Levomenol

Identification

Generic Name
Levomenol
DrugBank Accession Number
DB13153
Background

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.

Type
Small Molecule
Groups
Approved, Experimental
Structure
Thumb
Weight
Average: 222.372
Monoisotopic: 222.198365457
Chemical Formula
C15H26O
Synonyms
  • (-)-alpha-Bisabolol
  • alpha-(-)-bisabolol
  • alpha-bisabolol
  • Bisabolol
  • Kamillosan
  • Levomenol
  • α-(−)-bisabolol
External IDs
  • FEMA NO. 4666

Pharmacology

Indication

Levomenol has been known to elicit a number of potentially beneficial pharmacological effects, including anti-irritant, anti-inflammatory, and anti-microbial actions. Bisabolol is also demonstrated to enhance the percutaneous absorption of certain molecules

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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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.
DrugInteraction
FilgotinibThe serum concentration of Levomenol can be increased when it is combined with Filgotinib.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
IASO White Science EX SerumLiquid0.02 g/1mLTopicalIaso Inc2011-02-052018-03-12US flag
IASO White Science EX TonerLiquid0.02 g/1mLTopicalIaso Inc2011-02-012018-03-12US flag
Neogen Dermalogy White Truffle Laycure Oi LStick0.05 g/10gTopicalOutin Futures Corp.2016-11-012017-10-31US flag
PurpleU BAOBAB FACEOil0.07 g/15mLTopicalRecipe Co., Ltd.2017-10-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Seamoms Tamanu Oil MistLevomenol (0.5 g/100mL) + Adenosine (0.04 g/100mL)OilTopicalOneskin Cosmetics Co., Ltd.2021-01-27Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
IASO White Science EX SerumLevomenol (0.02 g/1mL)LiquidTopicalIaso Inc2011-02-052018-03-12US flag
IASO White Science EX TonerLevomenol (0.02 g/1mL)LiquidTopicalIaso Inc2011-02-012018-03-12US flag
Neogen Dermalogy White Truffle Laycure Oi LLevomenol (0.05 g/10g)StickTopicalOutin Futures Corp.2016-11-012017-10-31US flag
PurpleU BAOBAB FACELevomenol (0.07 g/15mL)OilTopicalRecipe Co., Ltd.2017-10-01Not applicableUS flag
Seamoms Tamanu Oil MistLevomenol (0.5 g/100mL) + Adenosine (0.04 g/100mL)OilTopicalOneskin Cosmetics Co., Ltd.2021-01-27Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alcohol / Aliphatic homomonocyclic compound / Bisabolane sesquiterpenoid / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Sesquiterpenoid / Tertiary alcohol
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
sesquiterpenoid (CHEBI:125) / Bisabolane sesquiterpenoids, Bisabolanes (C09621) / Bisabolane sesquiterpenoids (LMPR0103060001)
Affected organisms
Not Available

Chemical Identifiers

UNII
24WE03BX2T
CAS number
23089-26-1
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][C@@]1(CCC(C)=CC1)[C@@](C)(O)CCC=C(C)C

References

General References
  1. Pubchem [Link]
  2. NCBI [Link]
  3. BASG Product Information: Sensicutan (bisabolol/heparin sodium) topical ointment [Link]
KEGG Compound
C09621
PubChem Compound
442343
PubChem Substance
347829263
ChemSpider
390796
BindingDB
50382730
RxNav
19461
ChEBI
125
ChEMBL
CHEMBL1096927
ZINC
ZINC000001849759
Wikipedia
Bisabolol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentOnychomycosis1
1CompletedTreatmentWounds and Injuries1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidTopical0.02 g/1mL
StickTopical0.05 g/10g
OilTopical0.07 g/15mL
OilTopical
OintmentTopical
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

Transporters

Kind
Protein
Organism
Humans
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
Humans
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 20, 2016 03:12 / Updated on February 21, 2021 18:54