5949-44-0

Basic information

• Product Name: Testosterone undecanoate
• Synonyms: TESTOSTERONE UNDECANOATE;TESTOSTERONE UNDECANOILATE;17-beta-hydroxy-5-alpha-androstan-3-onundecanoate;testosterone,undecanoate(ester);andriol;4-ANDROSTEN-17BETA-OL-3-ONE 17-UNDECANOATE;4-ANDROSTEN-17-BETA-OL-3-ONE UNDECANOATE;17-[(1-oxoundecyl)oxy]-androst-4-en-3-one
• CAS NO: 5949-44-0
• Molecular Formula: C₃₀H₄₈O₃
• Molecular Weight: 456.7
• EINECS: 227-712-6
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids;Steroid and Hormone;Finished Steroid and Hormone;API;testosterone
• Mol File: 5949-44-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 59-61°C
• Boiling Point: 550.7 °C at 760 mmHg
• Flash Point: 230.3 °C
• Appearance: White crystalline powder
• Density: 1.03 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: Controlled Substance, -20?C Freezer
• CAS DataBase Reference: Testosterone undecanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Testosterone undecanoate(5949-44-0)
• EPA Substance Registry System: Testosterone undecanoate(5949-44-0)

Safety Data

• Hazardous Substances Data: 5949-44-0(Hazardous Substances Data)

Usage

Description

Testosterone undecanoate, sold under the brand names Andriol and Aveed among others, is an androgen and anabolic steroid (AAS) medication that is used mainly in the treatment of low testosterone levels in men. which includes hormone therapy for transgender men. It is taken by mouth or given by injection into muscle.Testosterone Undecanoate is the undecanoate ester form of the androgen testosterone, with gonadotropin-secretory inhibiting and hormone replacement activity. As testosterone inhibits the secretion of gonadotropins from the pituitary gland, administration of testosterone decreases the secretion of luteinizing hormone (LH). By inhibiting LH secretion, the growth of Leydig cells, which are normally stimulated by LH to produce testosterone, may be suppressed. In addition, this agent promotes the maintenance of male sex characteristics and can be used for testosterone replacement in hypogonadal males.

Chemical Properties

White Solid

Uses

Testosterone undecanoate is the ester prodrug of testosterone and has a midchain fatty acid at the 17Beta position. It is available as an intramuscular injection and as an oral capsule, and is indicated for treatment of testosterone deficiency. It should be noted that testosterone undecanoate is only indicated for treatment of hypogonadal conditions with structural or genetic etiologies and should not be used to manage "age-related hypogonadism".

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

Definition

ChEBI: Testosterone undecanoate is a steroid ester. It is a metabolite of Testosterone. It is a promising androgen for male hormonal contraception.

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.

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

Upstream product

• 17746-05-3 undecanoyl chloride 
• 58-22-0 testosterone 
• 63-05-8 Androstenedione 
• 975-57-5 3,3-(ethylenedioxy)-5-androsten-17β-ol 
• 26614-48-2 17β-hydroxy-3-ethoxyandrosta-3,5-diene 
• 972-46-3 3-ethoxyandrosta-3,5-dien-17-one 

Relevant articles and documents

Synthesis method of alkyl acid testosterone

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

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.