Terpinen-4-ol
Star0
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAcetylcholinesterase inhibitorHumans UApoptosis regulator Bcl-2 regulatorHumans UE3 ubiquitin-protein ligase XIAP downregulatorHumans UIntestinal-type alkaline phosphatase downregulatorHumans UNuclear factor NF-kappa-B downregulatorHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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
- 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
- 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]
- External Links
- Human Metabolome Database
- HMDB0035833
- KEGG Compound
- C17073
- PubChem Compound
- 11230
- PubChem Substance
- 347828987
- ChemSpider
- 10756
- 1314261
- ChEBI
- 78884
- ChEMBL
- CHEMBL507795
- Wikipedia
- Terpinen-4-ol
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Seborrheic Blepharitis 1 1 Completed Treatment Chronic Blepharitis 1
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
Property Value Source Water Solubility 2.5 mg/mL ALOGPS logP 2.81 ALOGPS logP 2.33 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 20 Chemaxon pKa (Strongest Basic) -0.61 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 48.31 m3·mol-1 Chemaxon Polarizability 18.7 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 137.4944801 predictedDarkChem Lite v0.1.0 [M-H]- 139.22624 predictedDeepCCS 1.0 (2019) [M+H]+ 138.3138801 predictedDarkChem Lite v0.1.0 [M+H]+ 142.33983 predictedDeepCCS 1.0 (2019) [M+Na]+ 137.7049801 predictedDarkChem Lite v0.1.0 [M+Na]+ 151.63728 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
1. DetailsAcetylcholinesterase
- 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
- 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]
2. DetailsApoptosis regulator Bcl-2
- 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
- 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]
3. DetailsE3 ubiquitin-protein ligase XIAP
- 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
- 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]
4. DetailsIntestinal-type alkaline phosphatase
- 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
- 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:
Name | UniProt ID |
---|---|
Nuclear factor NF-kappa-B p100 subunit | Q00653 |
Nuclear factor NF-kappa-B p105 subunit | P19838 |
References
- 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
1. DetailsCytochrome P450 2A6
- 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
- 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