Thymoquinone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Thymoquinone
Accession Number
DB16447
Description

Thymoquinone is a natural compound with widespread protective effects, including anti-oxidative, anti-inflammatory, immunomodulatory, anti-cancer, and anti-microbial.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 164.204
Monoisotopic: 164.083729626
Chemical Formula
C10H12O2
Synonyms
  • 2-Isopropyl-5-methyl-p-benzoquinone
  • p-Cymene-2,5-dione
  • p-Mentha-3,6-diene-2,5-dione
  • Thymoquinon
External IDs
  • NSC-2228

Pharmacology

Pharmacology
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Indication
Not Available
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action

Thymoquinone is a natural compound with widespread protective effects, including anti-oxidative, anti-inflammatory, immunomodulatory, anti-cancer, and anti-microbial. It is able to induce apoptosis, regulate pro- and anti- apopotitic genes, and inhibit cancer metastasis through JNK and p38 activation. Its anti-inflammatory effects are attributed to its inhibition of inflammatory cytokines and processes, including pathways associated with 5-LO, COX, and PGD2.

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
Adverse Effects
Medicalerrors
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Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified

Chemical Identifiers

UNII
O60IE26NUF
CAS number
490-91-5
InChI Key
KEQHJBNSCLWCAE-UHFFFAOYSA-N
InChI
InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3
IUPAC Name
2-methyl-5-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
SMILES
CC(C)C1=CC(=O)C(C)=CC1=O

References

General References
  1. Shaterzadeh-Yazdi H, Noorbakhsh MF, Hayati F, Samarghandian S, Farkhondeh T: Immunomodulatory and Anti-inflammatory Effects of Thymoquinone. Cardiovasc Hematol Disord Drug Targets. 2018;18(1):52-60. doi: 10.2174/1871529X18666180212114816. [PubMed:29437018]
  2. Imran M, Rauf A, Khan IA, Shahbaz M, Qaisrani TB, Fatmawati S, Abu-Izneid T, Imran A, Rahman KU, Gondal TA: Thymoquinone: A novel strategy to combat cancer: A review. Biomed Pharmacother. 2018 Oct;106:390-402. doi: 10.1016/j.biopha.2018.06.159. Epub 2018 Jul 11. [PubMed:29966985]
  3. Darakhshan S, Bidmeshki Pour A, Hosseinzadeh Colagar A, Sisakhtnezhad S: Thymoquinone and its therapeutic potentials. Pharmacol Res. 2015 May-Jun;95-96:138-58. doi: 10.1016/j.phrs.2015.03.011. Epub 2015 Mar 28. [PubMed:25829334]
  4. Velagapudi R, El-Bakoush A, Lepiarz I, Ogunrinade F, Olajide OA: AMPK and SIRT1 activation contribute to inhibition of neuroinflammation by thymoquinone in BV2 microglia. Mol Cell Biochem. 2017 Nov;435(1-2):149-162. doi: 10.1007/s11010-017-3064-3. Epub 2017 May 27. [PubMed:28551846]
  5. Gholamnezhad Z, Havakhah S, Boskabady MH: Preclinical and clinical effects of Nigella sativa and its constituent, thymoquinone: A review. J Ethnopharmacol. 2016 Aug 22;190:372-86. doi: 10.1016/j.jep.2016.06.061. Epub 2016 Jun 27. [PubMed:27364039]
Human Metabolome Database
HMDB0034732
ChemSpider
9861
BindingDB
166686
ChEBI
113532
ChEMBL
CHEMBL1672002
ZINC
ZINC000000164367
PDBe Ligand
IMW
Wikipedia
Thymoquinone
PDB Entries
4hco

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19) / Immunodeficiencies1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP2.55ChemAxon
pKa (Strongest Basic)-7.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.89 m3·mol-1ChemAxon
Polarizability17.84 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Drug created on January 21, 2021 01:31 / Updated on January 24, 2021 06:04