CIANIDANOL

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 Search

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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10383482
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

Primary Target	Pharmacology	Potency
Cyclooxygenase-2 86 Target ID: CHEMBL230 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11858749	Inhibitor 3315	93.3 µM [IC50]
Cyclooxygenase-1 57 Target ID: CHEMBL221 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11858749	Inhibitor 3315	36.7 µM [IC50]
superoxide anion generation 3 Target ID: GO:0042554 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10425115	Inhibitor 3315	13.1 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Chronic hepatitis 2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3520204	Primary	Approved 4033	Cianidanol Approved Use Cianidanol was introduced in 1976 as an adjunct in the treatment of liver disorders Launch Date 1.89215998E11
Overweight Sources: https://www.drugs.com/otc/110166/label.jpg	Preventing	Withdrawn	Unknown Approved Use Unknown
Friedreich ataxia 4 Sources: https://clinicaltrials.gov/ct2/show/NCT02660112	Primary	Phase II 394	Unknown Approved Use Unknown
Cervical cancer 16 Sources: https://clinicaltrials.gov/ct2/show/NCT00303823	Preventing	Phase II 394	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibitory activity of flavonoids and tannins against HIV-1 protease.	2000 Sep	10993207
Estimation of procyanidin chain length.	2001	11400393
Biological actions of oligomeric procyanidins: proliferation of epithelial cells and hair follicle growth.	2001	11400385
Inhibition of in vitro low-density lipoprotein oxidation by oligomeric procyanidins present in chocolate and cocoas.	2001	11400384
Characterization of antioxidant effect of procyanidins.	2001	11400383
Mechanism of antioxidant effect of catechins.	2001	11400369
Measurement of trans-resveratrol, (+)-catechin, and quercetin in rat and human blood and urine by gas chromatography with mass selective detection.	2001	11400362
Green tea: biochemical and biological basis for health benefits.	2001	11345896
Catechins in tea: chemistry and analysis.	2001	11263072
Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid.	2001 Apr	11380153
Phenolics and physico-chemical characteristics of persimmon during post-harvest storage.	2001 Apr	11379292
Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.	2001 Apr	11325231
Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus.	2001 Apr	11325228
Measurement of copper-binding sites on low density lipoprotein.	2001 Apr	11304478
Dietary catechins and epithelial cancer incidence: the Zutphen elderly study.	2001 Apr 15	11291060
Flavonoid B-ring chemistry and antioxidant activity: fast reaction kinetics.	2001 Apr 20	11302737
Separation of apple procyanidins into different degrees of polymerization by high-speed counter-current chromatography.	2001 Apr 27	11358256
Separation of phenolic compounds by high-performance liquid chromatography with absorbance and fluorimetric detection.	2001 Apr 6	11330794
Effects of de-alcoholated red wine and its phenolic fractions on platelet aggregation.	2001 Feb	11383321
Catechin intake and associated dietary and lifestyle factors in a representative sample of Dutch men and women.	2001 Feb	11305629
Nutrient distribution and phenolic antioxidants in air-classified fractions of beach pea (Lathyrus maritimus L.).	2001 Feb	11262051
Tea catechins inhibit cholesterol oxidation accompanying oxidation of low density lipoprotein in vitro.	2001 Feb	11239828
Effects of pH and metal ions on antioxidative activities of catechins.	2001 Jan	11272815
Polyphenolic compounds from Geranium pratense and their free radical scavenging activities.	2001 Jan	11219813
Combination cancer chemoprevention with green tea extract and sulindac shown in intestinal tumor formation in Min mice.	2001 Jan	11206275
Quantitative analysis of polymeric procyanidins (Tannins) from grape (Vitis vinifera) seeds by reverse phase high-performance liquid chromatography.	2001 Jan	11170555
Thiolysis-HPLC characterization of apple procyanidins covering a large range of polymerization states.	2001 Jan	11170553
Influence of metal ions on flavonoid protection against asbestos-induced cell injury.	2001 Jan 1	11361008
(+)-Catechin inhibits intestinal tumor formation and suppresses focal adhesion kinase activation in the min/+ mouse.	2001 Jan 1	11196148
Comparative efficacy as antioxidants between ascorbic acid and epigallocatechin gallate on cells of two human lymphoblastoid lines.	2001 Jan 15	11172912
Induction of apoptosis by green tea catechins in human prostate cancer DU145 cells.	2001 Jan 26	11228105
Is the cancer protective effect correlated with growth inhibitions by green tea (-)-epigallocatechin gallate mediated through an antioxidant mechanism?	2001 Jan 26	11146219
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	11368873
Black tea extract, thearubigin fraction, counteracts the effect of tetanus toxin in mice.	2001 Jun	11395929
Atmospheric carbon dioxide, irrigation, and fertilization effects on phenolic and nitrogen concentrations in loblolly pine (Pinus taeda) needles.	2001 Jun	11390305
Formation and identification of 4'-O-methyl-(-)-epigallocatechin in humans.	2001 Jun	11353745
Green tea polyphenolic antioxidants and skin photoprotection (Review).	2001 Jun	11351267
Green tea polyphenols: novel irreversible inhibitors of dopa decarboxylase.	2001 Jun 1	11374875
The role of inducible-nitric oxide in cocaine-induced kindling.	2001 Mar	11361036
Antioxidant effects of water extracts from barley (Hordeum vulgare L.) prepared under different roasting temperatures.	2001 Mar	11312880
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001 Mar	11258977
Antimutagenic activity of green tea and black tea extracts studied in a dynamic in vitro gastrointestinal model.	2001 Mar 1	11239964
Stereospecificity in membrane effects of catechins.	2001 Mar 14	11248221
EGCG, a major component of green tea, inhibits tumour growth by inhibiting VEGF induction in human colon carcinoma cells.	2001 Mar 23	11259102
The effects of phenolic components of tea on the production of pro- and anti-inflammatory cytokines by human leukocytes in vitro.	2001 Mar 7	11243706
Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea.	2001 Mar 8	11259050
Combination effect of lignin F and natural products.	2001 Mar-Apr	11396189
Furanocoumarins from the aerial parts of Dorstenia contrajerva.	2001 May	11395259
Fast determination of procyanidins and other phenolic compounds in food samples by micellar electrokinetic chromatography using acidic buffers.	2001 May	11386670
Water-soluble antioxidants inhibit macrophage recognition of oxidized erythrocytes.	2001 May	11379784

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

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Name

Type

Language

CIANIDANOL

Official Name

English

(+)-CATECHIN [USP-RS]

Common Name

English

CATECHIN

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