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Androgens and anabolic steroids
Testosterone propionate
Другие языки:

Testosterone propionate

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Testosterone propionate
Testosterone propionate.svg
Testosterone propionate molecule ball.png
Clinical data
Trade names Testoviron, others
Other names TP; Testosterone propanoate; Testosterone 17β-propanoate; Propionyltestosterone; NSC-9166
Routes of
administration		 Intramuscular injection, buccal
Drug class Androgen; Anabolic steroid; Androgen ester
Legal status
Legal status
Pharmacokinetic data
Bioavailability Oral: very low
Intramuscular: very high
Metabolism Liver
Elimination half-life Intramuscular: 0.8 days (~20 hours)
Excretion Urine
Identifiers
  • [(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] propanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.319
Chemical and physical data
Formula C22H32O3
Molar mass 344.495 g·mol−1
3D model (JSmol)
  • CCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
  • InChI=1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1
  • Key:PDMMFKSKQVNJMI-BLQWBTBKSA-N

Testosterone propionate, sold under the brand name Testoviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It has also been used to treat breast cancer in women. It is given by injection into muscle usually once every two to three days.

Side effects of testosterone propionate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. Testosterone supplementation is also known to reduce the threshold for aggressive behaviors in men. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy. Testosterone propionate is a testosterone ester and a relatively short-acting prodrug of testosterone in the body. Because of this, it is considered to be a natural and bioidentical form of testosterone.

Testosterone propionate was discovered in 1936 and was introduced for medical use in 1937. It was the first testosterone ester to be marketed, and was the major form of testosterone used in medicine until about 1960. The introduction of longer-acting testosterone esters like testosterone enanthate, testosterone cypionate, and testosterone undecanoate starting in the 1950s resulted in testosterone propionate mostly being superseded. As such, it is rarely used today. In addition to its medical use, testosterone propionate is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.

Medical uses

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

Testosterone propionate is used primarily in androgen replacement therapy. It is specifically approved for the treatment of hypogonadism in men, breast cancer, low sexual desire, delayed puberty in boys, and menopausal symptoms.

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
Sublingual Testosteroneb Testoral Tablet 5–10 mg 1–4x/day
Methyltestosteroneb Metandren, Oreton Methyl Tablet 10–30 mg/day
Buccal Testosterone Striant Tablet 30 mg 2x/day
Methyltestosteroneb Metandren, Oreton Methyl Tablet 5–25 mg/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.
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.
Androgen/anabolic steroid dosages for breast cancer
Route Medication Form Dosage
Oral Methyltestosterone Tablet 30–200 mg/day
Fluoxymesterone Tablet 10–40 mg 3x/day
Calusterone Tablet 40–80 mg 4x/day
Normethandrone Tablet 40 mg/day
Buccal Methyltestosterone Tablet 25–100 mg/day
Injection (IM or SC) Testosterone propionate Oil solution 50–100 mg 3x/week
Testosterone enanthate Oil solution 200–400 mg 1x/2–4 weeks
Testosterone cypionate Oil solution 200–400 mg 1x/2–4 weeks
Mixed testosterone esters Oil solution 250 mg 1x/week
Methandriol Aqueous suspension 100 mg 3x/week
Androstanolone (DHT) Aqueous suspension 300 mg 3x/week
Drostanolone propionate Oil solution 100 mg 1–3x/week
Metenolone enanthate Oil solution 400 mg 3x/week
Nandrolone decanoate Oil solution 50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionate Oil solution 50–100 mg/week
Note: Dosages are not necessarily equivalent. Sources: See template.

Available forms

Testosterone propionate is usually provided as an oil solution for use by intramuscular injection. It was also previously available as an 30 mg or 50 mg aqueous suspension.Buccal tablets of testosterone propionate were previously available as well.

Side effects

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

Side effects of testosterone propionate include virilization among others.

Testosterone propionate is often a painful injection, which is attributed to its short ester chain.

Pharmacology

Pharmacodynamics

See also: Testosterone § Mechanism of action, and Anabolic steroid § Pharmacology
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 propionate 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 propionate is administered in oil via intramuscular injection. It has a relatively short elimination half-life and mean residence time of 2 days and 4 days, respectively. As such, it has a short duration of action and must be administered two to three times per week.

Intramuscular injection of testosterone propionate as an oil solution, aqueous suspension, and emulsion has been compared.

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 Testosterone enanthate. 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.

Chemistry

See also: Androgen ester and List of androgen esters

Testosterone propionate, or testosterone 17β-propanoate, is a synthetic androstane steroid and a derivative of testosterone. It is an androgen ester; specifically, it is the C17β propionate (propanoate) ester of testosterone.

Structural properties of major testosterone esters
Androgen Structure Ester Relative
mol. weight 		Relative
T contentb 		logPc
Position(s) Moiet(ies) Type Lengtha
Testosterone Testosteron.svg – – – – 1.00 1.00 3.0–3.4
Testosterone propionate Testosterone propionate.svg C17β Propanoic acid Straight-chain fatty acid 3 1.19 0.84 3.7–4.9
Testosterone isobutyrate Testosterone isobutyrate.svg C17β Isobutyric acid Aromatic fatty acid – (~3) 1.24 0.80 4.9–5.3
Testosterone isocaproate Testosterone isocaproate.svg C17β Isohexanoic acid Branched-chain fatty acid – (~5) 1.34 0.75 4.4–6.3
Testosterone caproate Testosterone caproate.svg C17β Hexanoic acid Straight-chain fatty acid 6 1.35 0.75 5.8–6.5
Testosterone phenylpropionate Testosterone phenpropionate.svg C17β Phenylpropanoic acid Aromatic fatty acid – (~6) 1.46 0.69 5.8–6.5
Testosterone cypionate Testosterone cypionate.svg C17β Cyclopentylpropanoic acid Cyclic carboxylic acid – (~6) 1.43 0.70 5.1–7.0
Testosterone enanthate Testosterone enanthate.svg C17β Heptanoic acid Straight-chain fatty acid 7 1.39 0.72 3.6–7.0
Testosterone decanoate Testosterone decanoate.svg C17β Decanoic acid Straight-chain fatty acid 10 1.53 0.65 6.3–8.6
Testosterone undecanoate Testosterone undecanoate.svg C17β Undecanoic acid Straight-chain fatty acid 11 1.58 0.63 6.7–9.2
Testosterone buciclated Testosterone buciclate.svg C17β Bucyclic acide Aromatic carboxylic acid – (~9) 1.58 0.63 7.9–8.5
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 = Experimental or predicted octanol/water partition coefficient (i.e., lipophilicity/hydrophobicity). Retrieved from PubChem, ChemSpider, and DrugBank. d = Never marketed. e = Bucyclic acid = trans-4-Butylcyclohexane-1-carboxylic acid. Sources: See individual articles.

History

Testosterone esters were synthesized for the first time in 1936, and were found to have greatly improved potency relative to testosterone. Among the esters synthesized, testosterone propionate was the most potent, and for this reason, was selected for further development, subsequently being marketed. Testosterone propionate was introduced in 1937 by Schering AG in Germany under the brand name Testoviron. It was the first commercially available form of testosterone, and the first testosterone ester, to be introduced. The medication was the major form of testosterone used medically before 1960.Buccal testosterone propionate tablets were introduced for medical use in the mid-to-late 1940s under the brand name Oreton Buccal Tablets. An aqueous suspension of testosterone propionate was marketed by Ciba by 1950. In the 1950s, longer-acting testosterone esters like testosterone enanthate and testosterone cypionate were introduced and superseded testosterone propionate. Although rarely used nowadays due to its short duration, testosterone propionate remains medically available.

Society and culture

Generic names

Testosterone propionate is the generic name of the drug and its USAN and BAN. It has also been referred to as testosterone propanoate or as propionyltestosterone.

Brand names

Testosterone propionate is or has been marketed under a variety of brand names, including, among numerous others:

  • Agrovirin
  • Andronate
  • Andrusol-P
  • Anertan
  • Masenate
  • Neo-Hombreol
  • Oreton
  • Perandren
  • Synandrol
  • Testoviron

Availability

Testosterone propionate is no longer available commercially in the United States except via a compounding pharmacy.

Legal status

Testosterone propionate, 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.


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