| Size | Price | Stock | Qty |
|---|---|---|---|
| 50g |
|
||
| Other Sizes |
| Targets |
The target enabled by 1H-Imidazole-5-carboxaldehyde is C17,20-lyase (CYP17A1), a cytochrome P450 enzyme expressed in the adrenal glands, testes, ovaries, and prostate cancer tissues. When derivatized into C17,20-lyase inhibitors, the imidazole nitrogen coordinates to the heme iron of the CYP17A1 active site, competitively inhibiting the enzyme. The aldehyde group provides a point for further modification (e.g., condensation with amines to form Schiff bases, or reduction to alcohols) to improve potency and selectivity. The parent aldehyde is not a direct inhibitor.
|
|---|---|
| ln Vitro |
The in vitro activity is not attributed to 1H-Imidazole-5-carboxaldehyde itself but to the C17,20-lyase inhibitors synthesized from it. For such inhibitors, typical in vitro assays involve incubation with human recombinant CYP17A1 or microsomes expressing CYP17A1. The substrate (e.g., 17alpha-hydroxyprogesterone) is incubated with the test compound (0.1-1000 nM) at 37degC for 30 minutes. The reaction product (androstenedione) is quantified by HPLC-MS/MS. Potent inhibitors show IC50 values in the low nanomolar range (e.g., 1-50 nM).
|
| ln Vivo |
No direct in vivo data for 1H-Imidazole-5-carboxaldehyde. However, C17,20-lyase inhibitors derived from it have demonstrated efficacy in animal models of prostate cancer. A typical study: Male SCID mice are subcutaneously implanted with human androgen-sensitive LNCaP or VCaP tumor cells (5×10⁶ cells/mouse). When tumors reach ~100-200 mm3, mice are treated orally with the inhibitor (10-100 mg/kg daily) or vehicle. Tumor volumes and serum testosterone levels are measured. Inhibitors significantly reduce tumor growth (by 50-80% vs. control) and suppress serum testosterone by >90%. No data for the aldehyde.
|
| Enzyme Assay |
1H-Imidazole-5-carboxaldehyde is not used directly in enzyme binding assays. For chemical synthesis of inhibitors from it, a typical protocol: To a solution of 1H-Imidazole-5-carboxaldehyde (0.001 mol, 96 mg) in absolute ethanol, add an amine (0.0011 mol) and stir at room temperature for 2-4 hours to form the imine. Add sodium borohydride (0.0015 mol) slowly, and stir for another 2 hours. Quench with water, extract with ethyl acetate, dry, and concentrate to yield the reduced amine product. The final compound is then characterized by NMR, HPLC-MS, and tested in CYP17A1 inhibition assays.
|
| Cell Assay |
1H-Imidazole-5-carboxaldehyde is not directly tested in cell-based assays. However, C17,20-lyase inhibitors derived from it are tested in androgen-sensitive prostate cancer cell lines (LNCaP, VCaP). A typical protocol: LNCaP cells are cultured in RPMI-1640 with 10% charcoal-stripped FBS (to remove androgens) and seeded in 96-well plates (10,000 cells/well). Cells are treated with serial dilutions of test compound (0.1 nM - 10 microM) for 72 hours. Cell viability is measured by CellTiter-Glo. Testosterone (10 nM) is added to stimulate proliferation, and the ability of the compound to block testosterone-induced growth is measured. IC50 values are reported. No cell studies use the aldehyde.
|
| Animal Protocol |
1H-Imidazole-5-carboxaldehyde is not administered to animals. However, for the development of C17,20-lyase inhibitors, in vivo xenograft studies are performed: 4-6 week old male athymic nude mice are injected subcutaneously with LNCaP cells (5×10⁶ in Matrigel). After tumors reach ~150 mm3, mice are randomized (n=10/group). Test compound is administered orally once daily at doses of 10, 30, and 100 mg/kg suspended in 0.5% methylcellulose. Control groups receive vehicle or abiraterone acetate (positive control, 100 mg/kg). Tumor volume and body weight are measured twice weekly for 28 days. Endpoint: tumor growth inhibition (TGI)%. No data for the aldehyde.
|
| ADME/Pharmacokinetics |
No pharmacokinetic data are available for 1H-Imidazole-5-carboxaldehyde. For abiraterone (the FDA-approved C17,20-lyase inhibitor), PK in humans: oral bioavailability variable (~10-20% due to extensive CYP3A4 metabolism), Cmax at 2-4 hours, terminal half-life ~12 hours, metabolized to delta⁴-abiraterone (active). The imidazole aldehyde would likely be rapidly metabolized by aldehyde dehydrogenase and would have low oral bioavailability. No PK studies exist.
|
| Toxicity/Toxicokinetics |
The safety profile of 1H-Imidazole-5-carboxaldehyde: May cause skin and eye irritation. Harmful if swallowed (oral LD50 500-2000 mg/kg predicted). May cause respiratory irritation if dust is inhaled. Not classified as a carcinogen or reproductive toxin. Use with adequate ventilation and PPE. The parent imidazole ring is a known hepatotoxin at high doses (due to CYP inhibition), but the aldehyde is not expected to be highly toxic at low working concentrations. Waste should be disposed according to local regulations.
|
| Additional Infomation |
Structure in the first source
1H-Imidazole-5-carboxaldehyde is not a drug; it is a research chemical intermediate. Its most significant pharmaceutical derivative is abiraterone acetate (Zytiga), which is FDA-approved (2011) for metastatic castration-resistant prostate cancer (mCRPC) and also for metastatic high-risk castration-sensitive prostate cancer (mHSPC). Abiraterone is a C17,20-lyase inhibitor that blocks androgen biosynthesis. However, abiraterone itself is not synthesized directly from this aldehyde; the aldehyde is used to prepare certain analogues and alternative inhibitors. The compound has also been used to synthesize antimalarial agents targeting plasmodial CYP51. No clinical trials involve the aldehyde itself. |
| Molecular Formula |
C4H4N2O
|
|---|---|
| Molecular Weight |
96.09
|
| Exact Mass |
96.032
|
| CAS # |
3034-50-2
|
| PubChem CID |
76428
|
| Appearance |
Off-white to yellow solid powder
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
367.8±15.0 °C at 760 mmHg
|
| Melting Point |
174-177 °C(lit.)
|
| Flash Point |
179.8±26.8 °C
|
| Vapour Pressure |
0.0±0.8 mmHg at 25°C
|
| Index of Refraction |
1.620
|
| LogP |
0.2
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
7
|
| Complexity |
74.1
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C([H])C1=C([H])N=C([H])N1[H]
|
| InChi Key |
ZQEXIXXJFSQPNA-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C4H4N2O/c7-2-4-1-5-3-6-4/h1-3H,(H,5,6)
|
| Chemical Name |
1H-imidazole-5-carbaldehyde
|
| 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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 10.4069 mL | 52.0346 mL | 104.0691 mL | |
| 5 mM | 2.0814 mL | 10.4069 mL | 20.8138 mL | |
| 10 mM | 1.0407 mL | 5.2035 mL | 10.4069 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
