Details of the Drug

General Information of Drug (ID: DMG2KW7)

Drug Name

Menthol

Synonyms

Hexahydrothymol; Levomenthol; Levomentholum; Menthacamphor; Menthomenthol; Neoisomenthol; Racementhol; Racementholum; Racementol; Headache crystals; Menthol natural; Menthol racemic; Menthol racemique; Menthol racemique [French]; Menthol solution; Menthyl alcohol; Peppermint camphor; Racemic menthol; Robitussin Cough Drops; M0321; M0545; D-Menthol; D-Neomenthol; Dl-Menthol; Fisherman's friend lozenges; L-Menthol; Levomenthol [INN:BAN]; Levomentholum [INN-Latin]; Menthol (USP); Menthol (VAN); Menthol natural, brazilian; NOOLISFMXDJSKH-KXUCPTDWBX; Rac-Menthol; Racementhol [INN:BAN]; Racementholum [INN-Latin]; Racementol [INN-Spanish]; Tra-kill tracheal mite killer; D,l-Menthol; Dl-Menthol (JP15); Fisherman's friendlozenges (TN); L-Menthol (JP15); L-Menthol (TN); L-Menthol (natural); Dl-3-p-Menthanol; P-Menthan-3-ol; RACEMIC MENTHOL U.S.P.; U.S.P. Menthol; D-(-)-Menthol; D-p-Menthan-3-ol; L-(-)-Menthol; Menthol, (1alpha,2beta,5alpha)-Isomer; Cis-1 ,3-trans-1,4-(+-)-menthol; Cis-1,3-trans-1,4-(+-)-menthol; (+)-Neo-menthol; (+)-p-Menthan-3-ol; (+-)-(1R*,3R*,4S*)-Menthol; (+-)-Menthol; (+/-)-Menthol; (+/-)-p-Menthan-3-ol; (-)-(1R,3R,4S)-Menthol; (-)-Menthyl alcohol; (-)-menthol; (-)-p-Menthan-3-ol; (-)-trans-p-Menthan-cis-ol; (1R)-(-)-Menthol; (1R,2S,5R)-Menthol; (1R,3R,4S)-(-)-MENTHOL; (1S, 2S, 5R)-(+)-Neomenthol; (1S,2R,5R)-(+)-Isomenthol; (1S,2R,5S)-(+)-Menthol; (1S,2R,5S)-Menthol; (1r,2s,5r)-(-)-menthol; (L)-MENTHOL; (R)-(-)-Menthol; 2-Isopropyl-5-methylcyclohexanol; 3-p-Menthol; 4-Isopropyl-1-methylcyclohexan-3-ol; 5-Methyl-2-(1-methylethyl)-cyclohexanol; 5-Methyl-2-(1-methylethyl)cyclohexanol; 5-methyl-2-(propan-2-yl)cyclohexanol; 5-methyl-2-propan-2-ylcyclohexan-1-ol

Indication

Disease Entry	ICD 11	Status	REF
Throat irritation	CA0Y	Approved	[1], [2]

Therapeutic Class

Antipruritics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

156.26

Topological Polar Surface Area (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C10H20O
IUPAC Name: 5-methyl-2-propan-2-ylcyclohexan-1-ol
Canonical SMILES: CC1CCC(C(C1)O)C(C)C
InChI: InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3
InChIKey: NOOLISFMXDJSKH-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 1254
ChEBI ID: CHEBI:25187
CAS Number: 89-78-1
DrugBank ID: DB14123
TTD ID: D04CSZ

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Long transient receptor potential channel 8 (TRPM8)	TTXDKTO	TRPM8_HUMAN	Activator	[3]
Transformation-sensitive protein p120 (TRPA1)	TTELV3W	TRPA1_HUMAN	Activator	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2471).
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 022029.
3	TRPV1-mediated itch in seasonal allergic rhinitis. Allergy. 2009 May;64(5):807-10.
4	Best of the 2009 AUA Annual Meeting: Highlights from the 2009 Annual Meeting of the American Urological Association, April 25-30, 2009, Chicago, IL. Rev Urol. 2009 Spring; 11(2): 82-107.
5	Inhibition of TRPM8 channels reduces pain in the cold pressor test in humans. J Pharmacol Exp Ther. 2014 Nov;351(2):259-69.
6	Effects of antagonists and heat on TRPM8 channel currents in dorsal root ganglion neuron activated by nociceptive cold stress and menthol. Neurochem Res. 2012 Feb;37(2):314-20.
7	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 500).
8	5-benzyloxytryptamine as an antagonist of TRPM8. Bioorg Med Chem Lett. 2010 Dec 1;20(23):7076-9.
9	Evolution of thermal response properties in a cold-activated TRP channel. PLoS One. 2009 May 29;4(5):e5741.
10	Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. Br J Pharmacol. 2004 Feb;141(4):737-45.
11	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
12	NPPB structure-specifically activates TRPA1 channels. Biochem Pharmacol. 2010 Jul 1;80(1):113-21.
13	Transient receptor potential A1 mediates acetaldehyde-evoked pain sensation. Eur J Neurosci. 2007 Nov;26(9):2516-23.
14	Resolvin D1 attenuates activation of sensory transient receptor potential channels leading to multiple anti-nociception. Br J Pharmacol. 2010 Oct;161(3):707-20.
15	An ion channel essential for sensing chemical damage. J Neurosci. 2007 Oct 17;27(42):11412-5.
16	ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29.
17	Transient receptor potential A1 is a sensory receptor for multiple products of oxidative stress. J Neurosci. 2008 Mar 5;28(10):2485-94.
18	TRPA1 and TRPV1 activation is a novel adjuvant effect mechanism in contact hypersensitivity. J Neuroimmunol. 2009 Feb 15;207(1-2):66-74.
19	Cox-dependent fatty acid metabolites cause pain through activation of the irritant receptor TRPA1. Proc Natl Acad Sci U S A. 2008 Aug 19;105(33):12045-50.
20	Cigarette smoke-induced neurogenic inflammation is mediated by alpha,beta-unsaturated aldehydes and the TRPA1 receptor in rodents. J Clin Invest. 2008 Jul;118(7):2574-82.