5949-44-0 Usage
Description
Testosterone undecanoate, also known as Andriol and Aveed, is an androgen and anabolic steroid (AAS) medication primarily used for the treatment of low testosterone levels in men. It is available as an intramuscular injection and an oral capsule, and is characterized as a white solid. Testosterone undecanoate is the undecanoate ester form of the androgen testosterone, with gonadotropin-secretory inhibiting and hormone replacement activity. It is a metabolite of testosterone and is considered a promising androgen for male hormonal contraception.
Uses
Used in Hormone Therapy:
Testosterone undecanoate is used as a hormone therapy agent for the treatment of low testosterone levels in men. It helps maintain male sex characteristics and is used for testosterone replacement in hypogonadal males.
Used in Transgender Hormone Therapy:
Testosterone undecanoate is used as a hormone therapy agent for transgender men, aiding in the development of male secondary sex characteristics.
Used in Treatment of Testosterone Deficiency:
Testosterone undecanoate is used as a treatment for testosterone deficiency, particularly in cases with structural or genetic etiologies. It is indicated for the treatment of hypogonadal conditions and is available in both injectable and oral forms.
Indications
JATENZO (testosterone undecanoate) is an androgen indicated for testosterone replacement therapy in adult males for conditions associated with a deficiency or absence of endogenous testosterone: Primary hypogonadism (congenital or acquired): testicular failure due to cryptorchidism, bilateral torsion, orchitis, vanishing testis syndrome, orchiectomy, Klinefelter syndrome, chemotherapy, or toxic damage from alcohol or heavy metals. These men usually have low serum testosterone concentrations and gonadotropins (follicle-stimulating hormone [FSH], luteinizing hormone [LH]) above the normal range. Hypogonadotropic hypogonadism (congenital or acquired): gonadotropin or luteinizing hormone-releasing hormone (LHRH) deficiency or pituitary-hypothalamic injury from tumors, trauma, or radiation. These men have low testosterone serum concentrations but have gonadotropins in the normal or low range.www.accessdata.fda.gov
Pharmacokinetics
Testosterone undecanoate is a prodrug of testos-terone esterified in the 17b-position with undecanoic acid. Following oral administration, thisprodrug is metabolized only partly in the intestinal wall, and the remaining fraction of testosterone undecanoate is absorbed via the lymphatic system, and hence, avoids first pass hepatic metabolism. After reaching the systemic circulation, testosterone undecanoate rapidly converts to free testosterone. The absolute bioavailability of testosterone following oral administration of testosterone undecanoate is estimated to be 7%. Recent studies in lymph duct cannulated dogs revealed that all of the testosterone undecanoate absorbed into the systemic circulation is due to lymphatic absorption of the prodrug, and more than 80% of the free testosterone in the plasma is contributed by systemic hydrolysis of the lymphatically transported prodrug.
Side effects
Side effects of testosterone undecanoate include symptoms of masculinization like acne, increased hair growth, voice changes, hypertension, elevated liver enzymes, hypertriglyceridemia, and increased sexual desire. The drug is a prodrug of testosterone, the biological ligand of the androgen receptor (AR) and hence is an androgen and anabolic steroid. It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy. Testosterone undecanoate is a testosterone ester and a prodrug of testosterone in the body. Because of this, it is considered to be a natural and bioidentical form of testosterone.
Check Digit Verification of cas no
The CAS Registry Mumber 5949-44-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,9,4 and 9 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5949-44:
(6*5)+(5*9)+(4*4)+(3*9)+(2*4)+(1*4)=130
130 % 10 = 0
So 5949-44-0 is a valid CAS Registry Number.
InChI:InChI=1/C30H48O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h21,24-27H,4-20H2,1-3H3
5949-44-0Relevant articles and documents
Synthesis method of alkyl acid testosterone
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, (2020/12/10)
The invention discloses a synthesis method of alkyl acid testosterone, and belongs to the technical field of synthesis and processing of medicines. The method comprises the following steps of: taking4-androstenedione (4AD) as an initial raw material, firstly, carrying out enol ether protection on the keto group at the site 3, and reducing carbonyl at the site 17 into hydroxyl; or taking 4-androstenedione (4AD) as an initial raw material, firstly carrying out enol ether protection on the keto group at the site 3, then reducing carbonyl at the site 17 into hydroxyl, then carrying out hydrolysison the site 3 to obtain testosterone, and carrying out esterification and third-site hydrolysis to obtain the testosterone ester after testosterone third-site ketal protection. According to the method disclosed by the invention, the third site is protected during esterification reaction, the generation of impurities can be reduced, and an esterification reaction solvent is a water-insoluble organic solvent, so that after the reaction is completed, products can be directly extracted in a layered manner, a large amount of water does not need to be added to separate out the products, the amountof wastewater is reduced, the solvent can be recycled, and the process is more suitable for industrial production.
Method for synthesizing alkyl-acid testosterone compound
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Paragraph 0024; 0025; 0026; 0027; 0028, (2016/10/10)
The invention provides a method for synthesizing an alkyl-acid testosterone compound. The method comprises the step of subjecting a testosterone compound to the esterification reaction with the presence of a solvent and an alkali to obtain an alkyl-acid testosterone compound. According to the technical scheme of the method for synthesizing the alkyl-acid testosterone compound, the solvent is a water-soluble organic solvent. Therefore, after the reaction, the obtained product can be precipitated through adding water, so that the overall process is simplified.
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