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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24O10
Molecular Weight 424.3993
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GINKGOLIDE B

SMILES

C[C@]1([H])C(=O)O[C@@]2([H])[C@]([H])([C@]34[C@@]5([H])C[C@@]([H])(C(C)(C)C)[C@]64[C@]([H])(C(=O)O[C@@]6([H])O[C@@]3(C(=O)O5)[C@@]12O)O)O

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 424.3993
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.18 ng/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
16.36 ng × h/mL
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.24 h
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
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
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

Doses

DosePopulationAdverse 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:
unhealthy
n = 32
Health Status: unhealthy
Condition: multiple sclerosis
Sex: M+F
Food Status: UNKNOWN
Population Size: 32
Sources:
Other AEs: Hiccup...
Other AEs:
Hiccup (mild, 14 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy
n = 32
Health Status: unhealthy
Condition: multiple sclerosis
Sex: M+F
Food Status: UNKNOWN
Population Size: 32
Sources:
Overview

Overview

Drug as perpetrator​Drug as victim
PubMed

PubMed

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

Patents

Sample Use Guides

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
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 Jun 26 03:10:29 UTC 2021
Edited
by admin
on Sat Jun 26 03:10:29 UTC 2021
Record UNII
DF149B9460
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GINKGOLIDE B
MI  
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
GINKGOLIDE B [WHO-DD]
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)
Created by admin on Sat Jun 26 03:10:29 UTC 2021 , Edited by admin on Sat Jun 26 03:10:29 UTC 2021
Code System Code Type Description
FDA UNII
DF149B9460
Created by admin on Sat Jun 26 03:10:29 UTC 2021 , Edited by admin on Sat Jun 26 03:10:29 UTC 2021
PRIMARY
EVMPD
SUB184978
Created by admin on Sat Jun 26 03:10:29 UTC 2021 , Edited by admin on Sat Jun 26 03:10:29 UTC 2021
PRIMARY
CAS
15291-77-7
Created by admin on Sat Jun 26 03:10:29 UTC 2021 , Edited by admin on Sat Jun 26 03:10:29 UTC 2021
PRIMARY
PUBCHEM
11973122
Created by admin on Sat Jun 26 03:10:29 UTC 2021 , Edited by admin on Sat Jun 26 03:10:29 UTC 2021
PRIMARY
MERCK INDEX
M5731
Created by admin on Sat Jun 26 03:10:29 UTC 2021 , Edited by admin on Sat Jun 26 03:10:29 UTC 2021
PRIMARY Merck Index
MESH
C045856
Created by admin on Sat Jun 26 03:10:29 UTC 2021 , Edited by admin on Sat Jun 26 03:10:29 UTC 2021
PRIMARY
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