Testosterone propionate   中文名称: 丙酸睾酮

Androgen Receptor

与所有睾酮酯一样，丙酸睾酮在血浆中迅速水解为游离睾酮。睾酮通过两种不同的途径代谢为17酮类固醇。主要的活性代谢产物是雌二醇和二氢睾酮（DHT）。丙酸睾酮被迅速水解成睾酮。睾酮通过两种不同的途径代谢为17酮类固醇。主要的活性代谢产物是雌二醇和二氢睾酮（DHT）。消除途径：肌肉注射约90%的睾酮以睾酮及其代谢产物的葡萄糖醛酸和硫酸结合物的形式在尿液中排出；大约6%的剂量通过粪便排出，大部分以未结合的形式排出。

丙酸睾酮用于小母牛的兽医实践，以刺激最大限度的生长。丙酸睾酮的给药可以诱导与男性性发育相关的蛋白质的产生。临床试验表明，在给予丙酸睾酮后，血浆LH降低。

丙酸睾酮 (TP) 的配制 [13]
将丙酸睾酮 (TP) 溶解于丙酮-水混合液（1:3 体积比）中，于 70°C 加热 15 分钟。冷却后，与完全培养基混合，得到终浓度为 10⁻¹⁰ M、10⁻⁹ M、10⁻⁸ M、10⁻⁷ M 和 10⁻⁶ M 的 TP 溶液。细胞培养物中丙酮的最终体积为 0.3%，添加了 0.3% 丙酮的培养基用作载体对照。将骨髓间充质干细胞 (BM-MSCs) 分别与浓度为 10⁻⁶ M 至 10⁻¹⁰ M 的 TP 或载体对照孵育 24 小时，同时使用未处理的细胞作为空白对照。

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MB-MSCs 的细胞增殖测定 [13]
通过羧基荧光素琥珀酰亚胺酯 (CFSE) 染色测定 BM-MSCs 的增殖率，该方法依赖于细胞分裂时荧光染料在两个子细胞间的均等分配。在本研究中，将 2x10⁵ 个 BM-MSC 按一式三份接种于 6 孔组织培养板中，并孵育过夜使其贴壁。为标记细胞，弃去完全培养基，在含有终浓度为 5 µM CFSE 的 1 ml DMEM 中于 37°C 孵育细胞 20 分钟。弃去含有 CFSE 的培养基，然后用浓度为 10⁻⁶ M 至 10⁻¹⁰ M 的 TP 或载体对照处理细胞。24 小时孵育期结束时，通过胰蛋白酶消化收集细胞，用 DPBS 洗涤一次，并使用贝克曼库尔特 FC500 流式细胞仪进行检测。使用 CXP 软件进行分析。

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MB-MSCs 的细胞活力和凋亡测定 [13]
使用 ApopNexin Annexin V FITC 凋亡检测试剂盒，通过膜联蛋白 V/碘化丙啶 (PI) 染色，测定不同浓度 TP 对 MSCs 活力和凋亡率的影响。该方法的原理是同时分析在凋亡过程中逐渐丧失的膜不对称性和完整性。为此，将 2x10⁵ 个 BM-MSCs 按一式三份接种于 6 孔组织培养板中，并用浓度为 10⁻⁶ M 至 10⁻¹⁰ M 的 TP 或载体对照处理 24 小时，同时使用未处理的细胞作为对照。孵育结束后，通过胰蛋白酶消化收集细胞，用 DPBS 洗涤一次，然后根据制造商的说明，用 Annexin V-FITC 和 PI 进行标记。简言之，将细胞重悬于 1 ml Annexin V 结合缓冲液中，然后与试剂盒提供的 3 µl Annexin V FITC 和 2 µl PI 在室温避光条件下孵育 15 分钟。孵育结束后将细胞置于冰上，并立即使用贝克曼库尔特 FC500 流式细胞仪进行分析。使用 CXP 软件进行分析。

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TP 处理后 BM-MSCs 的表征 [13]
通过检测细胞表面标志物和评估 BM-MSCs 的分化能力，确定浓度为 10⁻⁸ M 的 TP 对 BM-MSCs 特征特性的影响。对于免疫表型分析，将 2x10⁵ 个 BM-MSCs 按一式三份接种于 6 孔组织培养板中，在 10⁻⁸ M TP 存在下孵育 24 小时，然后通过胰蛋白酶消化收集细胞并用上述抗体进行标记。立即使用贝克曼库尔特 DxFLEX 流式细胞仪读取数据，并使用 CytExpert 软件进行分析。对于 BM-MSCs 分化能力的评估，将 1x10⁴ 个 BM-MSCs 接种于 96 孔细胞培养板中，待细胞融合度达 80% 时，使用市售的软骨形成、成骨和成脂分化试剂盒（无论是否添加 10⁻⁸ M TP）诱导分化。每周更换两次分化培养基。分化第 21 天，用 10% 中性缓冲福尔马林溶液固定细胞。分别通过阿利新蓝、茜素红和油红 O 染色评估软骨形成、成骨和成脂分化。

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BM-MSCs 与 K562 细胞系的共培养 [13]
K562 细胞系 (ATCC #CCL-243) 在补充有 10% 胎牛血清 (FBS) 和 1% 青霉素/链霉素抗生素溶液的 RPMI 培养基中培养。为评估 BM-MSCs 对 K562 细胞系的细胞毒性作用，将 BM-MSCs 接种于 35 mm 细胞培养皿中（1x10⁴ 个细胞/皿），并培养过夜使其贴壁。然后，弃去培养基，BM-MSCs 或先用 10⁻⁸ M TP 处理 24 小时，再与 K562 细胞（1x10⁵ 个细胞/皿）共培养额外的 24 小时；或者，在 10⁻⁸ M TP 存在下将 K562 细胞加到 BM-MSCs 上，并孵育 24 小时。TP 对 K562 细胞的影响通过将其与补充了 10⁻⁸ M TP 的培养基孵育 24 小时来确定，而 BM-MSCs 对 K562 细胞的影响则通过共培养细胞 24 小时来评估。K562 细胞的活力通过用 4',6-二脒基-2-苯基吲哚 (DAPI) 在室温避光条件下孵育细胞 15 分钟进行标记来确定。使用贝克曼库尔特 DxFLEX 流式细胞仪读取细胞，并使用 CytExpert 软件进行分析。

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共聚焦显微镜检查 [13]
为评估 TP 处理后 BM-MSC 的极化和细胞形态，将细胞以每孔 2x10⁴ 个细胞的密度接种于 8 孔腔室载玻片中，孵育过夜使其贴壁，然后用 10⁻⁸ M TP 处理 24 小时。如先前文献23所述对载玻片进行固定和透化处理，然后用抗 CXCL9 PE和抗 CXCL5 APC抗体，或用 F-肌动蛋白探针鬼笔环肽 (Alexa Fluor 555 偶联) 于 4°C 孵育过夜进行标记。用 DAPI 复染细胞核，并用 FluoroShield 封片剂封片。使用蔡司 LSM 780 共聚焦显微镜拍摄显微照片。

Absorption
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.
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. From the rest of the dose, approximately 6% of a dose is excreted in the feces, mostly in the unconjugated form.
Volume of Distribution
The registered volume of distribution for testosterone propionate is in the range of 75-120 L/kg.
Clearance
Testosterone propionate has a reduced clearance rate compared to testosterone. The reported clearance rate is of approximately 2000 ml/min.
Biological Half-Life
Testosterone propionate possesses a relatively short half-life compared with other testosterone esters at approximately 4.5 days.

Absorption, Distribution and Excretion
Testosterone propionate is slowly absorbed after intramuscular injection. This slow absorption is due to the low polarity of its ester group. Compared to testosterone heptanate or testosterone cyclopentylpropionate, testosterone propionate is absorbed more slowly, thus requiring more frequent injections. Its absorption parameters (AUC and residence time) are 180–210 ng·h/ml and 40–60 h, respectively. Approximately 90% of the intramuscularly injected dose of testosterone is excreted in the urine as glucuronic acid and sulfate conjugates, which are testosterone and its metabolites. About 6% of the remaining dose is excreted in the feces, primarily in unconjugated form. The volume of distribution of testosterone propionate is 75–120 L/kg. The clearance of testosterone propionate is lower than that of testosterone. The reported clearance is approximately 2000 ml/min.

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Metabolism/Metabolites
Like all testosterone esters, testosterone propionate is rapidly hydrolyzed in plasma to free testosterone. Testosterone is metabolized to 17-ketosteroids via two distinct pathways. The main active metabolites are estradiol and dihydrotestosterone (DHT).
Excretion pathway: After intramuscular injection of testosterone, approximately 90% of the dose is excreted in the urine as glucuronic acid and sulfate conjugates; approximately 6% of the dose is excreted in the feces, primarily in unconjugated form.

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Biological half-life
Compared to other testosterone esters, testosterone propionate has a relatively short half-life of approximately 4.5 days.

Toxicity Summary
Testosterone exerts its effects in humans and other vertebrates primarily through two mechanisms: activation of androgen receptors (either directly or in the form of dihydrotestosterone), and conversion to estradiol, which activates certain estrogen receptors. Free testosterone (T) is transported to the cytoplasm of target cells, where it can bind to androgen receptors or be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds even more strongly to the same androgen receptor than T, thus its androgenic potency is approximately 2.5 times that of T. Structural changes occur in the T-receptor or DHT-receptor complex, allowing it to enter the nucleus and bind directly to specific nucleotide sequences in chromosomal DNA. These binding regions are called hormone response elements (HREs), which influence the transcriptional activity of certain genes, thus producing androgenic effects. Protein Binding 98% of testosterone in plasma is bound to sex hormone-binding globulin, while 2% remains free or bound to albumin and other proteins.

[1] Archives of General Psychiatry, 57, 133-140;

[2] Personality and Individual Differences, 28, 437-445;

[3] Am J Physiol Endocrinol Metab 2003 Jan 7;

[4] J Investig Med. 1997 Oct;45(8):441-7;

[5] J Clin Endocrinol Metab. 1986 Dec;63(6):1361-4;

[6] J Clin Endocrinol Metab. 1997 Feb;82(2):407-13;

[7] Am J Physiol Endocrinol Metab. 2002 Mar;282(3):E601-7;

[8] Curr Opin Clin Nutr Metab Care. 2004 May;7(3):271-7;

[9] Curr Pharm Biotechnol. 2004 Oct;5(5):459-70;

[10] Metabolism. 1991 Apr;40(4):368-77;

[11]] J Lab Clin Med. 1995 Mar;125(3):326-33;

[12] Zhonghua Nan Ke Xue. 2003;9(4):248-51.

[13] Balkan Med J. 2023 Mar 8;40(2):117–123.

Testosterone propionate is an odorless white or pale yellow crystal, or a white or milky white crystalline powder. (NTP, 1992)
Testosterone propionate is a steroid ester.
Testosterone propionate is a slow-release anabolic steroid with a short half-life. It is a synthetic androsterone steroid derivative of testosterone, existing as 17β-testosterone propionate. Testosterone propionate was initially developed by Watson Laboratories and approved by the FDA on February 5, 1974. Currently, this drug is no longer used in humans, but its veterinary products are still available over-the-counter.
Testosterone propionate is a short-acting, oil-based injectable form of testosterone. Testosterone inhibits the pituitary gland from secreting gonadotropins and inhibits the ovaries from producing estrogen, thereby reducing endogenous estrogen levels. In addition, this drug can promote the maintenance of male sexual characteristics and is suitable for testosterone replacement therapy in men with hypogonadism. (NCI04)
Testosterone ester, with the 17β position replaced by a propionate ester.
Testosterone ester, with its 17β position replaced by a propionate ester.
See also: Testosterone (with active moiety); Estradiol benzoate; Testosterone propionate (component).

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Drug Indications
Testosterone propionate is used in veterinary practice for heifers to promote their maximum growth.

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Mechanism of Action
Testosterone's effects in humans and other vertebrates are primarily achieved through two mechanisms: activation of androgen receptors (directly or in the form of dihydrotestosterone), and conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported to the cytoplasm of target tissue cells, where it can bind to androgen receptors or be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. These binding sites are called hormone response elements (HREs), which influence the transcriptional activity of certain genes, thus producing androgenic effects.

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Pharmacodynamics
Administration of testosterone propionate induces the production of proteins associated with male sexual development. Clinical trials have shown that administration of testosterone propionate reduces plasma luteinizing hormone (LH) levels.

C22H32O3

344.495

344.235

57-85-2

5995

Typically exists as solid at room temperature

1.1±0.1 g/cm3

454.6±45.0 °C at 760 mmHg

118-123 °C

196.3±28.8 °C

0.0±1.1 mmHg at 25°C

1.538

4.9

43.37

0

3

3

25

621

6

O(C(C([H])([H])C([H])([H])[H])=O)[C@@]1([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C([H])([H])C4=C([H])C(C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])[C@@]21C([H])([H])[H])=O

PDMMFKSKQVNJMI-BLQWBTBKSA-N

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

[(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

Enarmon Androlon Testosterone propionate

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO: ~30 mg/ml
DMF: ~30 mg/ml
Ethanol: ~2 mg/ml

注意: 如下所列的是一些常用的体内动物实验溶解配方，主要用于溶解难溶或不溶于水的产品（水溶度<1 mg/mL）。 建议您先取少量样品进行尝试，如该配方可行，再根据实验需求增加样品量。

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注射用配方1: DMSO : Tween 80： Saline = 10 : 5 : 85 (如： 100 μL DMSO → 50 μL Tween 80 → 850 μL Saline)
*生理盐水/Saline的制备：将0.9g氯化钠/NaCl溶解在100 mL ddH ₂ O中，得到澄清溶液。
注射用配方 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL DMSO → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)
注射用配方 3: DMSO : Corn oil = 10 : 90 (如： 100 μL DMSO → 900 μL Corn oil)
示例: 以注射用配方 3 (DMSO : Corn oil = 10 : 90) 为例说明, 如果要配制 1 mL 2.5 mg/mL的工作液, 您可以取 100 μL 25 mg/mL 澄清的 DMSO 储备液，加到 900 μL Corn oil/玉米油中, 混合均匀。

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注射用配方 4: DMSO : 20% SBE-β-CD in Saline = 10 : 90 [如：100 μL DMSO → 900 μL (20% SBE-β-CD in Saline)]
*20% SBE-β-CD in Saline的制备（4°C，储存1周）：将2g SBE-β-CD (磺丁基-β-环糊精) 溶解于10mL生理盐水中，得到澄清溶液。
注射用配方 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (如： 500 μL 2-Hydroxypropyl-β-cyclodextrin (羟丙基环胡精)→ 500 μL Saline)
注射用配方 6: DMSO : PEG300 : Castor oil : Saline = 5 : 10 : 20 : 65 (如： 50 μL DMSO → 100 μL PEG300 → 200 μL Castor oil → 650 μL Saline)
注射用配方 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (如： 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
注射用配方 8: 溶解于Cremophor/Ethanol (50 : 50), 然后用生理盐水稀释。
注射用配方 9: EtOH : Corn oil = 10 : 90 (如： 100 μL EtOH → 900 μL Corn oil)
注射用配方 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL EtOH → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)

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口服配方 1: 悬浮于0.5% CMC Na (羧甲基纤维素钠)
口服配方 2: 悬浮于0.5% Carboxymethyl cellulose (羧甲基纤维素)
示例: 以口服配方 1 (悬浮于 0.5% CMC Na)为例说明, 如果要配制 100 mL 2.5 mg/mL 的工作液, 您可以先取0.5g CMC Na并将其溶解于100mL ddH2O中，得到0.5%CMC-Na澄清溶液；然后将250 mg待测化合物加到100 mL前述 0.5%CMC Na溶液中，得到悬浮液。

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口服配方 3: 溶解于 PEG400 (聚乙二醇400)
口服配方 4: 悬浮于0.2% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 5: 溶解于0.25% Tween 80 and 0.5% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 6: 做成粉末与食物混合

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注意: 以上为较为常见方法，仅供参考， InvivoChem并未独立验证这些配方的准确性。具体溶剂的选择首先应参照文献已报道溶解方法、配方或剂型，对于某些尚未有文献报道溶解方法的化合物，需通过前期实验来确定（建议先取少量样品进行尝试），包括产品的溶解情况、梯度设置、动物的耐受性等。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。