339068-25-6

339068-25-6 structure

Name: HET-0016
Chemical Name: N'-(4-butyl-2-methylphenyl)-N-hydroxymethanimidamide
CAS Number: 339068-25-6
Molecular Formula: C₁₂H₁₈N₂O
Molecular Weight: 206.284
Catalog: Signaling Pathways Metabolic Enzyme/Protease Cytochrome P450
Create Date: 2017-08-15 10:01:01
Modify Date: 2024-01-06 13:03:19
HET0016 is a potent and selective 20-hydroxyeicosatetraenoic acid (20-HETE) synthase inhibitor, with IC50 values of 17.7 nM, 12.1 nM and 20.6 nM for recombinant CYP4A1-, CYP4A2- and CYP4A3-catalyzed 20-HETE synthesis, respectively. HET0016 also is a selective CYP450 inhibitor, which has been shown to inhibit angiogenesis and tumor growth[1][2].

Name	N'-(4-butyl-2-methylphenyl)-N-hydroxymethanimidamide
Synonyms	Methanimidamide, N'-(4-butyl-2-methylphenyl)-N-hydroxy- N'-(4-Butyl-2-methylphenyl)-N-hydroxyimidoformamide het0016 N-(4-butyl-2-methylphenyl)-N'-hydroxyiminoformamide hms1445d06

Description	HET0016 is a potent and selective 20-hydroxyeicosatetraenoic acid (20-HETE) synthase inhibitor, with IC50 values of 17.7 nM, 12.1 nM and 20.6 nM for recombinant CYP4A1-, CYP4A2- and CYP4A3-catalyzed 20-HETE synthesis, respectively. HET0016 also is a selective CYP450 inhibitor, which has been shown to inhibit angiogenesis and tumor growth[1][2].
Related Catalog	Research Areas >> Cardiovascular Disease Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450
Target	17.7 nM (CYP4A1), 12.1 nM (CYP4A2), 20.6 nM (CYP4A3)[1], CYP450[2]
In Vitro	HET0016 is a selective, non-competitive and irreversible inhibitor of CYP4A [1]. HET0016 (100 μM; 24 hours, 48 hours) decreases migration and invasion of breast cancer metastatic cells [2]. Cell Proliferation Assay[2] Cell Line: MDA-MB-231 cells Concentration: 100 μM Incubation Time: 24 hours, 48 hours Result: Decreased migration and invasion of breast cancer metastatic cells
In Vivo	HET0016 (10 mg/kg/day; i.v.; for 3 weeks) reduces tumor volume and lung metastasis in an immunocompetent breast cancer mouse model[2]. HET0016 reduces the metalloproteinases’ levels in the lungs via PI3K/AKT pathway in mice[2]. HET0016 decreases expression of pro-inflammatory and growth factors and granulocytic MDSCs population in lung microenvironment[2]. HET0016 protects BBB dysfunction after I/R by regulating the expression of MMP-9 and tight junction proteins[3]. Animal Model: 4–5 weeks female Balb/c mice (16-18 g)[2] Dosage: 10 mg/kg/day Administration: Intravenously; 5 days a week; for 3 weeks; starting from day 15 of tumor implantation Result: Reduced tumor volume and lung metastasis.
References	[1]. Seki T, et al. 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]. Borin TF, et al. HET0016 decreases lung metastasis from breast cancer in immune-competent mouse model. PLoS One. 2017 Jun 13;12(6):e0178830. [3]. Liu Y, et al. 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.

Density	1.0±0.1 g/cm3
Boiling Point	356.9±52.0 °C at 760 mmHg
Molecular Formula	C₁₂H₁₈N₂O
Molecular Weight	206.284
Flash Point	169.7±30.7 °C
Exact Mass	206.141907
PSA	44.62000
LogP	4.13
Vapour Pressure	0.0±0.8 mmHg at 25°C
Index of Refraction	1.524

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