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Teprenone

Cat No.:V29649 Purity: ≥98%
Teprenone is an antiulcer drug that is an inducer of heat shock proteins.
Teprenone
Teprenone Chemical Structure CAS No.: 6809-52-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
Other Sizes

Other Forms of Teprenone:

  • (5E,9E,13E)-Teprenone
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Teprenone is an antiulcer drug that is an inducer of heat shock proteins.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Teprenone is an inducer of HSP. Teprenone (geranylgeranyl acetone, 1 μM) effectively inhibits ethanol-induced exfoliation and lowers lactate dehydrogenase (LDH) release from stomach mucosal cells. Teprenone (1 μM) steadily elevates HSC70 levels and rapidly accumulates stress-induced concentrations of HSP90, HSP70, and HSP60 within 30-60 minutes. Teprenone also activates heat shock factor 1[1]. Teprenone (0-20 μM) modestly enhances the viability of human umbilical vein endothelial cells (HUVEC) after irradiation (IR). Teprenone (10 μM) showed no effect on HUVEC migration and invasion but increased HUVEC tube formation and wound healing with or without IR. Teprenone (10 μM) also increases angiogenesis by increasing VEGF and eNOS production in HUVEC [3].
ln Vivo
In comparison to rats given with a vehicle, rats treated with teprenone (200 mg/kg, p.o.) exhibit increased stress in their mucosa and an accumulation of HSP70 mRNA. Improve that accumulation. After a stress load of two and four hours, rats treated with teprenone (200 mg/kg) orally can dramatically reduce the formation of ulcers [1]. Retinal ganglion cells (RGC) in rats treated with 200 mg/kg teprenone on a daily basis express HSP72. Teprenone mitigated optic nerve damage, enhanced HSP72, decreased the amount of TUNEL-positive cells in the RGC layer, and greatly decreased RGC loss (measured following an increase in intraocular pressure, or IOP) in a rat model of glaucoma [2]. Mitigation of radiation-induced intestinal damage in mice can be achieved by teprenone (200 mg/kg, orally)[3].
References

[1]. Geranylgeranylacetone induces heat shock proteins in cultured guinea pig gastric mucosal cells and rat gastric mucosa. Gastroenterology. 1996 Aug;111(2):345-57.

[2]. Retinal ganglion cell protection with geranylgeranylacetone, a heat shock protein inducer, in a rat glaucoma model. Trans Am Ophthalmol Soc. 2003;101:39-50; discussion 50-1.

[3]. Geranylgeranylacetone Ameliorates Intestinal Radiation Toxicity by Preventing Endothelial Cell Dysfunction. Int J Mol Sci. 2017 Oct 7;18(10).

Additional Infomation
Teprenone is a terpene ketone in which a (9E,13E)-geranylgernayl group is bonded to one of the alpha-methyls of acetone (it is a mixture of 5E- and 5Z-geoisomers in a 3:2 ratio). It has a role as an anti-ulcer drug, a cardioprotective agent, a hepatoprotective agent, a nephroprotective agent, a neuroprotective agent and a Hsp70 inducer. It is a methyl ketone and a terpene ketone. It contains a geranylgeranyl group.
Mechanism of Action
Teprenone acts as an anti-ulcer and gastric mucoprotective agent used to treat gastric ulcers and gastritis. Currently, the full mechanisms of action are still unclear.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C23H38O
Molecular Weight
330.5472
Exact Mass
330.292
CAS #
6809-52-5
Related CAS #
(5E,9E,13E)-Teprenone;3796-63-2
PubChem CID
5282199
Appearance
Colorless to light yellow liquid
Density
0.9±0.1 g/cm3
Boiling Point
442.2±24.0 °C at 760 mmHg
Flash Point
168.0±9.8 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.483
LogP
8.2
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
12
Heavy Atom Count
24
Complexity
482
Defined Atom Stereocenter Count
0
SMILES
O=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])[H]
InChi Key
HUCXKZBETONXFO-NJFMWZAGSA-N
InChi Code
InChI=1S/C23H38O/c1-19(2)11-7-12-20(3)13-8-14-21(4)15-9-16-22(5)17-10-18-23(6)24/h11,13,15,17H,7-10,12,14,16,18H2,1-6H3/b20-13+,21-15+,22-17+
Chemical Name
(5E,9E,13E)-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one
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 (e.g. under nitrogen), 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 Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~302.53 mM)
Ethanol : ~50 mg/mL (~151.26 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (7.56 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 (7.56 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), suspension solution; with ultrasonication.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.56 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly.


Solubility in Formulation 4: ≥ 2.5 mg/mL (7.56 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% 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 EtOH stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of 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 5: 2.5 mg/mL (7.56 mM) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH 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.

Solubility in Formulation 6: ≥ 2.5 mg/mL (7.56 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (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 EtOH stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0253 mL 15.1263 mL 30.2526 mL
5 mM 0.6051 mL 3.0253 mL 6.0505 mL
10 mM 0.3025 mL 1.5126 mL 3.0253 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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