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アンドロゲン

Testosterone Propionate

HCID 5995
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
57-85-2
標準SMILES
CCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
PDMMFKSKQVNJMI-BLQWBTBKSA-N
分子式
C22H32O3
平均分子量
344.5 g/mol
単同位体質量
344.23514488

概要

Testosterone propionate appears as odorless white or yellowish-white crystals or a white or creamy-white crystalline powder. (NTP, 1992)

名称と識別子

優先名称
Testosterone Propionate
IUPAC
[(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] propanoate
現地名
アンドロゲン
英語名
Testosterone propionate
分子式
C22H32O3
分子量
344.5

名称と別名

testosterone propionate57-85-2Bio-testiculinaEnarmonAndrotest PAndrolonAndrotestonAquavironHormotestonTestodetTestodrinTestogen
名称をさらに表示
プロピオン酸テストステロンアンドロテストP17β-プロピオニルオキシアンドロスタ-4-エン-3-オンテストステロン17-プロピオナートネオ-ホンブレオール3-オキソアンドロスタ-4-エン-17β-オールプロピオナートテストゲン17β-(プロパノイルオキシ)アンドロスタ-4-エン-3-オンテストドリンテストステロンプロパノアートテストニクテストステロンプロピオン酸エステルテストキシルテストステロンプロピオナートテストシドプロピオン酸3-オキソアンドロスタ-4-エン-17β-イルエナルモンビオ-テストクリナトストリンテストルモールAndrogennsc9166Test PropTestosteron propionate3-Oxoandrost-4-en-17-yl propionateOkasa-masculOrchisterone

物性

構造計算による物性

XLogP
4.4
極性表面積
43.4 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
3
重原子数
25
形式電荷
0
複雑度
621

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202]
SpringerMaterials PropertiesCrystal structure
LogP3.72
Solubility · 2 件

less than 1 mg/mL at 76.1 °F (NTP, 1992)

5.02e-03 g/L

Human Drugs · 3 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Animal DrugsActive Ingredients (Testosterone Propionate) -> FDA Greenbook
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point · 2 件

244 to 252 °F (NTP, 1992)

118-123 °C

Physical Description · 2 件

Testosterone propionate appears as odorless white or yellowish-white crystals or a white or creamy-white crystalline powder. (NTP, 1992)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H302 (96.6%): 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 87 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationTestosterone propionate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Androst-4-en-3-one, 17-(1-oxopropoxy)-, (17.beta.)-: Human health tier I assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 件

SYMPTOMS: Symptoms of exposure to this compound include increased retention of nitrogen, calcium, sodium, potassium, chloride and phosphate which results in increased skeletal weight; water retention, increased vascularity of the skin, hypercalcemia, increased bone growth and stomatitis. In males, small doses ma cause increased number of spermatozoa produced, while large doses may cause suppressed formation of spermatozoa. In women, this compound may cause suppression of ovarian activity and menstruation, symptoms of virilism, atrophy of the breasts and endometrial tissue, increased libido and suppressed lactation. Other symptoms in women include male-pattern hirsuitism, deepening of the voice, acne and hypertrophy of the clitoris. Other symptoms of exposure to this type of compound through ingestion include menstrual irregularities, excessive body hair, prominent musculature, sustained erections, edema, jaundice, hepatic adenocarcinoma and feminization in males. In children, this chemical may cause serious disturbances of growth and of sexual and osseous development.

化学と産業

薬理情報

Protein BindingEven 98% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound or bound to albumin and other proteins.
PharmacodynamicsThe administration of testosterone propionate can induce production of proteins related to male sexual development. Clinical trials have shown a decrease in plasma LH after the administration of testosterone propionate.
Mechanism of Action · 1 件

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 5alpha-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5alpha-reductase. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.

Biological Half-LifeTestosterone propionate possesses a relatively short half-life compared with other testosterone esters at approximately 4.5 days.
Metabolism/Metabolites · 2 件

As all testosterone esters, testosterone propionate is rapidly hydrolysed into free testosterone in plasma. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).

Testosterone propionate is rapidly hydrolysed into testosterone. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT). Route of Elimination: About 90% of a dose of testosterone given intramuscularly is excreted in the urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites; about 6% of a dose is excreted in the feces, mostly in the unconjugated form.

Absorption, Distribution and Excretion · 4 件

Testosterone propionate presents a slow absorption from the intramuscular site of administration. This slow absorption is due to the presence of the less polar ester group. The absorption rate of testosterone propionate generates a frequent injection requirement when compared with testosterone enanthate or testosterone cypionate. It presents absorption parameters of AUC and residence time of 180-210 ng h/ml and 40-60 h, respectively.

関連反応

0 件
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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
oretonpropionate
TestoniqueTestormolTestrexTostrinNeo-HombreolMasenateOrchistinPantestin

データベース識別子

CAS
57-85-2
PubChem CID
5995
DTXSID
DTXSID9036515
ChEMBL
CHEMBL1170
ChEBI
CHEBI:9466
UNII
WI93Z9138A
EC Number
200-351-1
Nikkaji
J4.584E

Solid

Collision Cross Section · 2 件

191.1 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9036515]

188.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
118 · 118-123 °C
比旋光度
25 · D25 +83 to +90° (100 mg in 10 ml dioxane)
沸点
419.57 °C · 419.57°C (rough estimate)
比重(密度)
1.0906 · 1.0906 (rough estimate)
屈折率
1.5 · 1.5000 (estimate)
貯蔵温度
-20 °C · Store at -20°C
溶解性
10 mg/mL · エタノール: 10 mg/mL
外見
個体
色
白い
由来生物
synthetic (organic)
水溶解度
24.5 ℃で<0.1g/100mL · 24.5℃で<0.1g/100mL
Merck
13 · 13,9255
BRN
3221760 · 3221760
InChI
1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1
InChIKey
PDMMFKSKQVNJMI-BLQWBTBKSA-N
SMILES
[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])OC(=O)CC
CAS データベース
57 · 57-85-2(CAS DataBase Reference)
NISTの化学物質情報
-17 · Androstene-17(beta)-propionate-3-one,delta8-(57-85-2)
EPAの化学物質情報
Testosterone propionate (57-85-2)

化学的性質

化学的特性Testosterone Propionate occurs as white or almost white powder or colourless to pale yellow, crystals or crystalline powder. It is freely soluble in methanol and in ethanol, and practically insoluble in water.

Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Reactivity ProfileTESTOSTERONE PROPIONATE is sensitive to light. Incompatible with alkalis and oxidizing agents. (NTP, 1992).
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (96.6%)

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Personal Protective Equipment (PPE) · 1 件

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

毒性情報

Toxicity Summary · 1 件

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 SymptomsSide effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

wgk
3
tsca
TSCA listed
rtecs
XA3115000
ridadr
2811
毒性
LD50 oral in rat: 1gm/kg
hs_code
29372900
risk_code
45-22-63
hazard_code
T
safety_code
53-36/37-45
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Carc. 2Repr. 1A
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
危険度評価(NFPA 704基準/消防庁データ)
人的[青]=1

About 90% of a dose of testosterone given intramuscularly is excreted in the urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites. From the rest of the dose, approximately 6% of a dose is excreted in the feces, mostly in the unconjugated form.

The registered volume of distribution for testosterone propionate is in the range of 75-120 L/kg.

Testosterone propionate has a reduced clearance rate compared to testosterone. The reported clearance rate is of approximately 2000 ml/min.

Cellular LocationsCytoplasm

用途と製造

UsesTestosterone propionate is an anabolic steroid and a short ester form of testosterone that becomes active in the body. It is often used for muscle mass building.
Use Classification · 2 件

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Pharmaceuticals

General Manufacturing InformationAndrost-4-en-3-one, 17-(1-oxopropoxy)-, (17.beta.)-: INACTIVE
応用分野 · 3 件

解説男性ホルモン,雄性ホルモンともいう男性の副性器の活性の刺激,男性性欲の発達,去勢後の男性性徴の衰退の阻止などの活性を示す物質の総称で,通常はアンドロステロン,テストステロンなどの男性ホルモンを指す.

使用Testosterone propionate is an is an androgen and anabolic steroid (AAS) medication, which directs the development of the male phenotype during embryogenesis and at puberty. It has been widely used by athletes and bodybuilders for physical performance enhancement. Testosterone propionate has also been used for studying its effects on pregnant ewes.

一般的な説明Testosterone propionate appears as odorless white or yellowish-white crystals or a white or creamy-white crystalline powder. (NTP, 1992)

調製方法 · 1 件

純化方法Crystallise the propionate from aqueous EtOH, or Et2O/pet ether (m 121o), and it has max at 240nm (EtOH), and [] 20 +114o (c 1, CHCl3). Also purify it by HPLC. [Ercol & de Ruggieri J Am Chem Soc 75 650, 652 1953, polymorphism: Brandst.tter-Kuhnert & Kofler Mickokim Acta 847, 850 1959, Beilstein 8 IV 977.]

上流・下流製品情報

上流原料

テストステロンプロピオン酸無水物プロピオニルクロリドピリジン

下流製品

4-クロロ-17β-プロピオニルオキシアンドロスタ-4-エン-3-オン

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