CIANIDANOL

First approved in 2011

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H14O6
Molecular Weight	290.2681
Optical Activity	( + )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C3=CC=C(O)C(O)=C3

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	290.2681
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-2 201 Target ID: CHEMBL230 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11858749	Inhibitor 8504	93.3 µM [IC50]
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11858749	Inhibitor 8504	36.7 µM [IC50]
superoxide anion generation 11 Target ID: GO:0042554 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10425115	Inhibitor 8504	13.1 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Chronic hepatitis 10 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3520204	Primary	Approved 8583	Cianidanol Approved Use Cianidanol was introduced in 1976 as an adjunct in the treatment of liver disorders Launch Date 1975
Overweight 2 Sources: https://www.drugs.com/otc/110166/label.jpg	Preventing	Withdrawn	Unknown Approved Use Unknown
Friedreich ataxia 12 Sources: https://clinicaltrials.gov/ct2/show/NCT02660112	Primary	Phase II 1147	Unknown Approved Use Unknown
Cervical cancer 40 Sources: https://clinicaltrials.gov/ct2/show/NCT00303823	Preventing	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
78.3 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10617953/	35 mg single, oral dose: 35 mg route of administration: Oral experiment type: SINGLE co-administered:		CIANIDANOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
306 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10617953/	35 mg single, oral dose: 35 mg route of administration: Oral experiment type: SINGLE co-administered:		CIANIDANOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10617953/	35 mg single, oral dose: 35 mg route of administration: Oral experiment type: SINGLE co-administered:		CIANIDANOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
4.1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20732774/			CIANIDANOL plasma	Homo sapiens

Doses

Dose	Population	Adverse events
2.25 g 3 times / day multiple, oral Studied dose Dose: 2.25 g, 3 times / day Route: oral Route: multiple Dose: 2.25 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3520204/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/3520204/	Disc. AE: Pyrexia, Skin eruption... AEs leading to discontinuation/dose reduction: Pyrexia Skin eruption Sources: https://pubmed.ncbi.nlm.nih.gov/3520204/
1 mg 3 times / day multiple, oral Studied dose Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3896964/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3896964/	Disc. AE: Fever, Haemolysis... AEs leading to discontinuation/dose reduction: Fever (25%) Haemolysis (6.25%) Urticaria (6.25%) Sources: https://pubmed.ncbi.nlm.nih.gov/3896964/

AEs

AE	Significance	Dose	Population
Pyrexia	Disc. AE	2.25 g 3 times / day multiple, oral Studied dose Dose: 2.25 g, 3 times / day Route: oral Route: multiple Dose: 2.25 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3520204/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/3520204/
Skin eruption	Disc. AE	2.25 g 3 times / day multiple, oral Studied dose Dose: 2.25 g, 3 times / day Route: oral Route: multiple Dose: 2.25 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3520204/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/3520204/
Fever	25% Disc. AE	1 mg 3 times / day multiple, oral Studied dose Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3896964/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3896964/
Haemolysis	6.25% Disc. AE	1 mg 3 times / day multiple, oral Studied dose Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3896964/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3896964/
Urticaria	6.25% Disc. AE	1 mg 3 times / day multiple, oral Studied dose Dose: 1 mg, 3 times / day Route: oral Route: multiple Dose: 1 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3896964/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3896964/

PubMed

Title	Date	PubMed
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.	2001-07-10	11368873
Combination effect of lignin F and natural products.	2001-06-09	11396189
Black tea is a powerful chemopreventor of reactive oxygen and nitrogen species: comparison with its individual catechin constituents and green tea.	2001-06-01	11374887
Green tea polyphenols: novel irreversible inhibitors of dopa decarboxylase.	2001-06-01	11374875
Black tea extract, thearubigin fraction, counteracts the effect of tetanus toxin in mice.	2001-06	11395929
Atmospheric carbon dioxide, irrigation, and fertilization effects on phenolic and nitrogen concentrations in loblolly pine (Pinus taeda) needles.	2001-06	11390305
Formation and identification of 4'-O-methyl-(-)-epigallocatechin in humans.	2001-06	11353745
Nutrition and metabolism.	2001-06	11353337
Green tea polyphenol epigallocatechin inhibits DNA replication and consequently induces leukemia cell apoptosis.	2001-06	11351279
Green tea polyphenolic antioxidants and skin photoprotection (Review).	2001-06	11351267
Unusually large numbers of electrons for the oxidation of polyphenolic antioxidants.	2001-05-03	11325537
Furanocoumarins from the aerial parts of Dorstenia contrajerva.	2001-05	11395259
Fast determination of procyanidins and other phenolic compounds in food samples by micellar electrokinetic chromatography using acidic buffers.	2001-05	11386670
Water-soluble antioxidants inhibit macrophage recognition of oxidized erythrocytes.	2001-05	11379784
A tea catechin suppresses the expression of the high-affinity IgE receptor Fc epsilon RI in human basophilic KU812 cells.	2001-05	11368631
Chemiluminescence of hemoglobin and identification of related compounds with the hemoglobin chemiluminescence in plasma.	2001-05	11367578
[Polyphenol constituents from Salacia species: quantitative analysis of mangiferin with alpha-glucosidase and aldose reductase inhibitory activities].	2001-05	11360491
The in vitro inhibitory effect of tannin derivatives on 3-hydroxy-3-methylglutaryl-coenzyme a reductase on vero cells.	2001-05	11359999
Green tea polyphenol (-)-epigallocatechin-3-gallate treatment to mouse skin prevents UVB-induced infiltration of leukocytes, depletion of antigen-presenting cells, and oxidative stress.	2001-05	11358979
Anti-interferon gamma action of epigallocatechin-3-gallate mediated by specific inhibition of STAT1 activation.	2001-05	11344123
Separation of apple procyanidins into different degrees of polymerization by high-speed counter-current chromatography.	2001-04-27	11358256
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.	2001-04-16	11311209
Separation of phenolic compounds by high-performance liquid chromatography with absorbance and fluorimetric detection.	2001-04-06	11330794
Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid.	2001-04	11380153
Phenolics and physico-chemical characteristics of persimmon during post-harvest storage.	2001-04	11379292
Inhibitory effect of (+)-catechin on the growth of influenza A/PR/8 virus in MDCK cells.	2001-04	11345695
Specific antioxidant activity of caffeoyl derivatives and other natural phenolic compounds: LDL protection against oxidation and decrease in the proinflammatory lysophosphatidylcholine production.	2001-04	11325231
Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus.	2001-04	11325228
The role of inducible-nitric oxide in cocaine-induced kindling.	2001-03	11361036
Antioxidant effects of water extracts from barley (Hordeum vulgare L.) prepared under different roasting temperatures.	2001-03	11312880
Identification of procyanidins and anthocyanins in blueberries and cranberries (Vaccinium spp.) using high-performance liquid chromatography/mass spectrometry.	2001-03	11312849
Color and stability of pigments derived from the acetaldehyde-mediated condensation between malvidin 3-O-glucoside and (+)-catechin.	2001-03	11312838
Studies in polyphenol chemistry and bioactivity. 3.(1,2) stereocontrolled synthesis of epicatechin-4alpha,8-epicatechin, an unnatural isomer of the B-type procyanidins.	2001-02-23	11312959
Effects of de-alcoholated red wine and its phenolic fractions on platelet aggregation.	2001-02	11383321
Evaluation of antioxidant activity of epigallocatechin gallate in biphasic model systems in vitro.	2001-02	11330830
Catechin intake and associated dietary and lifestyle factors in a representative sample of Dutch men and women.	2001-02	11305629
Influence of metal ions on flavonoid protection against asbestos-induced cell injury.	2001-01-01	11361008
Pharmacokinetics and system linearity of tea catechins in rat.	2001-01	11334265
Inhibitory effect of epigallocatechin-gallate on brain tumor cell lines in vitro.	2001-01	11305413
Modulation of the biosynthesis of some phenolic compounds in Olea europaea L. fruits: their influence on olive oil quality.	2001-01	11305254
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
Inhibition of carcinogenesis by dietary polyphenolic compounds.	2001	11375442
Green tea: biochemical and biological basis for health benefits.	2001	11345896
Epigallocatechin gallate protects U937 cells against nitric oxide-induced cell cycle arrest and apoptosis.	2001	11329619
Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate-induced neuronal death.	2001	11321476

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 `Mon Mar 31 17:46:12 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:12 GMT 2025`
Record UNII	8R1V1STN48
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CATECHIN

Preferred Name

English

CIANIDANOL

Official Name

English

(+)-CYANIDANOL-3

Common Name

English

(+)-CATECHIN [USP-RS]

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 [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

Cianidanol [WHO-DD]

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