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Testosterone undecanoate

CAS No.5949-44-0
Chemical Name:Testosterone undecanoate
CBNumber:CB3123991
Molecular Formula:C30H48O3
Formula Weight:456.71
MOL File:5949-44-0.mol

Testosterone undecanoate Property

Melting point 59-61°C
Boiling point 550.7±50.0 °C(Predicted)
Density 1.03±0.1 g/cm3(Predicted)
storage temp. Controlled Substance, -20°C Freezer
solubility DMSO : 10 mg/mL (21.90 mM; Need ultrasonic and warming)
form Solid
color White to Off-White
InChIKey UDSFVOAUHKGBEK-JCROKFDDNA-N
SMILES C[C@]12CCC(=O)C=C1CC[C@@]1([H])[C@]3([H])CC[C@H](OC(=O)CCCCCCCCCC)[C@@]3(C)CC[C@]21[H] |&1:1,10,12,16,30,34,r|
CAS DataBase Reference 5949-44-0(CAS DataBase Reference)
FDA UNII H16A5VCT9C
NCI Drug Dictionary testosterone undecanoate
UNSPSC Code 12352200
NACRES NA.24

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H351-H360-H302-H362
Precautionary statements P264-P270-P301+P312-P330-P501-P201-P260-P263-P264-P270-P308+P313-P201-P202-P281-P308+P313-P405-P501

Testosterone undecanoate Chemical Properties,Usage,Production

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