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| Clinical data | |
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| Trade names | Andractim, others |
| Other names | Stanolone; Dihydrotestosterone; DHT; 5α-Dihydrotestosterone; 5α-DHT |
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| Routes of administration | Transdermal (gel),in the cheek,under the tongue,intramuscular injection (asesters) |
| Drug class | Androgen;Anabolic steroid |
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| Pharmacokinetic data | |
| Bioavailability | Oral: Very low[2] Transdermal: 10%[2][3] IM injection: 100%[3] |
| Metabolism | Liver |
| Eliminationhalf-life | Transdermal: 2.8 hours[4] |
| Excretion | Urine |
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| IUPHAR/BPS | |
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| Chemical and physical data | |
| Formula | C19H30O2 |
| Molar mass | 290.447 g·mol−1 |
| 3D model (JSmol) | |
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Androstanolone, orstanolone, also known asdihydrotestosterone (DHT) and sold under the brand nameAndractim among others, is anandrogen andanabolic steroid (AAS) medication andhormone which is used mainly in the treatment oflow testosterone levels in men.[2] It is also used to treatbreast development andsmall penis in males.[2] Compared totestosterone, androstanolone (DHT) is less likely toaromatize intoestrogen, and therefore it shows less pronouncedestrogenic side effects, such asgynecomastia andwater retention. On the other hand, androstanolone (DHT) show more significantandrogenic side effects, such asacne,hair loss andprostate enlargement.
It has strongandrogenic effects andmuscle-building effects, as well as relatively weakestrogenic effects.[2]
It is typically given as agel forapplication to the skin, but can also be used as anester byinjection into muscle.[2][5]
Side effects of androstanolone includesymptoms ofmasculinization likeacne,increased hair growth,voice changes, and increasedsexual desire.[2] The medication is anaturally occurring androgen and anabolic steroid and hence is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone and DHT.[2][6]
Androstanolone was discovered in 1935 and was introduced for medical use in 1953.[2][7][8][9] It is used mostly inFrance andBelgium.[2][10][11] The drug has been used by weightlifters to increase performance due to its powerful androgenic properties.[12][13] The medication is acontrolled substance in many countries and so non-medical use is generally illicit.[2]
Androstanolone is available inpharmaceuticalformulations formedical use as an androgen.[5] It is used mainly as a form ofandrogen replacement therapy in the treatment of malehypogonadism and is specifically approved for this indication in certain countries.[14][15][16][17][18][19][11] However, it is no longer recommended for this purpose due to biological differences from testosterone such as lack of estrogenic effects and partial androgenic effects.[20]Topical androstanolone is useful in the treatment ofgynecomastia.[21] Similarly,androstanolone enanthate viaintramuscular injection has been found to be effective in the treatment persistentpubertalgynecomastia.[22] The medication has also been used as a topical gel to treatsmall penis in pre- and peripubertal boys withmild orpartial androgen insensitivity syndrome.[23][2][24]
Androstanolone was found to be effective in the treatment of advancedbreast cancer in women in the 1950s, although it was used in very high doses and caused severevirilization.[25][26][27] It was used as amicrocrystallineaqueous suspension byintramuscular injection.[28][29][30] Shortly thereafter,drostanolone propionate (2α-methylandrostanolone propionate) was developed for this use instead of androstanolone due to its superiorpharmacokinetics and was introduced for this indication in theUnited States andEurope in the early 1960s.[31][32][33][34]
Androstanolone was used at a dose of 25 mg sublingually two to three times per day in androgen replacement therapy for men.[35] This is also theanabolic dosage of androstanolone in men.[35]
| 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/2–4× 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 | |
| Sublingual | Testosteroneb | Testoral | Tablet | 5–10 mg 1–4×/day |
| Methyltestosteroneb | Metandren, Oreton Methyl | Tablet | 10–30 mg/day | |
| Buccal | Testosterone | Striant | Tablet | 30 mg 2×/day |
| Methyltestosteroneb | 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, Testosteronb | Suppository | 40 mg 2–3×/day |
| Injection (IMTooltip intramuscular injection orSCTooltip subcutaneous injection) | Testosterone | Andronaq, Sterotate, Virosterone | Aqueous suspension | 10–50 mg 2–3×/week |
| Testosterone propionateb | Testoviron | Oil solution | 10–50 mg 2–3×/week | |
| Testosterone enanthate | Delatestryl | Oil solution | 50–250 mg 1x/1–4 weeks | |
| 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 phenylacetateb | 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 buciclatea | – | 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. | ||||
| 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 orSCTooltip 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. | ||||
Androstanolone is available as a 2.5%hydroalcoholicgel giventransdermally in doses of 5 or 10 g/day (brand name Andractim).[20] The medication was previously available as a 10 mgoraltablet with 300 mgL-lysine (brand name Lysinex) and as a 25 mgsublingual tablet (brand names Anabolex, Anaprotin, Anabolene, Anaboleen, Proteina).[35][36] The medication has also been marketed in the form of severalandrostanolone esters, includingandrostanolone benzoate (brand names Ermalone-Amp, Hermalone, Sarcosan),androstanolone enanthate (brand name Anaboleen Depot),androstanolone propionate (brand name Pesomax), andandrostanolone valerate (brand name Apeton), which are provided asoil solutions forintramuscular injection at regular intervals.[37]
Adverse effects of androstanolone are similar to those of other AAS and includeandrogenic side effects likeoily skin,acne,seborrhea, increasedfacial/body hairgrowth,scalp hair loss, and increasedaggressiveness andsex drive.[38][6] In women, androstanolone can cause partially irreversiblevirilization, for instancevoice deepening,hirsutism,clitoromegaly,breast atrophy, andmuscle hypertrophy, as well asmenstrual disturbances and reversibleinfertility.[38][6] In men, the medication may also causehypogonadism,testicular atrophy, and reversible infertility at sufficiently high dosages.[38][6]
Androstanolone can have adverse effects on thecardiovascular system, especially with long-term administration of high dosages.[38] AAS like androstanolone stimulateerythropoiesis (red blood cell production) and increasehematocrit levels and at high dosages can causepolycythemia (overproduction of red blood cells), which can greatly increase the risk ofthrombic events such asembolism andstroke.[38] Unlike many other AAS, androstanolone is notaromatized into estrogens and hence has no risk ofestrogenic side effects likegynecomastia,fluid retention, oredema.[38][6][39][40] In addition, as it is not a17α-alkylated AAS and is administered parenterally, androstanolone has no risk ofhepatotoxicity.[38][6]
It has been theorized that androstanolone may have less risk ofbenign prostatic hyperplasia andprostate cancer than testosterone because it is not aromatized into estrogens.[39][40] This is relevant because estrogens are thought to possibly be necessary for the manifestation of these diseases.[39] In accordance, androstanolone has been found to not increaseprostate gland size in men.[40] Conversely, due to lack of aromatization into estrogens, androstanolone therapy for androgen replacement may result in decreasedbone mineral density, incomplete effects in thebrain, and undesirable changes incholesterol levels.[39]
| Medication | Ratioa |
|---|---|
| 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 | 1:2–1:30 |
| Oxymetholone | 1:2–1:9 |
| Oxandrolone | 1:3–1:13 |
| Stanozolol | 1:1–1:30 |
| Nandrolone | 1:3–1:16 |
| Ethylestrenol | 1:2–1:19 |
| Norethandrolone | 1:1–1:20 |
| Notes: In rodents.Footnotes:a = Ratio of androgenic to anabolic activity.Sources: See template. | |
Androstanolone is apotentagonist of the AR. It has anaffinity (Kd) of 0.25 to 0.5 nM for the human AR, which is about 2- to 3-fold higher than that oftestosterone (Kd = 0.4 to 1.0 nM)[41] and thedissociation rate of androstanolone from the AR is also about 5-fold slower than that of testosterone.[42] TheEC50 of androstanolone for activation of the AR is 0.13 nM, which is about 5-fold stronger than that of testosterone (EC50 = 0.66 nM).[43] Inbioassays, androstanolone has been found to be 2.5- to 10-fold more potent than testosterone.[41] Upon intramuscular injection in rats, androstanolone is about 1.5- to 2.5-fold the potency of testosterone.[35]
Unlike testosterone and various other AAS, androstanolone cannot bearomatized, and for this reason, poses no risk ofestrogenicside effects likegynecomastia at any dosage.[44] In addition, androstanolone cannot bemetabolized by5α-reductase (as it is already 5α-reduced), and for this reason, is not potentiated in so-called "androgenic" tissues like theskin,hair follicles, andprostate gland, thereby improving its ratio ofanabolic toandrogenic effects. However, androstanolone is nonetheless described as a very poor anabolic agent.[38] This is attributed to its high affinity as asubstrate for3α-hydroxysteroid dehydrogenase (3α-HSD), which is highly expressed inskeletal muscle and inactivates androstanolone into3α-androstanediol, a metabolite with very weak AR activity.[38] Unlike androstanolone, testosterone is very resistant to metabolism by 3α-HSD, and so is not similarly inactivated in skeletal muscle.[38] For the preceding reasons, androstanolone has been described as a "partial androgen".[20]
Thebioavailability of androstanolone differs considerably depending on itsroute of administration.[2][3] Itsoral bioavailability is very low, and androstanolone has been considered to be ineffective by the oral route.[2] However, it has been used orally, and is described as a weak AAS by this route.[35] Thetransdermal bioavailability of androstanolone is approximately 10%.[2][3] Its bioavailability withintramuscular injection, on the other hand, is complete (100%).[3]
Doses of topical androstanolone gel of 16, 32, and 64 mg have been found to produce total testosterone and DHT levels in the low, mid, and high normal adult male range, respectively.[39]
Theplasma protein binding of androstanolone is about 98.5 to 99.0%.[45] It is bound 50 to 80% tosex hormone-binding globulin, 20 to 40% toalbumin, and less than 0.5% tocorticosteroid-binding globulin, with about 1.0 to 1.5% circulating freely or unbound.[45]
Theterminal half-life of androstanolone in the circulation (53 minutes) is longer than that of testosterone (34 minutes), and this may account for some of the difference in their potency.[46] A study of transdermal androstanolone and testosterone therapy reported terminal half-lives of 2.83 hours and 1.29 hours, respectively.[4]
Androstanolone, also known as 5α-androstan-17β-ol-3-one or as 5α-dihydrotestosterone (5α-DHT), is anaturally occurringandrostanesteroid with aketone group at the C3 position and ahydroxyl group at the C17β position.[37][47] It is thederivative of testosterone in which thedouble bond between the C4 and C5 positions has beenreduced orhydrogenated.[37][47]
Several C17βesterprodrugs of androstanolone, includingandrostanolone benzoate,androstanolone enanthate,androstanolone propionate, andandrostanolone valerate, have been developed and introduced for medical use as AAS. Conversely,dihydrotestosterone acetate,dihydrotestosterone butyrate, anddihydrotestosterone formate have been developed but have not been marketed.[37][48]
Synthetic derivatives of androstanolone (DHT) that have been developed as AAS include:[2]
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Androstanolone was first discovered and synthesized in 1935 byAdolf Butenandt and his colleagues.[7][8] It was first introduced for medical use in 1953, under the brand nameNeodrol in theUnited States,[9][49][50] and was subsequently marketed in theUnited Kingdom and otherEuropean countries.[9] Transdermal androstanolone gel has been available inFrance since 1982.[51]
When used as a drug, androstanolone is referred to asandrostanolone (INNTooltip International Nonproprietary Name) or asstanolone (BANTooltip British Approved Name) rather than as DHT.[5][37][47][10]
Brand names of androstanolone include Anaboleen, Anabolex, Anaprotin (UK), Andractim (formerly AndroGel-DHT) (FR,BE,LU), Androlone, Apeton, Gelovit (ES), Neodrol, Ophtovital (DE), Pesomax (IT), Stanaprol, and Stanolone, among others.[5][37][47][14][52][10][11]
The availability of pharmaceutical androstanolone is limited; it is not available in theUnited States orCanada,[53][54] but it is or has been available in certainEuropean countries, including theUnited Kingdom,Germany,France,Spain,Italy,Belgium, andLuxembourg.[47][14][10][11][35]
The available formulations of androstanolone includebuccal orsublingualtablets (Anabolex, Stanolone),topical gels (Andractim, Gelovit, Ophtovital), and, asesters inoil,injectables likeandrostanolone propionate (Pesomax) andandrostanolone valerate (Apeton).[5][14][52][35]Androstanolone benzoate (Ermalone-Amp, Hermalone, Sarcosan) andandrostanolone enanthate (Anaboleen Depot) are additional androstanolone esters that are available for medical use in some countries.[37] Androstanolone esters act asprodrugs of androstanolone in the body and have a long-lastingdepot effect when given viaintramuscular injection.[5]
Androstanolone, along with other AAS, is aschedule IIIcontrolled substance in theUnited States under theControlled Substances Act.[55]
Androstanolone is on theWorld Anti-Doping Agency's list of prohibited substances,[56] and is therefore banned from use in most major sports.
In the early- to mid-2000s, transdermal or topical androstanolone was under development in theUnited States for the treatment ofhypogonadism (as a form ofandrogen replacement therapy), maleosteoporosis, andcachexia (incancer patients) and inAustralia for the treatment ofbenign prostatic hyperplasia (BPH).[57][58][14] It reachedphase IIclinical trials for hypogonadism and BPH andphase III clinical studies for cachexia but development was ultimately never completed for these indications in these specific countries.[57][58][14] Although androstanolone itself has not been approved for cachexia in any country, anorally activesyntheticderivative of androstanolone,oxandrolone (2-oxa-17α-methylandrostanolone), is approved and used for this indication in the United States.[59][60]
Topical androgens like androstanolone have been used and studied in the treatment ofcellulite in women.[61] Topical androstanolone on the abdomen has also been found to significantly decrease subcutaneous abdominal fat in women, and hence may be useful for improving body silhouette.[61] However, men andhyperandrogenic women have higher amounts of abdominal fat than healthy women, and androgen therapy has been found to increase abdominal fat inpostmenopausal women andtransgender men.[62]
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