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Testosterone propionate

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Testosterone propionate
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	CA: Schedule IV US: Schedule III
Pharmacokinetic data
Bioavailability	Oral: very low Intramuscular: very high
Metabolism	Liver
Eliminationhalf-life	Intramuscular: 0.8 days (~20 hours)^[1]^[2]^[3]
Excretion	Urine
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] propanoate
CAS Number	57-85-2
PubChemCID	5995
DrugBank	DB01420
ChemSpider	5774
UNII	WI93Z9138A
KEGG	D00959
ChEBI	CHEBI:9466
ChEMBL	ChEMBL1170
CompTox Dashboard(EPA)	DTXSID9036515
ECHA InfoCard	100.000.319
Chemical and physical data
Formula	C₂₂H₃₂O₃
Molar mass	344.495 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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 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 nameTestoviron among others, is anandrogen andanabolic steroid (AAS) medication which is used mainly in the treatment oflow testosterone levels in men.^[4]^[1]^[5] It has also been used to treatbreast cancer in women.^[6] It is given byinjection into muscle usually once every two to three days.^[5]^[7]^[8]

Side effects of testosterone propionate includesymptoms ofmasculinization likeacne,increased hair growth,voice changes, and increasedsexual desire.^[5] Testosterone supplementation is also known to reduce the threshold foraggressive behavior in men.^[9] The drug is asynthetic androgen and anabolic steroid and hence is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone anddihydrotestosterone (DHT).^[10]^[5] It has strongandrogenic effects and moderateanabolic effects, which make it useful for producing masculinization and suitable forandrogen replacement therapy.^[5] Testosterone propionate is atestosterone ester and a relatively short-actingprodrug oftestosterone 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 liketestosterone enanthate,testosterone cypionate, andtestosterone 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 toimprove physique and performance.^[5] The drug is acontrolled substance in many countries and so non-medical use is generally illicit.^[5]

Medical uses

[edit]

Testosterone propionate is used primarily inandrogen replacement therapy. It is specifically approved for the treatment ofhypogonadism in men,breast cancer,low sexual desire,delayed puberty in boys, andmenopausal symptoms.^[14]

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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/2–4× 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
Sublingual	Testosterone^b	Testoral	Tablet	5–10 mg 1–4×/day
Sublingual	Methyltestosterone^b	Metandren, Oreton Methyl	Tablet	10–30 mg/day
Buccal	Testosterone	Striant	Tablet	30 mg 2×/day
Buccal	Methyltestosterone^b	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, Testosteron^b	Suppository	40 mg 2–3×/day
Injection (IMTooltip intramuscular injection or SCTooltip subcutaneous injection)	Testosterone	Andronaq, Sterotate, Virosterone	Aqueous suspension	10–50 mg 2–3×/week
	Testosterone propionate^b	Testoviron	Oil solution	10–50 mg 2–3×/week
	Testosterone enanthate	Delatestryl	Oil solution	50–250 mg 1x/1–4 weeks
	Testosterone enanthate	Xyosted	Auto-injector	50–100 mg 1×/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 1×/3–5 weeks
	Mixed testosterone esters	Sustanon 100, Sustanon 250	Oil solution	50–250 mg 1×/2–4 weeks
	Testosterone undecanoate	Aveed, Nebido	Oil solution	750–1,000 mg 1×/10–14 weeks
	Testosterone buciclate^a	–	Aqueous suspension	600–1,000 mg 1×/12–20 weeks
Implant	Testosterone	Testopel	Pellet	150–1,200 mg/3–6 months
Notes: Men produce about 3 to 11 mg of 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.

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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
Transdermal	Testosterone	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
	Mixed testosterone esters	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 μgtestosterone 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.

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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 (IMTooltip intramuscular injection or SCTooltip subcutaneous injection)	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

[edit]

Testosterone propionate is usually provided as anoil solution for use by intramuscular injection.^[5] It was also previously available as an 30 mg or 50 mgaqueous suspension.^[15]Buccal tablets of testosterone propionate were previously available as well.^[5]

Side effects

[edit]

Side effects of testosterone propionate includevirilization among others.^[5]

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

Pharmacology

[edit]

Pharmacodynamics

[edit]

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Androgenic vs. anabolic activity ratio
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	1:2–1:3
Oxymetholone	1:2–1:9
Oxandrolone	1:13–1:3
Stanozolol	1:1–1:3
Nandrolone	1:3–1:16
Ethylestrenol	1:2–1:19
Norethandrolone	1:1–1:2
Notes: In rodents.Footnotes:^a = Ratio of androgenic to anabolic activity.Sources: See template.

Testosterone propionate is aprodrug of testosterone and is an androgen andanabolic–androgenic steroid (AAS). That is, it is anagonist of theandrogen receptor (AR).

Pharmacokinetics

[edit]

Testosterone propionate is administered in oil viaintramuscular injection.^[1]^[2] It has a relatively shortelimination half-life andmean residence time of 2 days and 4 days, respectively.^[1]^[2] As such, it has a shortduration of action and must be administered two to three times per week.^[16]

Intramuscular injection of testosterone propionate as anoil solution,aqueous suspension, andemulsion has been compared.^[17]

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Pharmacokinetics of testosterone esters
Testosterone ester	Form	Route	T_maxTooltip Time to peak levels	t_1/2Tooltip Elimination half-life	MRTTooltip Mean residence time
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 toTestosterone enanthate.Footnotes:^a = Never marketed.Sources: See template.

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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

[edit]

Testosterone propionate, or testosterone 17β-propanoate, is asynthetic androstane steroid and aderivative oftestosterone.^[18]^[19] It is anandrogen ester; specifically, it is the C17βpropionate (propanoate)ester of testosterone.^[18]^[19]

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Structural properties of major testosterone esters
Androgen	Structure	Ester				Relative mol. weight	Relative T content^b	logP^c
Androgen	Structure	Position(s)	Moiet(ies)	Type	Length^a	Relative mol. weight	Relative T content^b	logP^c
Testosterone		–	–	–	–	1.00	1.00	3.0–3.4
Testosterone propionate		C17β	Propanoic acid	Straight-chain fatty acid	3	1.19	0.84	3.7–4.9
Testosterone isobutyrate		C17β	Isobutyric acid	Branched-chain fatty acid	– (~3)	1.24	0.80	4.9–5.3
Testosterone isocaproate		C17β	Isohexanoic acid	Branched-chain fatty acid	– (~5)	1.34	0.75	4.4–6.3
Testosterone caproate		C17β	Hexanoic acid	Straight-chain fatty acid	6	1.35	0.75	5.8–6.5
Testosterone phenylpropionate		C17β	Phenylpropanoic acid	Aromatic fatty acid	– (~6)	1.46	0.69	5.8–6.5
Testosterone cypionate		C17β	Cyclopentylpropanoic acid	Cyclic carboxylic acid	– (~6)	1.43	0.70	5.1–7.0
Testosterone enanthate		C17β	Heptanoic acid	Straight-chain fatty acid	7	1.39	0.72	3.6–7.0
Testosterone decanoate		C17β	Decanoic acid	Straight-chain fatty acid	10	1.53	0.65	6.3–8.6
Testosterone undecanoate		C17β	Undecanoic acid	Straight-chain fatty acid	11	1.58	0.63	6.7–9.2
Testosterone buciclate^d		C17β	Bucyclic acid^e	Cyclic carboxylic acid	– (~9)	1.58	0.63	7.9–8.5
Footnotes:^a = Length ofester incarbon atoms forstraight-chain fatty acids or approximate length of ester in carbon atoms foraromatic orcyclic fatty acids.^b = Relative testosterone content by weight (i.e., relativeandrogenic/anabolic potency).^c = Experimental or predictedoctanol/water partition coefficient (i.e.,lipophilicity/hydrophobicity). Retrieved fromPubChem,ChemSpider, andDrugBank.^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 bySchering AG inGermany 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 propionatetablets were introduced for medical use in the mid-to-late 1940s under the brand name Oreton Buccal Tablets.^[21]^[22]^[23] Anaqueous suspension of testosterone propionate was marketed byCiba 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 thegeneric 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 astestosterone propanoate or aspropionyltestosterone.^[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 theUnited States except via a compounding pharmacy.^[27]

Legal status

[edit]

Testosterone propionate, along with other AAS, is aschedule III controlled substance in theUnited States under theControlled Substances Act and aschedule IV controlled substance inCanada under theControlled Drugs and Substances Act.^[28]^[29]

References

[edit]

^^a ^b ^c ^d ^eNieschlag 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.
^^a ^b ^cBehre 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.
^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.
^^a ^b ^c ^d ^e ^f ^gBehre 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.
^^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^qLlewellyn W (2011).Anabolics. Molecular Nutrition Llc. pp. 357–361, 413, 426, 607, 677.ISBN 978-0-9828280-1-4.
^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.
^^a ^bBecker KL (2001).Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185, 1187.ISBN 978-0-7817-1750-2.
^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.
^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.
^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.
^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.
^^a ^b ^cKorenchevsky 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.
^^a ^bChapple 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.
^"Testosterone propionate".AdisInsight. Springer Nature Switzerland AG.
^^a ^bKahr 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.
^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.
^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 978-0-470-71515-4.ISSN 1935-4657.{{cite book}}:ISBN / Date incompatibility (help)
^^a ^b ^c ^d ^eElks 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.
^^a ^b ^c ^d ^eIndex Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1002–1004.ISBN 978-3-88763-075-1.
^Escamilla RF (February 1960)."Newer hormonal preparations".California Medicine.92 (2):121–124.PMC 1578009.PMID 13849734.
^The Mississippi Doctor. 1946. p. 7.
^The Midwestern Druggist ... 1948. p. 28.
^"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.
^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.
^^a ^b ^cMorton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media.ISBN 978-94-011-4439-1.
^^a ^b ^c"Testosterone".Drugs.com.
^"Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved16 November 2016.
^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.
^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.

v t e Testosterone
Topics	Testosterone (as a hormone) Testosterone (as a medication) Pharmacodynamics of testosterone Pharmacokinetics of testosterone Androgen (as a hormone) Androgen/anabolic steroid (as a medication) Androgen replacement therapy Masculinizing hormone therapy
Esters	Androgen ester Testosterone ester Testosterone buciclate Testosterone caproate Testosterone cypionate Testosterone decanoate Testosterone enanthate Testosterone isobutyrate Testosterone isocaproate Testosterone phenylpropionate Testosterone propionate Testosterone undecanoate Mixed testosterone esters
Related	Dihydrotestosterone (DHT; androstanolone) Methyltestosterone Nandrolone (19-nortestosterone) Dehydroepiandrosterone (DHEA; prasterone) Estradiol

Androgens andantiandrogens

Androgens
(incl.AASTooltip anabolic–androgenic steroid)

ARTooltip Androgen receptoragonists

19-Nortestosterone derivatives:Bolandiol dipropionate
Nandrolone esters (e.g.,nandrolone decanoate,nandrolone phenylpropionate)
Norclostebol
Norclostebol acetate
Oxabolone cipionate (oxabolone cypionate)
Trenbolone acetate
Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)

17α-Alkylated dihydrotestosterone derivatives:Androisoxazole
Furazabol
Mebolazine (dimethazine)
Mestanolone
Oxandrolone
Oxymetholone
Stanozolol

17α-Alkylated 19-nortestosterone derivatives:Ethylestrenol
Mibolerone
Norethandrolone
Normethandrone (methylestrenolone, normethisterone)
Propetandrol (propethandrol)

17α-Vinyltestosterone derivatives:Norvinisterone (vinylnortestosterone)

17α-Ethynyltestosterone derivatives:Danazol
Gestrinone
Progestins (e.g.,ethisterone (ethynyltestosterone),levonorgestrel,norgestrel,norethisterone (norethindrone),lynestrenol,norgestrienone)
Tibolone

Progesterone derivatives:Medroxyprogesterone acetate

Progonadotropins

Antiestrogens (e.g.,tamoxifen,clomifene)
GnRH agonists (e.g.,GnRH (gonadorelin),leuprorelin)
Gonadotropins (e.g.,LHTooltip luteinizing hormone,hCGTooltip human chorionic gonadotropin)

Antiandrogens

ARTooltip Androgen receptorantagonists

Steroidogenesis
inhibitors

5α-Reductase	Alfatradiol Dutasteride Epristeride Finasteride Saw palmetto extract
Others	Abiraterone acetate +niraparib Aminoglutethimide Bifluranol Cyproterone acetate Flutamide Ketoconazole Nilutamide Seviteronel^† Spironolactone

Antigonadotropins

Others

Androstenedione immunogens:Androvax (androstenedione albumin)
Ovandrotone albumin (Fecundin)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgen receptor modulators; Estrogens and antiestrogens; Progestogens and antiprogestogens; List of androgens/anabolic steroids

Androgen receptor modulators

ARTooltip Androgen receptor

Agonists	Testosterone derivatives:4-Androstenediol 4-Dehydroepiandrosterone (4-DHEA) 4-Hydroxytestosterone 4,17α-Dimethyltestosterone 5-Androstenedione 11-Ketotestosterone 11β-Hydroxyandrostenedione Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione) Androstenediol (5-androstenediol) Androstenediol 3β-acetate Androstenediol 17β-acetate Androstenediol diacetate Androstenediol dipropionate Androstenedione (4-androstenedione) Atamestane Boldenone Boldenone undecylenate Boldione (1,4-androstadienedione) Clostebol Clostebol acetate Clostebol caproate Clostebol propionate Cloxotestosterone Cloxotestosterone acetate Dehydroandrosterone DHEA (androstenolone, prasterone; 5-DHEA) DHEA enanthate (prasterone enanthate) DHEA sulfate Exemestane Formestane Plomestane Quinbolone Silandrone Testosterone^# (+dutasteride) Testosterone esters Polytestosterone phloretin phosphate 5α-Dihydrotestosterone derivatives:1-Androstenediol 1-Androstenedione 1-Androsterone (1-andro, 1-DHEA) 1-Testosterone 3α-Androstanediol 5α-Androst-2-en-17-one 7β-Hydroxyepiandrosterone 11-Ketodihydrotestosterone Androsterone Bolazine Bolazine capronate Dihydroethyltestosterone Dihydrofluoxymesterone Dihydromethylandrostenediol Dihydrotestosterone (DHT) (androstanolone, stanolone) Dihydrotestosterone esters Drostanolone Drostanolone propionate Epiandrosterone Epitiostanol Mepitiostane Mesabolone Mesterolone Mesterolone cipionate Methyldiazinol Nisterime Nisterime acetate Prostanozol Stenbolone Stenbolone acetate Testifenon (testiphenon, testiphenone) 19-Nortestosterone derivatives:7α-Methyl-19-norandrostenedione (MENT dione, trestione) 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione 19-Nordehydroepiandrosterone Bolandiol Bolandiol dipropionate Bolandione (19-nor-4-androstenedione) Bolmantalate (nandrolone adamantoate) Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate) Methoxydienone (methoxygonadiene) Nandrolone Nandrolone esters Norclostebol Norclostebol acetate Normethandrone (methylestrenolone, normethisterone) Oxabolone Oxabolone cipionate (oxabolone cypionate) Trenbolone Trenbolone acetate Trenbolone enanthate Trenbolone hexahydrobenzylcarbonate Trenbolone undecanoate Trendione Trestolone (MENT) Trestolone acetate Trestolone enanthate 5α-Dihydro-19-nortestosterone derivatives:5α-Dihydronandrolone 5α-Dihydrotrestolone 19-Norandrosterone 17α-Alkylated testosterone derivatives:Bolasterone Calusterone Chlorodehydromethylandrostenediol (CDMA) Chlorodehydromethyltestosterone (CDMT) Chloromethylandrostenediol (CMA) Enestebol Ethyltestosterone Fluoxymesterone Formebolone Hydroxystenozole Metandienone (methandrostenolone) Methandriol (methylandrostenediol) Methandriol bisenanthoyl acetate Methandriol diacetate Methandriol dipropionate Methandriol propionate Methylclostebol (chloromethyltestosterone) Methyltestosterone (+esterified estrogens) Methyltestosterone 3-hexyl ether Oxymesterone Penmesterol Tiomesterone 17α-Alkylated 5α-dihydrotestosterone derivatives:Androisoxazole Desoxymethyltestosterone Furazabol Mebolazine (dimethazine) Mestanolone Metenolone Metenolone acetate Metenolone enanthate Methasterone Methyl-1-testosterone Methylepitiostanol Methylstenbolone Oxandrolone Oxymetholone Stanozolol 17α-Alkylated 19-nortestosterone derivatives:Bolenol Dimethyldienolone Dimethyltrienolone Ethyldienolone Ethylestrenol Methyldienolone Methylhydroxynandrolone (MOHN, MHN) Metribolone Mibolerone Norboletone Norethandrolone Propetandrol RU-2309 Tetrahydrogestrinone 17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:5α-Dihydronorethandrolone 5α-Dihydronormethandrone 17α-Vinyltestosterone derivatives:Norvinisterone (vinylnortestosterone) 17α-Vinyl-19-nortestosterone derivatives:Vinyltestosterone 17α-Ethynyltestosterone derivatives:Danazol Ethinylandrostenediol Ethandrostate Ethisterone (ethynyltestosterone) 5α-Dihydro-17α-ethynyltestosterone derivatives:17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol Dihydroethisterone 17α-Ethynyl-19-nortestosterone derivatives:Δ⁴-Tibolone Desogestrel Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel esters (e.g.,levonorgestrel butanoate) Lynestrenol Lynestrenol phenylpropionate Norethisterone Norethisterone esters (e.g.,norethisterone acetate,norethisterone enanthate) Norgestrel Norgestrienone Quingestanol Quingestanol acetate Tibolone 5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:5α-Dihydrolevonorgestrel 5α-Dihydronorethisterone Progesterone derivatives:6α-Methylprogesterone Medroxyprogesterone acetate Megestrol acetate Others/unsorted:3-Keto-5α-abiraterone 5α-Androstane Alternariol Cl-4AS-1 Drupanol Trilostane ZM-182345
SARMsTooltip Selective androgen receptor modulator	Nonsteroidal:198RL26 ACP-105 AC-262,536 Acetothiolutamide Acetoxolutamide Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4) BMS-564,929 DTIB Enobosarm (ostarine, MK-2866, GTx-024, S-22) FTBU-1 GLPG-0492 GSK2881078 GSK-4336A GSK-8698 LG121071 (LGD-121071) LGD-2226 LGD-2941 (LGD-122941) LGD-3303 LGD-4033 LY305 JNJ-26146900 JNJ-28330835 JNJ-37654032 OPK-88004 (LY-2452473, TT-701) ORM-11984 PF-06260414 R-1 RU-59063 S-1 S-23 S-40503 S-101479 Vosilasarm Steroidal:EM-9017 MK-0773 S42 TFM-4AS-1 YK-11
Antagonists	Steroidal:7α-Thioprogesterone 7α-Thiospironolactone 7α-Thiomethylspironolactone 11α-Hydroxyprogesterone 15β-Hydroxycyproterone acetate Abiraterone Abiraterone acetate Allyltestosterone Benorterone BOMT Canrenoic acid Canrenone Chlormadinone acetate Clascoterone Clometerone Cyproheptadine Cyproterone Cyproterone acetate Delanterone Delmadinone acetate Dicirenone Dienogest Drospirenone DU-41165 Edogestrone EM-4350 EM-5854 EM-5855 EM-6537 Epitestosterone Galeterone Guggulsterone Ludaterone Medrogestone Megestrol acetate Mespirenone Metogest Mexrenone Mifepristone Nomegestrol acetate Nordinone Osaterone Osaterone acetate Oxendolone Potassium canrenoate Promegestone Prorenone Rosterolone RU-15328 SC-5233 (spirolactone) Spironolactone Spirorenone Spiroxasone Topterone Trimegestone Trimethyltrienolone (R-2956) Zanoterone Nonsteroidal:5N-Bicalutamide AA560 Antarlides Arabilin Apalutamide Atraric acid AZD-3514 Bakuchiol Bavdegalutamide BAY-1024767 Bicalutamide Bisphenols (e.g.,BADGE,BFDGE,bisphenol A,bisphenol F,bisphenol S) BMS-501949 BMS-570511 BMS-641988 CH5137291 Cimetidine Cioteronel Cyanonilutamide Darolutamide DDT (via metabolitep,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 Fenarimol Flutamide Hydroxyflutamide Inocoterone Inocoterone acetate Ketoconazole Ketodarolutamide Lavender oil LG-105 LG-120907 LGD-1331 Linuron Masofaniten Methiocarb N-Butylbenzenesulfonamide N-Desmethylapalutamide N-Desmethylenzalutamide Nilutamide ONC1-13B Pentomone PF-998425 Phenothrin Prochloraz Procymidone Proxalutamide Pyrilutamide Ralaniten (EPI-002) Ralaniten acetate (EPI-506) RD-162 Rezvilutamide Ro 2-7239 Ro 5-2537 RU-22930 RU-56187 RU-57073 RU-58642 RU-58841 Seviteronel Thalidomide Topilutamide (fluridil) Valproic acid Vinclozolin YM-580 YM-92088 YM-175735

GPRC6A

Agonists	Cations (incl.aluminium,calcium,gadolinium,magnesium,strontium,zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl.L-arginine,L-lysine,L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone

See also: Receptor/signaling modulators; Androgens and antiandrogens; Estrogen receptor modulators; Progesterone receptor modulators; List of androgens and anabolic steroids

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists	Steroidal:2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g.,testosterone andesters,methyltestosterone,metandienone (methandrostenolone),nandrolone andesters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent-Estradiol Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estradiol esters Lipoidal estradiol Polyestradiol phosphate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol esters Polyestriol phosphate Estrofurate Estrogenic substances Estromustine Estrone Estrone esters Estrone methyl ether Estropipate Etamestrol (eptamestrol) Ethinylandrostenediol Ethandrostate Ethinylestradiol Ethinylestradiol 3-benzoate Ethinylestradiol sulfonate Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Nonsteroidal:(R,R)-THC (S,S)-THC 2,8-DHHHC β-LGND1 β-LGND2 (GTx-878) AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Butestrol Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestrol diacetate Diethylstilbestrol Diethylstilbestrol esters Dimestrol (dianisylhexene) Dimethylstilbestrol Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Elacestrant ERB-196 (WAY-202196) Erteberel (SERBA-1, LY-500307) Estrobin (DBE) Fenestrel FERb 033 Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol esters ICI-85966 (Stilbostat) M2613 meso-Butestrol meso-Hexestrol Mestilbol Methallenestril Methestrol Methestrol dipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-3296 SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-169916 WAY-200070 WAY-204688 (SIM-688) WAY-214156 Unknown/unsorted:ERB-26 ERA-45 ERB-79 ZK-283197 Xenoestrogens:Anise-related (e.g.,anethole,anol,dianethole,dianol,photoanethole) Chalconoids (e.g.,isoliquiritigenin,phloretin,phlorizin (phloridzin),wedelolactone) Coumestans (e.g.,coumestrol,psoralidin) Flavonoids (incl.7,8-DHF,8-prenylnaringenin,apigenin,baicalein,baicalin,biochanin A,calycosin,catechin,daidzein,daidzin,ECG,EGCG,epicatechin,equol,formononetin,glabrene,glabridin,genistein,genistin,glycitein,kaempferol,liquiritigenin,mirificin,myricetin,naringenin,penduletin,pinocembrin,prunetin,puerarin,quercetin,tectoridin,tectorigenin) Lavender oil Lignans (e.g.,enterodiol,enterolactone,nyasol (cis-hinokiresinol)) Metalloestrogens (e.g.,cadmium) Pesticides (e.g.,alternariol,dieldrin,endosulfan,fenarimol,HPTE,methiocarb,methoxychlor,triclocarban,triclosan) Phytosteroids (e.g.,digitoxin (digitalis),diosgenin,guggulsterone) Phytosterols (e.g.,β-sitosterol,campesterol,stigmasterol) Resorcylic acid lactones (e.g.,zearalanone,α-zearalenol,β-zearalenol,zearalenone,zeranol (α-zearalanol),taleranol (teranol, β-zearalanol)) Steroid-like (e.g.,deoxymiroestrol,miroestrol) Stilbenoids (e.g.,resveratrol,rhaponticin) Synthetic xenoestrogens (e.g.,alkylphenols,bisphenols (e.g.,BPA,BPF,BPS),DDT,parabens,PBBs,PHBA,phthalates,PCBs) Others (e.g.,agnuside,rotundifuran)
Mixed (SERMsTooltip Selective estrogen receptor modulators)	2-Phenylbenzofuran 2-Phenyl-1-benzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Camizestrant Chlorotrianisene Clomifene Clomifenoxide CN-55945-27 Cyclofenil D-15413 Desmethylchlorotrianisene Droloxifene Enclomifene Endoxifen Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LN-1643 LN-2299 LY-117018 Menerba Miproxifene Miproxifene phosphate MRL-37 Nafoxidine Nitromifene NNC 45-0095 NNC 45-0320 NNC 45-0781 NNC 45-1506 Ormeloxifene Ospemifene Panomifene Pipendoxifene Promensil Raloxifene Rimostil (P-081) Spironolactone SS1010 Tamoxifen TAS-108 (SR-16234) Toremifene Trioxifene TZE-5323 U-11555A U-11634 Y-134 Zindoxifene Zuclomifene
Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate EM-800 (SCH-57050) Epitiostanol ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I,II,III,IV) ICI-164384 MDL-101906 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-39411 RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703 Coregulator-binding modulators:ERX-11 Noncompetitive inhibitors:Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT,o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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