TETRAPRENYLACETONE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H38O
Molecular Weight	330.5472
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C

InChI

InChIKey=HUCXKZBETONXFO-NJFMWZAGSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C23H38O
Molecular Weight	330.5472
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	3
Optical Activity	NONE

Description
Sources: http://www.shijiebiaopin.net/upload/product/201431323032020.pdf
Curator's Comment: Description was created based on several sources including http://www.ncbi.nlm.nih.gov/pubmed/26345206

Tetraprenylacetone (Geranylgeranylacetone) is an anti-peptic ulcer drug developed and approved in Japan in 1984. Tetraprenylacetone is shown to suppress H. pylori induced tissue and cell injury and inflammatory reaction, so it is expected to show beneficial effects on H. pylori-infected tissues. Tetraprenylacetone is used to treat patients suffering from peptic ulcers and gastritis. In Japan it is sold under the brand name Selbex.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis 156 Target ID: map04210 Sources: http://www.ncbi.nlm.nih.gov/pubmed/27470333	Activator 1447
Chaperone protein DnaK Helicobacter pylori NCTC 11637 ATCC 43504 2 Target ID: Chaperone protein DnaK Helicobacter pylori NCTC 11637 ATCC 43504 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26345206	Modulator 846	0.076 mM [Kd]
Heat shock 70 kDa protein 1 6 Target ID: CHEMBL5460 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26345206	Modulator 846	0.02 mM [Kd]
Interleukin-8 3 Target ID: CHEMBL2157 Sources: http://www.ncbi.nlm.nih.gov/pubmed/15068414	Inhibitor 8504
mucin 5AC, oligomeric mucus/gel-forming 2 Target ID: 682837.0 Gene Symbol: Muc5ac Sources: http://www.ncbi.nlm.nih.gov/pubmed/16240224	Activator 1447
mucin 6, oligomeric mucus/gel-forming 2 Target ID: 282586.0 Gene Symbol: Muc6 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16240224	Activator 1447
Hsp70 [Homo sapiens] 2 Target ID: Hsp70 [Homo sapiens] Sources: http://www.ncbi.nlm.nih.gov/pubmed/17684364	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gastric ulcer 74 Sources: http://www.shijiebiaopin.net/upload/product/201431323032020.pdf	Primary		Approved 8583	Selbex Approved Use Improvement of gastric mucosal lesions (erosion, hemorrhage, redness and edema) in the following diseases: Acute gastritis and acute exacerbation stage of chronic gastritis and Gastric ulcers Launch Date 1984
Gastritis 46 Sources: http://www.shijiebiaopin.net/upload/product/201431323032020.pdf	Primary		Approved 8583	Selbex Approved Use Improvement of gastric mucosal lesions (erosion, hemorrhage, redness and edema) in the following diseases: Acute gastritis and acute exacerbation stage of chronic gastritis and Gastric ulcers Launch Date 1984

C_max

Value	Dose	Co-administered	Analyte	Population
246.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17482416/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		TETRAPRENYLACETONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
851.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17482416/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		TETRAPRENYLACETONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.38 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17482416/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		TETRAPRENYLACETONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Doses

Dose	Population	Adverse events
100 mg 3 times / day multiple, oral Highest studied dose Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8794786/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/8794786/	Sources: https://pubmed.ncbi.nlm.nih.gov/8794786/
50 mg 3 times / week multiple, oral Studied dose Dose: 50 mg, 3 times / week Route: oral Route: multiple Dose: 50 mg, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/25100080/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25100080/	Disc. AE: Angina pectoris... AEs leading to discontinuation/dose reduction: Angina pectoris (1.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/25100080/

AEs

AE	Significance	Dose	Population
Angina pectoris	1.3% Disc. AE	50 mg 3 times / week multiple, oral Studied dose Dose: 50 mg, 3 times / week Route: oral Route: multiple Dose: 50 mg, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/25100080/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25100080/

PubMed

Title	Date	PubMed
Geranylgeranylacetone induces apoptosis via the intrinsic pathway in human melanoma cells.	2016-08	27470333
Suppression of Alzheimer's disease-related phenotypes by geranylgeranylacetone in mice.	2013	24098472

Patents

Sample Use Guides

In Vivo Use Guide

Capsules 50 mg: The usual adult dosage for oral use is 3 capsules (150 mg of teprenone) daily in three divided doses after meals. The dosage may be adjusted depending on the patient’s age and symptoms. Fine Granules 10%: The usual adult dosage for oral use is 1.5 g (150 mg of teprenone) daily in three divided doses after meals. The dosage may be adjusted depending on the patient’s age and symptoms.

Route of Administration: Oral

In Vitro Use Guide

Human melanoma cell lines G361, SK-MEL-2, and SK-MEL-5 were treated with GGA (Tetraprenylacetone) at various doses (1-100uM). GGA significantly reduced the viability of G361, SK-MEL-2, and SK-MEL-5 human melanoma cells at concentrations above 10uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:04:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:46 GMT 2025`
Record UNII	57B67OXM8F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRAPRENYLACETONE

Systematic Name

English

5,9,13,17-NONADECATETRAEN-2-ONE, 6,10,14,18-TETRAMETHYL-, (E,E,E)-

Preferred Name

English

(E,E,E)-GERANYLGERANYL ACETONE

Common Name

English

5,9,13,17-NONADECATETRAEN-2-ONE, 6,10,14,18-TETRAMETHYL-, (5E,9E,13E)-

Systematic Name

English

Code System Code Type Description

FDA UNII

57B67OXM8F

Created by admin on Mon Mar 31 18:04:46 GMT 2025 , Edited by admin on Mon Mar 31 18:04:46 GMT 2025

PRIMARY

CAS

3796-63-2

Created by admin on Mon Mar 31 18:04:46 GMT 2025 , Edited by admin on Mon Mar 31 18:04:46 GMT 2025

PRIMARY

EPA CompTox

DTXSID901166719

Created by admin on Mon Mar 31 18:04:46 GMT 2025 , Edited by admin on Mon Mar 31 18:04:46 GMT 2025

PRIMARY

PUBCHEM

5282199

Created by admin on Mon Mar 31 18:04:46 GMT 2025 , Edited by admin on Mon Mar 31 18:04:46 GMT 2025

PRIMARY

Details

SMILES

InChI

DescriptionSources: http://www.shijiebiaopin.net/upload/product/201431323032020.pdfCurator's Comment: Description was created based on several sources including http://www.ncbi.nlm.nih.gov/pubmed/26345206

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Doses

AEs

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.shijiebiaopin.net/upload/product/201431323032020.pdf
Curator's Comment: Description was created based on several sources including http://www.ncbi.nlm.nih.gov/pubmed/26345206

C_max

T_1/2