GENTIOPICRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H20O9
Molecular Weight	356.3246
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@@H](O[C@@H]2OC=C3C(=O)OCC=C3[C@H]2C=C)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=DUAGQYUORDTXOR-GPQRQXLASA-N

InChI=1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C16H20O9
Molecular Weight	356.3246
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23419353 | https://www.ncbi.nlm.nih.gov/pubmed/15537172 | https://www.ncbi.nlm.nih.gov/pubmed/27394986 | https://www.ncbi.nlm.nih.gov/pubmed/22521634 | https://www.ncbi.nlm.nih.gov/pubmed/24584520

Gentiopicrin is a naturally occurring iridoid glycoside. It is a bioactive component of gentian species of medical plants. It has proved to be the strongest inhibitor of myeloperoxidase. It could be absorbed rapidly in mice, but with a low bioavailability, and could distribute to tissues extensively. Gentiopicrin has been reported to be effective against inflammatory conditions such as rheumatoid arthritis, liver illness, fever, digestive and intestinal disorders. Gentiopicrin treatment can exert anti-inflammatory effects on experimental acute colitis through attenuating the expression levels of TNF-α, IL-1β, IL-6, iNOS and COX-2, and it may present the therapeutic potential in the treatment of colitis. The drug inhibits reserpine-induced pain/depression dyad by downregulating GluN2B receptors in the amygdala. Gentiopicrin injection was approved by SFDA for the treatment of acute jaundice and chronic active hepatitis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 2A6 16 Target ID: CHEMBL5282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23419353	Inhibitor 8504
Cytochrome P450 2E1 25 Target ID: P05181 Gene ID: 1571.0 Gene Symbol: CYP2E1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23419353	Inhibitor 8504
Myeloperoxidase 6 Target ID: CHEMBL2439 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22521634	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Acute hepatitis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23419353	Primary	Approved 8583	Unknown Approved Use Unknown
Colitis 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27394986	Primary	Preclinical	Unknown Approved Use Unknown
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27175624 https://www.ncbi.nlm.nih.gov/pubmed/24584520	Primary	Preclinical	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 150 inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2E1 1060		CYP1A2 832 CYP2B6 669

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	no
CYP1A2 2333	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	no
CYP2B6 1160	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	no
CYP3A4 2633	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	no
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	no
CYP2A6 911	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	yes
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23419353/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/88708#section=Biological-Test-Results Page: 91.0

PubMed

Title	Date	PubMed
Anti-apoptotic activity of gentiopicroside in D-galactosamine/lipopolysaccharide-induced murine fulminant hepatic failure.	2010-10-06	20558151
Antimicrobial activity of Gentiana lutea L. extracts.	2009-08-15	19678535
Gentiopicrin-producing endophytic fungus isolated from Gentiana macrophylla.	2009-08	19200701
[Preparative separation of gentiopicrin from Radix Gentianae by high-speed counter-current chromatography with macroporous resin].	2007-12	18338594
[Determination of iridoids and triterpenes in herb of Swertia pseudochinesis by RP-HPLC].	2007-12	18330241
[Investigation on explovitage of Gentiana straminea].	2007-10	18300487
[Preparative separation of gentiopicrin from Gentiana scabra bunge by high speed counter current chromatography].	2007-07	17944185
Ethnobotanical remarks on Central and Southern Italy.	2007-05-30	17537240
[Determination of ginsenoside rd in human plasma by LC/MS/MS].	2006-09	17212051
[Inhibition of extracts from 17 Chinese herbs on periodontal pathogenic microbes].	2006-08	16955176
[Determination gentiopicrin in biyanqingdu granulae by SPE-HPLC].	2005-06	16209272
Simultaneous determination of some active ingredients in anti-viral preparations of traditional Chinese medicine by micellar electrokinetic chromatography.	2004-11	15386499

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 200, 100, and 50mg/kg once a day for 7days

Route of Administration: Oral

In Vitro Use Guide

50, 500, and 1,500 ug/mL of gentiopicrin exhibited no significant toxicity to chondrocytes (P>0.05) after 24h.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:53:24 GMT 2025` Edited by `admin` on `Mon Mar 31 19:53:24 GMT 2025`
Record UNII	0WE09Z21RC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-606402

Preferred Name

English

GENTIOPICRIN

Common Name

English

GENTIOPICRIN [MI]

Common Name

English

GENTIOPICROSIDE

Common Name

English

(5R,6S)-5-ETHENYL-6-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,6-DIHYDRO-1H,3H-PYRANO(3,4-C)PYRAN-1-ONE

Common Name

English

Code System Code Type Description

MERCK INDEX

m5702