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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H14O6
Molecular Weight 290.2686
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIANIDANOL

SMILES

c1cc(c(cc1[C@]2([H])[C@]([H])(Cc3c(cc(cc3O2)O)O)O)O)O

InChI

InChIKey=PFTAWBLQPZVEMU-DZGCQCFKSA-N
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1

HIDE SMILES / InChI
Molecular Formula C15H14O6
Molecular Weight 290.2686
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/3896964

Cianidanol is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. One of the polyphenols present in green tea, (+)-catechin (Cianidanol), has been studied for its effects on animal models of hepatitis, as well as in human clinical studies. Pure (+)-catechin (also known as (+)- cyanidanol-3 – trade name Catergen) has been used to treat hepatitis since 1976. This compound has been shown to be an efficient immune stimulator, promoting activation of macrophages, cytotoxic-T-lymphocytes, and natural killer cells in mice. Several clinical studies demonstrate the effectiveness of (+)-catechin in the treatment of viral hepatitis. Pure (+)-catechin has been found to cause hemolysis in some patients, possibly by the promotion of antibody formation against (+)-catechin, which might cross-react with red blood cells. However, there are no reports in the literature of green tea, green tea extracts, or green tea polyphenols causing this side-effect.

Approval Year

2011
553
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7728
 93.3 µM [IC50]
Inhibitor
7728
 36.7 µM [IC50]
Inhibitor
7728
 13.1 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8043
Cianidanol

Approved Use

Cianidanol was introduced in 1976 as an adjunct in the treatment of liver disorders

Launch Date

1.89215998E11
Preventing
Withdrawn
Unknown

Approved Use

Unknown
Primary
Phase II
1101
Unknown

Approved Use

Unknown
Preventing
Phase II
1101
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Biological evaluation of proanthocyanidin dimers and related polyphenols.
1999 Jul
Suppression by flavonoids of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells: structure-activity relationship.
2000 Jul
Inhibitory activity of flavonoids and tannins against HIV-1 protease.
2000 Sep
Estimation of procyanidin chain length.
2001
Biological actions of oligomeric procyanidins: proliferation of epithelial cells and hair follicle growth.
2001
Inhibition of in vitro low-density lipoprotein oxidation by oligomeric procyanidins present in chocolate and cocoas.
2001
Characterization of antioxidant effect of procyanidins.
2001
Mechanism of antioxidant effect of catechins.
2001
Catechins in tea: chemistry and analysis.
2001
Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
2001 Apr
Separation of apple procyanidins into different degrees of polymerization by high-speed counter-current chromatography.
2001 Apr 27
Effects of de-alcoholated red wine and its phenolic fractions on platelet aggregation.
2001 Feb
Nutrient distribution and phenolic antioxidants in air-classified fractions of beach pea (Lathyrus maritimus L.).
2001 Feb
Tea catechins inhibit cholesterol oxidation accompanying oxidation of low density lipoprotein in vitro.
2001 Feb
Green tea polyphenol (-)-epigallocatechin-3-gallate treatment of human skin inhibits ultraviolet radiation-induced oxidative stress.
2001 Feb
Detrimental effect of cancer preventive phytochemicals silymarin, genistein and epigallocatechin 3-gallate on epigenetic events in human prostate carcinoma DU145 cells.
2001 Feb 1
Studies in polyphenol chemistry and bioactivity. 3.(1,2) stereocontrolled synthesis of epicatechin-4alpha,8-epicatechin, an unnatural isomer of the B-type procyanidins.
2001 Feb 23
Pharmacokinetics and system linearity of tea catechins in rat.
2001 Jan
Antioxidant benzoylated flavan-3-ol glycoside from Celastrus orbiculatus.
2001 Jan
Degradation of green tea catechins in tea drinks.
2001 Jan
Quantitative analysis of polymeric procyanidins (Tannins) from grape (Vitis vinifera) seeds by reverse phase high-performance liquid chromatography.
2001 Jan
Influence of metal ions on flavonoid protection against asbestos-induced cell injury.
2001 Jan 1
Comparative efficacy as antioxidants between ascorbic acid and epigallocatechin gallate on cells of two human lymphoblastoid lines.
2001 Jan 15
Is the cancer protective effect correlated with growth inhibitions by green tea (-)-epigallocatechin gallate mediated through an antioxidant mechanism?
2001 Jan 26
Protective effects of (-)-epigallocatechin-3-gallate on UVA- and UVB-induced skin damage.
2001 Jan-Feb
Green tea catechins enhance tumor development in the colon without effects in the lung or thyroid after pretreatment with 1,2-Dimethylhydrazine or 2,2'-dihydroxy-di-n-propylnitrosamine in male F344 rats.
2001 Jul 10
Black tea extract, thearubigin fraction, counteracts the effect of tetanus toxin in mice.
2001 Jun
Atmospheric carbon dioxide, irrigation, and fertilization effects on phenolic and nitrogen concentrations in loblolly pine (Pinus taeda) needles.
2001 Jun
Formation and identification of 4'-O-methyl-(-)-epigallocatechin in humans.
2001 Jun
The role of inducible-nitric oxide in cocaine-induced kindling.
2001 Mar
Antioxidant effects of water extracts from barley (Hordeum vulgare L.) prepared under different roasting temperatures.
2001 Mar
Polyphenols from Eucalyptus ovata.
2001 Mar
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
The effects of phenolic components of tea on the production of pro- and anti-inflammatory cytokines by human leukocytes in vitro.
2001 Mar 7
Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea.
2001 Mar 8
Combination effect of lignin F and natural products.
2001 Mar-Apr
Furanocoumarins from the aerial parts of Dorstenia contrajerva.
2001 May
Fast determination of procyanidins and other phenolic compounds in food samples by micellar electrokinetic chromatography using acidic buffers.
2001 May
[Polyphenol constituents from Salacia species: quantitative analysis of mangiferin with alpha-glucosidase and aldose reductase inhibitory activities].
2001 May
The in vitro inhibitory effect of tannin derivatives on 3-hydroxy-3-methylglutaryl-coenzyme a reductase on vero cells.
2001 May
Green tea polyphenol (-)-epigallocatechin-3-gallate treatment to mouse skin prevents UVB-induced infiltration of leukocytes, depletion of antigen-presenting cells, and oxidative stress.
2001 May
Patents

Patents

JP2000060427A
2
JP2000204182A
2
JP2000279498A
2
JP2000314083A
2
JP2001086932A
2
JP2001269191A
2
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2
JP2002087939A
2
JP2002114617A
2
JP2002142677A
2
JP2002224202A
2
JP2002360185A
2
JP2002363078A
2
JP2002536305A
4
JP2003500452A
11
JP2003532634A
63
JP2004041186A
2
JP2004129668A
2
JP2004147508A
2
JP2004352644A
5
JP2004359674A
2
JP2005021103A
2
JP2005104850A
7
JP2005237361A
2
JP2005245307A
2
JP2005261406A
2
JP2005290081A
2
JP2005295988A
2
JP2005314421A
2
JP2006025681A
2
JP2006042703A
2
JP2006042728A
2
JP2006067828A
2
JP2006096740A
2
JP2006166771A
2
JP2006180815A
2
JP2006206482A
2
JP2006206483A
2
JP2006218375A
2
JP2006219506A
2
JP2006271401A
2
JP2007020525A
2
JP2007022935A
2
JP2007089561A
2
JP2007104967A
4
JP2007126373A
2
JP2007143528A
3
JP2007254508A
2
JP2007267656A
2
JP2007289159A
2
JP2008212013A
2

Sample Use Guides

In Vivo Use Guide
Take 1~3 packet daily
Route of Administration: Oral
In Vitro Use Guide
The in vitro effect of the drug was assessed using cianidanol at 10(-6), 10(-5) and 10(-4) M concentrations.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:57:50 UTC 2021
Edited
by admin
on Sat Jun 26 05:57:50 UTC 2021
Record UNII
8R1V1STN48
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIANIDANOL
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
(+)-CATECHIN [USP-RS]
Common Name English
CATECHIN
MI   VANDF  
Common Name English
D-CATECHOL
Common Name English
(+)-CATECHOL
Systematic Name English
(+)-CATECHIN (CONSTITUENT OF MARITIME PINE) [DSC]
Common Name English
CIANIDANOL [INN]
Common Name English
2H-1-BENZOPYRAN-3,5,7-TRIOL, 2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R,3S)-
Systematic Name English
(+)-CATECHIN
Common Name English
CATECHIN, D-
Common Name English
(+)-CATECHIN (CONSTITUENT OF GRAPE SEEDS OLIGOMERIC PROANTHOCYANIDINS) [DSC]
Common Name English
CIANIDANOL [WHO-DD]
Common Name English
CIANIDANOL [MART.]
Common Name English
CIANIDOL
Common Name English
CATECHIN [VANDF]
Common Name English
(+)-CATECHIN (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT) [DSC]
Common Name English
CATECHIN [MI]
Common Name English
NSC-2819
Code English
CATECHUIC ACID
Common Name English
CIANIDANOL [JAN]
Common Name English
CATERGEN
Common Name English
CATECHINIC ACID
Common Name English
Classification Tree Code System Code
LIVERTOX 414
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
DSLD 119 (Number of products:75)
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
Code System Code Type Description
CAS
154-23-4
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
WIKIPEDIA
CATECHIN
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
NCI_THESAURUS
C63654
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
USP_CATALOG
1096790
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY USP-RS
RXCUI
1367177
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY RxNorm
FDA UNII
8R1V1STN48
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL311498
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
EVMPD
SUB06226MIG
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
MESH
D002392
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
EPA CompTox
154-23-4
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
PUBCHEM
9064
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-825-1
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
DRUG BANK
DB14086
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
INN
4804
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
DRUG CENTRAL
629
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY
MERCK INDEX
M3172
Created by admin on Sat Jun 26 05:57:50 UTC 2021 , Edited by admin on Sat Jun 26 05:57:50 UTC 2021
PRIMARY Merck Index
Related Record Type Details
THEOBROMA GRANDIFLORUM SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
The compound was screened for it's antioxidant capacity in the DPPH assay, and displayed a high antioxidant activity, with an IC50 value of 49.0 uM.
HISTIDINE DECARBOXYLASE
TARGET -> INHIBITOR
BILBERRY
PARENT -> CONSTITUENT ALWAYS PRESENT
VIBURNUM OPULUS BARK
PARENT -> CONSTITUENT ALWAYS PRESENT
COCOA
PARENT -> CONSTITUENT ALWAYS PRESENT
Secondary metabolite detected in developing cacao seeds.
MARITIME PINE
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
GREEN TEA LEAF
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
IN-VITRO
Related Record Type Details
Structure of MECIADANOL
METABOLITE -> PARENT
Related Record Type Details
Structure of CIANIDANOL
ACTIVE MOIETY
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