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.,[4][2][5][6] which includes hormone therapy for transgender men.[7][8][9] 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.[6][10]

Testosterone undecanoate

Clinical data
Pronunciation	/tɛˈstɒstəroʊn ənˈdɛkənoʊeɪt/ teh-STOS-tə-rohn ən-DEK-ə-noh-ayt
Trade names	Oral: Andriol, Jatenzo, others IM: Aveed, Nebido, others
Other names	TU; Testosterone undecylate; Testosterone 17β-undecanoate; ORG-538; CLR-610
AHFS/Drugs.com	Monograph
MedlinePlus	a614041
License data	US DailyMed: Testosterone_undecanoate
Pregnancy category	AU: D [1] US: X (Contraindicated) [1]
Routes of administration	By mouth, intramuscular injection
Drug class	Androgen; Anabolic steroid; Androgen ester
ATC code	G03BA03 (WHO)
Legal status
Legal status	CA: Schedule IV US: Schedule III
Pharmacokinetic data
Bioavailability	Oral: 3–7% Intramuscular: high
Protein binding	High (testosterone)
Metabolism	Liver
Metabolites	Testosterone, undecanoic acid, metabolites of testosterone
Elimination half-life	In TSO: 20.9 days (i.m.)[2][3] In CO: 33.9 days (i.m.)[2][3]
Excretion	~90% Urine, 6% feces
Identifiers
IUPAC name [(8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] undecanoate
CAS Number	5949-44-0^Y
PubChem CID	65157
DrugBank	DB13946^Y
ChemSpider	58664^Y
UNII	H16A5VCT9C
KEGG	D06087^Y
ChEBI	CHEBI:135741^Y
ChEMBL	ChEMBL2107067^Y
ECHA InfoCard	100.025.193
Chemical and physical data
Formula	C30H48O3
Molar mass	456.711 g·mol^−1
3D model (JSmol)	Interactive image
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
InChI InChI=1S/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/t24-,25-,26-,27-,29-,30-/m0/s1^N Key:UDSFVOAUHKGBEK-CNQKSJKFSA-N^N
(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.[6] The drug is a prodrug of testosterone, the biological ligand of the androgen receptor (AR) and hence is an androgen and anabolic steroid.[11][6] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy.[6] Testosterone undecanoate is a testosterone ester and a prodrug of testosterone in the body.[5][4][2] Because of this, it is considered to be a natural and bioidentical form of testosterone.[12]

Testosterone undecanoate was introduced in China for use by injection and in Europe for use by mouth in the 1970s.[13][14] It became available for use by injection in Europe in the early to mid 2000s and in the United States in 2014.[15][16] A formulation for use by mouth is not currently available in the United States but is pending approval as of 2018.[17] Along with testosterone enanthate, testosterone cypionate, and testosterone propionate, testosterone undecanoate is one of the most widely used testosterone esters.[11][2][6] 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.[18][4][2][3][6] In addition to its medical use, testosterone undecanoate is used to improve physique and performance.[6] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[6]

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.[19][20][21] As an intramuscular injection, it is administered at a dosage of 1,000 mg once every 12 weeks.[10] Conversely, oral testosterone undecanoate must be taken two or three times a day with food.[10][22]

Androgen replacement therapy formulations and dosages used in men

Route	Medication	Major brand names	Form	Dosage
Oral	Testosterone^a	–	Tablet	400–800 mg/day (in divided doses)
	Testosterone undecanoate	Andriol, Jatenzo	Capsule	40–80 mg/2–4x day (with meals)
	Methyltestosterone^b	Android, Metandren, Testred	Tablet	10–50 mg/day
	Fluoxymesterone^b	Halotestin, Ora-Testryl, Ultandren	Tablet	5–20 mg/day
	Metandienone^b	Dianabol	Tablet	5–15 mg/day
	Mesterolone^b	Proviron	Tablet	25–150 mg/day
Buccal	Testosterone	Striant	Tablet	30 mg 2x/day
	Methyltestosterone^b	Metandren, Oreton Methyl	Tablet	5–25 mg/day
Sublingual	Testosterone^b	Testoral	Tablet	5–10 mg 1–4x/day
	Methyltestosterone^b	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, Testosteron^b	Suppository	40 mg 2–3x/day
Injection (IM or SC)	Testosterone	Andronaq, Sterotate, Virosterone	Aqueous suspension	10–50 mg 2–3x/week
	Testosterone propionate^b	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 phenylacetate^b	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 buciclate^a	–	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 acetate^a	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
Lynestrenol^a	Orgametril, others	Progestin	Oral	5–10 mg/day
Finasteride^b	Propecia, Proscar	5α-Reductase inhibitor	Oral	1 mg/day
Dutasteride^b	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
	Normethandrone^a	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 propionate^a	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 isobutyrate^a	Femandren M, Folivirin	Aqueous suspension	25–50 mg 1x/4–6 weeks
	Mixed testosterone esters	Climacteron^a	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 enanthate^a	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 effects

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

Side effects of testosterone undecanoate include virilization among others.[6]

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.[23] 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.[24] 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

Medication	Ratio^a
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).

Pharmacokinetics

Testosterone undecanoate has a very long elimination half-life and mean residence time when given as a depot intramuscular injection.[25][2][3] 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.[2][3] 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).[25] Testosterone undecanoate is administered via intramuscular injection once every three months or so.[10][26]

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 buciclate^a	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 esters^a	Oil solution	Triolandren	10–20 days
Mixed testosterone esters^b	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 esters^c	Oil solution	Sustanon 250	28 days
Testosterone undecanoate	Oil solution	Aveed, Nebido	100 days
Testosterone buciclate^d	Aqueous suspension	20 Aet-1, CDB-1781^e	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.

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.[27][28] It is an androgen ester; specifically, it is the C17β undecylate (undecanoate) ester of testosterone.[27][28] A related testosterone ester with a similarly very long duration is testosterone buciclate.[4][5]

Structural properties of major testosterone esters

Androgen	Structure	Ester				Relative mol. weight	Relative T content^b	Duration^c
		Position	Moiety	Type	Length^a			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 buciclate^d		C17β	Bucyclic acid^e	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.

History

In the late 1970s, testosterone undecanoate was introduced for oral use in Europe,[13] although intramuscular testosterone undecanoate had already been in use in China for several years.[14] Intramuscular testosterone undecanoate was not introduced in Europe and the United States until much later, in the early to mid 2000s and 2014, respectively.[15][16] Testosterone undecanoate was approved in the United States after three previous rejections due to safety concerns.[29]

Society and culture

Generic names

Testosterone undecanoate is the generic name of the drug and its USAN and BAN.[27][28][30][31] It is also referred to as testosterone undecylate.[27][28][30][31]

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.[27][28][30][31]

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.[6][32][33] It is approved in over 100 countries worldwide.[32][6] Oral testosterone undecanoate is available in Canada, Europe, Mexico, Asia, and elsewhere but not in the United States.[32][34] 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.[6][32][33]

Legal status

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.[35][36]

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.[37] 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.[38]

Oral testosterone undecanoate

Recently, two different oral formulations of testosterone undecanoate were developed for the treatment of hypogonadism in the United States.[39][40]

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.[41] Clarus has stated it expects Jatenzo to be available in United States pharmacies before the end of 2019,[42] however, it is unclear when Jatenzo will be available for sale as it is currently the subject of a lawsuit alleging patent infringement.[43] 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.[44]

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External links

• "Testosterone undecanoate". Drug Information Portal. U.S. National Library of Medicine.