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

Identification

Generic Name
Terpinen-4-ol
DrugBank Accession Number
DB12816
Background

Terpinen-4-ol is under investigation in clinical trial NCT01647217 (Demodex Blepharitis Treatment Study).

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 154.253
Monoisotopic: 154.1357652
Chemical Formula
C10H18O
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAcetylcholinesterase
inhibitor
Humans
UApoptosis regulator Bcl-2
regulator
Humans
UE3 ubiquitin-protein ligase XIAP
downregulator
Humans
UIntestinal-type alkaline phosphatase
downregulator
Humans
UNuclear factor NF-kappa-B
downregulator
Humans
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
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Toxicity

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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Menthane monoterpenoids
Alternative Parents
Monocyclic monoterpenoids / Tertiary alcohols / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homomonocyclic compound / Hydrocarbon derivative / Monocyclic monoterpenoid / Organic oxygen compound / Organooxygen compound / P-menthane monoterpenoid / Tertiary alcohol
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
tertiary alcohol, terpineol (CHEBI:78884) / Menthane monoterpenoids (C17073)
Affected organisms
Not Available

Chemical Identifiers

UNII
L65MV77ZG6
CAS number
562-74-3
InChI Key
WRYLYDPHFGVWKC-UHFFFAOYSA-N
InChI
InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3
IUPAC Name
4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol
SMILES
CC(C)C1(O)CCC(C)=CC1

References

General References
  1. Chooluck K, Singh RP, Sathirakul K, Derendorf H: Plasma and dermal pharmacokinetics of terpinen-4-ol in rats following intravenous administration. Pharmazie. 2013 Feb;68(2):135-40. [Article]
Human Metabolome Database
HMDB0035833
KEGG Compound
C17073
PubChem Compound
11230
PubChem Substance
347828987
ChemSpider
10756
RxNav
1314261
ChEBI
78884
ChEMBL
CHEMBL507795
Wikipedia
Terpinen-4-ol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentSeborrheic Blepharitis1
1CompletedTreatmentChronic Blepharitis1

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
Water Solubility2.5 mg/mLALOGPS
logP2.81ALOGPS
logP2.33ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)20ChemAxon
pKa (Strongest Basic)-0.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.31 m3·mol-1ChemAxon
Polarizability18.7 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-006x-9100000000-575f0430fad8f36207fc
GC-MS Spectrum - EI-BGC-MSsplash10-022l-9500000000-3f2e9ea1f5b3757fe0ee
Mass Spectrum (Electron Ionization)MSsplash10-00dl-9200000000-42c59760ac8ce71b2738
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-0900000000-6ab97f1e60330835e91d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-6900000000-04567bac2f7cdff17fbb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-100r-9200000000-348297fc0a82a249f6ce
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-cf6571639c99834988f8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-08b8295cc319afc2225c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gw0-8900000000-e34fafe0d516af6cb77f
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
References
  1. Dohi S, Terasaki M, Makino M: Acetylcholinesterase inhibitory activity and chemical composition of commercial essential oils. J Agric Food Chem. 2009 May 27;57(10):4313-8. doi: 10.1021/jf804013j. Epub 2009 Apr 9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
General Function
Ubiquitin protein ligase binding
Specific Function
Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells. Regulates cell death by controlling the mitochondrial membrane permeability. Appea...
Gene Name
BCL2
Uniprot ID
P10415
Uniprot Name
Apoptosis regulator Bcl-2
Molecular Weight
26265.66 Da
References
  1. Wu CS, Chen YJ, Chen JJ, Shieh JJ, Huang CH, Lin PS, Chang GC, Chang JT, Lin CC: Terpinen-4-ol Induces Apoptosis in Human Nonsmall Cell Lung Cancer In Vitro and In Vivo. Evid Based Complement Alternat Med. 2012;2012:818261. doi: 10.1155/2012/818261. Epub 2011 Jun 20. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Zinc ion binding
Specific Function
Multi-functional protein which regulates not only caspases and apoptosis, but also modulates inflammatory signaling and immunity, copper homeostasis, mitogenic kinase signaling, cell proliferation,...
Gene Name
XIAP
Uniprot ID
P98170
Uniprot Name
E3 ubiquitin-protein ligase XIAP
Molecular Weight
56684.41 Da
References
  1. Wu CS, Chen YJ, Chen JJ, Shieh JJ, Huang CH, Lin PS, Chang GC, Chang JT, Lin CC: Terpinen-4-ol Induces Apoptosis in Human Nonsmall Cell Lung Cancer In Vitro and In Vivo. Evid Based Complement Alternat Med. 2012;2012:818261. doi: 10.1155/2012/818261. Epub 2011 Jun 20. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Not Available
Specific Function
Alkaline phosphatase activity
Gene Name
ALPI
Uniprot ID
P09923
Uniprot Name
Intestinal-type alkaline phosphatase
Molecular Weight
56811.695 Da
References
  1. Wu CS, Chen YJ, Chen JJ, Shieh JJ, Huang CH, Lin PS, Chang GC, Chang JT, Lin CC: Terpinen-4-ol Induces Apoptosis in Human Nonsmall Cell Lung Cancer In Vitro and In Vivo. Evid Based Complement Alternat Med. 2012;2012:818261. doi: 10.1155/2012/818261. Epub 2011 Jun 20. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...

Components:
References
  1. Chaiyana W, Anuchapreeda S, Leelapornpisid P, Phongpradist R, Viernstein H, Mueller M: Development of Microemulsion Delivery System of Essential Oil from Zingiber cassumunar Roxb. Rhizome for Improvement of Stability and Anti-Inflammatory Activity. AAPS PharmSciTech. 2017 May;18(4):1332-1342. doi: 10.1208/s12249-016-0603-2. Epub 2016 Aug 8. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Miyazawa M, Haigou R: Determination of cytochrome P450 enzymes involved in the metabolism of (-)-terpinen-4-ol by human liver microsomes. Xenobiotica. 2011 Dec;41(12):1056-62. doi: 10.3109/00498254.2011.596230. [Article]

Drug created at October 21, 2016 00:28 / Updated at June 27, 2022 17:21