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

Similar Structures

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

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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

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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: Improve decision support & research outcomes
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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.

Drug	Interaction
Integrate drug-drug interactions in your software
Apalutamide	The serum concentration of Levomenol can be decreased when it is combined with Apalutamide.
Ceftobiprole medocaril	The serum concentration of Levomenol can be increased when it is combined with Ceftobiprole medocaril.
Elexacaftor	The serum concentration of Levomenol can be increased when it is combined with Elexacaftor.
Encorafenib	The serum concentration of Levomenol can be increased when it is combined with Encorafenib.
Filgotinib	The serum concentration of Levomenol can be increased when it is combined with Filgotinib.

Food Interactions

No interactions found.

Products

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Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
IASO White Science EX Serum	Liquid	0.02 g/1mL	Topical	Iaso Inc	2011-02-05	2018-03-12
IASO White Science EX Toner	Liquid	0.02 g/1mL	Topical	Iaso Inc	2011-02-01	2018-03-12
Neogen Dermalogy White Truffle Laycure Oi L	Stick	0.05 g/10g	Topical	Outin Futures Corp.	2016-11-01	2017-10-31
PurpleU BAOBAB FACE	Oil	0.07 g/15mL	Topical	Recipe Co., Ltd.	2017-10-01	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Intense Multi Ampoule Balm Vita C	Levomenol (0.05 g/10g) + alpha-Tocopherol acetate (0.3 g/10g)	Liquid	Topical	Nature Republic Co., Ltd.	2022-03-01	Not applicable
NEWSTEM Rx IPL VITA C Energy Ampoule	Levomenol (0.5 g/100g) + Adenosine (0.04 g/100g) + Ascorbic acid (13.5 g/100g)	Liquid	Topical	Yj Lab Co., Ltd.	2022-01-02	Not applicable
Seamoms Tamanu Oil Mist	Levomenol (0.5 g/100mL) + Adenosine (0.04 g/100mL)	Oil	Topical	Oneskin Cosmetics Co., Ltd.	2021-01-27	Not applicable
Sensicutan - Salbe	Levomenol (0.3 g) + Heparin sodium (20000 IU)	Ointment	Topical	Harras Pharma Curarina Arzneimittel Gmb H Arzneimittelforschung Und Vertrieb	2001-12-07	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
IASO White Science EX Serum	Levomenol (0.02 g/1mL)	Liquid	Topical	Iaso Inc	2011-02-05	2018-03-12
IASO White Science EX Toner	Levomenol (0.02 g/1mL)	Liquid	Topical	Iaso Inc	2011-02-01	2018-03-12
Intense Multi Ampoule Balm Vita C	Levomenol (0.05 g/10g) + alpha-Tocopherol acetate (0.3 g/10g)	Liquid	Topical	Nature Republic Co., Ltd.	2022-03-01	Not applicable
Neogen Dermalogy White Truffle Laycure Oi L	Levomenol (0.05 g/10g)	Stick	Topical	Outin Futures Corp.	2016-11-01	2017-10-31
NEWSTEM Rx IPL VITA C Energy Ampoule	Levomenol (0.5 g/100g) + Adenosine (0.04 g/100g) + Ascorbic acid (13.5 g/100g)	Liquid	Topical	Yj Lab Co., Ltd.	2022-01-02	Not applicable

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

Pubchem [Link]
NCBI [Link]
BASG Product Information: Sensicutan (bisabolol/heparin sodium) topical ointment [Link]

External Links

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

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Onychomycosis	1
1	Completed	Treatment	Wounds and Injuries	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Liquid	Topical	0.02 g/1mL
Liquid	Topical
Stick	Topical	0.05 g/10g
Oil	Topical	0.07 g/15mL
Oil	Topical
Ointment	Topical

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0729 mg/mL	ALOGPS
logP	4.76	ALOGPS
logP	3.91	Chemaxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-0.47	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	4	Chemaxon
Refractivity	72.19 m³·mol^-1	Chemaxon
Polarizability	28.29 Å³	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052b-4900000000-25a7aa21476e3e7e1390
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-0090000000-29715d4df85d92334d15
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0596-9700000000-22bf66cba48f1b59f507
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-1790000000-a51af2f534b8e4d2c909
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-08mi-3910000000-6fd64c757e97dd508dc8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0aou-9100000000-9c8f20013d16c0f691b2
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	167.6245613	predicted	DarkChem Lite v0.1.0
[M-H]-	167.2734613	predicted	DarkChem Lite v0.1.0
[M-H]-	166.7967613	predicted	DarkChem Lite v0.1.0
[M-H]-	153.06496	predicted	DeepCCS 1.0 (2019)
[M+H]+	168.0192613	predicted	DarkChem Lite v0.1.0
[M+H]+	167.5233613	predicted	DarkChem Lite v0.1.0
[M+H]+	167.1692613	predicted	DarkChem Lite v0.1.0
[M+H]+	155.46053	predicted	DeepCCS 1.0 (2019)
[M+Na]+	167.5119613	predicted	DarkChem Lite v0.1.0
[M+Na]+	167.3180613	predicted	DarkChem Lite v0.1.0
[M+Na]+	166.4137613	predicted	DarkChem Lite v0.1.0
[M+Na]+	161.83762	predicted	DeepCCS 1.0 (2019)

Transporters

Details1. Solute carrier organic anion transporter family member 1B1

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

ChEMBL [Link]
UniProt [Link]

Details2. Solute carrier organic anion transporter family member 1B3

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

ChEMBL [Link]
UniProt [Link]
KEGG [Link]

Drug created at November 20, 2016 03:12 / Updated at February 21, 2021 18:54

Levomenol

Identification

Structure for Levomenol (DB13153)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Transporters

References

References