Testosterone undecanoate

Testosterone undecanoate, sold for use by mouth under the brand names Andriol and Jatenzo and for use by injection under the brand names Aveed and Nebido, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men.[3][1][4][5], which includes hormone therapy for transgender men.[6][7][8] It is taken by mouth two to three times per day with food or given by injection into muscle once every 3.5 days to 2 weeks, depending on individual response.[5][9]

Testosterone undecanoate
Clinical data
Pronunciation/tɛˈstɒstəroʊn ənˈdɛkənoʊeɪt/ teh-STOS-tə-rohn ən-DEK-ə-noh-ayt
Trade namesOral: Andriol, Jatenzo, others
IM: Aveed, Nebido, others
Other namesTU; Testosterone undecylate; Testosterone 17β-undecanoate; ORG-538; CLR-610
Pregnancy
category
  • US: X (Contraindicated)
    Routes of
    administration    		By mouth, intramuscular injection
    Drug classAndrogen; Anabolic steroid; Androgen ester
    ATC code
    Legal status
    Legal status
    Pharmacokinetic data
    BioavailabilityOral: 3–7%
    Intramuscular: high
    Protein bindingHigh (testosterone)
    MetabolismLiver
    MetabolitesTestosterone, undecanoic acid, metabolites of testosterone
    Elimination half-lifeIn TSO: 20.9 days (i.m.)[1][2]
    In CO: 33.9 days (i.m.)[1][2]
    Excretion~90% Urine, 6% feces
    Identifiers
    CAS Number
    PubChem CID
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    ECHA InfoCard100.025.193
    Chemical and physical data
    FormulaC30H48O3
    Molar mass456.711 g·mol−1
    3D model (JSmol)
      (verify)

    Side effects of testosterone undecanoate include symptoms of masculinization like acne, increased hair growth, voice changes, hypertension, elevated liver enzymes, hypertiglyceridemia, and increased sexual desire.[5] The drug is a prodrug of testosterone, the biological ligand of the androgen receptor (AR) and hence is an androgen and anabolic steroid.[10][5] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy.[5] Testosterone undecanoate is a testosterone ester and a prodrug of testosterone in the body.[4][3][1] Because of this, it is considered to be a natural and bioidentical form of testosterone.[11]

    Testosterone undecanoate was introduced in China for use by injection and in Europe for use by mouth in the 1970s.[12][13] It became available for use by injection in Europe in the early to mid 2000s and in the United States in 2014.[14][15] A formulation for use by mouth is not currently available in the United States but is pending approval as of 2018.[16] Along with testosterone enanthate, testosterone cypionate, and testosterone propionate, testosterone undecanoate is one of the most widely used testosterone esters.[10][1][5] However, it has advantages over other testosterone esters in that it can be taken by mouth and in that it has a far longer duration when given by injection.[17][3][1][2][5] In addition to its medical use, testosterone undecanoate is used to improve physique and performance.[5] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[5]

    Medical uses
    See also: Androgen replacement therapy § Medical uses, and Anabolic steroid § Medical

    Testosterone undecanoate is used in androgen replacement therapy. It is specifically approved only for the treatment of hypogonadism.[18][19][20] As an intramuscular injection, it is administered at a dosage of 1,000 mg once every 12 weeks.[9] Conversely, oral testosterone undecanoate must be taken two or three times a day with food.[9][21]

    Androgen replacement therapy formulations and dosages used in men
    RouteMedicationMajor brand namesFormDosage
    OralTestosteronea–Tablet400–800 mg/day (in divided doses)
    Testosterone undecanoateAndriol, JatenzoCapsule40–80 mg/2–4x day (with meals)
    MethyltestosteronebAndroid, Metandren, TestredTablet10–50 mg/day
    FluoxymesteronebHalotestin, Ora-Testryl, UltandrenTablet5–20 mg/day
    MetandienonebDianabolTablet5–15 mg/day
    MesterolonebProvironTablet25–150 mg/day
    BuccalTestosteroneStriantTablet30 mg 2x/day
    MethyltestosteronebMetandren, Oreton MethylTablet5–25 mg/day
    SublingualTestosteronebTestoralTablet5–10 mg 1–4x/day
    MethyltestosteronebMetandren, Oreton MethylTablet10–30 mg/day
    IntranasalTestosteroneNatestoNasal spray11 mg 3x/day
    TransdermalTestosteroneAndroGel, Testim, TestoGelGel25–125 mg/day
    Androderm, AndroPatch, TestoPatchNon-scrotal patch2.5–15 mg/day
    TestodermScrotal patch4–6 mg/day
    AxironAxillary solution30–120 mg/day
    Androstanolone (DHT)AndractimGel100–250 mg/day
    RectalTestosteroneRektandron, TestosteronbSuppository40 mg 2–3x/day
    Injection (IM or SC)TestosteroneAndronaq, Sterotate, VirosteroneAqueous suspension10–50 mg 2–3x/week
    Testosterone propionatebTestovironOil solution10–50 mg 2–3x/week
    Testosterone enanthateDelatestrylOil solution50–250 mg 1x/1–4 weeks
    XyostedAuto-injector50–100 mg 1x/week
    Testosterone cypionateDepo-TestosteroneOil solution50–250 mg 1x/1–4 weeks
    Testosterone isobutyrateAgovirin DepotAqueous suspension50–100 mg 1x/1–2 weeks
    Mixed testosterone estersSustanon 100, Sustanon 250Oil solution50–250 mg 1x/2–4 weeks
    Testosterone undecanoateAveed, NebidoOil solution750–1,000 mg 1x/10–14 weeks
    Testosterone buciclatea–Aqueous suspension600–1,000 mg 1x/12–20 weeks
    ImplantTestosteroneTestopelPellet150–1,200 mg/3–6 months
    Notes: Men produce about 3 to 11 mg testosterone per day (mean 7 mg/day in young men). Footnotes: a = Never marketed. b = No longer used and/or no longer marketed. Sources: See template.
    Medications and dosages used in masculinizing hormone therapy for transgender men
    MedicationBrand namesTypeRouteDosage
    Testosterone undecanoateAndriol, JatenzoAndrogenOral40–80 mg/2–3x day (with meals)
    TestosteroneStriantAndrogenBuccal30 mg 2x/day
    NatestoNasal spray11 mg 3x/day
    AndroGel, othersTransdermal gel25–100 mg/day
    Androderm, othersTransdermal patch2.5–10 mg/day
    AxironAxillary solution30–120 mg/day
    TestopelSubcutaneous implant150–600 mg/3–6 months
    Testosterone enanthateDelatestryl, othersAndrogenInjection (IM or SC)50–100 mg/week or 100–250 mg/2–4 weeks
    Testosterone cypionateDepo-Testosterone, othersAndrogenInjection (IM or SC)50–100 mg/week or 100–250 mg/2–4 weeks
    Testosterone isobutyrateAgovirin DepotAndrogenInjection (IM or SC)50–100 mg/week
    Mixed testosterone estersSustanon 250, othersAndrogenInjection (IM or SC)250 mg/2–3 weeks or 500 mg/3–6 weeks
    Testosterone undecanoateAveed, Nebido, othersAndrogenInjection (IM or SC)750–1,000 mg/10–14 weeks
    GnRH analogueVariousGnRH modulatorParenteral (various)Variable
    ElagolixOrilissaGnRH antagonistOral150 mg/day or 200 mg/twice a day
    Medroxyprogesterone acetateaProvera, othersProgestinOral5–10 mg/day
    Depo-Provera, othersInjection (IM)150 mg/3 months
    Depo-SubQ Provera 104Injection (SC)104 mg/3 months
    LynestrenolaOrgametril, othersProgestinOral5–10 mg/day
    FinasteridebPropecia, Proscar5α-Reductase inhibitorOral1 mg/day
    DutasteridebAvodart5α-Reductase inhibitorOral0.5 mg/day
    Notes: Testes produce 3 to 11 mg testosterone per day (mean 7 mg/day in young men). Footnotes: a = For suppression of menses. b = For prevention/treatment of scalp hair loss. Sources: See template.
    Androgen replacement therapy formulations and dosages used in women
    RouteMedicationMajor brand namesFormDosage
    OralTestosterone undecanoateAndriol, JatenzoCapsule40–80 mg 1x/1–2 days
    MethyltestosteroneMetandren, EstratestTablet0.5–10 mg/day
    FluoxymesteroneHalotestinTablet1–2.5 mg 1x/1–2 days
    NormethandroneaGinecosideTablet5 mg/day
    TiboloneLivialTablet1.25–2.5 mg/day
    Prasterone (DHEA)b–Tablet10–100 mg/day
    SublingualMethyltestosteroneMetandrenTablet0.25 mg/day
    TransdermalTestosteroneIntrinsaPatch150–300 μg/day
    AndroGelGel, cream1–10 mg/day
    VaginalPrasterone (DHEA)IntrarosaInsert6.5 mg/day
    InjectionTestosterone propionateaTestovironOil solution25 mg 1x/1–2 weeks
    Testosterone enanthateDelatestryl, Primodian DepotOil solution25–100 mg 1x/4–6 weeks
    Testosterone cypionateDepo-Testosterone, Depo-TestadiolOil solution25–100 mg 1x/4–6 weeks
    Testosterone isobutyrateaFemandren M, FolivirinAqueous suspension25–50 mg 1x/4–6 weeks
    Mixed testosterone estersClimacteronaOil solution150 mg 1x/4–8 weeks
    Omnadren, SustanonOil solution50–100 mg 1x/4–6 weeks
    Nandrolone decanoateDeca-DurabolinOil solution25–50 mg 1x/6–12 weeks
    Prasterone enanthateaGynodian DepotOil solution200 mg 1x/4–6 weeks
    ImplantTestosteroneTestopelPellet50–100 mg 1x/3–6 months
    Notes: Premenopausal women produce about 230 ± 70 μg testosterone per day (6.4 ± 2.0 mg testosterone per 4 weeks), with a range of 130 to 330 μg per day (3.6–9.2 mg per 4 weeks). Footnotes: a = Mostly discontinued or unavailable. b = Over-the-counter. Sources: See template.

    Side effects
    See also: Anabolic steroid § Adverse effects, and Androgen replacement therapy § Adverse effects

    Side effects of testosterone undecanoate include virilization among others.[5]

    Anaphylaxis

    The Reandron 1000 formulation (Nebido in the United States) contains 1,000 mg of testosterone undecanoate suspended in castor oil with benzyl benzoate for solubilization and as a preservative, and is administered by intramuscular injection. As an excipient in Reandron 1000, benzyl benzoate has been reported as a cause of anaphylaxis (a serious life-threatening allergic reaction) in a case in Australia.[22] Bayer includes this report in information for health professionals and recommends that physicians "should be aware of the potential for serious allergic reactions" to preparations of this type.[23] In Australia, reports to the Adverse Drug Reactions Advisory Committee (ADRAC), which evaluates reports of adverse drug reactions for the Therapeutic Goods Administration (TGA), show several reports of allergic reactions since the anaphylaxis case from 2011.

    Pharmacology

    Pharmacodynamics
    See also: Testosterone § Mechanism of action, and Anabolic steroid § Pharmacology
    Androgenic vs. anabolic activity
    of androgens/anabolic steroids
    MedicationRatioa
    Testosterone~1:1
    Androstanolone (DHT)~1:1
    Methyltestosterone~1:1
    Methandriol~1:1
    Fluoxymesterone1:1–1:15
    Metandienone1:1–1:8
    Drostanolone1:3–1:4
    Metenolone1:2–1:30
    Oxymetholone1:2–1:9
    Oxandrolone1:3–1:13
    Stanozolol1:1–1:30
    Nandrolone1:3–1:16
    Ethylestrenol1:2–1:19
    Norethandrolone1:1–1:20
    Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

    Testosterone undecanoate is a prodrug of testosterone and is an androgen and anabolic–androgenic steroid (AAS). That is, it is an agonist of the androgen receptor (AR).

    Pharmacokinetics

    Testosterone undecanoate has a very long elimination half-life and mean residence time when given as a depot intramuscular injection.[24][1][2] Its elimination half-life is 20.9 days and its mean residence time is 34.9 days in tea seed oil, while its elimination half-life is 33.9 days and its mean residence time is 36.0 days in castor oil.[1][2] These values are substantially longer than those of testosterone enanthate (which, in castor oil, has values of 4.5 days and 8.5 days, respectively).[24] Testosterone undecanoate is administered via intramuscular injection once every three months or so.[9][25]

    Pharmacokinetics of testosterone esters
    Testosterone esterFormRoute of administrationElimination half-lifeMean residence time
    Testosterone undecanoateOil-filled capsulesOral1.6 hours3.7 hours
    Testosterone propionateOil solutionIntramuscular injection0.8 days1.5 days
    Testosterone enanthateCastor oil solutionIntramuscular injection4.5 days8.5 days
    Testosterone undecanoateTea seed oil solutionIntramuscular injection20.9 days34.9 days
    Testosterone undecanoateCastor oil solutionIntramuscular injection33.9 days36.0 days
    Testosterone buciclateaAqueous suspensionIntramuscular injection29.5 days60.0 days
    Notes: Testosterone cypionate has very similar pharmacokinetics to TE. Footnotes: a = Never marketed. Sources: See template.
    Parenteral durations of androgens/anabolic steroids
    MedicationFormMajor brand namesDuration
    TestosteroneAqueous suspensionAndronaq, Sterotate, Virosterone2–3 days
    Testosterone propionateOil solutionAndroteston, Perandren, Testoviron3–4 days
    Testosterone phenylpropionateOil solutionTestolent8 days
    Testosterone isobutyrateAqueous suspensionAgovirin Depot, Perandren M14 days
    Mixed testosterone estersaOil solutionTriolandren10–20 days
    Mixed testosterone estersbOil solutionTestosid Depot14–20 days
    Testosterone enanthateOil solutionDelatestryl14–20 days
    Testosterone cypionateOil solutionDepovirin14–20 days
    Mixed testosterone esterscOil solutionSustanon 25028 days
    Testosterone undecanoateOil solutionAveed, Nebido100 days
    Testosterone buciclatedAqueous suspension20 Aet-1, CDB-1781e90–120 days
    Nandrolone phenylpropionateOil solutionDurabolin10 days
    Nandrolone decanoateOil solutionDeca Durabolin21 days
    MethandriolAqueous suspensionNotandron, Protandren8 days
    Methandriol bisenanthoyl acetateOil solutionNotandron Depot16 days
    Metenolone acetateOil solutionPrimobolan3 days
    Metenolone enanthateOil solutionPrimobolan Depot14 days
    Note: All are via i.m. injection. Footnotes: a = TP, TV, and TUe. b = TP and TKL. c = TP, TPP, TiCa, and TD. d = Studied but never marketed. e = Developmental code names. Sources: See template.

    Chemistry
    See also: Androgen ester and List of androgen esters

    Testosterone undecanoate, or testosterone 17β-undecanoate, is a synthetic androstane steroid and a derivative of testosterone.[26][27] It is an androgen ester; specifically, it is the C17β undecylate (undecanoate) ester of testosterone.[26][27] A related testosterone ester with a similarly very long duration is testosterone buciclate.[3][4]

    Structural properties of major testosterone esters
    AndrogenStructureEsterRelative
    mol. weight    		Relative
    T contentb    		Durationc
    PositionMoietyTypeLengthaRankGroup
    Testosterone
    		––––1.001.0011Short
    Testosterone propionate
    		C17βPropanoic acidStraight-chain fatty acid31.190.8410Short
    Testosterone isobutyrate
    		C17βIsobutyric acidAromatic fatty acid– (~3)1.240.809Moderate
    Testosterone cypionate
    		C17βCyclopentylpropanoic acidAromatic fatty acid– (~6)1.430.708Moderate
    Testosterone phenylpropionate
    		C17βPhenylpropanoic acidAromatic fatty acid– (~6)1.460.697Moderate
    Testosterone isocaproate
    		C17βIsohexanoic acidBranched-chain fatty acid– (~5)1.340.756Moderate
    Testosterone caproate
    		C17βHexanoic acidStraight-chain fatty acid61.350.755Moderate
    Testosterone enanthate
    		C17βHeptanoic acidStraight-chain fatty acid71.390.724Moderate
    Testosterone decanoate
    		C17βDecanoic acidStraight-chain fatty acid101.530.653Long
    Testosterone undecanoate
    		C17βUndecanoic acidStraight-chain fatty acid111.580.632Long
    Testosterone buciclated
    		C17βBucyclic acideAromatic carboxylic acid– (~9)1.580.631Long
    Footnotes: a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative testosterone content by weight (i.e., relative androgenic/anabolic potency). c = Duration by intramuscular or subcutaneous injection in oil solution (except TiB and TB, which are in aqueous suspension). d = Never marketed. e = Bucyclic acid = trans-4-Butylcyclohexane-1-carboxylic acid. Sources: See individual articles.

    History

    In the late 1970s, testosterone undecanoate was introduced for oral use in Europe,[12] although intramuscular testosterone undecanoate had already been in use in China for several years.[13] Intramuscular testosterone undecanoate was not introduced in Europe and the United States until much later, in the early to mid 2000s and 2014, respectively.[14][15] Testosterone undecanoate was approved in the United States after three previous rejections due to safety concerns.[28]

    Society and culture

    Generic names

    Testosterone undecanoate is the generic name of the drug and its USAN and BAN.[26][27][29][30] It is also referred to as testosterone undecylate.[26][27][29][30]

    Brand names

    Testosterone undecanoate is or has been marketed under a variety of brand names, including Andriol, Androxon, Aveed, Cernos Depot, Jatenzo, Nebido, Nebido-R, Panteston, Reandron 1000, Restandol, and Undestor.[26][27][29][30]

    Availability
    See also: List of androgens/anabolic steroids available in the United States

    Intramuscular testosterone undecanoate is available in the United States, Canada, Europe, and elsewhere in the world.[5][31][32] It is approved in over 100 countries worldwide.[31][5] Oral testosterone undecanoate is available in Canada, Europe, Mexico, Asia, and elsewhere but not in the United States.[31][33] Intramuscular testosterone undecanoate is marketed most commonly as Nebido in Canada and Europe and as Aveed in the United States while oral testosterone undecanoate is marketed most commonly as Andriol.[5][31][32]

    Testosterone undecanoate, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act and a schedule IV controlled substance in Canada under the Controlled Drugs and Substances Act.[34][35]

    Research

    Non-alcoholic steatohepatitis

    In 2013, a phase II clinical trial testing intramuscular testosterone undecanoate for the treatment of non-alcoholic steatohepatitis (NASH) was initiated in the United Kingdom.[36] In the United States in 2018, Lipocine Inc. began investigating the potential of using an oral testosterone undecanoate formulation, known as LPCN-1144, in patients with NASH.[37]

    Oral testosterone undecanoate

    Recently, two different oral formulations of testosterone undecanoate were developed for the treatment of hypogonadism in the United States.[38][39]

    On March 27, 2019, the United States Food and Drug Administration (FDA) approved Jatenzo (testosterone undecanoate), an oral testosterone capsule to treat men with certain forms of hypogonadism. The FDA granted the approval of Jatenzo to Clarus Therapeutics.[40] Clarus has stated it expects Jatenzo to be available in United States pharmacies before the end of 2019,[41] however, it is unclear when Jatenzo will be available for sale as it is currently the subject of a lawsuit alleging patent infringement.[42] The suit was filed by Lipocine Inc., who has also developed an oral testosterone undecanoate drug, Tlando, which (as of May 2019) is under review at the FDA.[43]

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    42. Lipocine Seeks Injunction Against the Marketing of Clarus Therapeutics' JATENZO® for Testosterone Replacement Therapy
    43. Lipocine Announces TLANDO™ NDA PDUFA Action Date of November 9, 2019
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