| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
|
||
| 25mg | |||
| 50mg | |||
| 100mg | |||
| 250mg | |||
| 500mg | |||
| Other Sizes |
| Targets |
21-Hydroxypregnenolone is a precursor in the adrenal steroidogenesis pathway. It is formed by the 21-hydroxylation of pregnenolone, catalyzed by the enzyme cytochrome P450 21-hydroxylase (CYP21A2, also known as 21-hydroxylase). This enzyme is responsible for the conversion of 17alpha-hydroxyprogesterone to 11-deoxycortisol and of progesterone to 11-deoxycorticosterone in the cortisol and aldosterone synthesis pathways, respectively. 21-Hydroxypregnenolone itself is a substrate for 11beta-hydroxylase in the biosynthesis of corticosterone. Deficiencies in 21-hydroxylase lead to congenital adrenal hyperplasia, characterized by impaired cortisol synthesis and androgen excess.
|
|---|---|
| ln Vitro |
In vitro, 21-hydroxypregnenolone is used as a substrate in enzyme assays to study 21-hydroxylase and other steroidogenic enzymes. The compound can be converted to corticosterone by 11beta-hydroxylase in adrenal tissue preparations. In cultured adrenal cells (e.g., Y1 mouse adrenocortical cells or H295R human adrenocortical carcinoma cells), 21-hydroxypregnenolone stimulates steroid production. The compound also serves as a precursor for the synthesis of other steroids including aldosterone and cortisol. Its activity is primarily as a metabolic intermediate rather than a pharmacologically active compound with direct receptor-mediated effects. In research settings, 21-hydroxypregnenolone is used to elucidate the biochemical pathways of adrenal steroidogenesis.
|
| ln Vivo |
In vivo, 21-hydroxypregnenolone is an intermediate in the adrenal steroidogenic pathway. It is produced in the adrenal cortex and is rapidly converted to downstream steroid hormones. Plasma levels of 21-hydroxypregnenolone are regulated by ACTH (adrenocorticotropic hormone) and reflect adrenal cortex activity. In conditions of 21-hydroxylase deficiency (congenital adrenal hyperplasia), levels of 21-hydroxypregnenolone and other steroid precursors are elevated. The compound does not have direct pharmacological effects but serves as a biomarker of adrenal function and steroidogenic activity. It is used in clinical diagnostics to assess adrenal enzyme activity and to monitor patients with adrenal disorders.
|
| Enzyme Assay |
In vitro enzyme assays for 21-hydroxypregnenolone typically involve measuring 21-hydroxylase or 11beta-hydroxylase activity using adrenal microsomal or mitochondrial preparations. For 21-hydroxylase assays, adrenal microsomes are incubated with [3H]- or [14C]-labeled pregnenolone or 17alpha-hydroxyprogesterone as substrate in buffer containing NADPH as cofactor. The reaction is carried out at 37degC for 10-30 minutes and stopped by organic solvent extraction. Steroid products (including 21-hydroxypregnenolone, 11-deoxycorticosterone, and corticosterone) are separated by TLC or HPLC and quantified by liquid scintillation counting or mass spectrometry. For 11beta-hydroxylase activity, adrenal mitochondria are used with 21-hydroxypregnenolone as substrate. Enzyme kinetics (Km, Vmax) are determined from substrate concentration curves.
|
| Cell Assay |
In vitro cellular assays for 21-hydroxypregnenolone are performed using adrenocortical cell lines such as H295R (human) or Y1 (mouse) cells that express steroidogenic enzymes. Cells are cultured in DMEM/F12 medium supplemented with charcoal-stripped FBS and ITS (insulin, transferrin, selenium) premix. Cells are seeded in 24- or 96-well plates and treated with 21-hydroxypregnenolone (0.1-100 microM) or with forskolin/ACTH to stimulate steroidogenesis. After 24-48 hours of incubation, medium is collected for steroid measurement by ELISA, RIA, or LC-MS/MS. Steroid production (corticosterone, aldosterone, cortisol) is quantified to assess the conversion of 21-hydroxypregnenolone to downstream products. Cell viability is assessed by MTT assay to ensure compound effects are not due to cytotoxicity.
|
| Animal Protocol |
In vivo studies involving 21-hydroxypregnenolone are typically conducted in rodent models to study adrenal steroidogenesis or to model congenital adrenal hyperplasia. In typical protocols, rats or mice are administered ACTH or dexamethasone to stimulate or suppress adrenal function. Blood samples are collected at various time points, and plasma steroid levels (including 21-hydroxypregnenolone) are measured by LC-MS/MS or RIA. In adrenal insufficiency models, the compound may be administered exogenously to assess metabolic conversion. For pharmacokinetic studies, 21-hydroxypregnenolone is administered intraperitoneally or intravenously, and plasma concentrations are measured over time. The compound is also used in tracer studies with radiolabeled substrates to track steroid biosynthesis pathways.
|
| ADME/Pharmacokinetics |
21-Hydroxypregnenolone (CAS#: 1164-98-3) has molecular formula C21H32O3 and molecular weight 332.48. The compound's chemical name is (3beta)-3,21-dihydroxypregn-5-en-20-one. It is a white to off-white solid and is soluble in organic solvents such as ethanol, DMSO, and methanol. The compound has a role as a mouse metabolite and is a steroid natural product. In the adrenal cortex, 21-hydroxypregnenolone is synthesized from pregnenolone by 21-hydroxylase (CYP21A2) and is further metabolized to corticosterone by 11beta-hydroxylase. The compound is used in research to study steroidogenesis and adrenal function.
|
| Toxicity/Toxicokinetics |
Toxicological information for 21-hydroxypregnenolone is limited as it is an endogenous metabolite. As a naturally occurring steroid, the compound is not considered highly toxic. However, at supraphysiological concentrations, it may cause endocrine effects. Standard laboratory precautions should be observed when handling the compound, including the use of personal protective equipment. The compound should be stored at -20degC, protected from light and moisture. It is intended for research use only and is not for human therapeutic applications. Disposal should follow institutional guidelines for chemical waste.
|
| References | |
| Additional Infomation |
21-Hydroxypregnenolone is a hydroxypregnenolone, meaning that the 21-position of pregnenolone is replaced by a hydroxyl group. It exerts its metabolic effects in mice. It is a hydroxypregnenolone, a 21-hydroxy steroid, and a primary α-hydroxy ketone.
21-Hydroxypregnenolone (CAS#: 1164-98-3) is a steroidal natural product and endogenous metabolite that serves as a key intermediate in adrenal steroidogenesis, specifically in the biosynthesis of corticosterone. The compound is formed from pregnenolone by 21-hydroxylation and is further converted to corticosterone by 11beta-hydroxylase. 21-Hydroxypregnenolone is used in research to study steroid hormone biosynthesis, adrenal function, and endocrine disorders such as congenital adrenal hyperplasia. The compound has a ChEMBL ID of CHEMBL1908012 and a KEGG ID of C05485. It is not approved as a therapeutic agent but serves as an important research tool for endocrinology and steroid biochemistry. |
| Molecular Formula |
C21H32O3
|
|---|---|
| Molecular Weight |
332.47700
|
| Exact Mass |
332.235
|
| CAS # |
1164-98-3
|
| PubChem CID |
247020
|
| Appearance |
White to off-white solid powder
|
| Density |
1.15g/cm3
|
| Boiling Point |
483.4ºC at 760mmHg
|
| Flash Point |
260.2ºC
|
| Vapour Pressure |
2.26E-11mmHg at 25°C
|
| Index of Refraction |
1.567
|
| LogP |
3.487
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
24
|
| Complexity |
567
|
| Defined Atom Stereocenter Count |
7
|
| SMILES |
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)CO)CC=C4[C@@]3(CC[C@@H](C4)O)C
|
| InChi Key |
MOIQRAOBRXUWGN-WPWXJNKXSA-N
|
| InChi Code |
InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h3,14-18,22-23H,4-12H2,1-2H3/t14-,15-,16-,17-,18+,20-,21-/m0/s1
|
| Chemical Name |
2-hydroxy-1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ≥ 25 mg/mL (~75.19 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2 mg/mL (6.02 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2 mg/mL (6.02 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0077 mL | 15.0385 mL | 30.0770 mL | |
| 5 mM | 0.6015 mL | 3.0077 mL | 6.0154 mL | |
| 10 mM | 0.3008 mL | 1.5038 mL | 3.0077 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
