of surgery.
Veterinary and Animal Reproductive Applications
In the fields of veterinary medicine and animal reproduction, the product serves as a highly effective reproductive regulatory agent. With its precise control over animal reproductive cycles, it is widely used in the reproductive management and research of livestock, aquatic animals, and laboratory animals, significantly improving reproductive efficiency and advancing the development of animal husbandry, aquaculture, and life science research.
(I) Livestock (Cattle, Pigs, Sheep)
Reproductive efficiency in livestock directly impacts the economic benefits of animal husbandry. Issues in natural reproduction, such as irregular estrus, delayed ovulation, and low conception rates, severely restrict the development of large-scale farming. As a synthetic GnRH analog, alarelin acetate effectively modulates the reproductive endocrine system of livestock, enabling estrus synchronization and ovulation induction, optimizing breeding cycles, and improving artificial insemination conception rates, thus providing technical support for large-scale and standardized farming.
Its specific applications in cattle, pigs, sheep, and other livestock are mainly reflected in two aspects:First, estrus synchronization. Uniform administration of the product to a group of livestock eliminates the randomness of natural estrus, allowing the herd to enter estrus collectively within 7–10 days. This facilitates unified management and centralized breeding by farmers, reducing labor costs and improving farming efficiency. For example, in dairy cattle farming, estrus synchronization enables centralized breeding and calving, optimizing lactation cycles and increasing milk yield.
In pig farming, it promotes synchronized estrus and conception in sows, realizing batch production and improving piglet survival rates.Second, ovulation induction and enhanced conception rates. For livestock with weak estrus signs or ovulatory disorders, administration of the product precisely induces follicular maturation and ovulation, resolving issues such as delayed or failed ovulation. Meanwhile, the drug improves the fertilization capacity of sperm and egg, significantly increasing artificial insemination conception rates. It is especially suitable for the breeding of elite breeding stock, accelerating the genetic improvement process.
(II) Aquatic Animals (Fish and Shrimp)
In aquaculture, the reproductive efficiency of fish and shrimp directly determines production yield and economic benefits. Under natural conditions, gonadal development in fish and shrimp is susceptible to environmental factors including water temperature, light, and water quality, leading to problems such as immature gonads, difficult spawning induction, and low fecundity, which restrict the large-scale development of aquaculture. As a highly effective reproductive regulatory agent, the product effectively induces gonadal development and promotes spawning in fish and shrimp, increasing fecundity and fertilization rates, thus ensuring stable and high yields in aquaculture.
FAQ
What is the use of alarelin acetate?
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Alarelin acetate, a synthetic gonadotropin-releasing hormone (GnRH) analogue, is widely used to manage endometriosis and hormone-sensitive malignancies. Although its safety profile is generally favorable, we report the first documented case of severe hepatotoxicity associated with alarelin acetate administration.
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