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Details

Stereochemistry ACHIRAL
Molecular Formula C22H22O5
Molecular Weight 366.4071
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CYCLOVALONE

SMILES

COC1=C(O)C=CC(C=C2CCCC(=CC3=CC(OC)=C(O)C=C3)C2=O)=C1

InChI

InChIKey=DHKKONBXGAAFTB-OTYYAQKOSA-N
InChI=1S/C22H22O5/c1-26-20-12-14(6-8-18(20)23)10-16-4-3-5-17(22(16)25)11-15-7-9-19(24)21(13-15)27-2/h6-13,23-24H,3-5H2,1-2H3/b16-10+,17-11+

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/cyclovalone.html | https://www.ncbi.nlm.nih.gov/pubmed/3783484 | https://www.ncbi.nlm.nih.gov/pubmed/9538139

Cyclovalone is a synthetic curcumin derivative in which the keto-enolic system is replaced by a cyclohexanone ring. Cyclovalone is a choleretic and cholagogic agent which stimulates the formation and secretion of bile, and also has an anti-inflammatory effect.

Originator

Sources: Journal de Pharmacie et de Chimie (1928), 7, 162-73

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2094253
Sources: Majalah Farmasi Indonesia (1998), 9, (4), 180-185.
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Vanilone Infantile

Approved Use

Unknown
Primary
Vanilone Infantile

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling.
1998 Oct 8
Patents

Sample Use Guides

Oral. First 2 days of therapy in a daily dose of 300 mg, then - 400 mg. Multiplicity of admission - 3-4 r / day. The course of treatment is 3-4 weeks.
Route of Administration: Oral
In Vitro Use Guide
For these studies the LNCaP and PC-3 human prostate cancer cell lines were obtained from ATC. These cells were maintained in RPMI (LNCaP cells) or DMEM-S12 (PC-3 cells) media containing 10% fetal calf serum and 1% penicillinstreptomycin. To assess BMHPC (Cyclovalone) effects on cell proliferation, LNCaP or PC-3 cells were seeded in 24-well plates (5,000 cells/well) containing 1.0 ml of RPMI (LNCaP cells) or DMEM-S12 medium and allowed to attach for 72 h. Following attachment (day 0), the medium was replaced with fresh medium and the cells were treated with 5 fil of ethanol (controls) or BMHPC (0.2-10 mkg/ml tissue culture medium) added in 5 mkl absolute ethanol. The cells were grown in the presence of BMHPC for 2-9 days and medium and the drug were replaced every 48 h. Cell number was determined by hemocytometer counts at the times indicated in the text and figure legends and DNA content per well was determined by the Burton assay
Name Type Language
CYCLOVALONE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
Cyclovalone [WHO-DD]
Common Name English
NSC-26727
Code English
CYCLOVALONE [MI]
Common Name English
CYCLOVALONE [MART.]
Common Name English
cyclovalone [INN]
Common Name English
2,6-DIVANILLYLIDENECYCLOHEXANONE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C66913
Created by admin on Fri Dec 15 17:15:41 GMT 2023 , Edited by admin on Fri Dec 15 17:15:41 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL17205
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PRIMARY
SMS_ID
100000083777
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PRIMARY
MERCK INDEX
m1099
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PRIMARY Merck Index
MESH
C010704
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PRIMARY
FDA UNII
6M4YJ3FA16
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PRIMARY
ECHA (EC/EINECS)
209-438-9
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PRIMARY
DRUG CENTRAL
762
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PRIMARY
EVMPD
SUB06865MIG
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PRIMARY
CAS
579-23-7
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PRIMARY
NCI_THESAURUS
C81040
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PRIMARY
PUBCHEM
11366
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EPA CompTox
DTXSID7046386
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PRIMARY
INN
1456
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PRIMARY
NSC
26727
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PRIMARY