Testosterone undecanoate

Base Information

• Chemical Name: Testosterone undecanoate
• CAS No.: 5949-44-0
• Molecular Formula: C30H48O3
• Molecular Weight: 456.709
• Hs Code.: 2937290024
• European Community (EC) Number: 227-712-6
• UNII: H16A5VCT9C
• DSSTox Substance ID: DTXSID90863661
• Nikkaji Number: J61.334G
• Wikipedia: Testosterone_undecanoate
• Wikidata: Q15410178
• NCI Thesaurus Code: C1249
• RXCUI: 37864
• Pharos Ligand ID: 4RGNGJF1LZZR
• Metabolomics Workbench ID: 154684
• ChEMBL ID: CHEMBL2107067
• Mol file: 5949-44-0.mol

Synonyms:Andriol;Nebido;Pantestone;Restandol;testosterone undecanoate;testosterone undecylate;Undestor

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Chemical Property of Testosterone undecanoate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 39-42°C(lit.)
• Refractive Index: 1.522
• Boiling Point: 550.7 °C at 760 mmHg
• Flash Point: 230.3 °C
• PSA: 43.37000
• Density: 1.03 g/cm³
• LogP: 7.96090
• Storage Temp.: Controlled Substance, -20?C Freezer
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 456.36034539
• Heavy Atom Count: 33
• Complexity: 739

Purity/Quality:

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC(=O)OC1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
• Isomeric SMILES: CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
• Recent ClinicalTrials: Patient Satisfaction After Switching to Oral Testosterone Undecanoate
• Recent EU Clinical Trials: Impact of peri-operative tEstosterone levels oN Functional and oncological Outcomes following RadiCal prostatEctomy
• Recent NIPH Clinical Trials: Administration test of dutasteride, bazedoxifene acetate and testosterone undecanoate preparation to healthy adult males
• 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.
• 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

Technology Process of Testosterone undecanoate

There total 8 articles about Testosterone undecanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.15%

undecanoyl chloride (17746-05-3) + 3,3-(ethylenedioxy)-5-androsten-17β-ol (975-57-5) → testosterone undecanoate (5949-44-0)

Guidance literature:

undecanoyl chloride; 3,3-(ethylenedioxy)-5-androsten-17β-ol; With dmap; triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

With hydrogenchloride; In water;

Reference yield: 96.0%

undecanoyl chloride (17746-05-3) + testosterone (58-22-0) → testosterone undecanoate (5949-44-0)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h; Solvent; Reagent/catalyst; Inert atmosphere;

Reference yield:

3-ethoxyandrosta-3,5-dien-17-one (972-46-3) → testosterone undecanoate (5949-44-0)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium borohydride; pyridine / ethanol / 60 °C

2: hydrogenchloride / water; tetrahydrofuran / 20 - 30 °C

3: orthoformic acid triethyl ester; toluene-4-sulfonic acid / 40 °C / Inert atmosphere

4: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; potassium borohydride; toluene-4-sulfonic acid; triethylamine; orthoformic acid triethyl ester; In tetrahydrofuran; ethanol; dichloromethane; water;

upstream raw materials:

undecanoyl chloride

testosterone

3-ethoxyandrosta-3,5-dien-17-one

17β-hydroxy-3-ethoxyandrosta-3,5-diene

Refernces

• 1、 -. "Synthesis method of alkyl acid testosterone". . . Retrieved 2020/12/10.