Physicochemical Properties
| Molecular Formula | C₁₂H₁₈N₂O |
| Molecular Weight | 206.28 |
| Exact Mass | 206.141 |
| CAS # | 339068-25-6 |
| PubChem CID | 2727594 |
| Appearance | White to off-white solid powder |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 356.9±52.0 °C at 760 mmHg |
| Flash Point | 169.7±30.7 °C |
| Vapour Pressure | 0.0±0.8 mmHg at 25°C |
| Index of Refraction | 1.524 |
| LogP | 4.13 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 15 |
| Complexity | 194 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | LYNOGBKNFIHKLE-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C12H18N2O/c1-3-4-5-11-6-7-12(10(2)8-11)13-9-14-15/h6-9,15H,3-5H2,1-2H3,(H,13,14) |
| Chemical Name | N'-(4-butyl-2-methylphenyl)-N-hydroxymethanimidamide |
| Synonyms | HET0016; HET-0016 |
| 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) |
Biological Activity
| ln Vitro | HET0016 inhibits CYP4A in a selective, non-competitive, and irreversible manner [1]. Breast cancer metastatic cells are less likely to migrate and invade when exposed to HET0016 (100 μM) for 24 or 48 hours [2]. |
| ln Vivo | In an immunocompetent mouse model of breast cancer, HET0016 (10 mg/kg/day; intravenously; for 3 weeks) decreases tumor volume and lung metastases [2]. By inhibiting the PI3K/AKT pathway, HET0016 lowers the amounts of metalloproteinases in the lungs of mice [2]. In the lung microenvironment, HET0016 decreases the expression of growth factors, pro-inflammatory factors, and granulocyte MDSC populations [2]. By controlling the expression of tight junction proteins and MMP-9, HET0016 prevents BBB dysfunction following I/R [3]. |
| Cell Assay |
Cell proliferation assay[2] Cell Types: MDA-MB-231 Cell Tested Concentrations: 100 μM Incubation Duration: 24 hrs (hours), 48 hrs (hours) Experimental Results: diminished migration and invasion of breast cancer metastatic cells |
| Animal Protocol |
Animal/Disease Models: 4-5 weeks female balb/c (Bagg ALBino) mouse (16-18 g) [2] Doses: 10 mg/kg/day Route of Administration: intravenous (iv) (iv)injection; 5 days per week; for 3 weeks; from tumor implantation Results started on day 15: reduction in tumor volume and lung metastases. |
| References |
[1]. Cytochrome P450 4A isoform inhibitory profile of N-hydroxy-N'-(4-butyl-2-methylphenyl)-formamidine (HET0016), a selective inhibitor of 20-HETE synthesis. Biol Pharm Bull. 2005 Sep;28(9):1651-4. [2]. HET0016 decreases lung metastasis from breast cancer in immune-competent mouse model. PLoS One. 2017 Jun 13;12(6):e0178830. [3]. The protective effect of HET0016 on brain edema and blood-brain barrier dysfunction after cerebral ischemia/reperfusion. Brain Res. 2014 Jan 28;1544:45-53. |
| Additional Infomation | HET0016 is a member of toluenes. |
Solubility Data
| Solubility (In Vitro) |
DCM : 12.5 mg/mL (~60.60 mM) DMSO : ~5 mg/mL (~24.24 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2 mg/mL (9.70 mM) in 20% HP-β-CD in Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8478 mL | 24.2389 mL | 48.4778 mL | |
| 5 mM | 0.9696 mL | 4.8478 mL | 9.6956 mL | |
| 10 mM | 0.4848 mL | 2.4239 mL | 4.8478 mL |