| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Other Sizes |
| Targets |
CYP17
Abiraterone metabolite 1 targets CYP17A1 (17alpha-hydroxylase/17,20-lyase), a key enzyme in the androgen biosynthesis pathway. As a 5beta-reduced metabolite of abiraterone, this compound retains the ability to inhibit CYP17A1, thereby blocking androgen synthesis. CYP17A1 catalyzes the conversion of pregnenolone and progesterone to dehydroepiandrosterone (DHEA) and androstenedione, respectively, which are precursors to testosterone and other androgens. By inhibiting this enzyme, abiraterone and its metabolites reduce androgen levels in the body, which is the primary mechanism for treating prostate cancer. |
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| ln Vitro |
Abiraterone blocks androgen synthesis and prolongs survival in patients with castration-resistant prostate cancer, which is otherwise driven by intratumoral androgen synthesis. Abiraterone is metabolized in patients to Δ(4)-abiraterone (D4A), which has even greater anti-tumour activity and is structurally similar to endogenous steroidal 5α-reductase substrates, such as testosterone. Here, we show that D4A is converted to at least three 5α-reduced and three 5β-reduced metabolites in human serum. The initial 5α-reduced metabolite, 3-keto-5α-abiraterone, is present at higher concentrations than D4A in patients with prostate cancer taking abiraterone, and is an androgen receptor agonist, which promotes prostate cancer progression. In a clinical trial of abiraterone alone, followed by abiraterone plus dutasteride (a 5α-reductase inhibitor), 3-keto-5α-abiraterone and downstream metabolites were depleted by the addition of dutasteride, while D4A concentrations rose, showing that dutasteride effectively blocks production of a tumour-promoting metabolite and permits D4A accumulation. Furthermore, dutasteride did not deplete the three 5β-reduced metabolites, which were also clinically detectable, demonstrating the specific biochemical effects of pharmacological 5α-reductase inhibition on abiraterone metabolism. Our findings suggest a previously unappreciated and biochemically specific method of clinically fine-tuning abiraterone metabolism to optimize therapy.[1]
In vitro, Abiraterone metabolite 1 acts by inhibiting CYP17A1, thereby blocking androgen synthesis. As a 5beta-reduced metabolite of abiraterone, this compound retains biological activity similar to that of the parent drug. The metabolite has a molecular weight of 351.52 and is soluble in DMSO at 25 mg/mL (71.12 mM). Its in vitro activity is relevant for understanding the pharmacological profile of abiraterone and its metabolites in the treatment of prostate cancer. |
| ln Vivo |
In vivo, Abiraterone metabolite 1 contributes to the overall pharmacological effect of abiraterone therapy. Abiraterone inhibits CYP17A1, blocks androgen synthesis, and prolongs survival in prostate cancer patients. As an active metabolite, Abiraterone metabolite 1 (delta⁴-abiraterone, D4A) is formed in the body following abiraterone administration and may contribute to the drug's therapeutic and side effect profile. The compound is used as a research tool to study abiraterone metabolism and pharmacology.
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| Enzyme Assay |
Abiraterone metabolite 1 is not typically used in receptor binding assays. The compound is a metabolite of abiraterone and its activity is assessed through CYP17A1 enzyme inhibition assays. In these assays, CYP17A1 enzyme activity is measured by monitoring the conversion of radiolabeled or mass-tagged substrates to products. Abiraterone metabolite 1 is incubated with the enzyme and substrate at varying concentrations, and product formation is quantified by HPLC, LC-MS, or radiometric detection to determine inhibitory potency. Nonspecific activity is determined in control reactions without inhibitor.
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| Cell Assay |
Cellular assays for Abiraterone metabolite 1 are performed using prostate cancer cell lines that express CYP17A1 and are sensitive to androgen deprivation. Cells are cultured in appropriate media and treated with Abiraterone metabolite 1 at varying concentrations for defined time periods. The effects on cell viability and proliferation are assessed using standard assays such as MTT or CellTiter-Glo. Androgen synthesis and signaling are assessed by measuring the levels of androgens and androgen receptor target gene expression. The compound is typically dissolved in DMSO and diluted in cell culture media for treatment.
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| Animal Protocol |
Abiraterone metabolite 1 is used in pharmacokinetic and pharmacodynamic studies of abiraterone. In animal models, abiraterone is administered, and plasma and tissue samples are collected at various time points to measure the levels of abiraterone and its metabolites, including Abiraterone metabolite 1. The compound's contribution to the overall pharmacological effect is assessed by correlating metabolite levels with efficacy and toxicity endpoints. The compound is soluble in DMSO at 25 mg/mL for formulation for in vivo studies.
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| ADME/Pharmacokinetics |
Abiraterone metabolite 1 has a molecular weight of 351.52 and a molecular formula of C24H33NO. The compound is a 5beta-reduced metabolite of abiraterone. As a metabolite of a clinically used drug, its pharmacokinetic properties are studied in the context of abiraterone metabolism and disposition. The compound is soluble in DMSO at 25 mg/mL (71.12 mM). It is stable as a powder at -20degC for up to 3 years and in solution at -80degC for 1 year.
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| Toxicity/Toxicokinetics |
Comprehensive toxicology data for Abiraterone metabolite 1 are not extensively documented as the compound is a metabolite rather than a therapeutic agent itself. The compound is intended for research use only and is not approved for human therapeutic applications. The safety profile of Abiraterone metabolite 1 is studied in the context of abiraterone pharmacology and toxicology. Standard laboratory safety practices should be followed when handling this compound, including the use of appropriate personal protective equipment.
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| References | |
| Additional Infomation |
Abiraterone metabolite 1, also known as delta⁴-abiraterone (D4A) or 3beta-OH-5alpha-Abi, is a 5beta-reduced metabolite of abiraterone. Abiraterone is a steroidal agent that inhibits CYP17A1, blocks androgen synthesis, and prolongs survival in prostate cancer. As an active metabolite, Abiraterone metabolite 1 retains CYP17A1 inhibitory activity and is used as a research tool to study abiraterone metabolism and pharmacology. The compound is for research purposes only.
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| Molecular Formula |
C24H33NO
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| Molecular Weight |
351.524926900864
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| Exact Mass |
351.256
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| CAS # |
1940176-03-3
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| PubChem CID |
122638979
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| Appearance |
White to off-white solid powder
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| LogP |
5.4
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
26
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| Complexity |
585
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| Defined Atom Stereocenter Count |
7
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| SMILES |
C[C@@]12C(C3C=NC=CC=3)=CC[C@H]1[C@@H]1CC[C@@H]3C[C@H](CC[C@]3(C)[C@H]1CC2)O
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| InChi Key |
UNJQRCXVHBZVTM-JSIIKIRASA-N
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| InChi Code |
InChI=1S/C24H33NO/c1-23-11-9-18(26)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-4,7,13,15,17-19,21-22,26H,5-6,8-12,14H2,1-2H3/t17-,18+,19+,21+,22+,23+,24-/m1/s1
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| Chemical Name |
(3S,5R,8R,9S,10S,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
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| Synonyms |
Abiraterone metabolite 1; 1940176-03-3; (3S,5R,8R,9S,10S,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3beta,5beta)-17-(3-Pyridinyl)androst-16-en-3-ol; SCHEMBL18170331;
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ≥ 25 mg/mL (~71.12 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (7.11 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.11 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 25.0 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8448 mL | 14.2239 mL | 28.4479 mL | |
| 5 mM | 0.5690 mL | 2.8448 mL | 5.6896 mL | |
| 10 mM | 0.2845 mL | 1.4224 mL | 2.8448 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.
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