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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 3
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
0.076 mM [Kd]
0.02 mM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Selbex
Primary
Selbex

Cmax

ValueDoseCo-administeredAnalytePopulation
246.9 ng/mL
50 mg single, oral
TETRAPRENYLACETONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
851.7 ng × h/mL
50 mg single, oral
TETRAPRENYLACETONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.38 h
50 mg single, oral
TETRAPRENYLACETONE plasma
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
57B67OXM8F
Record Status Validated (UNII)
Record Version