GINKGOLIDE B

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H24O10
Molecular Weight	424.3986
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12OC(=O)[C@H](O)[C@@]13[C@@H](C[C@H]4OC(=O)[C@]5(O2)[C@@]6(O)[C@H](C)C(=O)O[C@@]6([H])[C@@H](O)[C@]345)C(C)(C)C

InChI

InChIKey=SQOJOAFXDQDRGF-ZMVGXLHTSA-N

InChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)26/h6-11,15,21-22,26H,5H2,1-4H3/t6-,7+,8-,9-,10+,11+,15+,17+,18+,19-,20-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H24O10
Molecular Weight	424.3986
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8691847 | https://www.ncbi.nlm.nih.gov/pubmed/12757407
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17543184 https://www.ncbi.nlm.nih.gov/pubmed/12914542

Ginkgolide B belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure. Ginkgolide B is one of the ginkgolides isolated from the leaves of the Ginkgo biloba tree. The Ginkgolide B is the most potent antagonist of platelet activating factor (PAF) and exhibits therapeutic action in a variety of diseases mainly by the PAF receptor. The ginkgolide B possesses a number of beneficial effects such as anti-inflammatory, anti-allergic, antioxidant, and neuroprotective effects. It promotes the proliferation, migration and adhesion of endothelial progenitor cells, and the induction of angiogenesis through vascular endothelial factor (VEGF). Ginkgolide B is considered a valid non-pharmacological (or nutraceutical) approach to the prophylaxis of both migraine with and without aura. Effects of ginkgolide B include reduction of Ca2+-stimulated intracellular events, scavenging of free radicals, modulation of central nervous system glutamatergic transmission and reduction of antiplatelet activating factor (PAF) levels in brain. Ginkgolide B is an active component of EGb, a standardised extract of Ginkgo biloba leaves. Ginkgolide B is one of the major components of EGb-761.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Platelet activating factor receptor 20 Target ID: CHEMBL250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2820421 \| https://www.ncbi.nlm.nih.gov/pubmed/9871752	Antagonist 2778		0.128 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Migraine 103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23695070 https://www.ncbi.nlm.nih.gov/pubmed/22437495 https://www.ncbi.nlm.nih.gov/pubmed/20464618	Primary	Preclinical	Unknown Approved Use Unknown
Acute pancreatitis 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18720532 https://www.ncbi.nlm.nih.gov/pubmed/17589953	Primary	Basic research	Unknown Approved Use Unknown
Multiple sclerosis 104 Sources: https://clinicaltrials.gov/ct2/show/NCT00841321	Primary	Phase II 1132	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13130383	Primary	Phase II 1132	Unknown Approved Use Unknown
Intrauterine growth restriction 2 Sources: https://clinicaltrials.gov/ct2/show/NCT02425436	Primary	Phase II 1132	Unknown Approved Use Unknown
Colitis-associated cancer 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25755731	Primary	Basic research	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
4.18 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430/	524.56 μg single, oral dose: 524.56 μg route of administration: Oral experiment type: SINGLE co-administered:	GINKGOLIDE B plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.73 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430/	147.45 μg single, oral dose: 147.45 μg route of administration: Oral experiment type: SINGLE co-administered:	GINKGOLIDE B plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.99 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430/	836.46 μg single, oral dose: 836.46 μg route of administration: Oral experiment type: SINGLE co-administered:	GINKGOLIDE B plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
16.36 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430/	524.56 μg single, oral dose: 524.56 μg route of administration: Oral experiment type: SINGLE co-administered:	GINKGOLIDE B plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.75 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430/	147.45 μg single, oral dose: 147.45 μg route of administration: Oral experiment type: SINGLE co-administered:	GINKGOLIDE B plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
82.77 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430/	836.46 μg single, oral dose: 836.46 μg route of administration: Oral experiment type: SINGLE co-administered:	GINKGOLIDE B plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
3.24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430/	524.56 μg single, oral dose: 524.56 μg route of administration: Oral experiment type: SINGLE co-administered:	GINKGOLIDE B plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430/	147.45 μg single, oral dose: 147.45 μg route of administration: Oral experiment type: SINGLE co-administered:	GINKGOLIDE B plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.57 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430/	836.46 μg single, oral dose: 836.46 μg route of administration: Oral experiment type: SINGLE co-administered:	GINKGOLIDE B plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
180 mg 2 times / day multiple, intravenous Highest studied dose Dose: 180 mg, 2 times / day Route: intravenous Route: multiple Dose: 180 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7897422	unhealthy n = 32 Health Status: unhealthy Condition: multiple sclerosis Sex: M+F Food Status: UNKNOWN Population Size: 32 Sources: https://pubmed.ncbi.nlm.nih.gov/7897422	Other AEs: Hiccup... Other AEs: Hiccup (mild, 14 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/7897422

AEs

AE	Significance	Dose	Population
Hiccup	mild, 14 patients	180 mg 2 times / day multiple, intravenous Highest studied dose Dose: 180 mg, 2 times / day Route: intravenous Route: multiple Dose: 180 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7897422	unhealthy n = 32 Health Status: unhealthy Condition: multiple sclerosis Sex: M+F Food Status: UNKNOWN Population Size: 32 Sources: https://pubmed.ncbi.nlm.nih.gov/7897422

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781 inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478	rCYP2D6 1 rCYP1A2 1 rCYP3A 3 rOATs/rOATPs 1 rCYP2E1 1 rCYP2C9 1 P-gp 1537	CYP3A 129 CYP1A2 701 MRP2 111 CYP2B6 547 UGT1A1 69 P-gp 257

Drug as perpetrator

Target	Modality	Activity
MRP2 475	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/19034627/	likely
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15133536/	no [Inhibition 160 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15133536/	no [Inhibition 168 uM]
CYP1A2 1692	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/19034627/	no
CYP1A2 1692	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/410#sid=11114166	no
CYP2C19 1553	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/899#sid=11114166	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/891#sid=11114166	no
CYP3A 298	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/19356072/	no
CYP2B6 1001	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/19034627/	yes
CYP3A4 1925	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/19034627/	yes
P-gp 1650	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/19034627/	yes
UGT1A1 254	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/19034627/	yes
hPXR 2	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/19034627/	yes

Drug as victim

Target	Modality	Activity
rOATs/rOATPs 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25589475/	likely
rCYP2D6 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18298904/	major
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=11114166	no
rCYP1A2 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18298904/	no
rCYP2C9 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18298904/	no
rCYP2E1 1	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18298904/	no
rCYP3A 3	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18298904/	no

Sourcing

Vendor/Aggregator	ID	URL
MolPort	MolPort-003-983-580	https://www.molport.com/shop/molecule-link/MolPort-003-983-580
MolPort	MolPort-004-955-260	https://www.molport.com/shop/molecule-link/MolPort-004-955-260
Molnova	M18066	https://www.molnova.com/en/serch-list.html?keywords=M18066
TargetMol	T2751	https://www.targetmol.com/search?keyword=T2751
TimTec	ST057159	http://www.echemstore.com/catalogsearch/result/?q=ST057159
eMolecules	295160737	https://orderbb.emolecules.com/search/#?query=295160737
eMolecules	48605111	https://orderbb.emolecules.com/search/#?query=48605111
eMolecules	6878282	https://orderbb.emolecules.com/search/#?query=6878282
eNovation Chemicals	D512358	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D512358&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-7132817410	https://mcule.com/MCULE-7132817410/

PubMed

Title	Date	PubMed
24 hour emergency dental service. Minneapolis District Dental Society.	1967 Dec	5241084
Fine specificity of a rabbit antibody interacting with human IgG Fc receptor-like molecules.	1990 Sep	2147423
Ginkgolide B, a constituent of Ginkgo biloba, facilitates glutamate exocytosis from rat hippocampal nerve terminals.	2005 May 9	15910800

Patents

Sample Use Guides

In Vivo Use Guide

One group of migrane patients received nutraceutical preparation A containing 80 mg ginkgolide B, 20 mg coenzyme Q10, 1.6 mg riboflavin and 300 mg magnesium. Preparation wasadministered twice daily for 6 months

Route of Administration: Oral

In Vitro Use Guide

Ginkgolide B (10 uM) reduced the apoptotic damage induced by serum deprivation (24h) or treatment with staurosporine (200 nM, 24h) in cultured chick embryonic neurons. Ginkgolide B (1uM) protected the hippocampal neurons from neonatal rats against damage caused by glutamate (1 uM, 1 h) as evaluated by trypan blue staining.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:15:37 GMT 2023` Edited by `admin` on `Sat Dec 16 05:15:37 GMT 2023`
Record UNII	DF149B9460
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GINKGOLIDE B

Common Name

English

Ginkgolide B [WHO-DD]

Common Name

English

BN-52051

Code

English

9H-1,7A-(EPOXYMETHANO)-1H,6AH-CYCLOPENTA(C)FURO(2,3-B)FURO(3',2':3,4)CYCLOPENTA(1,2-D)FURAN-5,9,12(4H)-TRIONE, 3-(1,1-DIMETHYLETHYL)HEXAHYDRO-4,7B,11-TRIHYDROXY-8-METHYL-, (1R,3S,3AS,4R,6AR,7AR,7BR,8S,10AS,11R,11AR)-

Common Name

English

GINKGOLIDE A, 1-HYDROXY-, (1.BETA.)-

Common Name

English

BN-52021

Code

English

GINKGOLIDE B [MI]

Common Name

English

5H-DICYCLOPENTA(B,C)FURAN-3,5A(6H)-DIACETIC ACID, 6-TERT-BUTYL-3A-CARBOXYHEXAHYDRO-.ALPHA.5A,1,2,3,5,8-HEXAHYDROXY-.ALPHA.3-METHYL-, TRI-.GAMMA.-LACTONE

Common Name

English

GINKGOLIDES, GINKGOLIDE B

Common Name

English

GINKGOLIDE B (CONSTITUENT OF GINKGO) [DSC]

Common Name

English

Classification Tree Code System Code

DSLD

2519 (Number of products:2)