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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

Targets

Targets

Primary TargetPharmacologyConditionPotency
93.2999999999999972 µM [IC50]
36.7000000000000028 µM [IC50]
13.0999999999999996 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Cianidanol

Approved Use

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

Launch Date

189216000000
Preventing
Primary
Preventing
PubMed

PubMed

TitleDatePubMed
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
Measurement of trans-resveratrol, (+)-catechin, and quercetin in rat and human blood and urine by gas chromatography with mass selective detection.
2001
Inhibition of carcinogenesis by dietary polyphenolic compounds.
2001
Epigallocatechin gallate protects U937 cells against nitric oxide-induced cell cycle arrest and apoptosis.
2001
Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death.
2001
Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid.
2001 Apr
Phenolics and physico-chemical characteristics of persimmon during post-harvest storage.
2001 Apr
Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.
2001 Apr
Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus.
2001 Apr
Measurement of copper-binding sites on low density lipoprotein.
2001 Apr
Growth inhibitory effect of green tea extract and (-)-epigallocatechin in Ehrlich ascites tumor cells involves a cellular thiol-dependent activation of mitogenic-activated protein kinases.
2001 Apr 16
Flavonoid B-ring chemistry and antioxidant activity: fast reaction kinetics.
2001 Apr 20
Separation of apple procyanidins into different degrees of polymerization by high-speed counter-current chromatography.
2001 Apr 27
Separation of phenolic compounds by high-performance liquid chromatography with absorbance and fluorimetric detection.
2001 Apr 6
Effects of de-alcoholated red wine and its phenolic fractions on platelet aggregation.
2001 Feb
Catechin intake and associated dietary and lifestyle factors in a representative sample of Dutch men and women.
2001 Feb
Apoptosis-inducing activity of high molecular weight fractions of tea extracts.
2001 Feb
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
Inhibitory effect of epigallocatechin-gallate on brain tumor cell lines in vitro.
2001 Jan
Modulation of the biosynthesis of some phenolic compounds in Olea europaea L. fruits: their influence on olive oil quality.
2001 Jan
Influence of metal ions on flavonoid protection against asbestos-induced cell injury.
2001 Jan 1
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
Nutrition and metabolism.
2001 Jun
Green tea polyphenol epigallocatechin inhibits DNA replication and consequently induces leukemia cell apoptosis.
2001 Jun
Black tea is a powerful chemopreventor of reactive oxygen and nitrogen species: comparison with its individual catechin constituents and green tea.
2001 Jun 1
Green tea polyphenols: novel irreversible inhibitors of dopa decarboxylase.
2001 Jun 1
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
Identification of procyanidins and anthocyanins in blueberries and cranberries (Vaccinium spp.) using high-performance liquid chromatography/mass spectrometry.
2001 Mar
Color and stability of pigments derived from the acetaldehyde-mediated condensation between malvidin 3-O-glucoside and (+)-catechin.
2001 Mar
Polyphenols from Eucalyptus ovata.
2001 Mar
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
Water-soluble antioxidants inhibit macrophage recognition of oxidized erythrocytes.
2001 May
A tea catechin suppresses the expression of the high-affinity IgE receptor Fc epsilon RI in human basophilic KU812 cells.
2001 May
Chemiluminescence of hemoglobin and identification of related compounds with the hemoglobin chemiluminescence in plasma.
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
Anti-interferon gamma action of epigallocatechin-3-gallate mediated by specific inhibition of STAT1 activation.
2001 May
A new murine oxidative stress model associated with senescence.
2001 May 15
Unusually large numbers of electrons for the oxidation of polyphenolic antioxidants.
2001 May 3
Patents

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
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