EPIGALLOCATECHIN GALLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H18O11
Molecular Weight	458.3717
Optical Activity	( - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC1=CC(O)=C2C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C4=CC(O)=C(O)C(O)=C4

InChI

InChIKey=WMBWREPUVVBILR-WIYYLYMNSA-N

InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H18O11
Molecular Weight	458.3717
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Epigallocatechin-3-gallate (EGCG), the major polyphenol from green tea, has the potential to impact a variety of human diseases. EGCG functions as a powerful antioxidant, preventing oxidative damage in healthy cells, but also as an antiangiogenic and antitumor agent and as a modulator of tumor cell response to chemotherapy. It was shown, that EGCG can inhibit 5-cytosine DNA methyltransferase (DNMT) activity and reactivate methylation-silenced genes in cancer cells and another of the probable mechanisms by EGCG exercise their anti-tumor property is through the suppression of the NFκB signaling pathway. EGCG has emerged as a potential neuroprotective agent for the treatment of neurological disorders associated with harmful effects of reactive oxygen species. The neuroprotective mechanism of action is probably based on several factors, including EGCG's modulation of several signal transduction pathways, its influence on the expression of genes regulating cell survival or programmed cell death, as well as its modulation of mitochondrial function. A phase II/III trial of oral Sunphenon epigallocatechin-3-gallate in patients with progressive multiple sclerosis has been completed. In addition, EGCG was in phase III clinical trials for the treatment of multiple system atrophy and for patients with Duchenne Muscular Dystrophy ((DMD). DMD is the most frequent neuromuscular condition to occur in childhood and youth.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA (cytosine-5)-methyltransferase 1 10	Inhibitor 8,504		6.89 µM [Ki]
NF-kappa B signaling pathway 87	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Multiple sclerosis 107	Primary	Phase III 665	Unknown
Multiple system atrophy 1	Primary	Phase III 665	Unknown
Duchenne muscular dystrophy 18	Primary	Phase III 665	Unknown

C_max

Value	Dose	Analyte	Population
73.7 ng/mL	200 mg single, oral	EPIGALLOCATECHIN GALLATE plasma	Homo sapiens
438.5 ng/mL	800 mg single, oral	EPIGALLOCATECHIN GALLATE serum	Homo sapiens
169.1 ng/mL	600 mg single, oral	EPIGALLOCATECHIN GALLATE serum	Homo sapiens
111.8 ng/mL	400 mg single, oral	EPIGALLOCATECHIN GALLATE serum	Homo sapiens

AUC

Value	Dose	Analyte	Population
22.5 μg × min/mL	200 mg single, oral	EPIGALLOCATECHIN GALLATE plasma	Homo sapiens
161.4 μg × min/mL	800 mg single, oral	EPIGALLOCATECHIN GALLATE serum	Homo sapiens
101.9 μg × min/mL	600 mg single, oral	EPIGALLOCATECHIN GALLATE serum	Homo sapiens
35.4 μg × min/mL	400 mg single, oral	EPIGALLOCATECHIN GALLATE serum	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
118 min	200 mg single, oral	EPIGALLOCATECHIN GALLATE plasma	Homo sapiens
114 min	800 mg single, oral	EPIGALLOCATECHIN GALLATE serum	Homo sapiens
183.7 min	600 mg single, oral	EPIGALLOCATECHIN GALLATE serum	Homo sapiens
162.3 min	400 mg single, oral	EPIGALLOCATECHIN GALLATE serum	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
1600 mg single, oral Highest studied dose	healthy, ADULT
800 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT	Other AEs: Headache, Stomach ache...

Showing 1 to 2 of 2 entries

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AEs

Show entries

AE	Significance	Dose	Population
Headache	25%	800 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT
Dizziness	grade 1, 12.5%	800 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT
Muscle pain	grade 1, 12.5%	800 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT
Stomach ache	grade 1, 12.5%	800 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT
Abdominal pain	grade 1, 25%	800 mg 1 times / day multiple, oral Highest studied dose	healthy, ADULT

Showing 1 to 5 of 6 entries

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PubMed

Show entries

Title	Date	PubMed
Pharmacokinetics of the green tea derivative, EGCG, by the topical route of administration in mouse and human skin.	1999	10071985
Polyphenolic antioxidant (-)-epigallocatechin-3-gallate from green tea reduces UVB-induced inflammatory responses and infiltration of leukocytes in human skin.	1999 Feb	10048310
Green tea and cancer chemoprevention.	1999 Jul 16	10518005
A new concept of tumor promotion by tumor necrosis factor-alpha, and cancer preventive agents (-)-epigallocatechin gallate and green tea--a review.	2000	10757128
Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data.	2000 Jan-Feb	10769631

Showing 1 to 5 of 37 entries

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Patents

Sample Use Guides

In Vivo Use Guide

Sunphenon EGCG (Epigallo Catechin Gallate) 200-800mg (1-4 capsules)

Route of Administration: Oral

In Vitro Use Guide

Epigallocatechin gallate (EGCG) could inhibit the viability and invasion, and induce the apoptosis, of bladder cancer T24 cells. The apoptosis of bladder cancer cells was notably increased by 20 µm EGCG. In addition, 20 µm EGCG inhibited bladder cancer cell viability. However, 10 µm EGCG did not exhibit any significant inhibitory effect on T24 cell viability. The effect of EGCG on the invasive ability of the bladder cancer cells was then investigated, which demonstrated that 10 µm and 20 µm of EGCG significantly inhibited invasion compared with the control group.