Identification

Name
Levomenol
Accession Number
DB13153
Type
Small Molecule
Groups
Approved, Experimental
Description

Bisabolol, or more formally α-(−)-bisabolol or also known as levomenol, (-)-alpha-Bisabolol is found in fats and oils. (-)-alpha-Bisabolol is isolated from essential oil of Matricaria chamomilla (German chamomile) (-)-alpha-Bisabolol belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units.

Structure
Thumb
Synonyms
  • (-)-alpha-Bisabolol
  • alpha-(-)-bisabolol
  • alpha-bisabolol
  • Bisabolol
  • Kamillosan
  • Levomenol
  • α-(−)-bisabolol
External IDs
FEMA NO. 4666
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
IASO White Science EX SerumLiquid.02 mL/mLTopicalIaso Inc2011-02-05Not applicableUs
IASO White Science EX TonerLiquid.02 mL/mLTopicalIaso Inc2011-02-01Not applicableUs
Neogen Dermalogy White Truffle Laycure Oi LStick.05 g/10gTopicalOutin Futures Corp.2016-11-012017-11-07Us
Categories
UNII
24WE03BX2T
CAS number
23089-26-1
Weight
Average: 222.372
Monoisotopic: 222.198365457
Chemical Formula
C15H26O
InChI Key
RGZSQWQPBWRIAQ-CABCVRRESA-N
InChI
InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1
IUPAC Name
(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
SMILES
[H][[email protected]@]1(CCC(C)=CC1)[[email protected]@](C)(O)CCC=C(C)C

Pharmacology

Indication

Levomenol is known to have anti-irritant, anti-inflammatory and anti-microbial properties. Bisabolol is also demonstrated to enhance the percutaneous absorption of certain molecules

Structured Indications
Not Available
Pharmacodynamics

Levomenol is an anti-inflammatory and natural moisturizing agent that has been found to diminish the signs of photodamage, reduce pruritus, and ameliorate skin texture and elasticity.

Mechanism of action
Not Available
Absorption

The purpose of the present investigations was to study the cutaneous absorption of sesquiterpenic alcohol, the major active principle of chamomile. For these investigations 14C-labelled levomenol ((-)-6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol; (-)-alpha-bisabolol) was prepared by biochemical incorporation of [14C]-acetate into the molecule. 5 h after topical application of the radiolabelled substance onto nude mice half of the radioactivity was found in the skin. The other part was measured in tissue and organes. 90% of this radioactivity was analysed as intact levomenol.

Volume of distribution

To demonstrate the distribution of the substance in the skin a part of this tissue was cutted into horizontal slices by a cryotome. From the slices autoradiograms were produced. The densitometric measuration showed that there was a fast penetration of levomenol into the skin. 5 h after the topical application the substance was displaced from outermost to innermost areas. From these results a fast cutaneous absorption and a long therapeutical effect of the antiphlogistic and spasmolytic levomenol in the skin can be expected.

Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
EltrombopagThe serum concentration of Levomenol can be increased when it is combined with Eltrombopag.Approved
TeriflunomideThe serum concentration of Levomenol can be increased when it is combined with Teriflunomide.Approved
Food Interactions
Not Available

References

General References
  1. Pubchem [Link]
  2. Wikipedia [Link]
  3. NCBI [Link]
External Links
KEGG Compound
C09621
PubChem Compound
442343
PubChem Substance
347829263
ChemSpider
390796
BindingDB
50382730
ChEBI
125
ChEMBL
CHEMBL1096927
Wikipedia
Bisabolol

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidTopical.02 mL/mL
StickTopical.05 g/10g
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0729 mg/mLALOGPS
logP4.76ALOGPS
logP3.91ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-0.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.19 m3·mol-1ChemAxon
Polarizability28.29 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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Sesquiterpenoids
Direct Parent
Sesquiterpenoids
Alternative Parents
Tertiary alcohols / Hydrocarbon derivatives
Substituents
Bisabolane sesquiterpenoid / Sesquiterpenoid / Tertiary alcohol / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Alcohol / Aliphatic homomonocyclic compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
sesquiterpenoid (CHEBI:125) / Bisabolane sesquiterpenoids, Bisabolanes (C09621) / Bisabolane sesquiterpenoids (LMPR0103060001)

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. ChEMBL [Link]
  2. UniProt [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. ChEMBL [Link]
  2. UniProt [Link]
  3. KEGG [Link]

Drug created on November 19, 2016 20:12 / Updated on November 09, 2017 05:19