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
Testosterone isobutyrate.svg
Testosterone isobutyrate molecule ball.png
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 Edit this at Wikidata
Chemical and physical data
FormulaC23H34O3
Molar mass358.514 g/mol g·mol−1
3D model (JSmol)

Medical usesEdit

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

Route Medication Major brand names Form Dosage
Oral Testosteronea Tablet 400–800 mg/day (in divided doses)
Testosterone undecanoate Andriol, Jatenzo Capsule 40–80 mg/2–4x day (with meals)
Methyltestosteroneb Android, Metandren, Testred Tablet 10–50 mg/day
Fluoxymesteroneb Halotestin, Ora-Testryl, Ultandren Tablet 5–20 mg/day
Metandienoneb Dianabol Tablet 5–15 mg/day
Mesteroloneb Proviron Tablet 25–150 mg/day
Buccal Testosterone Striant Tablet 30 mg 2x/day
Methyltestosteroneb Metandren, Oreton Methyl Tablet 5–25 mg/day
Sublingual Testosteroneb Testoral Tablet 5–10 mg 1–4x/day
Methyltestosteroneb Metandren, Oreton Methyl Tablet 10–30 mg/day
Intranasal Testosterone Natesto Nasal spray 11 mg 3x/day
Transdermal Testosterone AndroGel, Testim, TestoGel Gel 25–125 mg/day
Androderm, AndroPatch, TestoPatch Non-scrotal patch 2.5–15 mg/day
Testoderm Scrotal patch 4–6 mg/day
Axiron Axillary solution 30–120 mg/day
Androstanolone (DHT) Andractim Gel 100–250 mg/day
Rectal Testosterone Rektandron, Testosteronb Suppository 40 mg 2–3x/day
Injection (IM or SC) Testosterone Andronaq, Sterotate, Virosterone Aqueous suspension 10–50 mg 2–3x/week
Testosterone propionateb Testoviron Oil solution 10–50 mg 2–3x/week
Testosterone enanthate Delatestryl Oil solution 50–250 mg 1x/1–4 weeks
Xyosted Auto-injector 50–100 mg 1x/week
Testosterone cypionate Depo-Testosterone Oil solution 50–250 mg 1x/1–4 weeks
Testosterone isobutyrate Agovirin Depot Aqueous suspension 50–100 mg 1x/1–2 weeks
Testosterone phenylacetateb Perandren, Androject Oil solution 50–200 mg 1x/3–5 weeks
Mixed testosterone esters Sustanon 100, Sustanon 250 Oil solution 50–250 mg 1x/2–4 weeks
Testosterone undecanoate Aveed, Nebido Oil solution 750–1,000 mg 1x/10–14 weeks
Testosterone buciclatea Aqueous suspension 600–1,000 mg 1x/12–20 weeks
Implant Testosterone Testopel Pellet 150–1,200 mg/3–6 months
Notes: Men produce about 3 to 11 mg testosterone per day (mean 7 mg/day in young men). Footnotes: a = Never marketed. b = No longer used and/or no longer marketed. Sources: See template.

Medications and dosages used in masculinizing hormone therapy for transgender men

Medication Brand names Type Route Dosage
Testosterone undecanoate Andriol, Jatenzo Androgen Oral 40–80 mg/2–3x day (with meals)
Testosterone Striant Androgen Buccal 30 mg 2x/day
Natesto Nasal spray 11 mg 3x/day
AndroGel, others Transdermal gel 25–100 mg/day
Androderm, others Transdermal patch 2.5–10 mg/day
Axiron Axillary solution 30–120 mg/day
Testopel Subcutaneous implant 150–600 mg/3–6 months
Testosterone enanthate Delatestryl, others Androgen Injection (IM or SC) 50–100 mg/week or 100–250 mg/2–4 weeks
Testosterone cypionate Depo-Testosterone, others Androgen Injection (IM or SC) 50–100 mg/week or 100–250 mg/2–4 weeks
Testosterone isobutyrate Agovirin Depot Androgen Injection (IM or SC) 50–100 mg/week
Mixed testosterone esters Sustanon 250, others Androgen Injection (IM or SC) 250 mg/2–3 weeks or 500 mg/3–6 weeks
Testosterone undecanoate Aveed, Nebido, others Androgen Injection (IM or SC) 750–1,000 mg/10–14 weeks
GnRH analogue Various GnRH modulator Parenteral (various) Variable
Elagolix Orilissa GnRH antagonist Oral 150 mg/day or 200 mg/twice a day
Medroxyprogesterone acetatea Provera, others Progestin Oral 5–10 mg/day
Depo-Provera, others Injection (IM) 150 mg/3 months
Depo-SubQ Provera 104 Injection (SC) 104 mg/3 months
Lynestrenola Orgametril, others Progestin Oral 5–10 mg/day
Finasterideb Propecia, Proscar 5α-Reductase inhibitor Oral 1 mg/day
Dutasterideb Avodart 5α-Reductase inhibitor Oral 0.5 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

Route Medication Major brand names Form Dosage
Oral Testosterone undecanoate Andriol, Jatenzo Capsule 40–80 mg 1x/1–2 days
Methyltestosterone Metandren, Estratest Tablet 0.5–10 mg/day
Fluoxymesterone Halotestin Tablet 1–2.5 mg 1x/1–2 days
Normethandronea Ginecoside Tablet 5 mg/day
Tibolone Livial Tablet 1.25–2.5 mg/day
Prasterone (DHEA)b Tablet 10–100 mg/day
Sublingual Methyltestosterone Metandren Tablet 0.25 mg/day
Transdermal Testosterone Intrinsa Patch 150–300 μg/day
AndroGel Gel, cream 1–10 mg/day
Vaginal Prasterone (DHEA) Intrarosa Insert 6.5 mg/day
Injection Testosterone propionatea Testoviron Oil solution 25 mg 1x/1–2 weeks
Testosterone enanthate Delatestryl, Primodian Depot Oil solution 25–100 mg 1x/4–6 weeks
Testosterone cypionate Depo-Testosterone, Depo-Testadiol Oil solution 25–100 mg 1x/4–6 weeks
Testosterone isobutyratea Femandren M, Folivirin Aqueous suspension 25–50 mg 1x/4–6 weeks
Mixed testosterone esters Climacterona Oil solution 150 mg 1x/4–8 weeks
Omnadren, Sustanon Oil solution 50–100 mg 1x/4–6 weeks
Nandrolone decanoate Deca-Durabolin Oil solution 25–50 mg 1x/6–12 weeks
Prasterone enanthatea Gynodian Depot Oil solution 200 mg 1x/4–6 weeks
Implant Testosterone Testopel Pellet 50–100 mg 1x/3–6 months
Notes: Premenopausal women produce about 230 ± 70 μg testosterone per day (6.4 ± 2.0 mg testosterone per 4 weeks), with a range of 130 to 330 μg per day (3.6–9.2 mg per 4 weeks). Footnotes: a = Mostly discontinued or unavailable. b = Over-the-counter. Sources: See template.

Available formsEdit

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 effectsEdit

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

PharmacologyEdit

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

Medication Form Major brand names Duration
Testosterone Aqueous suspension Andronaq, Sterotate, Virosterone 2–3 days
Testosterone propionate Oil solution Androteston, Perandren, Testoviron 3–4 days
Testosterone phenylpropionate Oil solution Testolent 8 days
Testosterone isobutyrate Aqueous suspension Agovirin Depot, Perandren M 14 days
Mixed testosterone estersa Oil solution Triolandren 10–20 days
Mixed testosterone estersb Oil solution Testosid Depot 14–20 days
Testosterone enanthate Oil solution Delatestryl 14–28 days
Testosterone cypionate Oil solution Depovirin 14–28 days
Mixed testosterone estersc Oil solution Sustanon 250 28 days
Testosterone undecanoate Oil solution Aveed, Nebido 100 days
Testosterone buciclated Aqueous suspension 20 Aet-1, CDB-1781e 90–120 days
Nandrolone phenylpropionate Oil solution Durabolin 10 days
Nandrolone decanoate Oil solution Deca Durabolin 21–28 days
Methandriol Aqueous suspension Notandron, Protandren 8 days
Methandriol bisenanthoyl acetate Oil solution Notandron Depot 16 days
Metenolone acetate Oil solution Primobolan 3 days
Metenolone enanthate Oil solution Primobolan Depot 14 days
Note: All are via i.m. injection. Footnotes: a = TP, TV, and TUe. b = TP and TKL. c = TP, TPP, TiCa, and TD. d = Studied but never marketed. e = Developmental code names. Sources: See template.

ChemistryEdit

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

Androgen Structure Ester Relative
mol. weight
Relative
T contentb
Durationc
Position Moiety Type Lengtha Rank Group
Testosterone   1.00 1.00 11 Short
Testosterone propionate   C17β Propanoic acid Straight-chain fatty acid 3 1.19 0.84 10 Short
Testosterone isobutyrate   C17β Isobutyric acid Aromatic fatty acid – (~3) 1.24 0.80 9 Moderate
Testosterone cypionate   C17β Cyclopentylpropanoic acid Aromatic fatty acid – (~6) 1.43 0.70 8 Moderate
Testosterone phenylpropionate   C17β Phenylpropanoic acid Aromatic fatty acid – (~6) 1.46 0.69 7 Moderate
Testosterone isocaproate   C17β Isohexanoic acid Branched-chain fatty acid – (~5) 1.34 0.75 6 Moderate
Testosterone caproate   C17β Hexanoic acid Straight-chain fatty acid 6 1.35 0.75 5 Moderate
Testosterone enanthate   C17β Heptanoic acid Straight-chain fatty acid 7 1.39 0.72 4 Moderate
Testosterone decanoate   C17β Decanoic acid Straight-chain fatty acid 10 1.53 0.65 3 Long
Testosterone undecanoate   C17β Undecanoic acid Straight-chain fatty acid 11 1.58 0.63 2 Long
Testosterone buciclated   C17β Bucyclic acide Aromatic carboxylic acid – (~9) 1.58 0.63 1 Long
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.

HistoryEdit

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 cultureEdit

Brand namesEdit

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]

AvailabilityEdit

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]

See alsoEdit

ReferencesEdit

  1. ^ a b c d e f g h i j k l m n o p q r s t u v w x y William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 314–322. ISBN 978-0-9828280-1-4.
  2. ^ a b Hans Schuermann; Rudolf Doepfmer (13 March 2013). Fertilitätsstörungen beim Manne. Springer-Verlag. pp. 260–. ISBN 978-3-642-94784-1.
  3. ^ a b 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. ^ a b http://www.sukl.cz/download/pil/PI15789.pdf
  8. ^ a b 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. ^ a b 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. ^ a b 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. ^ a b 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. ^ a b c 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. ^ a b c 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. ^ a b 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. ^ a b "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".

External linksEdit