Testosterone isobutyrate

Testosterone isobutyrate, sold under the brand names Agovirin-Depot and Perandren M among others, is an androgen and anabolic steroid medication and a testosterone ester which is used for indications such as low testosterone levels in men and delayed puberty in boys.[1][4] It is available only in the Czech Republic and Slovakia.[1] The medication is administered by injection into muscle once every 1 to 2 weeks in males.[1] Unlike most other testosterone esters, which are provided as oil solutions, testosterone isobutyrate is formulated as a microcrystalline aqueous suspension.[1]

Testosterone isobutyrate
Clinical data
Trade namesAgovirin-Depot, Perandren M, Testocryst, Virex-Cryst
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
ATC code
Pharmacokinetic data
MetabolitesTestosterone
Duration of action~2 weeks[1][2][3]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.013.293
Chemical and physical data
FormulaC23H34O3
Molar mass358.522 g·mol−1
3D model (JSmol)

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

Testosterone isobutyrate is used in the treatment of hypogonadism in men and delayed puberty in adolescent boys.[1] It is also used in the treatment of Klinefelter's syndrome, aplastic anemia, Cushing's syndrome (as an anabolic to preserve lean body mass), postmenopausal osteoporosis in women, advanced breast cancer in women, breast pain in women, and cachexia.[1] Testosterone isobutyrate has been used in masculinizing hormone therapy for transgender men as well.[5][6]

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
BuccalTestosteroneStriantTablet30 mg 2x/day
MethyltestosteronebMetandren, Oreton MethylTablet5–25 mg/day
SublingualTestosteronebTestoralTablet5–10 mg 1–4x/day
MethyltestosteronebMetandren, Oreton MethylTablet10–30 mg/day
IntranasalTestosteroneNatestoNasal spray11 mg 3x/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 (IM or SC)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.
Medications and dosages used in masculinizing hormone therapy for transgender men
MedicationBrand namesTypeRouteDosage
Testosterone undecanoateAndriol, JatenzoAndrogenOral40–80 mg/2–3x day (with meals)
TestosteroneStriantAndrogenBuccal30 mg 2x/day
NatestoNasal spray11 mg 3x/day
AndroGel, othersTransdermal gel25–100 mg/day
Androderm, othersTransdermal patch2.5–10 mg/day
AxironAxillary solution30–120 mg/day
TestopelSubcutaneous implant150–600 mg/3–6 months
Testosterone enanthateDelatestryl, othersAndrogenInjection (IM or SC)50–100 mg/week or 100–250 mg/2–4 weeks
Testosterone cypionateDepo-Testosterone, othersAndrogenInjection (IM or SC)50–100 mg/week or 100–250 mg/2–4 weeks
Testosterone isobutyrateAgovirin DepotAndrogenInjection (IM or SC)50–100 mg/week
Mixed testosterone estersSustanon 250, othersAndrogenInjection (IM or SC)250 mg/2–3 weeks or 500 mg/3–6 weeks
Testosterone undecanoateAveed, Nebido, othersAndrogenInjection (IM or SC)750–1,000 mg/10–14 weeks
GnRH analogueVariousGnRH modulatorParenteral (various)Variable
ElagolixOrilissaGnRH antagonistOral150 mg/day or 200 mg/twice a day
Medroxyprogesterone acetateaProvera, othersProgestinOral5–10 mg/day
Depo-Provera, othersInjection (IM)150 mg/3 months
Depo-SubQ Provera 104Injection (SC)104 mg/3 months
LynestrenolaOrgametril, othersProgestinOral5–10 mg/day
FinasteridebPropecia, Proscar5α-Reductase inhibitorOral1 mg/day
DutasteridebAvodart5α-Reductase inhibitorOral0.5 mg/day
Notes: Testes produce 3 to 11 mg testosterone per day (mean 7 mg/day in young men). Footnotes: a = For suppression of menses. b = For prevention/treatment of scalp hair loss. Sources: See template.
Androgen replacement therapy formulations and dosages used in women
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.

Available forms
See also: Estradiol benzoate/testosterone isobutyrate

Testosterone isobutyrate is provided in the form of a 25 mg/mL microcrystalline aqueous suspension packaged in 2 mL ampoules (5 ampoules per box).[1] This equates to a dose of 50 mg per ampoule.[1] Testosterone isobutyrate (25 mg) is also available in combination with estradiol benzoate (2.5 mg) under the brand name Folivirin (1 mL ampoules).[7][8][9][10][11]

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

Side effects of testosterone isobutyrate include virilization among others.[1]

Pharmacology
See also: Testosterone § Mechanism of action, and Anabolic steroid § Pharmacology

Testosterone isobutyrate is a prodrug of testosterone, and hence is an agonist of the androgen receptor, the biological target of endogenous androgens like testosterone and dihydrotestosterone.[1] It produces both androgenic and anabolic effects, as well as weak estrogenic effects due to metabolism of testosterone into estradiol.[1]

In contrast to most other testosterone esters, which are used as amorphous oil solutions, testosterone isobutyrate is provided in the form of a microcrystalline aqueous suspension.[1] It has very low water solubility and forms a long-lasting microcrystalline depot within muscle upon intramuscular injection.[1] This respository slowly dissolves over time.[1] As a result, testosterone isobutyrate has a prolonged duration of action of approximately 2 weeks.[1][2][3] It is administered at intervals of once every 1 to 2 weeks in men.[1] Microcrystalline testosterone isobutyrate in aqueous suspension requires a larger needle (21 gauge) than oil solutions due to the presence of solid crystals in the suspension.[1] It can produce local irritation, pain, and redness upon injection.[1]

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
See also: Androgen ester and List of androgen esters § Testosterone esters

Testosterone isobutyrate, or testosterone 17β-(2-methylpropanoate), is a synthetic androstane steroid and a derivative of testosterone.[12][13] It is an androgen ester; specifically, it is the C17β 2-methylpropanoate (isobutyrate) ester of testosterone.[12][13]

Structural properties of major testosterone esters
AndrogenStructureEsterRelative
mol. weight		Relative
T contentb		Durationc
PositionMoietyTypeLengthaRankGroup
Testosterone––––1.001.0011Short
Testosterone propionateC17βPropanoic acidStraight-chain fatty acid31.190.8410Short
Testosterone isobutyrateC17βIsobutyric acidAromatic fatty acid– (~3)1.240.809Moderate
Testosterone cypionateC17βCyclopentylpropanoic acidAromatic fatty acid– (~6)1.430.708Moderate
Testosterone phenylpropionateC17βPhenylpropanoic acidAromatic fatty acid– (~6)1.460.697Moderate
Testosterone isocaproateC17βIsohexanoic acidBranched-chain fatty acid– (~5)1.340.756Moderate
Testosterone caproateC17βHexanoic acidStraight-chain fatty acid61.350.755Moderate
Testosterone enanthateC17βHeptanoic acidStraight-chain fatty acid71.390.724Moderate
Testosterone decanoateC17βDecanoic acidStraight-chain fatty acid101.530.653Long
Testosterone undecanoateC17βUndecanoic acidStraight-chain fatty acid111.580.632Long
Testosterone buciclatedC17βBucyclic acideAromatic carboxylic acid– (~9)1.580.631Long
Footnotes: a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative testosterone content by weight (i.e., relative androgenic/anabolic potency). c = Duration by intramuscular or subcutaneous injection in oil solution (except TiB and TB, which are in aqueous suspension). d = Never marketed. e = Bucyclic acid = trans-4-Butylcyclohexane-1-carboxylic acid. Sources: See individual articles.

History

Microcrystalline testosterone isobutyrate in aqueous suspension was first described in 1952.[1][14] It was introduced for medical use shortly thereafter.[1] Around the same time, testosterone enanthate in oil solution was introduced for medical use.[1] It became the dominant long-acting injectable form of testosterone, and limited the commercial success of testosterone isobutyrate.[1] The combination of microcrystalline estradiol benzoate and testosterone isobutyrate in aqueous suspension was introduced under the brand name Femandren M by 1953.[15]

Society and culture

Brand names

Brand names of testosterone isobutyrate include Agovirin-Depot, Perandren M, Testocryst, and Virex-Cryst.[12][13][16][17][16] It has also been marketed in combination with estradiol benzoate under the brand names Femandren M and Folivirin.[7][8][9][10][11]

Availability

Testosterone isobutyrate is available only in the Czech Republic and Slovakia.[1][17] It was originally manufactured by the pharmaceutical company SPOFA[18] intermittently manufactured by Biotika,[1] and is now manufactured by BB Pharma.[19]

gollark: But we got it for phone charging. Eventually. Sort of. Ish.
gollark: That's probably the main problem - nobody really wants a standard.
gollark: Ideally stackable, too.
gollark: Just standardize a form factor with however-many-volt terminals and probably a serial link for communicating with a control computer.
gollark: With decent interfaces.

See also

References
  1. William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 314–322. ISBN 978-0-9828280-1-4.
  2. Hans Schuermann; Rudolf Doepfmer (13 March 2013). Fertilitätsstörungen beim Manne. Springer-Verlag. pp. 260–. ISBN 978-3-642-94784-1.
  3. Joachim Ufer (1960). Hormontherapie in der Frauenheilkunde: Grundlagen und Praxis. Gruyter. p. 153.
  4. http://www.sukl.cz/download/pil/PI15709.pdf
  5. Heresová J, Pobisová Z, Hampl R, Stárka L (December 1986). "Androgen administration to transsexual women. II. Hormonal changes". Exp. Clin. Endocrinol. 88 (2): 219–23. doi:10.1055/s-0029-1210600. PMID 3556412.
  6. Hampl R, Hána V, Heresová J, Brzek A, Marek J, Stárka L (January 1989). "Srovnání vylucování trí v Ceskoslovensku registrovaných androgenů" [Comparison of the excretion of 3 androgens registered in Czechoslovakia]. Sbornik Lekarsky (in Czech). 91 (1): 16–20. ISSN 0036-5327. PMID 2717876.
  7. http://www.sukl.cz/download/pil/PI15789.pdf
  8. Kubíková, Drahomíra (2014). "Menopauzální symptomy a hormonální substituční terapie" [Menopausal symptoms and hormone replacement therapy]. Praktické Lékárenství (in Czech). 10 (2): 68–73. ISSN 1801-2434.
  9. Marek Josef; a kolektiv (14 May 2010). Farmakoterapie vnitřních nemocí: 4., zcela přepracované a doplněné vydání. Grada Publishing a.s. pp. 380–. ISBN 978-80-247-9524-9. In addition, testosterone isobutyrate in FOLIVIRIN, Biotika, an injection containing 25 mg testosterone isobutyrate and 2.5 mg estradiol benzoate is available. It is applied every 4-6 weeks depending on the effect.
  10. Georg Arends; Heinrich Zörnig; Hermann Hager; Georg Frerichs, Walther Kern (14 December 2013). Hagers Handbuch der pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Drogisten, Ärzte u. Medizinalbeamte. Springer-Verlag. pp. 1163–. ISBN 978-3-662-36329-4.
  11. Hans Hermann Julius Hager; Walther Kern; Paul Heinz List; Hermann Josef Roth (29 July 2013). Hagers Handbuch der Pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Ärzte und Medizinalbeamte: Wirkstoffgruppen II Chemikalien und Drogen (A-AL). Springer-Verlag. pp. 109, 141, 178. ISBN 978-3-662-25655-8.
  12. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–642. ISBN 978-1-4757-2085-3.
  13. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1.
  14. Drescher H (April 1952). "Unsere Erfahrungen mit einer neuartigen Testosteron-isobutyrat-Kristallsuspension" [Experiences with a New Testosterone Isobutyrate Crystal Suspension]. Dtsch. Med. Wochenschr. (in German). 77 (14): 431–2. doi:10.1055/s-0028-1115985. PMID 12988767.
  15. Ciba Symposium: 1953/57:Index. Ciba. 1953. p. 197. Femandren M. C'est le nom des nouvelles ampoules cristallines destinées au traitement associé œs- trogène-androgène. Elles renferment, sous forme de microcristaux, 2,5 mg de mono- benzoate d'œstradiol et 50 mg d'isobutyra- te de testostérone; elles sont indiquées pour traiter les cas où il convient d'administrer simultanément de l'hormone femelle et de l'hormone mâle et où il importe aussi d'obtenir un effet prolongé, par exemple lors de symptômes d'insuffisance à la ménopause ou après castration. L'effet d'une injection se prolonge pendant 3-6 semaines.
  16. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
  17. "Testosterone".
  18. K. Lissak (6 December 2012). Hormones and Brain Function. Springer Science & Business Media. pp. 145–. ISBN 978-1-4684-2007-4.
  19. "Agovirin Injection - bbpharma.sk".
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