Art. -Nr.: HY-13219

Tepoxalin

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Tepoxalin is an orally active dual inhibitor of Cyclooxygenase/Lipoxygenase, with IC₅₀ values of 4.6 μM (sheep cyclooxygenase), 2.85 μM (rat cyclooxygenase), 0.15 μM (rat 5-lipoxygenase), and 3.0 μM (h12-lipoxygenase), respectively. Tepoxalin inhibits ROS production and NF-κB activation. Tepoxalin suppresses the production of thromboxane B₂, leukotriene B₄, prostaglandins and cytokines, and blocks platelet aggregation. Tepoxalin exhibits potent anti-inflammatory activity in rats with adjuvant-induced arthritis. Tepoxalin possesses analgesic activity. Tepoxalin shows no ulcerogenic activity within the anti-inflammatory dose range. Tepoxalin can be used in studies related to adjuvant-induced arthritis, skin inflammation and Alzheimer's disease.

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Reinheit: 98.46%
CAS. Nr.: 103475-41-8
Formel: C₂₀H₂₀ClN₃O₃
Molecular Weight:385.84

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

Tepoxalin Chemical Structure

CAS. Nr.: 103475-41-8

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target^[1]

Sheep cyclooxygenase

4.6 μM (IC₅₀)

Rat cyclooxygenase

2.85 μM (IC₅₀)

Rat 5-lipoxygenase

0.15 μM (IC₅₀)

h12-lipoxygenase

3.0 μM (IC₅₀)

Alle COX Isoform-spezifische Produkte anzeigen :

Alle Lipoxygenase Isoform-spezifische Produkte anzeigen :

Alle NF-κB Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
RBL-1	IC₅₀	0.15 μM Compound: Tepoxalin	Inhibitory activity against 5-lipoxygenase (5-LO) in intact rat barophilic leukemia cells (RBL-1) Inhibitory activity against 5-lipoxygenase (5-LO) in intact rat barophilic leukemia cells (RBL-1)	[PMID: 10230624]
RBL-1	IC₅₀	0.15 μM Compound: Tepoxalin	The compound was tested for inhibitory activity against 5-Lipoxygenase in rat RBL-1 The compound was tested for inhibitory activity against 5-Lipoxygenase in rat RBL-1	[PMID: 1635053]
RBL-1	IC₅₀	1.7 μM Compound: Tepoxalin	Inhibitory activity against 5-lipoxygenase (5-LO) using broken rat barophilic leukemia cells (RBL-1) Inhibitory activity against 5-lipoxygenase (5-LO) using broken rat barophilic leukemia cells (RBL-1)	[PMID: 10230624]
RBL-1	IC₅₀	2.85 μM Compound: Tepoxalin	Inhibitory activity against cyclooxygenase (COX) in intact rat barophilic leukemia cells (RBL-1) Inhibitory activity against cyclooxygenase (COX) in intact rat barophilic leukemia cells (RBL-1)	[PMID: 10230624]
RBL-1	IC₅₀	4.2 μM Compound: Tepoxalin	Inhibitory activity against Cyclooxygenase (COX) using broken rat barophilic leukemia cells (RBL-1) Inhibitory activity against Cyclooxygenase (COX) using broken rat barophilic leukemia cells (RBL-1)	[PMID: 10230624]

In Vitro

Tepoxalin inhibits ovine seminal vesicle cyclooxygenase with an IC₅₀ of 4.6 μM^[1].
Tepoxalin inhibits cyclooxygenase in RBL-1 lysates with an IC₅₀ of 2.85 μM^[1].
Tepoxalin inhibits cyclooxygenase activity in intact RBL-1 cells with an IC₅₀ of 4.2 μM^[1].
Tepoxalin inhibits the production of thromboxane B₂ in peripheral blood leukocytes stimulated by calcium ionophore A-23187, with an IC₅₀ of 0.01 μM^[1].
Tepoxalin inhibits the production of thromboxane B₂ in whole blood stimulated by calcium ionophore A-23187, with an IC₅₀ of 0.08 μM^[1].
Tepoxalin inhibits epinephrine-induced platelet aggregation with an IC₅₀ of 0.045 μM^[1].
Tepoxalin inhibits lipoxygenase in RBL-1 lysates with an IC₅₀ of 0.15 μM^[1].
Tepoxalin inhibits lipoxygenase activity in intact RBL-1 cells with an IC₅₀ of 1.7 μM^[1].
Tepoxalin inhibits the production of leukotriene B₄ in peripheral blood leukocytes stimulated by calcium ionophore A-23187, with an IC₅₀ of 0.07 μM^[1].
Tepoxalin inhibits leukotriene B4 production in whole blood stimulated by the calcium ionophore A-23187, with an IC₅₀ of 1.57 μM^[1].
Tepoxalin inhibits platelet 12-lipoxygenase with an IC₅₀ of 3.0 μM^[1].
Tepoxalin weakly inhibits 15-lipoxygenase with an IC₅₀ of 157 μM^[1].
Tepoxalin inhibits PMA-induced Mac-1 upregulation and PMA-induced IL-8 production in HL60 granulocytes^[2].
Tepoxalin (1-30 μM; 16 h-96 h) potently inhibits the proliferation of activated peripheral blood lymphocytes (PBL) and IL-2-dependent T lymphoblasts, with the strongest inhibitory activity against PBL stimulated by PMA, PMA + ionomycin, and IL-2 (IC₅₀ values 1.36-2.75 μM), while exerting minimal effects on spontaneously proliferating or growth factor-dependent cell lines; in addition, it synergizes with suboptimal doses of cyclosporin A (CsA) to inhibit OKT3-stimulated PBL proliferation^[3].
Tepoxalin (1-50 μM; 30 min pre-incubation; 24 h LPS stimulation) potently inhibits LPS-induced IL-1β and IL-6 synthesis in primary rat microglia, with the maximum inhibitory effect observed at 10 μM^[4].
Tepoxalin (1-50 μM; 30 min pre-incubation; 24 h IL-1β stimulation) potently inhibits IL-1β-induced IL-6 synthesis in primary rat astrocytes, with the maximum inhibitory effect observed at 10 μM^[4].
Tepoxalin (1-50 μM; pre-incubation; 60 min IL-1β stimulation) dose-dependently inhibits IL-1β-induced IκB-α degradation in human U373 MG astrocytoma cells^[4].
Tepoxalin inhibits cyclooxygenase activity in purified ovine PGHS1 in a non-competitive and reversible manner, with an IC₅₀ of 0.1 μM, and this inhibitory effect cannot be reversed by excess heme^[5].
Tepoxalin inhibits the peroxidase activity of purified ovine PGHS1 with an IC₅₀ of 4 μM. This effect is independent of cyclooxygenase activity, can be reversed by excess heme, and does not inhibit unrelated peroxidases^[5].
Tepoxalin (20 μM; 1 h at 37°C) inhibits tert-butyl hydroperoxide-induced reactive oxygen species production and prostaglandin E₂ synthesis in Jurkat cells at a concentration of 20 μM^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Proliferation Assay^[3]

Cell Line:

human peripheral blood lymphocytes (PBLs), IL-2-dependent T cell blasts, Jurkat cells, PDGF-supplemented 3T3 cells, T47D cells, MCF7 cells
Concentration:

1-30 μM (stimulated PBLs, IL-2-dependent blasts); up to 20 μM (Jurkat, PDGF-supplemented 3T3, T47D, MCF7 cells); 10, 30 μM (timed addition assays); 2 μM (combination assay with CsA)
Incubation Time:

72-96 h (stimulated PBLs); 16 h (IL-2-dependent blasts); 3 days (Jurkat, PDGF-supplemented 3T3, T47D, MCF7 cells, combination assay); 48-72 h total (timed addition assays); 24 h (viability assays)
Result:

Suppressed PBL proliferation stimulated by OKT3, PMA, PMA + ionomycin, or IL-2, with mean IC₅₀ values of 5.9 μM, 1.36 μM, 1.6 μM, and 2.75 μM, respectively.
Caused near-complete suppression of IL-2-dependent blasts at 10 μM.
Exerted minimal effect on proliferation of Jurkat, PDGF-supplemented 3T3, T47D, or MCF7 cells at concentrations up to 20 μM.
Showed equivalent potency when added at culture initiation or 48 hours post-OKT3 stimulation.
Co-administration of 2 μM tepoxalin with 0.1 nM CsA resulted in 40% suppression of OKT3-stimulated PBL proliferation, and with 0.4 nM CsA resulted in 45% suppression.
Maintained 90-95% cell viability at 20 μM after 24 hours.

Real Time qPCR^[3]

Cell Line:

human PBLs, IL-2-dependent T cell blasts
Concentration:

30 μM (OKT3-stimulated PBLs); 1-30 μM (PMA + ionomycin-stimulated PBLs); 15, 30 μM (PMA-stimulated PBLs); 10 μM (IL-2-dependent blasts)
Incubation Time:

2 h pre-incubation, then 2, 4, or 21 h post-OKT3 stimulation; 2 h pre-incubation, then 4 h post-PMA + ionomycin stimulation; 2 h pre-incubation, then 4 h post-PMA stimulation; 2 h (IL-2-dependent blasts)
Result:

Caused only minimal (≤1.8-fold) reduction in OKT3-induced IL-2 mRNA at 2, 4, and 21 hours post-stimulation.
Induced dose-dependent reduction of IL-2 mRNA in PMA + ionomycin-stimulated PBLs, with 2.7-fold reduction at 1 μM, 4.2-fold at 5 μM, 8.3-fold at 10 μM, and 12.5-fold at 30 μM.
Caused 6.1-fold reduction of IL-2 mRNA at 15 μM and 27-fold reduction at 30 μM in PMA-stimulated PBLs, with no effect on G3PDH mRNA levels.
Caused more than 4.5-fold reduction of IFN-γ mRNA in IL-2-dependent blasts at 10 μM.

Western Blot Analysis^[4]

Cell Line:

human U373 MG astrocytoma cells
Concentration:

1, 10, 25, 50 μM
Incubation Time:

pre-incubation; 60 min IL-1β stimulation
Result:

Dose-dependently inhibited IL-1β-induced degradation of 35 kDa IkB-α, with increasing recovery of IkB-α protein observed at higher concentrations.

In Vivo

Tepoxalin (1-173 mg/kg; p.o.) exhibits potent oral anti-inflammatory activity in adjuvant arthritic rats (ED₅₀ = 3.5 mg/kg) and lacks ulcerogenic activity in both arthritic rats and normal rats at doses up to 100 mg/kg (p.o.)^[1].
Tepoxalin (0.45 mg/kg; p.o.) exhibits potent oral analgesic activity in mice (ED₅₀ = 0.45 mg/kg) in the acetic acid-induced abdominal constriction assay^[1].
Tepoxalin (0.015-2.37 mg/kg; p.o.) exhibits oral dose-dependent inhibition of ex vivo eicosanoid production in dogs, with greater potency for prostaglandin synthesis (ED₅₀ = 0.015 mg/kg) than leukotriene synthesis (ED₅₀ = 2.37 mg/kg)^[1].
Tepoxalin (3-50 mg/kg; p.o.; 18 h and 1 h before stimulant injection) inhibits neutrophil migration into LPS- or TNF-α-induced murine cutaneous inflammatory sites in a dose-dependent manner, with a maximum 64.7% inhibition of LPS-induced MPO activity at 50 mg/kg, by suppressing NFκB-mediated upregulation of Mac-1 and E-selectin, and at the highest dose, ICAM-1^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

C57BL/6, B6D2F₁ (male, 8-12 weeks of age, intradermal injection of LPS or recombinant murine TNF-α-induced acute cutaneous inflammation)^[2]
Dosage:

3 mg/kg; 6 mg/kg; 12 mg/kg; 25 mg/kg; 50 mg/kg
Administration:

p.o.; 18 h and 1 h before stimulant injection
Result:

Inhibited LPS-induced MPO activity by 0% at 3 mg/kg, 33.6% at 6 mg/kg, 50.0% at 12 mg/kg, 54.3% at 25 mg/kg, and 64.7% at 50 mg/kg.
Inhibited TNF-α-induced MPO activity by 12.0% at 12 mg/kg, 54.7% at 25 mg/kg, and 61.2% at 50 mg/kg.
Reduced LPS-induced neutrophil extravasation and edema in skin tissue at 12, 25, and 50 mg/kg.
Suppressed LPS-induced upregulation of Mac-1 (CD18) on neutrophils and reduced E-selectin protein expression on vascular endothelial cells at 12, 25, and 50 mg/kg.
Reduced LPS-induced E-selectin mRNA levels to 6.3 × 10^-22 moles/μg RNA at 25 mg/kg and did not alter ICAM-1 mRNA levels.
Reduced LPS-induced E-selectin mRNA levels to 4.8 × 10^-22 moles/μg RNA and ICAM-1 mRNA levels to 9.7 × 10^-22 moles/μg RNA at 50 mg/kg.
Caused no change in total leukocyte numbers or lymphocyte:monocyte:neutrophil ratios at 50 mg/kg compared to vehicle controls.

Chemical Information

CAS. Nr. 103475-41-8
Appearance Solid
Molecular Weight 385.84
Formel C₂₀H₂₀ClN₃O₃
Color Off-white to yellow
SMILES

O=C(N(O)C)CCC1=NN(C2=CC=C(OC)C=C2)C(C3=CC=C(Cl)C=C3)=C1
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 100 mg/mL (259.17 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.5917 mL

12.9587 mL

25.9175 mL

5 mM

0.5183 mL

2.5917 mL

5.1835 mL

10 mM

0.2592 mL

1.2959 mL

2.5917 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.5 mg/mL (6.48 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: ≥ 2.5 mg/mL (6.48 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.5 mg/mL (6.48 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (289 KB)
SDS (393 KB)
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COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Argentieri DC, et al. Tepoxalin: a dual cyclooxygenase/5-lipoxygenase inhibitor of arachidonic acid metabolism with potent anti-inflammatory activity and a favorable gastrointestinal profile. J Pharmacol Exp Ther. 1994 Dec;271(3):1399-408. [Content Brief]

[2]. Zhou L, et al. Tepoxalin blocks neutrophil migration into cutaneous inflammatory sites by inhibiting Mac-1 and E-selectin expression. Eur J Immunol. 1996 Jan;26(1):120-9. [Content Brief]

[3]. Zhou L, et al. Tepoxalin, a novel immunosuppressive agent with a different mechanism of action from cyclosporin A. J Immunol. 1994 Dec 1;153(11):5026-37. PMID: 7963563. [Content Brief]

[4]. Fiebich BL, et al. The non-steroidal anti-inflammatory drug tepoxalin inhibits interleukin-6 and alpha1-anti-chymotrypsin synthesis in astrocytes by preventing degradation of IkappaB-alpha. Neuropharmacology. 1999;38(9):1325-1333. [Content Brief]

[5]. Tam SS, et al. Tepoxalin, a novel dual inhibitor of the prostaglandin-H synthase cyclooxygenase and peroxidase activities. J Biol Chem. 1995;270(23):13948-13955. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.5917 mL	12.9587 mL	25.9175 mL	64.7937 mL
	5 mM	0.5183 mL	2.5917 mL	5.1835 mL	12.9587 mL
	10 mM	0.2592 mL	1.2959 mL	2.5917 mL	6.4794 mL
	15 mM	0.1728 mL	0.8639 mL	1.7278 mL	4.3196 mL
	20 mM	0.1296 mL	0.6479 mL	1.2959 mL	3.2397 mL
	25 mM	0.1037 mL	0.5183 mL	1.0367 mL	2.5917 mL
	30 mM	0.0864 mL	0.4320 mL	0.8639 mL	2.1598 mL
	40 mM	0.0648 mL	0.3240 mL	0.6479 mL	1.6198 mL
	50 mM	0.0518 mL	0.2592 mL	0.5183 mL	1.2959 mL
	60 mM	0.0432 mL	0.2160 mL	0.4320 mL	1.0799 mL
	80 mM	0.0324 mL	0.1620 mL	0.3240 mL	0.8099 mL
	100 mM	0.0259 mL	0.1296 mL	0.2592 mL	0.6479 mL

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Tepoxalin

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Alle COX Isoform-spezifische Produkte anzeigen

Alle Lipoxygenase Isoform-spezifische Produkte anzeigen

Alle NF-κB Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Tepoxalin Related Classifications

HY-13219 Related Classifications