DrugBank: Ginkgo biloba (DB01381)

targets (6) enzymes (1)

Identification

Name

Ginkgo biloba

Accession Number

DB01381

Type

small molecule

Groups

approved, nutraceutical

Description

The extract of the Ginkgo leaves contains flavonoid glycosides and terpenoids (ginkgolides, bilobalides) and has been used pharmaceutically for hundreds of years. It has many alleged nootropic properties, and is mainly used as memory and concentration enhancer, and anti-vertigo agent. Ginkgo extract seems to have three effects on the human body: it improves blood flow (including microcirculation in small capillaries) to most tissues and organs; it protects against oxidative cell damage from free radicals; and it blocks many of the effects of PAF (platelet aggregation, blood clotting) that have been related to the development of a number of cardiovascular, renal, respiratory and CNS (Central Nervous System) disorders.

Structure

Synonyms

Adiantifolia
Bai Guo Ye
Baiguo
Fossil Tree
Ginkgo Folium
Herba Ginkgo Biloba
Japanese Silver Apricot
Kew Tree
Maidenhair Tree
Pei Go Su Ye
Salisburia Adiantifolia
Yen Xing
Yinhsing

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Not Available

CAS number

Not Available

Weight

Not Available

Chemical Formula

Not Available

InChI Key

Not Available

InChI

Not Available

IUPAC Name

Not Available

SMILES

Not Available

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Appears to be effective in: alleviating age-related memory impairment in some elderly people with mild to moderate age-related memory or cognitive impairment; improving cognitive function in healthy young to middle-aged people; improving symptoms of Alzheimer's, vascular or mixed dementia; improving damage to the visual field in patients with normal tension glaucoma; decreasing the number of painful attacks in patients with Raynaud's syndrome; and may improve symptoms of vertigo and dizziness in some patients.

Pharmacodynamics

The mechanism by which ginkgo biloba is thought to be effective for these conditions appears to be in part through active "ginkgolides" terpenoids and flavinoids that appear to inhibit platelet aggregation, neutrophil degranulation, and the induction of oxygen-free radical production

Mechanism of action

The compounds found in ginkgo may have a protective role in different stages of the decline of intellectual function via several mechanisms of action: vasoregulating activity of arteries, capillaries, and veins (increased blood flow); platelet activating factor (PAF) antagonism; homeostasis of inflammation and oxidative stress; and prevention of cell membrane damage causedby free radicals; and neurotransmission modulation. The most important substances are flavonoids (ginkgo flavone glycosides) and terpenoids (ginkgolides and bilobalide).The compounds inginkgo act to varying degrees as scavengers for free radicals.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Fresh seeds are toxic may cause death. Roasted seed and crude ginkgo plant should not be used orally. Consumption of greater than 10 roasted seeds may cause difficulty breathing, weak pulse, seizures, loss of consciousness, and shock. Standardized ginkgo leaf extracts have been used safely in trials lasting several weeks to six years; however, cases of spontaneous hemorrhages have been reported with the conventional use of the standardized extract. As with all medications, individual risk factors must be considered in the assessment of safety of this medication. This medication is well-tolerated at standard oral doses. Ginkgo biloba may cause gastrointestinal upset, headache, dizziness, palpitations, nausea, vomiting, lack of muscle tone and weakness.

Affected organisms

Not Available

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Dosage forms

Form	Route	Strength
Capsule	Oral	120 mg
Capsule	Oral	30 mg
Capsule	Oral	40 mg
Capsule	Oral	60 mg
Liquid	Oral
Solution / drops	Oral

Prices

Unit description	Cost	Unit
Ginkgo biloba 40 mg tablet	0.24 USD	tablet
Ginkgo biloba 120 mg caplet	0.19 USD	caplet
Sm ginkgo biloba 60 mg caplet	0.19 USD	caplet
Ginkgo 60 mg tablet	0.14 USD	tablet
Ra ginkgo biloba 40 mg tablet	0.11 USD	tablet
Ginkgo biloba 60 mg capsule	0.1 USD	capsule
Ginkgo biloba 50 mg tablet	0.09 USD	tablet
Ginkgo biloba 30 mg capsule	0.04 USD	capsule
Pv ginkgo biloba capsule	0.03 USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

solid

Experimental Properties

Not Available

Predicted Properties

Not Available

References

Synthesis Reference

Not Available

General Reference

Cohen AJ, Bartlik B: Ginkgo biloba for antidepressant-induced sexual dysfunction. J Sex Marital Ther. 1998 Apr-Jun;24(2):139-43. Pubmed

External Links

Resource	Link
PharmGKB	PA449758
Drug Product Database	889660
RxList	http://www.rxlist.com/cgi/generic/ginkgo.htm
Drugs.com	http://www.drugs.com/mtm/ginkgo.html
Wikipedia	http://en.wikipedia.org/wiki/Ginkgo_biloba

ATC Codes

N06DX02

AHFS Codes

92:02.00*

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (72.2 KB)

Interactions

Drug Interactions

Drug	Interaction
Abciximab	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Acenocoumarol	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Acetylsalicylic acid	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Alteplase	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Anagrelide	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Argatroban	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Bivalirudin	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Cilostazol	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Citalopram	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Clopidogrel	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Dabigatran etexilate	Additive anticoagulant/antiplatelet effects of gingko may increase bleed risk for patients on dabigatran. Concomitant therapy should be avoided.
Diclofenac	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Diflunisal	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Dipyridamole	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Enoxaparin	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Eptifibatide	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Escitalopram	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Etodolac	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Fenoprofen	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Fluoxetine	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Flurbiprofen	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Fluvoxamine	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Fondaparinux sodium	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Ginseng	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Heparin	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Ibuprofen	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Indomethacin	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Ketoprofen	Increased risk of bleeding due to additive antiplatelet properties of the two agents. Concomitant therapy should be avoided or monitored carefully for bleeding, bruising and altered mental status, which may be caused by CNS bleeds.
Ketorolac	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Lepirudin	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Meclofenamic acid	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Meloxicam	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Nabumetone	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Naproxen	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Oxaprozin	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Paroxetine	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Piroxicam	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Prasugrel	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Reteplase	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Rivaroxaban	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
S-Adenosylmethionine	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Sertraline	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Sulindac	Ginkgo biloba may enhance the anticoagulant effect of sulindac. Increased risk of bleeding, bruising and altered mental status due to CNS bleeds. Concomitant therapy should be avoided.
Tacrine	Ginkgo biloba may cause additive/toxic cholinergic effects when administered with Tacrine. Monitor for cholinergic toxicity.
Tenecteplase	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Tiaprofenic acid	Increased risk of bleeding due to additive antiplatelet properties of the two agents. Concomitant therapy should be avoided or monitored carefully for bleeding, bruising and altered mental status, which may be caused by CNS bleeds.
Ticlopidine	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Tirofiban	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Tolmetin	Increased risk of bleeding due to additive antiplatelet properties of the two agents. Concomitant therapy should be avoided or monitored carefully for bleeding, bruising and altered mental status, which may be caused by CNS bleeds.
Trazodone	Increased effect and toxicity of both agents
Urokinase	Increased risk of bleeding.
Warfarin	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.

Food Interactions

Not Available

Targets
1. Sodium-dependent noradrenaline transporter Pharmacological action: unknown Actions: inhibitor Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals Organism class: human UniProt ID: P23975 Gene: SLC6A2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Fehske CJ, Leuner K, Muller WE: Ginkgo biloba extract (EGb761) influences monoaminergic neurotransmission via inhibition of NE uptake, but not MAO activity after chronic treatment. Pharmacol Res. 2009 Jul;60(1):68-73. Epub 2009 Mar 21. Pubmed 2. Phospholipase A2, membrane associated Pharmacological action: unknown Actions: inhibitor Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2- acyl groups in 3-sn-phosphoglycerides Organism class: human UniProt ID: P14555 Gene: PLA2G2A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Kim HK, Son KH, Chang HW, Kang SS, Kim HP: Inhibition of rat adjuvant-induced arthritis by ginkgetin, a biflavone from ginkgo biloba leaves. Planta Med. 1999 Jun;65(5):465-7. Pubmed Weichel O, Hilgert M, Chatterjee SS, Lehr M, Klein J: Bilobalide, a constituent of Ginkgo biloba, inhibits NMDA-induced phospholipase A2 activation and phospholipid breakdown in rat hippocampus. Naunyn Schmiedebergs Arch Pharmacol. 1999 Dec;360(6):609-15. Pubmed Lim H, Son KH, Chang HW, Kang SS, Kim HP: Effects of anti-inflammatory biflavonoid, ginkgetin, on chronic skin inflammation. Biol Pharm Bull. 2006 May;29(5):1046-9. Pubmed 3. Glycine receptor subunit alpha-1 Pharmacological action: unknown Actions: antagonist The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing) Organism class: human UniProt ID: P23415 Gene: GLRA1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Heads JA, Hawthorne RL, Lynagh T, Lynch JW: Structure-activity analysis of ginkgolide binding in the glycine receptor pore. J Neurochem. 2008 May;105(4):1418-27. Epub 2008 Jan 21. Pubmed 4. Gamma-aminobutyric-acid receptor subunit alpha-1 Pharmacological action: unknown Actions: negative modulator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P14867 Gene: GABRA1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Hanrahan JR, Chebib M, Davucheron NL, Hall BJ, Johnston GA: Semisynthetic preparation of amentoflavone: A negative modulator at GABA receptors. Bioorg Med Chem Lett. 2003 Jul 21;13(14):2281-4. Pubmed 5. Gamma-aminobutyric-acid receptor subunit beta-2 Pharmacological action: unknown Actions: negative modulator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P47870 Gene: GABRB2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Hanrahan JR, Chebib M, Davucheron NL, Hall BJ, Johnston GA: Semisynthetic preparation of amentoflavone: A negative modulator at GABA receptors. Bioorg Med Chem Lett. 2003 Jul 21;13(14):2281-4. Pubmed 6. Gamma-aminobutyric acid receptor subunit gamma-2 Pharmacological action: unknown Actions: negative modulator GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel Organism class: human UniProt ID: P18507 Gene: GABRG2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Hanrahan JR, Chebib M, Davucheron NL, Hall BJ, Johnston GA: Semisynthetic preparation of amentoflavone: A negative modulator at GABA receptors. Bioorg Med Chem Lett. 2003 Jul 21;13(14):2281-4. Pubmed

Targets

1. Sodium-dependent noradrenaline transporter

Pharmacological action: unknown
Actions: inhibitor

Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: P23975 Link_out

Gene: SLC6A2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Fehske CJ, Leuner K, Muller WE: Ginkgo biloba extract (EGb761) influences monoaminergic neurotransmission via inhibition of NE uptake, but not MAO activity after chronic treatment. Pharmacol Res. 2009 Jul;60(1):68-73. Epub 2009 Mar 21. Pubmed

2. Phospholipase A2, membrane associated

Pharmacological action: unknown
Actions: inhibitor

Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2- acyl groups in 3-sn-phosphoglycerides

Organism class: human
UniProt ID: P14555 Link_out

Gene: PLA2G2A Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Kim HK, Son KH, Chang HW, Kang SS, Kim HP: Inhibition of rat adjuvant-induced arthritis by ginkgetin, a biflavone from ginkgo biloba leaves. Planta Med. 1999 Jun;65(5):465-7. Pubmed
Weichel O, Hilgert M, Chatterjee SS, Lehr M, Klein J: Bilobalide, a constituent of Ginkgo biloba, inhibits NMDA-induced phospholipase A2 activation and phospholipid breakdown in rat hippocampus. Naunyn Schmiedebergs Arch Pharmacol. 1999 Dec;360(6):609-15. Pubmed
Lim H, Son KH, Chang HW, Kang SS, Kim HP: Effects of anti-inflammatory biflavonoid, ginkgetin, on chronic skin inflammation. Biol Pharm Bull. 2006 May;29(5):1046-9. Pubmed

3. Glycine receptor subunit alpha-1

Pharmacological action: unknown
Actions: antagonist

The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing)

Organism class: human
UniProt ID: P23415 Link_out

Gene: GLRA1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Heads JA, Hawthorne RL, Lynagh T, Lynch JW: Structure-activity analysis of ginkgolide binding in the glycine receptor pore. J Neurochem. 2008 May;105(4):1418-27. Epub 2008 Jan 21. Pubmed

4. Gamma-aminobutyric-acid receptor subunit alpha-1

Pharmacological action: unknown
Actions: negative modulator

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P14867 Link_out

Gene: GABRA1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Hanrahan JR, Chebib M, Davucheron NL, Hall BJ, Johnston GA: Semisynthetic preparation of amentoflavone: A negative modulator at GABA receptors. Bioorg Med Chem Lett. 2003 Jul 21;13(14):2281-4. Pubmed

5. Gamma-aminobutyric-acid receptor subunit beta-2

Pharmacological action: unknown
Actions: negative modulator

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P47870 Link_out

Gene: GABRB2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Hanrahan JR, Chebib M, Davucheron NL, Hall BJ, Johnston GA: Semisynthetic preparation of amentoflavone: A negative modulator at GABA receptors. Bioorg Med Chem Lett. 2003 Jul 21;13(14):2281-4. Pubmed

6. Gamma-aminobutyric acid receptor subunit gamma-2

Pharmacological action: unknown
Actions: negative modulator

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P18507 Link_out

Gene: GABRG2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Hanrahan JR, Chebib M, Davucheron NL, Hall BJ, Johnston GA: Semisynthetic preparation of amentoflavone: A negative modulator at GABA receptors. Bioorg Med Chem Lett. 2003 Jul 21;13(14):2281-4. Pubmed

Enzymes
1. Cytochrome P450 2C9 Actions: inhibitor Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan UniProt ID: P11712 Gene: CYP2C9 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Yale SH, Glurich I: Analysis of the inhibitory potential of Ginkgo biloba, Echinacea purpurea, and Serenoa repens on the metabolic activity of cytochrome P450 3A4, 2D6, and 2C9. J Altern Complement Med. 2005 Jun;11(3):433-9. Pubmed Greenblatt DJ, von Moltke LL, Luo Y, Perloff ES, Horan KA, Bruce A, Reynolds RC, Harmatz JS, Avula B, Khan IA, Goldman P: Ginkgo biloba does not alter clearance of flurbiprofen, a cytochrome P450-2C9 substrate. J Clin Pharmacol. 2006 Feb;46(2):214-21. Pubmed

Enzymes

1. Cytochrome P450 2C9

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan

UniProt ID: P11712 Link_out

Gene: CYP2C9
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Yale SH, Glurich I: Analysis of the inhibitory potential of Ginkgo biloba, Echinacea purpurea, and Serenoa repens on the metabolic activity of cytochrome P450 3A4, 2D6, and 2C9. J Altern Complement Med. 2005 Jun;11(3):433-9. Pubmed
Greenblatt DJ, von Moltke LL, Luo Y, Perloff ES, Horan KA, Bruce A, Reynolds RC, Harmatz JS, Avula B, Khan IA, Goldman P: Ginkgo biloba does not alter clearance of flurbiprofen, a cytochrome P450-2C9 substrate. J Clin Pharmacol. 2006 Feb;46(2):214-21. Pubmed

Comments

Drug created on July 06, 2007 14:33 / Updated on February 14, 2012 11:47