テストステロン
テストステロン · アンドロリン · プリモテストン · ビロステロン · Δ4-アンドロステン-17β-オール-3-オン · オレトン-F · ホモステロン · テストリル

識別子と物理属性
| CAS No. | 58-22-0 |
|---|---|
| 分子式 | C19H28O2 |
| 平均分子量 | 288.4 g/mol |
| 単同位体質量 | 288.20893014 g/mol |
| SMILES | C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O |
| InChIKey | MUMGGOZAMZWBJJ-DYKIIFRCSA-N |
| PubChem CID | 6013 |
| ChEMBL | CHEMBL386630 |
| ChEBI | CHEBI:17347 |
| EC No. | 200-370-5 |
| DTXSID | DTXSID8022371 |
| 現地名 | テストステロン |
化学・物理的性質
| XLogP | 3.3 |
|---|---|
| 極性表面積 | 37.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 21 |
| 形式電荷 | 0 |
| 複雑度 | 508 |
| 物質分類 | Hormone |
| 医薬品 | DEA NFLIS-Drug Category -> SteroidsDEA Schedule III Controlled Substance -> Anabolic steroidsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds |
| 脂質 | Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202] |
| SpringerMaterials Properties | Chemical shift |
| LogP(分配係数) | log Kow = 3.323.13 |
| 臭い | Odorless |
| Color/Form | White needles from dilute acetoneNeedles from dilute acetoneWhite or slightly cream-white crystals or crystalline powder |
| 溶解度 | In water, 23.4 mg/L at 25 °CFreely soluble in dehydrogenated alcohol, chloroformsoluble in vegetable oils, alcohol, dioxane and other organic solventsslightly soluble in etherInsoluble in waterSoluble in ethanol, ethyl ether, acetoneIn ethanol: 1 in 5in chloroform: 1 in 2in diethyl ether: 1 in 100in ethyl oleate: 1 in 150. Sol in acetone, dioxane and fixed oils45% (w/v) 2-ヒドロキシプロピル-β-シクロデキストリン水溶液: 溶解度は 18.2mg/ml22.79mg/L(20℃) |
| Human Drugs | Breast FeedingLactationMilk, HumanAndrogensHormonesFDA approved drugs -> Active ingredient |
| Animal Drugs | Active Ingredients (Testosterone) -> FDA GreenbookPharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| 融点 | 152-156 °C |
| 比旋光度 | 101 º (c=1, dioxane 25 ºC) |
| 沸点 | 370.65°C (rough estimate) |
| 密度 | 1.0484 (rough estimate) |
| 屈折率 | 1.4709 (estimate) |
| 引火点 | 5 °C |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 粉 |
| pKa(酸解離定数) | 15.06±0.60(Predicted) |
| Merck | 13,9255 |
| BRN | 1915399 |
| ヘンリー定数 | 2.8×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定。可燃性。強力な酸化剤とは相容れない。 |
| 化粧品成分の機能 | スキンコンディショニング |
| InChI | 1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1 |
| InChIKey | MUMGGOZAMZWBJJ-DYKIIFRCSA-N |
| SMILES | C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2O |
| CAS データベース | 58-22-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Testosterone(58-22-0) |
| EPAの化学物質情報 | Testosterone (58-22-0) |
化学的特性
white crystalline odourless solid
安全性と法規制
| GHS 分類 | DangerH302 (64.9%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P263, P264, P270, P273, P280, P301+P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 231 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302: Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Hazard Traits - CarcinogenicityDEA schedule III controlled substanceDirective (EC) No 74/2003Status: Active Update: 22-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/25237Testosterone: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - Androst-4-en-3-one, 17-hydroxy-, (17.beta.)-: Human health tier I assessment |
| FDA 要件 | The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including testosterone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including testosterone cypionate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Testosterone cypionate/The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including testosterone enanthate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Testosterone enanthate/The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including testosterone undecanoate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Testosterone undecanoate/For more FDA Requirements (Complete) data for Testosterone (10 total), please visit the HSDB record page. |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides. |
用途
解説
(17β)-hydroxyandrost-4-en-3-one.C19H28O2(288.42).男性ホルモンの一つ.1935年,E. Laqueurらにより,ウシの睾丸から単離された.テストステロンは,睾丸の間質細胞からおもに分泌されるが,副腎皮質の網状層の細胞でも合成される前立腺や精嚢に多く分布している.1935年,A.F. Butenandt(ブテナント),L. Ruzicka(ルジチカ)らにより,デヒドロエピアンドロステロンより合成された.白色~微黄色の結晶または結晶性粉末.融点153~157 ℃.[α]20D+101~+105°(ジオキサン).UVλmax 238 nm.水に難溶,無水エタノールまたはクロロホルムに可溶.ジオキサンにやや溶けやすく,エーテルまたはごま油に溶けにくい.ヒトの血中濃度は男0.64 μg/dL,女0.034 μg/dL である.テストステロンは真の男性ホルモンとされており,前立腺や精嚢などの副性器および陰茎,陰嚢などの外性器の発育,さらに第二次性徴の発育にも重要な役割を果たしている.また,タンパク同化作用が強い.男性性器機能不全症,乳がん,更年期障害の治療に用いられている.森北出版「化学辞典(第2版)
用途
アンドロゲン受容体作動薬です。 薬物代謝酵素CYP3A4の基質であり、薬物代謝試験で使用されます。 テストステロンは代謝されると6β-ヒドロキシテストステロンに変換されます。
説明
Testosterone (Item No.15645) is an analytical reference material categorized as an anabolic androgenic steroid. Testosterone is an endogenous metabolite of androstenedione (Item Nos. ISO60161 | 15874) and estradiol (Item Nos. ISO60155 | 10006315). Anabolic steroids, including testosterone, have been used to enhance physical performance in athletes. Testosterone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.
使用
Secreted by the testis and is converted to dihydrotestosterone in the target tissue where is appears to mediate many of the biological actions of testosterone. CONTROLLED SUBSTANC
一般的な説明
Testosterone, 17β-hydroxyandrost-4-en-3-one, is a naturally occurring androgen in men. Inwomen, it mainly serves as a biosynthetic precursor to estradiolbut also has other hormonal effects. It is rapidly metabolizedto relatively inactive 17-ones, however,preventing significant oral activity. Testosterone is availablein a transdermal delivery system (patch), a gel formulation, abuccal system, and as implantable pellets.
製法・合成法
純化方法
Crystallise testosterone from aqueous acetone, hexane or isoPrOH. The long needles that separated from EtOH/AcOH were used for X-ray crystallography [Roberts et al. J Chem Soc Perkin Trans II 1978 1973.] The acetate [1045-69-8] crystallises from MeOH or aqueous Me2CO, with m 140-141o and [] D 20 +87.8o (c 1, EtOH). [Ruzicka et al. Helv Chim Acta 18 1478 1935 and 19 99, 842 1936, Beilstein 8 IV 974.]