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]
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| Clinical data | |
|---|---|
| Trade names | Agovirin-Depot, Perandren M, Testocryst, Virex-Cryst |
| Routes of administration | Intramuscular injection |
| Drug class | Androgen; Anabolic steroid; Androgen ester |
| ATC code | |
| Pharmacokinetic data | |
| Metabolites | Testosterone |
| Duration of action | ~2 weeks[1][2][3] |
| Identifiers | |
IUPAC name
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.013.293  |
| Chemical and physical data | |
| Formula | C23H34O3 |
| Molar mass | 358.514 g/mol g·mol−1 |
| 3D model (JSmol) | |
SMILES
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InChI
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Medical uses
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]
| 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 | |
| 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. | ||||
| 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. | ||||
| 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 forms
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
Side effects of testosterone isobutyrate include virilization among others.[1]
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]
| 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 | 14–20 days |
| Testosterone cypionate | Oil solution | Depovirin | 14–20 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 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
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]
| 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. | |||||||||
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
References
- William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 314–322. ISBN 978-0-9828280-1-4.
- Hans Schuermann; Rudolf Doepfmer (13 March 2013). Fertilitätsstörungen beim Manne. Springer-Verlag. pp. 260–. ISBN 978-3-642-94784-1.
- Joachim Ufer (1960). Hormontherapie in der Frauenheilkunde: Grundlagen und Praxis. Gruyter. p. 153.
- http://www.sukl.cz/download/pil/PI15709.pdf
- 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.
- 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.
- http://www.sukl.cz/download/pil/PI15789.pdf
- 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.
- 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.
- 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.
- 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.
- 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.
- Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1.
- 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.
- 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.
- 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.
- "Testosterone".
- K. Lissak (6 December 2012). Hormones and Brain Function. Springer Science & Business Media. pp. 145–. ISBN 978-1-4684-2007-4.
- "Agovirin Injection - bbpharma.sk".