| Size | Price | Stock | Qty |
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| 500mg |
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| Other Sizes |
| Targets |
Teprenone targets heat shock proteins (HSPs) as an inducer, particularly HSP70, HSPB8, and HSPB1. Induction of HSP70 expression is protective against the development of various diseases, including inflammatory bowel disease, hypoxic/ischemic brain injury, and spinal and bulbar muscular atrophy. The compound also exerts cytoprotective effects by promoting gastric mucus secretion, enhancing mucosal blood flow, and inhibiting reactive oxygen species formation. Teprenone has been shown to protect the myocardium from ischemia/reperfusion injury by activating heat shock proteins.
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| 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].
In vitro studies have demonstrated that Teprenone (1 microM) significantly prevents ethanol-induced cell shedding and reduces lactate dehydrogenase (LDH) release from gastric mucosal cells. The compound also gradually increases HSC70 levels in gastric mucosal cells. As an inducer of HSPs, Teprenone activates heat shock element binding activity, indicating that heat shock factor 1 is activated. The compound's cytoprotective effects have been characterized in various in vitro models of cellular stress, including oxidative stress and chemical injury. |
| 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].
In vivo studies have demonstrated that Teprenone causes rat stomach mucosa to accumulate heat shock proteins and protects the gastric mucosa in peptic ulcer disease. The compound has been shown to protect the myocardium from ischemia/reperfusion injury and exhibits cardioprotective, hepatoprotective, nephroprotective, and neuroprotective effects. In clinical settings, Teprenone is used for the treatment of gastric ulcers and prevention of NSAID-induced gastropathy. The compound is typically administered orally at a dose of 150 mg/day in three divided doses after meals. |
| Enzyme Assay |
The in vitro assays for Teprenone typically involve measuring heat shock protein induction and cytoprotective effects. For HSP induction studies, cells are treated with varying concentrations of Teprenone, and HSP70, HSPB8, and HSPB1 levels are measured using Western blotting or ELISA. Heat shock element binding activity is assessed using electrophoretic mobility shift assays to confirm heat shock factor 1 activation. For cytoprotection studies, cells are treated with Teprenone prior to exposure to stress-inducing agents such as ethanol, and cell viability and LDH release are measured.
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| Cell Assay |
Cellular assays for Teprenone are conducted using gastric mucosal cells, cardiomyocytes, hepatocytes, or neuronal cells. Cells are cultured in appropriate media and treated with varying concentrations of Teprenone (e.g., 1 microM). Cytoprotective effects are assessed by exposing cells to stress-inducing agents such as ethanol or oxidative stress, and measuring cell viability, LDH release, and markers of cell damage. HSP induction is confirmed by measuring HSP70, HSPB8, and HSPB1 levels using Western blotting or quantitative PCR. These assays confirm the compound's cytoprotective and HSP-inducing activities.
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| Animal Protocol |
In vivo animal studies for Teprenone are conducted in rat and mouse models. In rat models, Teprenone is administered orally, and its effects on gastric mucosa are assessed by measuring HSP accumulation in stomach tissue. Cardioprotective effects are studied in ischemia/reperfusion models, where the compound is administered before ischemia and myocardial damage is assessed. Hepatoprotective, nephroprotective, and neuroprotective effects are studied in appropriate disease models. These studies confirm the compound's in vivo efficacy and support its clinical use as an anti-ulcer and cytoprotective agent.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies in rats have shown that Teprenone metabolism follows a one-compartment model. In humans, following oral administration of a 50 mg capsule, the maximum plasma concentration (Cmax) was 246.9+/-85.4 ng/ml. The compound is highly lipophilic and is poorly absorbed when taken on an empty stomach; it should be taken after meals for optimal absorption. Teprenone is excreted primarily in breath, and the urinary recovery of unchanged compound in rats is 22%. The compound is not FDA-approved in the United States but is used in some Asian countries.
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| Toxicity/Toxicokinetics |
Toxicological data for Teprenone indicate that the compound is well-tolerated at therapeutic doses. The most common adverse effects are mild and include gastrointestinal disturbances. No significant toxicity has been reported with the use of Teprenone at recommended doses. The compound has been used clinically for the treatment of gastric ulcers and prevention of NSAID-induced gastropathy with a favorable safety profile. However, as with any medication, Teprenone should be used with caution in patients with specific medical conditions and under the supervision of a healthcare professional.
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| References |
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| Additional Infomation |
Teprenone is a terpenoid ketone in which a (9E,13E)-geranyl-geranyl group is linked to the α-methyl group of acetone (it is a mixture of 5E- and 5Z-geometric isomers in a 3:2 ratio). It possesses anti-ulcer, cardioprotective, hepatoprotective, nephroprotective, neuroprotective, and Hsp70-inducing effects. It is a methyl ketone and a terpenoid ketone containing a geranyl-geranyl group.
Mechanism of Action Teprenone is an anti-ulcer and gastric mucosal protectant used to treat gastric ulcers and gastritis. Currently, its complete mechanism of action is not fully understood. Teprenone (geranylgeranylacetone, GGA) is an anti-ulcer agent and HSP inducer used clinically in some Asian countries for the treatment of gastric ulcers and prevention of NSAID-induced gastropathy. The compound exerts cytoprotective effects by inducing HSP70, HSPB8, and HSPB1 expression, promoting gastric mucus secretion, enhancing mucosal blood flow, and inhibiting reactive oxygen species formation. Teprenone also exhibits cardioprotective, hepatoprotective, nephroprotective, and neuroprotective effects in preclinical studies. The compound is available as an oral medication and is not FDA-approved in the United States. |
| Molecular Formula |
C23H38O
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|---|---|
| Molecular Weight |
330.5472
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| Exact Mass |
330.292
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| CAS # |
6809-52-5
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| Related CAS # |
(5E,9E,13E)-Teprenone;3796-63-2
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| PubChem CID |
5282199
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
442.2±24.0 °C at 760 mmHg
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| Flash Point |
168.0±9.8 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.483
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| LogP |
8.2
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
12
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| Heavy Atom Count |
24
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| Complexity |
482
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| Defined Atom Stereocenter Count |
0
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| 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]
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| InChi Key |
HUCXKZBETONXFO-NJFMWZAGSA-N
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| 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+
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| Chemical Name |
(5E,9E,13E)-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~302.53 mM)
Ethanol : ~50 mg/mL (~151.26 mM) |
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| 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. View More
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. 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. |
| 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.
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.
Link: https://clinicaltrials.gov/ct2/show/NCT05672134
Conditions:Heart Failure With Preserved Ejection FractionLink: https://clinicaltrials.gov/ct2/show/NCT01397448
Conditions:Gastric or Duodenal Ulcers Caused by Low-dose AspirinLink: https://clinicaltrials.gov/ct2/show/NCT01190657
Conditions:Acute Gastritis|Gastric UlcerProducts are for research use only; We do not sell to patients
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