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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 of TETRAPRENYLACETONE

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
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

Curator's Comment: GGA (Tetraprenylacetone) is able to pass through blood brain barrier

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
PubMed

PubMed

TitleDatePubMed
Suppression of Alzheimer's disease-related phenotypes by geranylgeranylacetone in mice.
2013
Geranylgeranylacetone induces apoptosis via the intrinsic pathway in human melanoma cells.
2016 Aug
Patents

Patents

Sample Use Guides

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 Fri Dec 15 15:39:56 GMT 2023
Edited
by admin
on Fri Dec 15 15:39:56 GMT 2023
Record UNII
57B67OXM8F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TETRAPRENYLACETONE
Systematic Name English
(E,E,E)-GERANYLGERANYL ACETONE
Common Name English
5,9,13,17-NONADECATETRAEN-2-ONE, 6,10,14,18-TETRAMETHYL-, (E,E,E)-
Systematic 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 Fri Dec 15 15:39:57 GMT 2023 , Edited by admin on Fri Dec 15 15:39:57 GMT 2023
PRIMARY
CAS
3796-63-2
Created by admin on Fri Dec 15 15:39:57 GMT 2023 , Edited by admin on Fri Dec 15 15:39:57 GMT 2023
PRIMARY
PUBCHEM
5282199
Created by admin on Fri Dec 15 15:39:57 GMT 2023 , Edited by admin on Fri Dec 15 15:39:57 GMT 2023
PRIMARY