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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 of GINKGOLIDE B

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

Description

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 TargetPharmacologyConditionPotency
0.128 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
4.18 ng/mL
524.56 μg single, oral
GINKGOLIDE B plasma
Homo sapiens
1.73 ng/mL
147.45 μg single, oral
GINKGOLIDE B plasma
Homo sapiens
9.99 ng/mL
836.46 μg single, oral
GINKGOLIDE B plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
16.36 ng × h/mL
524.56 μg single, oral
GINKGOLIDE B plasma
Homo sapiens
7.75 ng × h/mL
147.45 μg single, oral
GINKGOLIDE B plasma
Homo sapiens
82.77 ng × h/mL
836.46 μg single, oral
GINKGOLIDE B plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.24 h
524.56 μg single, oral
GINKGOLIDE B plasma
Homo sapiens
2.34 h
147.45 μg single, oral
GINKGOLIDE B plasma
Homo sapiens
3.57 h
836.46 μg single, oral
GINKGOLIDE B plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

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.