Teprenone

Modify Date: 2024-01-02 20:05:25

Teprenone Structure
Teprenone structure
Common Name Teprenone
CAS Number 6809-52-5 Molecular Weight 330.55
Density 0.9±0.1 g/cm3 Boiling Point 442.2±24.0 °C at 760 mmHg
Molecular Formula C23H38O Melting Point N/A
MSDS Chinese USA Flash Point 168.0±9.8 °C

 Use of Teprenone


Teprenone is a anti-ulcer drug, and works as an inducer of heat shock proteins (HSPs).

 Names

Name teprenone
Synonym More Synonyms

 Teprenone Biological Activity

Description Teprenone is a anti-ulcer drug, and works as an inducer of heat shock proteins (HSPs).
Related Catalog
Target

HSP

In Vitro Teprenone is an inducer of HSPs. Teprenone (Geranylgeranylacetone, 1 μM) significantly prevents ethanol-induced exfoliation, and reduces lactate dehydrogenase (LDH) release in gastric mucosal cells. Teprenone (1 μM) gradually increases HSC70 level, and rapidly accumulates the stress-inducible HSP90, HSP70, and HSP60 concentrations within 30-60 min. Teprenone also activates the heat shock factor 1[1]. Teprenone (0-20 µM) slightly increases human umbilical vein endothelial cell (HUVEC) viability following irradiation (IR). Teprenone (10 µM) exhibits no effects on HUVEC migration and invasion, but enhances HUVEC tube formation and wound healing both with and without IR. Teprenone (10 µM) also promotes angiogenesis by inducing VEGF and eNOS expression in HUVECs[3].
In Vivo Teprenone (200 mg/kg, p.o.) results in the accumulation of HSP70 mRNA in rats, and the accumulation is enhanced by stress addition in the mucosa of Teprenone-pretreated rats compared with that of vehicle-pretreated rats. Teprenone (200 mg/kg, p.o.) markedly suppresses the ulcer formation after 2- and 4-hour stress loading in rats[1]. Teprenone (200 mg/kg daily) induces HSP72 in retinal ganglion cells (RGCs) from rat retinas. Teprenone significantly reduces the loss of RGCs (evaluated after intraocular pressure (IOP) elevation), lessens optic nerve damage, decreases the number of TUNEL-positive cells in the RGC layer, and increases HSP72 in a rat model of glaucoma[2]. Teprenone (200 mg/kg, p.o.) shows protective effect on radiation-induced intestinal injury in mice[3].
Cell Assay Human umbilical vein endothelial cells (HUVECs) are seeded onto 48-well plates at a density of 1 × 102 cells/well before Teprenone and/or radiation treatment. Cell viability is determined at 48 h after treatment using 0.5 mg/mL MTT solution in serum-free media. This solution is incubated with the cells for 2 h in the 37°C humidified atmosphere containing 5% CO2. Then, the MTT solution is removed, and the cells are dissolved in 100 µL of DMSO. Optical densities of the supernatants are measured at 540 nm with an ELISA spectrophotometer[3].
Animal Admin Male Wister strain rats weighing approximately 250 g are individually housed in wire-mesh cages in a room maintained at 23°C on a 12-hour light-dark cycle. Rats are allowed free access to a standard laboratory chow. Teprenone (200 mg/kg; as emulsion with 5% gum arabic and 0.008% α-tocopherol) or vehicle (5% gum arabic emulsion containing 0.008% α-tocopherol) is given orally in a volume of 5 mL/kg through a metal tubing attached to a 6-mL syringe. Two hours later, rats are placed in restraint cages and then vertically immersed in water at 23°C to the level of the xyphoid process. The rats are killed by decapitation at the indicated times[1].
References

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

[2]. Caprioli J, et al. 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]. Han NK, et al. Geranylgeranylacetone Ameliorates Intestinal Radiation Toxicity by Preventing Endothelial Cell Dysfunction. Int J Mol Sci. 2017 Oct 7;18(10).

 Chemical & Physical Properties

Density 0.9±0.1 g/cm3
Boiling Point 442.2±24.0 °C at 760 mmHg
Molecular Formula C23H38O
Molecular Weight 330.55
Flash Point 168.0±9.8 °C
PSA 17.07000
LogP 8.20
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.483
Storage condition ?20°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RA5391300
CHEMICAL NAME :
5,9,13,17-Nonadecatetraen-2-one, 6,10,14,18-tetramethyl-
CAS REGISTRY NUMBER :
6809-52-5
LAST UPDATED :
199110
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C23-H38-O
MOLECULAR WEIGHT :
330.61

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>15 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,703,1990
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,703,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,703,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,703,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3750 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 16,357,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,703,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,703,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,703,1990

 Safety Information

Hazard Codes Xi
Risk Phrases R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Phrases S26-S36/37/39
RIDADR NONH for all modes of transport
RTECS RA5391300
HS Code 2914190090

 Synthetic Route

 Customs

HS Code 2914190090
Summary 2914190090 other acyclic ketones without other oxygen function。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

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 Synonyms

5,9,13,17-Nonadecatetraen-2-one, 6,10,14,18-tetramethyl-, (E,E,E)-
Geranylgeranyl acetone
GGA
5,9,13,17-Nonadecatetraen-2-one, 6,10,14,18-tetramethyl-, (5E,9E,13E)-
geranylgeranylacetone
6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one
Teprenone
(5E,9E,13E)-6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one
(5E,9E,13E)-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one
E36U31
MFCD00866901
Selbex
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