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Methyltestosteron
METHYLTESTOSTERONE · 17α-Methyltestosterone · Androsten · Delatestryl · MESTERONE · METANDREN · Methyltestosterone CRS · 17ALPHA-METHYLTESTOSTERONE
Identifikatoren & physikalische Daten
| CAS No. | 58-18-4 |
|---|---|
| Summenformel | C20H30O2 |
| Durchschnittliche Molmasse | 302,5 g/mol |
| Monoisotopische Masse | 302,2245802 g/mol |
| SMILES | C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O |
| InChIKey | GCKMFJBGXUYNAG-HLXURNFRSA-N |
| PubChem CID | 6010 |
| ChEMBL | CHEMBL1395 |
| ChEBI | CHEBI:27436 |
| EC No. | 200-366-3 |
| DTXSID | DTXSID1033664 |
| Lokaler Name | Methyltestosteron |
Chemische & physikalische Eigenschaften
| XLogP | 3,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 550 |
| Arzneimittel | DEA NFLIS-Drug Category -> SteroidsDEA Schedule III Controlled Substance -> Anabolic steroidsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive CompoundsPharmaceuticals -> Listed in ZINC15 |
| Lipide | Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202] |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | log Kow = 3.36 |
| Geruch | Odorless |
| Color/Form | Crystals from hexaneWhite or creamy white crystals or crystalline powder |
| Löslichkeit | Soluble in alcohol, methanol, ether and other organic solventssparingly soluble in vegetable oilSoluble in ethanolIn water, 34 mg/L at 25 °C1.39e-02 g/LH2O: ≤0.5 mg/mL33.88mg/L(25 ºC) |
| Flammpunkt | 41 °F5 °C |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Animal Drugs | Pharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 161-166 °C323.6-334.4 °F162-168 °C(lit.) |
| Siedepunkt | 383.47°C (rough estimate) |
| Dichte | 1.0434 (rough estimate) |
| Brechungsindex | 1.4800 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | solid (photosensitive) |
| pKa (Säurekonstante) | 15.13±0.60(Predicted) |
| Farbe | white |
| Merck | 13,6148 |
| BRN | 2057425 |
| Henry-Konstante | 2.1×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Hauptanwendungen | clinical testing |
| InChI | 1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1 |
| InChIKey | GCKMFJBGXUYNAG-HLXURNFRSA-N |
| SMILES | C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C |
| CAS Datenbank | 58-18-4(CAS DataBase Reference) |
| NIST chemische Informationen | 17(Alpha)-methyl-delta4-androsten-17-(beta)-ol-3-one(58-18-4) |
| EPA chemische Informationen | Methyltestosterone (58-18-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302+H312+H332 (30%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 60 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Hazard Traits - Developmental ToxicityDEA schedule III controlled substance |
| Weitere Sicherheitsinformationen | IMAP assessments - Androst-4-en-3-one, 17-hydroxy-17-methyl-, (17.beta.)-: Environment tier I assessment |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methyltestosterone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation containing any quantity of the following substances, including its salts, isomers, and salts of isomers whenever the existence of such salts of isomers is possible within the specific chemical designation. DEA Code #: 4000Drug class: anabolic steroids. |
| Hazard Classes and Categories | Acute Tox. 4 (30%) |
| Lagerbedingungen | Commercially available preparations of methyltestosterone should be protected from light and stored in well-closed containers at a temperature less than 40 °C, preferably between 2-30 °C, unless otherwise specified by the manufacturer. |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Wechselwirkungen | ...Short- or long-term chronic admin of methyltestosterone...could change metabolism of ethylmorphine or hexobarbitone in hepatic microsomes of male or female rats by altering degree of binding of drugs to cytochrome p-450 and activity of NADPH cytochrome-c reductase...Methyltestosterone has been reported to increase plasma concentrations of cyclosporine and may increase the risk of nephrotoxicity.The metabolic effects of androgens may decrease blood glucose concentrations and insulin requirements in patients with diabetes.Methyltestosterone may potentiate the action of oral anticoagulants, causing bleeding in some patients. When methyltestosterone therapy is initiated in patients receiving oral anticoagulants, dosage reduction of the anticoagulant may be required to prevent an excessive hypoprothrombinemic response. Patients receiving oral anticoagulants also should be closely monitored when androgen therapy is discontinued. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,600(SRC), determined from a log Kow of 3.36(2) and a regression-derived equation(3), indicates that 17-methyltestosterone is expected to have low mobility in soil(SRC). Volatilization of 17-methyltestosterone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.7X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 17-Methyltestosterone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-8 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2005).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,600(SRC), determined from a log Kow of 3.36(2) and a regression-derived equation(3), indicates that 17-methyltestosterone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.7X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 77(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2005).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 17-methyltestosterone, which has an estimated vapor pressure of 1.8X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will solely exist in the particulate phase in the atmosphere. Particulate-phase 17-methyltestosterone may be removed from the air by wet and dry deposition(SRC). 17-Methyltestosterone does not absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis(SRC). |
| Expositionspfade | The methyl group aids to increase oral bioavailability. |
| Toxizitätsübersicht | IDENTIFICATION: Methyltestosterone is an anabolic steroid. Origin of the substance: Naturally-occurring anabolic steroids are synthesized in the testis, ovary and adrenal gland from cholesterol via pregnenolone. Synthetic anabolic steroids are based on the principal male hormone testosterone, modified in one of three ways: alkylation of the 17-carbonesterification of the 17-OH groupmodification of the steroid nucleus. Methyltestosterone is white or slightly yellowish-white, odorless, slightly hygroscopic, solid crystals. Practically insoluble in waterfreely soluble in chloroformsoluble in methyl alcoholsparingly soluble in vegetable oils. Indications: The only legitimate therapeutic indications for anabolic steroids are: replacement of male sex steroids in men who have androgen deficiency, for example as a result of loss of both testesthe treatment of certain rare forms of aplastic anemia which are or may be responsive to anabolic androgensthe drugs have been used in certain countries to counteract catabolic states, for example after major trauma. HUMAN EXPOSURE: Main risks and target organs: There is no serious risk from acute poisoning, but chronic use can cause harm. The main risks are those of excessive androgens: menstrual irregularities and virilization in women and impotence, premature cardiovascular disease and prostatic hypertrophy in men. Both men and women can suffer liver damage with oral anabolic steroids containing a substituted 17-alpha-carbon. Psychiatric changes can occur during use or after cessation of these agents. Summary of clinical effects: Acute overdosage can produce nausea and gastrointestinal upset. Chronic usage is thought to cause an increase in muscle bulk, and can cause an exaggeration of male characteristics and effects related to male hormones. Anabolic steroids can influence sexual function. They can also cause cardiovascular and hepatic damage. Acne and male-pattern baldness occur in both sexesirregular menses, atrophy of the breasts, and clitoromegaly in womenand testicular atrophy and prostatic hypertrophy in men. Contraindications: Known or suspected cancer of the prostate or (in men) breast. Pregnancy or breast-feeding or known cardiovascular disease is a relative contraindication. Oral: Anabolic steroids can be absorbed from the gastrointestinal tract, but many compounds undergo such extensive first-pass metabolism in the liver that they are inactive. Those compounds in which substitution of the 17-carbon protects the compound from the rapid hepatic metabolism are active orally. There are preparations of testosterone that can be taken sublingually. Parenteral: Intramuscular or deep subcutaneous injection is the principal route of administration of all the anabolic steroids except the 17-alpha-substituted steroids which are active orally. Absorption by route of exposure: The absorption after oral dosing is rapid for testosterone and probably for other anabolic steroids, but there is extensive first-pass hepatic metabolism for all anabolic steroids except those that are substituted at the 17-alpha position. The rate of absorption from subcutaneous or intramuscular depots depends on the product and its formulation. Absorption is slow for the lipid-soluble esters such as the cypionate or enanthate, and for oily suspensions. Distribution by route of exposure: The anabolic steroids are highly protein bound, and is carried in plasma by a specific protein called sex-hormone binding globulin. Biological half-life by route of exposure: The metabolism of absorbed drug is rapid, and the elimination half-life from plasma is very short. The duration of the biological effects is therefore determined almost entirely by the rate of absorption from subcutaneous or intramuscular depots, and on the de-esterification which precedes it. Metabolism: Free (de-esterified) anabolic androgens are metabolized by hepatic mixed function oxidases. Elimination by route of exposure: After administration of radiolabelled testosterone, about 90% of the radioactivity appears in the urine, and 6% in the fecesthere is some enterohepatic recirculation. Mode of action: Toxicodynamics: The toxic effects are an exaggeration of the normal pharmacological effects. Pharmacodynamics: Anabolic steroids bind to specific receptors present especially in reproductive tissue, muscle and fat. The anabolic steroids reduce nitrogen excretion from tissue breakdown in androgen deficient men. They are also responsible for normal male sexual differentiation. The ratio of anabolic body-building effects to androgenic (virilizing) effects may differ among the members of the class, but in practice all agents possess both properties to some degree. There is no clear evidence that anabolic steroids enhance overall athletic performance. Precocious prostatic cancer has been described after long-term anabolic steroid abuse. Cases where hepatic cancers have been associated with anabolic steroid abuse have been reported. Teratogenicity: Androgen ingestion by a pregnant mother can cause virilization of a female fetus. Main adverse effects: The adverse effects of anabolic steroids include weight gain, fluid retention, and abnormal liver function as measured by biochemical tests. Administration to children can cause premature closure of the epiphyses. Men can develop impotence and azoospermia. Women are at risk of virilization. Acute poisoning: Ingestion: Nausea and vomiting can occur. Parenteral exposure: Patients are expected to recover rapidly after acute overdosage, but there are few data. Body-builders use doses many times the standard therapeutic doses for these compounds but do not suffer acute toxic effects. Chronic poisoning: Ingestion: Hepatic damage, manifest as derangement of biochemical tests of liver function and sometimes severe enough to cause jaundicevirilization in womenprostatic hypertrophy, impotence and azoospermia in menacne, abnormal lipids, premature cardiovascular disease (including stroke and myocardial infarction), abnormal glucose tolerance, and muscular hypertrophy in both sexespsychiatric disturbances can occur during or after prolonged treatment. Parenteral exposure: Virilization in womenacne, abnormal lipids, premature cardiovascular disease (including stroke and myocardial infarction), abnormal glucose tolerance, and muscular hypertrophy in both sexes. Psychiatric disturbances can occur during or after prolonged treatment. Hepatic damage is not expected from parenteral preparations. Course, prognosis, cause of death: Patients with symptoms of acute poisoning are expected to recover rapidly. Patients who persistently abuse high doses of anabolic steroids are at risk of death from premature heart disease or cancer, especially prostatic cancer. Non-fatal but long-lasting effects include voice changes in women and fusion of the epiphyses in children. Other effects are reversible over weeks or months. Systematic description of clinical effects: Cardiovascular: Chronic ingestion of high doses of anabolic steroids can cause elevations in blood pressure, left ventricular hypertrophy and premature coronary artery disease. Neurological: Central nervous system: Stroke has been described in a young anabolic steroid abuser. Mania and psychotic symptoms of hallucination and delusion in anabolic steroid abusers. They also described depression after withdrawal from anabolic steroids. There is also considerable debate about the effects of anabolic steroids on aggressive behavior and on criminal behavior. Mood swings were significantly more common in normal volunteers during the active phase of a trial comparing methyltestosterone with placebo. Gastrointestinal: Acute ingestion of large doses can cause nausea and gastrointestinal upset. Hepatic: Orally active (17-alpha substituted) anabolic steroids can cause abnormalities of hepatic function, manifest as abnormally elevated hepatic enzyme activity in biochemical tests of liver function, and sometimes as overt jaundice. The histological abnormality of peliosis hepatitis has been associated with anabolic steroid use. Angiosarcoma and a case of hepatocellular carcinoma in an anabolic steroid user have been reported. Urinary: Men who take large doses of anabolic steroids can develop prostatic hypertrophy. Prostatic carcinoma has been described in young men who have abused anabolic steroids. Endocrine and reproductive systems: Small doses of anabolic steroids are said to increase libido, but larger doses lead to azoospermia and impotence. Testicular atrophy is a common clinical feature of long-term abuse of anabolic steroids, and gynecomastia can occur. Women develop signs of virilism, with increased facial hair, male pattern baldness, acne, deepening of the voice, irregular menses and clitoral enlargement. Dermatological: Acne occurs in both male and female anabolic steroids abusers. Women can develop signs of virilism, with increased facial hair and male pattern baldness. Eye, ear, nose, and throat: local effects: Changes in the larynx in women caused by anabolic steroids can result in a hoarse, deep voice. The changes are irreversible. Hematological: Anabolic androgens stimulate erythropoesis. Metabolic: Fluid and electrolyte disturbances: Sodium and water retention can occur, and result in edemahypercalcemia is also reported. Insulin resistance with a fall in glucose tolerance, and hypercholesterolemia with a fall in high density lipoprotein cholesterol, has been reported.The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5&alpha-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5&alpha-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. |
| Signs and Symptoms | Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation. |
| Soil Adsorption/Mobility | The Koc of 17-methyltestosterone is estimated as 1,600(SRC), using a log Kow of 3.36(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 17-methyltestosterone is expected to have low mobility in soil. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ In males, oligospermia, azoospermia, or reduced sperm function or ejaculatory volume resulting in possible infertility may occur during high-dose therapy with androgens if spermatogenesis is suppressed by a negative feedback mechanism. In females treated with androgens, amenorrhea may result, impairing fertility. In both females and males, fertility usually returns following cessation of therapy in females and dosage reduction or discontinuation in males. /Androgens//SIGNS AND SYMPTOMS/ Hepatic neoplasms have been associated with long-term, high-dose androgen therapy in humanssome cases were irreversible after androgen withdrawal. This effect is more likely with oral methylated androgens. /Androgens//SIGNS AND SYMPTOMS/ Gastrointestinal effects of prolonged use of high doses of orally active 17-alpha-androgens (e.g., methyltestosterone) have been associated with serious hepatic adverse effects (e.g., peliosis hepatitis, hepatic neoplasms , cholestatic hepatitis, and jaundice). Peliosis hepatitis can be a life-threatening or fatal complication ./SIGNS AND SYMPTOMS/ Methyltestosterone may cause fetal harm when administered to pregnant women. Androgenic effects including clitoral hypertrophy, labial fusion of the external genital fold to form a scrotal-like structure, abnormal vaginal development, and persistence of a urogenital sinus have occurred in the female offspring of women who were given androgens during pregnancy. The degree of masculinization is related to the amount of drug given to the woman and the age of the fetusmasculinization is most likely to occur in a female fetus when exposure to androgens occurs during the first trimester.For more Human Toxicity Excerpts (Complete) data for 17-METHYLTESTOSTERONE (11 total), please visit the HSDB record page. |
| Artificial Pollution Sources | 17-Methyltestosterone's production and use as androgen(1) and possible use as a performance enhancement drug in athletes(2) may result in its release to the environment through various waste streams(SRC). |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)MethyltestosteronevLess-DILI-concernWarnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Environmental Bioconcentration | An estimated BCF of 77 was calculated for 17-methyltestosterone(SRC), using a log Kow of 3.36(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 17-methyltestosterone is estimated as 4.7X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 17-methyltestosterone is expected to be essentially nonvolatile from moist soil(SRC) and water surfaces(2). 17-Methyltestosterone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-8 mm Hg(SRC), determined from a fragment constant method(3). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3249 |
| Zollcode | 29372900 |
| RTECS-Nr. | BV8400000 |
| R-Sätze (R) | 45-63-22-20-19-11-61-60-36/37/38-38-10 |
| Toxizität | man,TDLo,oral,39mg/kg/33W-I (39mg/kg),LIVER: "JAUNDICE, CHOLESTATIC",American Journal of Gastroenterology. Vol. 82, Pg. 461, 1987. |
| Gefahrensymbole | T,Xn,F,Xi |
| Sicherheitshinweise (S) | 53-36/37-45-24/25-22 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 InhalationCarc. 1BFlam. Liq. 2Repr. 1BSkin Irrit. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 58-18-4(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Methyltestosterone is a synthetic analog of testosterone that possesses all of the properties of testosterone, exhibiting stimulatory action on the development of male sex organs and secondary sex characteristics, although it is not degraded by enzymes in the gastrointestinal tract, and therefore it can only be taken orally
Verwenden
Androgen. It has been used as an androgenic agent. Controlled substance (anabolic steroid).