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Testosterone propionate

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]

Testosterone propionate
Clinical data
Trade namesTestoviron, others
Other namesTP; Testosterone propanoate; Testosterone 17β-propanoate; Propionyltestosterone; NSC-9166
Routes of
administration		Intramuscular injection, buccal
Drug classAndrogen; Anabolic steroid; Androgen ester
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: very low
Intramuscular: very high
MetabolismLiver
Elimination half-lifeIntramuscular: 0.8 days (~20 hours)[1][2][3]
ExcretionUrine
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 InfoCard100.000.319 Edit this at Wikidata
Chemical and physical data
FormulaC22H32O3
Molar mass344.495 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

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 edit

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.[14]

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
SublingualTestosteronebTestoralTablet5–10 mg 1–4x/day
MethyltestosteronebMetandren, Oreton MethylTablet10–30 mg/day
BuccalTestosteroneStriantTablet30 mg 2x/day
MethyltestosteronebMetandren, Oreton MethylTablet5–25 mg/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 (IMTooltip intramuscular injection or SCTooltip subcutaneous injection)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
Testosterone phenylacetatebPerandren, AndrojectOil solution50–200 mg 1x/3–5 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.
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.
Androgen/anabolic steroid dosages for breast cancer
RouteMedicationFormDosage
OralMethyltestosteroneTablet30–200 mg/day
FluoxymesteroneTablet10–40 mg 3x/day
CalusteroneTablet40–80 mg 4x/day
NormethandroneTablet40 mg/day
BuccalMethyltestosteroneTablet25–100 mg/day
Injection (IMTooltip intramuscular injection or SCTooltip subcutaneous injection)Testosterone propionateOil solution50–100 mg 3x/week
Testosterone enanthateOil solution200–400 mg 1x/2–4 weeks
Testosterone cypionateOil solution200–400 mg 1x/2–4 weeks
Mixed testosterone estersOil solution250 mg 1x/week
MethandriolAqueous suspension100 mg 3x/week
Androstanolone (DHT)Aqueous suspension300 mg 3x/week
Drostanolone propionateOil solution100 mg 1–3x/week
Metenolone enanthateOil solution400 mg 3x/week
Nandrolone decanoateOil solution50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionateOil solution50–100 mg/week
Note: Dosages are not necessarily equivalent. Sources: See template.

Available forms edit

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 edit

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

Pharmacodynamics edit

See also: Testosterone § Mechanism of action, and Anabolic steroid § Pharmacology
Androgenic vs. anabolic activity ratio
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 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 edit

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 esterFormRouteTmaxTooltip Time to peak levelst1/2Tooltip Elimination half-lifeMRTTooltip Mean residence time
Testosterone undecanoateOil-filled capsulesOral?1.6 hours3.7 hours
Testosterone propionateOil solutionIntramuscular injection?0.8 days1.5 days
Testosterone enanthateCastor oil solutionIntramuscular injection10 days4.5 days8.5 days
Testosterone undecanoateTea seed oil solutionIntramuscular injection13.0 days20.9 days34.9 days
Testosterone undecanoateCastor oil solutionIntramuscular injection11.4 days33.9 days36.0 days
Testosterone buciclateaAqueous 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
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 solutionDelatestryl14–28 days
Testosterone cypionateOil solutionDepovirin14–28 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 Durabolin21–28 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 edit

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.[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 ––––1.001.003.0–3.4
Testosterone propionate C17βPropanoic acidStraight-chain fatty acid31.190.843.7–4.9
Testosterone isobutyrate C17βIsobutyric acidBranched-chain fatty acid– (~3)1.240.804.9–5.3
Testosterone isocaproate C17βIsohexanoic acidBranched-chain fatty acid– (~5)1.340.754.4–6.3
Testosterone caproate C17βHexanoic acidStraight-chain fatty acid61.350.755.8–6.5
Testosterone phenylpropionate C17βPhenylpropanoic acidAromatic fatty acid– (~6)1.460.695.8–6.5
Testosterone cypionate C17βCyclopentylpropanoic acidCyclic carboxylic acid– (~6)1.430.705.1–7.0
Testosterone enanthate C17βHeptanoic acidStraight-chain fatty acid71.390.723.6–7.0
Testosterone decanoate C17βDecanoic acidStraight-chain fatty acid101.530.656.3–8.6
Testosterone undecanoate C17βUndecanoic acidStraight-chain fatty acid111.580.636.7–9.2
Testosterone buciclated C17βBucyclic acideCyclic 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 edit

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 edit

Generic names edit

Testosterone propionate is the generic name of the drug and its USANTooltip United States Adopted Name and BANTooltip 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 edit

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

  • Agrovirin
  • Andronate
  • Andrusol-P
  • Anertan[15]
  • Masenate
  • Neo-Hombreol
  • Oreton
  • Perandren
  • Synandrol
  • Testoviron

Availability edit

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

Legal status edit

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]

References edit

  1. ^ a b c d e 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. ^ a b c 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. ^ a b c d e f g 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. ^ a b c d e f g h i j k l m n o p q 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. ^ a b 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. ^ a b c 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. ^ a b 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. ^ a b 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. ^ a b c d e 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. ^ a b c d e 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. ^ a b c 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. ^ a b c "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.
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