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 8 to 12 weeks, depending on individual response.[5][9]

Testosterone undecanoate
Testosterone undecanoate.svg
Testosterone undecanoate molecule ball.png
Clinical data
Pronunciation/tɛˈstɒstərn ənˈdɛkənt/ 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%[citation needed]
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 Edit this at Wikidata
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 usesEdit

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

Route Medication Major brand names Form Dosage
Oral Testosteronea Tablet 400–800 mg/day (in divided doses)
Testosterone undecanoate Andriol, Jatenzo Capsule 40–80 mg/2–4x day (with meals)
Methyltestosteroneb Android, Metandren, Testred Tablet 10–50 mg/day
Fluoxymesteroneb Halotestin, Ora-Testryl, Ultandren Tablet 5–20 mg/day
Metandienoneb Dianabol Tablet 5–15 mg/day
Mesteroloneb Proviron Tablet 25–150 mg/day
Buccal Testosterone Striant Tablet 30 mg 2x/day
Methyltestosteroneb Metandren, Oreton Methyl Tablet 5–25 mg/day
Sublingual Testosteroneb Testoral Tablet 5–10 mg 1–4x/day
Methyltestosteroneb Metandren, Oreton Methyl Tablet 10–30 mg/day
Intranasal Testosterone Natesto Nasal spray 11 mg 3x/day
Transdermal Testosterone AndroGel, Testim, TestoGel Gel 25–125 mg/day
Androderm, AndroPatch, TestoPatch Non-scrotal patch 2.5–15 mg/day
Testoderm Scrotal patch 4–6 mg/day
Axiron Axillary solution 30–120 mg/day
Androstanolone (DHT) Andractim Gel 100–250 mg/day
Rectal Testosterone Rektandron, Testosteronb Suppository 40 mg 2–3x/day
Injection (IM or SC) Testosterone Andronaq, Sterotate, Virosterone Aqueous suspension 10–50 mg 2–3x/week
Testosterone propionateb Testoviron Oil solution 10–50 mg 2–3x/week
Testosterone enanthate Delatestryl Oil solution 50–250 mg 1x/1–4 weeks
Xyosted Auto-injector 50–100 mg 1x/week
Testosterone cypionate Depo-Testosterone Oil solution 50–250 mg 1x/1–4 weeks
Testosterone isobutyrate Agovirin Depot Aqueous suspension 50–100 mg 1x/1–2 weeks
Testosterone phenylacetateb Perandren, Androject Oil solution 50–200 mg 1x/3–5 weeks
Mixed testosterone esters Sustanon 100, Sustanon 250 Oil solution 50–250 mg 1x/2–4 weeks
Testosterone undecanoate Aveed, Nebido Oil solution 750–1,000 mg 1x/10–14 weeks
Testosterone buciclatea Aqueous suspension 600–1,000 mg 1x/12–20 weeks
Implant Testosterone Testopel Pellet 150–1,200 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

Medication Brand names Type Route Dosage
Testosterone undecanoate Andriol, Jatenzo Androgen Oral 40–80 mg/2–3x day (with meals)
Testosterone Striant Androgen Buccal 30 mg 2x/day
Natesto Nasal spray 11 mg 3x/day
AndroGel, others Transdermal gel 25–100 mg/day
Androderm, others Transdermal patch 2.5–10 mg/day
Axiron Axillary solution 30–120 mg/day
Testopel Subcutaneous implant 150–600 mg/3–6 months
Testosterone enanthate Delatestryl, others Androgen Injection (IM or SC) 50–100 mg/week or 100–250 mg/2–4 weeks
Testosterone cypionate Depo-Testosterone, others Androgen Injection (IM or SC) 50–100 mg/week or 100–250 mg/2–4 weeks
Testosterone isobutyrate Agovirin Depot Androgen Injection (IM or SC) 50–100 mg/week
Mixed testosterone esters Sustanon 250, others Androgen Injection (IM or SC) 250 mg/2–3 weeks or 500 mg/3–6 weeks
Testosterone undecanoate Aveed, Nebido, others Androgen Injection (IM or SC) 750–1,000 mg/10–14 weeks
GnRH analogue Various GnRH modulator Parenteral (various) Variable
Elagolix Orilissa GnRH antagonist Oral 150 mg/day or 200 mg/twice a day
Medroxyprogesterone acetatea Provera, others Progestin Oral 5–10 mg/day
Depo-Provera, others Injection (IM) 150 mg/3 months
Depo-SubQ Provera 104 Injection (SC) 104 mg/3 months
Lynestrenola Orgametril, others Progestin Oral 5–10 mg/day
Finasterideb Propecia, Proscar 5α-Reductase inhibitor Oral 1 mg/day
Dutasterideb Avodart 5α-Reductase inhibitor Oral 0.5 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

Route Medication Major brand names Form Dosage
Oral Testosterone undecanoate Andriol, Jatenzo Capsule 40–80 mg 1x/1–2 days
Methyltestosterone Metandren, Estratest Tablet 0.5–10 mg/day
Fluoxymesterone Halotestin Tablet 1–2.5 mg 1x/1–2 days
Normethandronea Ginecoside Tablet 5 mg/day
Tibolone Livial Tablet 1.25–2.5 mg/day
Prasterone (DHEA)b Tablet 10–100 mg/day
Sublingual Methyltestosterone Metandren Tablet 0.25 mg/day
Transdermal Testosterone Intrinsa Patch 150–300 μg/day
AndroGel Gel, cream 1–10 mg/day
Vaginal Prasterone (DHEA) Intrarosa Insert 6.5 mg/day
Injection Testosterone propionatea Testoviron Oil solution 25 mg 1x/1–2 weeks
Testosterone enanthate Delatestryl, Primodian Depot Oil solution 25–100 mg 1x/4–6 weeks
Testosterone cypionate Depo-Testosterone, Depo-Testadiol Oil solution 25–100 mg 1x/4–6 weeks
Testosterone isobutyratea Femandren M, Folivirin Aqueous suspension 25–50 mg 1x/4–6 weeks
Mixed testosterone esters Climacterona Oil solution 150 mg 1x/4–8 weeks
Omnadren, Sustanon Oil solution 50–100 mg 1x/4–6 weeks
Nandrolone decanoate Deca-Durabolin Oil solution 25–50 mg 1x/6–12 weeks
Prasterone enanthatea Gynodian Depot Oil solution 200 mg 1x/4–6 weeks
Implant Testosterone Testopel Pellet 50–100 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 effectsEdit

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

AnaphylaxisEdit

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.[citation needed]

PharmacologyEdit

PharmacodynamicsEdit

Androgenic vs. anabolic activity
of androgens/anabolic steroids

Medication Ratioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
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).

PharmacokineticsEdit

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 ester Form Route Tmax t1/2 MRT
Testosterone undecanoate Oil-filled capsules Oral ? 1.6 hours 3.7 hours
Testosterone propionate Oil solution Intramuscular injection ? 0.8 days 1.5 days
Testosterone enanthate Castor oil solution Intramuscular injection 10 days 4.5 days 8.5 days
Testosterone undecanoate Tea seed oil solution Intramuscular injection 13.0 days 20.9 days 34.9 days
Testosterone undecanoate Castor oil solution Intramuscular injection 11.4 days 33.9 days 36.0 days
Testosterone buciclatea Aqueous suspension Intramuscular injection 25.8 days 29.5 days 60.0 days
Notes: Testosterone cypionate has similar pharmacokinetics to TE. Footnotes: a = Never marketed. Sources: See template.

Parenteral durations of androgens/anabolic steroids

Medication Form Major brand names Duration
Testosterone Aqueous suspension Andronaq, Sterotate, Virosterone 2–3 days
Testosterone propionate Oil solution Androteston, Perandren, Testoviron 3–4 days
Testosterone phenylpropionate Oil solution Testolent 8 days
Testosterone isobutyrate Aqueous suspension Agovirin Depot, Perandren M 14 days
Mixed testosterone estersa Oil solution Triolandren 10–20 days
Mixed testosterone estersb Oil solution Testosid Depot 14–20 days
Testosterone enanthate Oil solution Delatestryl 14–28 days
Testosterone cypionate Oil solution Depovirin 14–28 days
Mixed testosterone estersc Oil solution Sustanon 250 28 days
Testosterone undecanoate Oil solution Aveed, Nebido 100 days
Testosterone buciclated Aqueous suspension 20 Aet-1, CDB-1781e 90–120 days
Nandrolone phenylpropionate Oil solution Durabolin 10 days
Nandrolone decanoate Oil solution Deca Durabolin 21–28 days
Methandriol Aqueous suspension Notandron, Protandren 8 days
Methandriol bisenanthoyl acetate Oil solution Notandron Depot 16 days
Metenolone acetate Oil solution Primobolan 3 days
Metenolone enanthate Oil solution Primobolan Depot 14 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.

ChemistryEdit

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

Androgen Structure Ester Relative
mol. weight
Relative
T contentb
Durationc
Position Moiety Type Lengtha Rank Group
Testosterone   1.00 1.00 11 Short
Testosterone propionate   C17β Propanoic acid Straight-chain fatty acid 3 1.19 0.84 10 Short
Testosterone isobutyrate   C17β Isobutyric acid Aromatic fatty acid – (~3) 1.24 0.80 9 Moderate
Testosterone cypionate   C17β Cyclopentylpropanoic acid Aromatic fatty acid – (~6) 1.43 0.70 8 Moderate
Testosterone phenylpropionate   C17β Phenylpropanoic acid Aromatic fatty acid – (~6) 1.46 0.69 7 Moderate
Testosterone isocaproate   C17β Isohexanoic acid Branched-chain fatty acid – (~5) 1.34 0.75 6 Moderate
Testosterone caproate   C17β Hexanoic acid Straight-chain fatty acid 6 1.35 0.75 5 Moderate
Testosterone enanthate   C17β Heptanoic acid Straight-chain fatty acid 7 1.39 0.72 4 Moderate
Testosterone decanoate   C17β Decanoic acid Straight-chain fatty acid 10 1.53 0.65 3 Long
Testosterone undecanoate   C17β Undecanoic acid Straight-chain fatty acid 11 1.58 0.63 2 Long
Testosterone buciclated   C17β Bucyclic acide Aromatic carboxylic acid – (~9) 1.58 0.63 1 Long
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.

HistoryEdit

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 cultureEdit

Generic namesEdit

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 namesEdit

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]

AvailabilityEdit

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]

Legal statusEdit

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]

ResearchEdit

Non-alcoholic steatohepatitisEdit

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 undecanoateEdit

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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  41. ^ Clarus Therapeutics Receives U.S. FDA Approval of JATENZO® (Testosterone Undecanoate Capsules for Oral Use) (CIII) for Testosterone Replacement Therapy in Certain Adult Men
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External linksEdit