Testosterone propionate

Last updated
Testosterone propionate
Testosterone propionate.svg
Testosterone propionate molecule ball.png
Clinical data
Trade names Testoviron, others
Other namesTP; 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) [1] [2] [3]
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 OOjs UI icon edit-ltr-progressive.svg
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. [4] [1] [5] It has also been used to treat breast cancer in women. [6] It is given by injection into muscle usually once every two to three days. [5] [7] [8]

Contents

Side effects of testosterone propionate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. [5] Testosterone supplementation is also known to reduce the threshold for aggressive behavior in men. [9] 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). [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 propionate is a testosterone ester and a relatively short-acting prodrug of testosterone in the body. [7] [4] [1] Because of this, it is considered to be a natural and bioidentical form of testosterone. [11]

Testosterone propionate was discovered in 1936 and was introduced for medical use in 1937. [12] [4] It was the first testosterone ester to be marketed, and was the major form of testosterone used in medicine until about 1960. [4] [5] 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. [4] [5] As such, it is rarely used today. [5] [13] In addition to its medical use, testosterone propionate 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

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. [14]

Androgen replacement therapy formulations and dosages used in men
RouteMedicationMajor brand namesFormDosage
Oral Testosterone aTablet400–800 mg/day (in divided doses)
Testosterone undecanoate Andriol, JatenzoCapsule40–80 mg/2–4x day (with meals)
Methyltestosterone bAndroid, Metandren, TestredTablet10–50 mg/day
Fluoxymesterone bHalotestin, Ora-Testryl, UltandrenTablet5–20 mg/day
Metandienone bDianabolTablet5–15 mg/day
Mesterolone bProvironTablet25–150 mg/day
Sublingual Testosterone bTestoralTablet5–10 mg 1–4x/day
Methyltestosterone bMetandren, Oreton MethylTablet10–30 mg/day
Buccal Testosterone StriantTablet30 mg 2x/day
Methyltestosterone bMetandren, Oreton MethylTablet5–25 mg/day
Transdermal Testosterone AndroGel, 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
Rectal Testosterone Rektandron, TestosteronbSuppository40 mg 2–3x/day
Injection (IM Tooltip intramuscular injection or SC Tooltip subcutaneous injection) Testosterone Andronaq, Sterotate, VirosteroneAqueous suspension10–50 mg 2–3x/week
Testosterone propionatebTestovironOil solution10–50 mg 2–3x/week
Testosterone enanthate DelatestrylOil solution50–250 mg 1x/1–4 weeks
XyostedAuto-injector50–100 mg 1x/week
Testosterone cypionate Depo-TestosteroneOil solution50–250 mg 1x/1–4 weeks
Testosterone isobutyrate Agovirin DepotAqueous suspension50–100 mg 1x/1–2 weeks
Testosterone phenylacetate bPerandren, AndrojectOil solution50–200 mg 1x/3–5 weeks
Mixed testosterone esters Sustanon 100, Sustanon 250Oil solution50–250 mg 1x/2–4 weeks
Testosterone undecanoate Aveed, NebidoOil solution750–1,000 mg 1x/10–14 weeks
Testosterone buciclate aAqueous suspension600–1,000 mg 1x/12–20 weeks
Implant Testosterone TestopelPellet150–1,200 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
RouteMedicationMajor brand namesFormDosage
Oral Testosterone undecanoate Andriol, JatenzoCapsule40–80 mg 1x/1–2 days
Methyltestosterone Metandren, EstratestTablet0.5–10 mg/day
Fluoxymesterone HalotestinTablet1–2.5 mg 1x/1–2 days
Normethandrone aGinecosideTablet5 mg/day
Tibolone LivialTablet1.25–2.5 mg/day
Prasterone (DHEA) bTablet10–100 mg/day
Sublingual Methyltestosterone MetandrenTablet0.25 mg/day
Transdermal Testosterone IntrinsaPatch150–300 μg/day
AndroGelGel, cream1–10 mg/day
Vaginal Prasterone (DHEA) IntrarosaInsert6.5 mg/day
Injection Testosterone propionateaTestovironOil solution25 mg 1x/1–2 weeks
Testosterone enanthate Delatestryl, Primodian DepotOil solution25–100 mg 1x/4–6 weeks
Testosterone cypionate Depo-Testosterone, Depo-TestadiolOil solution25–100 mg 1x/4–6 weeks
Testosterone isobutyrate aFemandren M, FolivirinAqueous suspension25–50 mg 1x/4–6 weeks
Mixed testosterone esters ClimacteronaOil solution150 mg 1x/4–8 weeks
Omnadren, SustanonOil solution50–100 mg 1x/4–6 weeks
Nandrolone decanoate Deca-DurabolinOil solution25–50 mg 1x/6–12 weeks
Prasterone enanthate aGynodian DepotOil solution200 mg 1x/4–6 weeks
Implant Testosterone TestopelPellet50–100 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
RouteMedicationFormDosage
Oral Methyltestosterone Tablet30–200 mg/day
Fluoxymesterone Tablet10–40 mg 3x/day
Calusterone Tablet40–80 mg 4x/day
Normethandrone Tablet40 mg/day
Buccal Methyltestosterone Tablet25–100 mg/day
Injection (IM Tooltip intramuscular injection or SC Tooltip subcutaneous injection)Testosterone propionateOil solution50–100 mg 3x/week
Testosterone enanthate Oil solution200–400 mg 1x/2–4 weeks
Testosterone cypionate Oil solution200–400 mg 1x/2–4 weeks
Mixed testosterone esters Oil solution250 mg 1x/week
Methandriol Aqueous suspension100 mg 3x/week
Androstanolone (DHT) Aqueous suspension300 mg 3x/week
Drostanolone propionate Oil solution100 mg 1–3x/week
Metenolone enanthate Oil solution400 mg 3x/week
Nandrolone decanoate Oil solution50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionate Oil solution50–100 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. [5] It was also previously available as an 30 mg or 50 mg aqueous suspension. [15] Buccal tablets of testosterone propionate were previously available as well. [5]

Side effects

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

Testosterone propionate is often a painful injection, which is attributed to its short ester chain. [5]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity
of androgens/anabolic steroids
MedicationRatioa
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. [1] [2] It has a relatively short elimination half-life and mean residence time of 2 days and 4 days, respectively. [1] [2] As such, it has a short duration of action and must be administered two to three times per week. [16]

Intramuscular injection of testosterone propionate as an oil solution, aqueous suspension, and emulsion has been compared. [17]

Pharmacokinetics of testosterone esters
Testosterone esterFormRoute Tmax Tooltip Time to peak levels t1/2 Tooltip Elimination half-life MRT Tooltip Mean residence time
Testosterone undecanoate Oil-filled capsulesOral ?1.6 hours3.7 hours
Testosterone propionateOil solutionIntramuscular injection ?0.8 days1.5 days
Testosterone enanthate Castor oil solutionIntramuscular injection10 days4.5 days8.5 days
Testosterone undecanoate Tea seed oil solutionIntramuscular injection13.0 days20.9 days34.9 days
Testosterone undecanoate Castor oil solutionIntramuscular injection11.4 days33.9 days36.0 days
Testosterone buciclate aAqueous suspensionIntramuscular injection25.8 days29.5 days60.0 days
Notes: Testosterone cypionate has similar pharmacokinetics to Testosterone enanthate. Footnotes:a = Never marketed. Sources: See template.
Parenteral durations of androgens/anabolic steroids
MedicationFormMajor brand namesDuration
Testosterone Aqueous suspensionAndronaq, Sterotate, Virosterone2–3 days
Testosterone propionateOil solutionAndroteston, Perandren, Testoviron3–4 days
Testosterone phenylpropionate Oil solutionTestolent8 days
Testosterone isobutyrate Aqueous suspensionAgovirin Depot, Perandren M14 days
Mixed testosterone esters aOil solutionTriolandren10–20 days
Mixed testosterone esters bOil solutionTestosid Depot14–20 days
Testosterone enanthate Oil solutionDelatestryl14–28 days
Testosterone cypionate Oil solutionDepovirin14–28 days
Mixed testosterone esters cOil solutionSustanon 25028 days
Testosterone undecanoate Oil solutionAveed, Nebido100 days
Testosterone buciclate dAqueous suspension20 Aet-1, CDB-1781e90–120 days
Nandrolone phenylpropionate Oil solutionDurabolin10 days
Nandrolone decanoate Oil solutionDeca Durabolin21–28 days
Methandriol Aqueous suspensionNotandron, Protandren8 days
Methandriol bisenanthoyl acetate Oil solutionNotandron Depot16 days
Metenolone acetate Oil solutionPrimobolan3 days
Metenolone enanthate Oil 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

Testosterone propionate, or testosterone 17β-propanoate, is a synthetic androstane steroid and a derivative of testosterone. [18] [19] It is an androgen ester; specifically, it is the C17β propionate (propanoate) ester of testosterone. [18] [19]

Structural properties of major testosterone esters
AndrogenStructureEsterRelative
mol. weight
Relative
T contentb
logPc
Position(s)Moiet(ies)TypeLengtha
Testosterone Testosteron.svg 1.001.003.0–3.4
Testosterone propionate Testosterone propionate.svg C17β Propanoic acid Straight-chain fatty acid31.190.843.7–4.9
Testosterone isobutyrate Testosterone isobutyrate.svg C17β Isobutyric acid Branched-chain fatty acid– (~3)1.240.804.9–5.3
Testosterone isocaproate Testosterone isocaproate.svg C17β Isohexanoic acid Branched-chain fatty acid– (~5)1.340.754.4–6.3
Testosterone caproate Testosterone caproate.svg C17β Hexanoic acid Straight-chain fatty acid61.350.755.8–6.5
Testosterone phenylpropionate Testosterone phenpropionate.svg C17β Phenylpropanoic acid Aromatic fatty acid– (~6)1.460.695.8–6.5
Testosterone cypionate Testosterone cypionate.svg C17β Cyclopentylpropanoic acid Cyclic carboxylic acid– (~6)1.430.705.1–7.0
Testosterone enanthate Testosterone enanthate.svg C17β Heptanoic acid Straight-chain fatty acid71.390.723.6–7.0
Testosterone decanoate Testosterone decanoate.svg C17β Decanoic acid Straight-chain fatty acid101.530.656.3–8.6
Testosterone undecanoate Testosterone undecanoate.svg C17β Undecanoic acid Straight-chain fatty acid111.580.636.7–9.2
Testosterone buciclate d Testosterone buciclate.svg C17β Bucyclic acid eCyclic carboxylic acid– (~9)1.580.637.9–8.5
Footnotes:a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic or cyclic 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. [12] Among the esters synthesized, testosterone propionate was the most potent, and for this reason, was selected for further development, subsequently being marketed. [12] Testosterone propionate was introduced in 1937 by Schering AG in Germany under the brand name Testoviron. [5] It was the first commercially available form of testosterone, and the first testosterone ester, to be introduced. [4] [20] The medication was the major form of testosterone used medically before 1960. [5] Buccal testosterone propionate tablets were introduced for medical use in the mid-to-late 1940s under the brand name Oreton Buccal Tablets. [21] [22] [23] An aqueous suspension of testosterone propionate was marketed by Ciba by 1950. [24] In the 1950s, longer-acting testosterone esters like testosterone enanthate and testosterone cypionate were introduced and superseded testosterone propionate. [4] Although rarely used nowadays due to its short duration, [13] testosterone propionate remains medically available. [5]

Society and culture

Generic names

Testosterone propionate is the generic name of the drug and its USAN Tooltip United States Adopted Name and BAN Tooltip British Approved Name. [18] [19] [25] [26] It has also been referred to as testosterone propanoate or as propionyltestosterone. [18] [19] [25] [26]

Brand names

Testosterone propionate is or has been marketed under a variety of brand names, including, among numerous others: [18] [19] [25] [26]

Availability

Testosterone propionate is no longer available commercially in the United States except via a compounding pharmacy. [27]

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. [28] [29]

Related Research Articles

<span class="mw-page-title-main">Nandrolone</span> Anabolic steroid

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.

<span class="mw-page-title-main">Nandrolone decanoate</span> Anabolic steroid

Nandrolone decanoate, sold under the brand name ROLON among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemias and wasting syndromes, as well as osteoporosis in menopausal women. It is given by injection into muscle or fat once every one to four weeks.

<span class="mw-page-title-main">Testosterone cypionate</span> Chemical compound

Testosterone cypionate, sold under the brand name Depo-Testosterone among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It is also used in hormone therapy for transgender men. It is given by injection into muscle or subcutaneously, once every one to four weeks, depending on clinical indication.

<span class="mw-page-title-main">Testosterone enanthate</span> Chemical compound

Testosterone enanthate is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It is also used in hormone therapy for transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks.

<span class="mw-page-title-main">Metenolone enanthate</span> Chemical compound

Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is given by injection into muscle. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. A related drug, metenolone acetate, is taken by mouth.

<span class="mw-page-title-main">Mesterolone</span> Chemical compound

Mesterolone, sold under the brand name Proviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels. It has also been used to treat male infertility, although this use is controversial. It is taken by mouth.

<span class="mw-page-title-main">Trestolone</span> Chemical compound

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.

<span class="mw-page-title-main">Drostanolone propionate</span> Chemical compound

Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no longer marketed. It is given by injection into muscle.

<span class="mw-page-title-main">Methandriol</span> Chemical compound

Methandriol, also known as methylandrostenediol, is an androgen and anabolic steroid (AAS) medication which was developed by Organon and is used in both oral and injectable formulations. It is an orally active 17α-alkylated AAS and a derivative of the endogenous androgen prohormone androstenediol.

<span class="mw-page-title-main">Testosterone undecanoate</span> Chemical compound

Testosterone undecanoate, sold under the brand names Andriol, Aveed and Nebido among others, is an androgen and anabolic steroid (AAS) medication that is used mainly in the treatment of low testosterone levels in men, It is taken by mouth or given by injection into muscle.

<span class="mw-page-title-main">Testosterone decanoate</span> Chemical compound

Testosterone decanoate is an androgen and anabolic steroid and a testosterone ester. It is a component of Sustanon, along with testosterone propionate, testosterone phenylpropionate, and testosterone isocaproate. The medication has not been marketed as a single-drug preparation. Testosterone decanoate has been investigated as a potential long-acting injectable male contraceptive. It has a longer duration of action than testosterone enanthate, but its duration is not as prolonged as that of testosterone undecanoate.

<span class="mw-page-title-main">Androgen ester</span> Class of chemical compounds

An androgen or anabolic steroid ester is an ester of an androgen/anabolic steroid (AAS) such as the natural testosterone or dihydrotestosterone (DHT) or the synthetic nandrolone (19-nortestosterone). Esterification renders AAS into metabolism-resistant prohormones of themselves, improving oral bioavailability, increasing lipophilicity, and extending the elimination half-life. In addition, with intramuscular injection, AAS esters are absorbed more slowly into the body, further improving the elimination half-life. Aside from differences in pharmacokinetics, these esters essentially have the same effects as the parent drugs. They are used in androgen replacement therapy (ART), among other indications. Examples of androgen esters include testosterone esters such as testosterone cypionate, testosterone enanthate, testosterone propionate, and testosterone undecanoate and nandrolone esters such as nandrolone decanoate and nandrolone phenylpropionate.

<span class="mw-page-title-main">Testosterone hexahydrobenzoate</span> Chemical compound

Testosterone hexahydrobenzoate (THHB), or testosterone cyclohexanecarboxylate (TCHC), sold under the brand names Testormon Depot, Sterandryl Retard, Tardosterandryl, and Testosteron-Depot among others, is an androgen and anabolic steroid medication and a testosterone ester. It is used by intramuscular injection and is provided in the form of ampoules containing 100 mg THHB in oil solution. THHB has comparable pharmacokinetics to those of testosterone cypionate and testosterone enanthate. The medication is no longer marketed. It was previously available in Great Britain.

<span class="mw-page-title-main">Testosterone phenylacetate</span> Chemical compound

Testosterone phenylacetate is an androgen and anabolic steroid and a testosterone ester. Analogously to estradiol benzoate having been one of the first estrogen esters to be introduced, testosterone phenylacetate was one of the first testosterone esters to be introduced. However, since its introduction, it has largely been replaced by other esters, such as testosterone propionate.

<span class="mw-page-title-main">Nandrolone hexyloxyphenylpropionate</span> Chemical compound

Nandrolone hexyloxyphenylpropionate, also known as 19-nortestosterone 17β-(3- phenyl)propionate, is a synthetic androgen and anabolic steroid and a nandrolone ester that is marketed in France, Denmark, Austria, Luxembourg, and Turkey. It has been studied as a potential long-acting injectable male contraceptive, though it has not been marketed for this indication. Approximately 70% of men became azoospermic, while the remaining men all became oligospermic. NHPP has a mean residence time in the body of 29.1 days and an elimination half-life in the body of 20.1 days.

<span class="mw-page-title-main">Nandrolone phenylpropionate</span> Anabolic steroid

Nandrolone phenylpropionate (NPP), or nandrolone phenpropionate, sold under the brand name Durabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used primarily in the treatment of breast cancer and osteoporosis in women. It is given by injection into muscle once every week. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.

<span class="mw-page-title-main">Testosterone buciclate</span> Chemical compound

Testosterone buciclate is a synthetic, injected anabolic–androgenic steroid (AAS) which was never marketed. It was developed in collaboration by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and the World Health Organization (WHO) in the 1970s and early 1980s for use in androgen replacement therapy for male hypogonadism and as a potential male contraceptive. It was first described in 1986. The medication is an androgen ester – specifically, the C17β buciclate (4-butylcyclohexane-1-carboxylate) ester of testosterone – and is a prodrug of testosterone with a very long duration of action when used as a depot via intramuscular injection. Testosterone buciclate is formulated as a microcrystalline aqueous suspension with a defined particle size of at least 75% in the range of 10 to 50 μm.

<span class="mw-page-title-main">Testosterone (medication)</span> Medication and naturally occurring steroid hormone

Testosterone (T) is a medication and naturally occurring steroid hormone. It is used to treat male hypogonadism, gender dysphoria, and certain types of breast cancer. It may also be used to increase athletic ability in the form of doping. It is unclear if the use of testosterone for low levels due to aging is beneficial or harmful. Testosterone can be used as a gel or patch that is applied to the skin, injection into a muscle, tablet that is placed in the cheek, or tablet that is taken by mouth.

<span class="mw-page-title-main">Androstanolone</span> Androgenic and anabolic steroid medication

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT) and sold under the brand name Andractim among others, is an androgen and anabolic steroid (AAS) medication and hormone which is used mainly in the treatment of low testosterone levels in men. It is also used to treat breast development and small penis in males. Compared to testosterone, androstanolone (DHT) is less likely to aromatize into estrogen, and therefore it shows less pronounced estrogenic side effects, such as gynecomastia and water retention. On the other hand, androstanolone (DHT) show more significant androgenic side effects, such as acne, hair loss and prostate enlargement.

<span class="mw-page-title-main">Pharmacokinetics of testosterone</span>

The pharmacology of testosterone, an androgen and anabolic steroid (AAS) medication and naturally occurring steroid hormone, concerns its pharmacodynamics, pharmacokinetics, and various routes of administration.

References

  1. 1 2 3 4 5 Nieschlag E, Behre HM (13 January 2010). "Testosterone Therapy". In Nieschlag E, Behre HM, Nieschlag S (eds.). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 441–446. ISBN   978-3-540-78355-8.
  2. 1 2 3 Behre HM, Abshagen K, Oettel M, Hübler D, Nieschlag E (May 1999). "Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies". European Journal of Endocrinology. 140 (5): 414–419. CiteSeerX   10.1.1.503.1752 . doi:10.1530/eje.0.1400414. PMID   10229906. S2CID   22597244.
  3. Rastrelli G, Reisman Y, Ferri S, Prontera O, Sforza A, Maggi M, Corona G (2019). "Testosterone Replacement Therapy". Sexual Medicine. Springer. pp. 79–93. doi:10.1007/978-981-13-1226-7_8. ISBN   978-981-13-1225-0. S2CID   240176927.
  4. 1 2 3 4 5 6 7 Behre HM, Nieschlag E (26 July 2012). "Testosterone preparations for clinical use in males". In Nieschlag E, Behre HM, Nieschlag S (eds.). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 9, 315–. ISBN   978-1-107-01290-5.
  5. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 357–361, 413, 426, 607, 677. ISBN   978-0-9828280-1-4.
  6. Bolour S, Braunstein G (2005). "Testosterone therapy in women: a review". International Journal of Impotence Research. 17 (5): 399–408. doi:10.1038/sj.ijir.3901334. PMID   15889125. S2CID   6461717.
  7. 1 2 Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185, 1187. ISBN   978-0-7817-1750-2.
  8. Payne AH, Hardy MP (28 October 2007). The Leydig Cell in Health and Disease. Springer Science & Business Media. pp. 423–. ISBN   978-1-59745-453-7.
  9. Geniole SN, Bird BM, McVittie JS, Purcell RB, Archer J, Carré JM (July 2020). "Is testosterone linked to human aggression? A meta-analytic examination of the relationship between baseline, dynamic, and manipulated testosterone on human aggression" (PDF). Hormones and Behavior. 123: 104644. doi:10.1016/j.yhbeh.2019.104644. PMID   31785281. S2CID   208515589.
  10. Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC   2439524 . PMID   18500378.
  11. Santoro N, Braunstein GD, Butts CL, Martin KA, McDermott M, Pinkerton JV (April 2016). "Compounded Bioidentical Hormones in Endocrinology Practice: An Endocrine Society Scientific Statement". The Journal of Clinical Endocrinology and Metabolism. 101 (4): 1318–1343. doi: 10.1210/jc.2016-1271 . PMID   27032319.
  12. 1 2 3 Korenchevsky V, Dennison M, Eldridge M (March 1937). "The prolonged treatment of castrated and ovariectomized rats with testosterone propionate". The Biochemical Journal. 31 (3): 475–485. doi:10.1042/bj0310475. PMC   1266958 . PMID   16746360.
  13. 1 2 Chapple CR, Steers WD (10 May 2011). Practical Urology: Essential Principles and Practice: Essential Principles and Practice. Springer Science & Business Media. pp. 228–. ISBN   978-1-84882-034-0.
  14. "Testosterone propionate". AdisInsight. Springer Nature Switzerland AG.
  15. 1 2 Kahr H (8 March 2013). Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur. Springer-Verlag. pp. 21–. ISBN   978-3-7091-5694-0.
  16. Lee C, Basaria S, Dobs AS (2009). "Hypogonadism and Hormone Replacement in Men with Cancers". In Yeung SJ, Escalante CP, Gagel RF (eds.). Medical Care of Cancer Patients. PMPH-USA. pp. 247–. ISBN   978-1-60795-008-0.
  17. Hamburger C (1952). "17-Ketosteroid Excretion and Modes of Administering Testosterone Preparations". Ciba Foundation Symposium - Steroid Hormone Administration (Book II of Colloquia on Endocrinology, Vol. 3). Novartis Foundation Symposia. John Wiley & Sons. pp. 304–322. doi:10.1002/9780470715154.ch7. ISBN   9780470715154. ISSN   1935-4657.
  18. 1 2 3 4 5 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–642. ISBN   978-1-4757-2085-3.
  19. 1 2 3 4 5 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1002–1004. ISBN   978-3-88763-075-1.
  20. Escamilla RF (February 1960). "Newer hormonal preparations". California Medicine. 92 (2): 121–124. PMC   1578009 . PMID   13849734.
  21. The Mississippi Doctor. 1946. p. 7.
  22. The Midwestern Druggist ... 1948. p. 28.
  23. "New Prescription Products". Journal of the American Pharmaceutical Association (Practical Pharmacy Ed.). 10 (4): 198–206. 1949. doi:10.1016/S0095-9561(16)31795-9. ISSN   0095-9561.
  24. Østergaard E (1950). "Employment of androgens in gynecology". Acta Obstetricia et Gynecologica Scandinavica. 30 (1): 106–127. doi:10.3109/00016345009154942. PMID   14777285. S2CID   30737118.
  25. 1 2 3 Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN   978-94-011-4439-1.
  26. 1 2 3 "Testosterone". Drugs.com.
  27. "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 16 November 2016.
  28. Bicerano J, Karch SB (21 December 2006). "Criminalistics: Introduction to Controlled Substances". In Karch SB (ed.). Drug Abuse Handbook (Second ed.). CRC Press. pp. 30–. ISBN   978-1-4200-0346-8.
  29. Lilley LL, Snyder JS, Rainforth SC (5 August 2016). Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. pp. 50–. ISBN   978-1-77172-066-3.