Menthol

Identification

Summary

Menthol is an organic compound used to treat mild to moderate muscle and joint pain.

Brand Names

Absorbine Jr Antifungal, Activon Arthritis, Bengay, Calazime Skin Protectant, Calmodrox, Calmoseptine Ointment, Capzasin Quick Relief, Chloraseptic Sore Throat, Chloraseptic Sore Throat + Cough, Delsym Cough Plus Soothing Action, Delsym Cough Relief Plus Soothing Action, Dendracin Neurodendraxcin, Fast Freeze, Flexall Ultra Plus, Gold Bond Maximum Relief, Icy Hot Arthritis, Ivy-dry Cream, Lidopro, Lidothol, Listerine Antiseptic, Max-freeze, Medi-derm, Medi-derm With Lidocaine, Medicaine Sting and Bite, Medrox, Men-phor, Orasep Reformulated Dec 2013, Ortho-nesic, Rematex, Salonpas Gel-patch, Salonpas Pain Relieving Patch, Sarna Sensitive, Sucrets, Tiger Balm, Vaporex, Vicks Vaporub, Xoten-C

Generic Name

Levomenthol
Commonly known or available as Menthol

DrugBank Accession Number

DB00825

Background

Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Forming clear or white waxy, crystalline substance, menthol is typically solid at room temperature. (-)-Menthol is the naturally-occurring and main form of menthol, and is assigned the (1R,2S,5R) configuration. Menthol mediates anesthetic properties and anti-irritating properties locally, thus it is widely used to relieve minor throat irritations.

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 156.2652
Monoisotopic: 156.151415262
Chemical Formula: C₁₀H₂₀O

Synonyms

(-)-Menthol
(−)-(1R,3R,4S)-menthol
(−)-menthol
(1alpha,2beta,5alpha)-5-methyl-2(1-methylethyl)cyclohexanol
(1R-(1-α,2-β,5-α))-5-methyl-2-(1-methylethyl)cyclohexanol
(1R,3R,4S)-(−)-menthol
L-menthol
Levomenthol
Lévomenthol
Levomentholum
Levomentol
Mentol

External IDs

FEMA NO. 2665, (-)-
NPO-11
NSC-62788

Pharmacology

Indication

Used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants.

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Associated Conditions

Associated Therapies

Sports Massage

Contraindications & Blackbox Warnings

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Pharmacodynamics

Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Menthol induces a cooling sensation on the skin upon inhalation, oral ingestion, or topical application by stimulating the cold-sensitive receptors expressed on the skin, without actually causing a drop in the skin temperature.

Mechanism of action

Menthol primarily activates the cold-sensitive TRPM8 receptors in the skin. Menthol, after topical application, causes a feeling of coolness due to stimulation of 'cold' receptors by inhibiting Ca++ currents of neuronal membranes. It may also yield analgesic properties via kappa-opioid receptor agonism.

Target	Actions	Organism
ATransient receptor potential cation channel subfamily M member 8	inducer	Humans
ATransient receptor potential cation channel subfamily A member 1	inducer	Humans
ATransient receptor potential cation channel subfamily V member 3	inducer	Humans
UKappa-type opioid receptor	agonist	Humans
AVoltage-dependent L-type calcium channel	antagonist	Humans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

Levomenthol
- p-Menthane-3,-8-diol

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Menthol, DL: ORAL (LD50): Acute: 2900 mg/kg [Rat], 3100 mg/kg [Mouse]. DERMAL (LD50): Acute: 5001 mg/kg Rabbit.

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
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Abametapir	The serum concentration of Levomenthol can be increased when it is combined with Abametapir.
Acebutolol	Levomenthol may increase the arrhythmogenic activities of Acebutolol.
Aceclofenac	The risk or severity of hyperkalemia can be increased when Levomenthol is combined with Aceclofenac.
Acemetacin	The risk or severity of hyperkalemia can be increased when Levomenthol is combined with Acemetacin.
Acetyldigitoxin	Acetyldigitoxin may increase the arrhythmogenic activities of Levomenthol.
Acrivastine	The risk or severity of QTc prolongation can be increased when Levomenthol is combined with Acrivastine.
Adenosine	Levomenthol may increase the arrhythmogenic activities of Adenosine.
Ajmaline	Levomenthol may increase the arrhythmogenic activities of Ajmaline.
Alclofenac	The risk or severity of hyperkalemia can be increased when Levomenthol is combined with Alclofenac.
Alfentanil	Alfentanil may increase the bradycardic activities of Levomenthol.

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Food Interactions

No interactions found.

Products

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Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
0 Degrees Pain Relieving	Gel	5 g/100mL	Topical	Rlabs, Llc	2016-04-01	2016-08-11
2 in 1 Relief Value Pack		0.05 g/1g	Topical	Performance Health, LLC	2020-09-30	Not applicable
21ST CENTURY CHILDREN'S VAPOR BALM	Ointment		Topical	21ST CENTURY PRODUCTS SDN. BHD.	2020-09-08	Not applicable
4Jointz	Cream	1.5 g/100g	Topical	Arp(usa) Pty Ltd	2017-01-31	Not applicable
A.C.C Fresh and Cooling Scalp Mist	Liquid	0.3 g/100mL	Topical	Nature4 Co., Ltd.	2019-10-01	Not applicable
A.C.C Fresh and Cooling Scalp Mist	Liquid	0.3 g/100mL	Topical	Nature4 Co., Ltd.	2017-07-26	2019-12-01
Abejas y Viboras Brand Roll-On	Gel	5 mg/100mL	Topical	MENPER DISTRIBUTORS INC.	2021-03-01	Not applicable
Absorbine	Gel	100 mg/1g	Topical	W.F. Young, Inc.	2011-01-10	2013-01-31
Absorbine Back	Patch	5000 mg/8h	Transdermal	DSE Healthcare Solutions, LLC	2013-10-15	2013-10-01
Absorbine BACK Therapeutic Pain Relief	Patch	5 g/100g	Topical	Teh Seng Pharmaceutical Mfg. Co., Ltd.	2013-10-10	2021-04-30

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
1st Medxpatch With Lidocaine 4%	Levomenthol (5 g/1) + Capsaicin (0.025 g/1) + Lidocaine (4 g/1) + Methyl salicylate (20 g/1)	Patch	Topical	1ST MEDX LLC	2018-03-15	Not applicable
1st RELIEF TOPICAL	Levomenthol (10 mg/1mL) + Lidocaine (40 mg/1mL)	Spray	Topical	1st Class Pharmaceuticals	2014-12-02	Not applicable
24 Alopecia Reliefshampoo	Levomenthol (0.3 g/100mL) + Panthenol (0.2 g/100mL) + Salicylic acid (0.25 g/100mL)	Shampoo	Topical	DERMA CENTRIC INC	2020-08-08	Not applicable
3x Medicated Mouth Sore Gel	Levomenthol (0.1 g/100g) + Benzocaine (20 g/100g) + Zinc chloride (0.15 g/100g)	Gel	Oral	HEB	2020-06-02	Not applicable
3x Medicated Mouth Sore Gel	Levomenthol (0.1 g/100g) + Benzocaine (20 g/100g) + Zinc chloride (0.15 g/100g)	Gel	Oral	CVS	2020-06-05	Not applicable
3X Medicated Mouth Sore Gel	Levomenthol (0.1 g/100g) + Benzocaine (20 g/100g) + Zinc chloride (0.15 g/100g)	Gel	Oral	Rite Aid	2020-06-05	Not applicable
3x Medicated Mouth Sore Gel	Levomenthol (0.1 g/100g) + Benzocaine (20 g/100g) + Zinc chloride (0.15 g/100g)	Gel	Oral	Lornamead	2020-06-05	Not applicable
3X Medicated Toothache and Gum Gel	Levomenthol (0.26 g/100g) + Benzocaine (20 g/100g) + Zinc chloride (0.15 g/100g)	Gel	Oral	Rite Aid	2020-05-06	Not applicable
3x Medicated Toothache and Gum Gel	Levomenthol (0.26 g/100g) + Benzocaine (20 g/100g) + Zinc chloride (0.15 g/100g)	Gel	Oral	CVS	2020-06-05	Not applicable
3x Medicated Toothache and Gum Gel	Levomenthol (0.26 g/100g) + Benzocaine (20 g/100g) + Zinc chloride (0.15 g/100g)	Gel	Oral	Lornamead	2020-06-05	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
1st Medxpatch With Lidocaine 4%-rx	Levomenthol (5 1/1) + Capsaicin (0.0375 1/1) + Lidocaine (4 1/1) + Methyl salicylate (20 1/1)	Patch	Topical	1ST MEDX LLC	2018-03-15	Not applicable
1st Medxpatch With Lidocaine 4%-rx	Levomenthol (5 1/1) + Capsaicin (0.0375 1/1) + Lidocaine (4 1/1) + Methyl salicylate (20 1/1)	Patch	Topical	Direct Rx	2020-10-14	Not applicable
24 Alopecia Reliefshampoo	Levomenthol (0.3 g/100mL) + Panthenol (0.2 g/100mL) + Salicylic acid (0.25 g/100mL)	Shampoo	Topical	DERMA CENTRIC INC	2020-08-08	Not applicable
4125 First Aid Kit	Levomenthol (0.33 g/100g) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4204 First Aid Kit	Levomenthol (7 mg/1) + Acetaminophen (325 mg/1) + Benzalkonium chloride (0.13 g/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4210 First Aid Kit	Levomenthol (7 mg/1) + Acetaminophen (325 mg/1) + Benzalkonium chloride (0.13 g/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4221 First Aid Kit	Levomenthol (0.33 g/100g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4230 First Aid Kit	Levomenthol (0.33 g/100g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4232 First Aid Kit	Levomenthol (0.33 g/100g) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4240 First Aid Kit	Levomenthol (0.33 g/100g) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Calcium carbonate (420 mg/1) + Isopropyl alcohol (0.7 mL/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable

Chemical Identifiers

UNII: BZ1R15MTK7
CAS number: 2216-51-5
InChI Key: NOOLISFMXDJSKH-KXUCPTDWSA-N
InChI: InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
IUPAC Name: (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
SMILES: CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O

References

Synthesis Reference

Tatsuo Higashiyama, Isao Sakata, "Menthol glycoside, process for preparing the same and method for releasing menthol therefrom." U.S. Patent US4038270, issued December, 1972.

US4038270

General References

Not Available

External Links

Human Metabolome Database: HMDB0003352
KEGG Drug: D00064
KEGG Compound: C00400
PubChem Compound: 16666
PubChem Substance: 46506513
ChemSpider: 15803
BindingDB: 50318482
RxNav: 236388
ChEBI: 15409
ChEMBL: CHEMBL470670
ZINC: ZINC000001482164
Therapeutic Targets Database: DAP000876
PharmGKB: PA164776605
Guide to Pharmacology: GtP Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Menthol

AHFS Codes

84:08.00 — Antipruritics and Local Anesthetics
84:24.04 — Basic Lotions and Liniments
52:92.00 — EENT Drugs, Miscellaneous
92:01.00* — Herbs and Natural Products
84:08.01* — Other Analgesics
48:01.00* — Other Cold and Cough Preparations

MSDS

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Back Pain Lower Back Chronic	1
4	Completed	Prevention	Abnormal Menstrual Cycle	1
4	Completed	Treatment	Actinic Keratosis (AK)	1
4	Completed	Treatment	Back Pain Lower Back Chronic	1
4	Completed	Treatment	Cervical Ripening / Induction of Labour	1
4	Completed	Treatment	Cessation, Smoking / Smoking	1
4	Completed	Treatment	Diaper Dermatitis	1
4	Completed	Treatment	Infertility	1
4	Completed	Treatment	Sub-acute Back Pain	1
4	Not Yet Recruiting	Treatment	Embryo Transfer	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Active and Innovative Inc.
Bergen Brunswig
Chain Drug
Chattem Chemicals Inc.
CVS Pharmacy
Dofs Laboratories
Gold Mints Products Co. Ltd.
Herbion Pakistan Pvt Ltd.
Hisamitsu Pharmaceuticals
Humco
Major Pharmaceuticals
Medicine Shop
Mentholatum Co.
Nutri Dyn Products Limited
Pfizer Inc.
Walgreen Co.

Dosage Forms

Form	Route	Strength
Ointment	Topical
Gel	Oral
Kit	Ophthalmic; Oral; Topical
Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical
Kit	Ophthalmic; Respiratory (inhalation); Topical
Kit	Ophthalmic; Topical
Cream	Oral
Liquid	Topical	0.3 g/100mL
Gel	Topical	5 mg/100mL
Ointment	Nasal
Gel	Topical	100 mg/1g
Patch	Transdermal	5000 mg/8h
Patch	Topical	5000 mg/1h
Liquid	Topical	1.27 g/100mL
Patch	Topical	6500 mg/1h
Patch	Topical	6500 mg/8h
Patch	Topical	5000 mg/8h
Liquid	Topical	40 mg/1mL
Liquid	Topical	0.0127 g/1mL
Patch	Transdermal	6500 mg/8h
Cream	Topical	28 g/90mL
Gel	Topical	12 mg/1mL
Cream	Topical	70 mg/1mL
Gel	Topical	80 mg/1mL
Liquid	Topical	80 g/1000g
Spray	Topical	80 g/1000g
Stick	Topical	0.05138 g/1g
Solution	Topical	35 mg/1mL
Cream	Topical	35 mg/1mL
Lozenge	Oral	7.6 1/1
Lozenge	Oral	8.6 1/1
Tape	Topical
Aerosol, spray	Percutaneous; Topical; Transdermal
Aerosol, spray	Cutaneous; Topical; Transdermal
Liquid	Topical	1.05 g/84g
Cream	Topical	0.2 g/4g
Patch	Topical	30 mg/1
Patch	Topical	2.5 mg/100mg
Ointment	Topical	0.31 g/100g
Gel	Topical	70 mg/1L
Spray	Topical	70 mg/1L
Spray	Topical	700 mL/1L
Ointment	Enteral
Liquid	Buccal
Spray	Topical	5 mL/100mL
Lotion	Topical	0.15 g/100g
Rinse	Oral
Mouthwash	Oral
Spray	Topical	5 g/100mL
Spray	Topical	10 g/100mL
Gel	Topical	3.2 g/100mL
Gel	Topical	3 g/100mL
Liquid	Topical	3 g/100mL
Gel	Topical	2.5 g/100mL
Gel	Topical	3.969 g/113.4g
Gel	Topical	3.969 g/90g
Cream	Topical	3.7 g/100g
Lotion	Topical	1 g/100g
Cream	Topical	12.5 mg/1g
Cream	Topical	1.4125 g/113g
Cream	Topical	8.5 mg/85g
Lozenge	Oral	2.8 mg/1
Patch	Topical	5 mg/100mg
Gel	Topical	1.25 g/100g
Powder	Topical	0.15 g/100g
Stick	Topical	1.34 g/57g
Gel, dentifrice	Topical	10 mg/1g
Cream	Topical	10 g/100g
Mouthwash	Buccal
Solution	Topical	100 mg/1mL
Patch	Topical; Transdermal
Cream	Topical	4 g/100g
Spray	Topical	9 g/100mL
Liquid	Respiratory (inhalation)	6 %
Stick	Topical	2.6 mg/1g
Cream	Topical	25 mg/1mL
Patch	Topical	4.62 g/100g
Liniment	Topical	3.7 g/100mL
Gel	Topical	3 g/120mL
Gel	Topical	2.4 mg/120mL
Gel	Topical	3 mg/120mL
Gel	Topical	1.5 g/60mL
Oil	Percutaneous; Topical; Transdermal
Gel	Topical
Tablet	Transmucosal
Ointment	Cutaneous
Gel	Topical	50 mg/1g
Patch	Topical	50 mg/1
Tablet, chewable	Oral
Gel	Topical	4.5 g/100g
Gel	Topical	5.085 g/113g
Spray	Topical	11.8 g/118mL
Lozenge	Oral	9.1 mg/1
Lozenge	Oral	5.97 mg/1
Liquid	Topical	4.2 mL/60mL
Gel	Topical	1 g/10mL
Gel	Topical	8.9 g/89mL
Lotion	Topical	5.11 g/113g
Gel	Topical	30 mg/1g
Gel	Topical	2.1 g/60mL
Gel	Topical	4.0 g/100mL
Gel	Topical	0.03 g/1g
Spray	Topical	105 mg/1mL
Patch	Topical	56 mg/1g
Gel	Topical	35 mg/1mL
Spray	Topical
Gel	Topical	105 mg/1mL
Stick	Topical	100 mg/1g
Stick	Topical	105 mg/1g
Liquid	Topical	105 mg/1mL
Solution	Topical
Gel	Topical	3.5 g
Spray	Topical	590 mg/1mL
Patch	Topical	0.156 g/1
Patch	Topical	0.348 g/1
Salve	Topical	1 g/100g
Salve	Topical	1.1 g/100g
Soap	Topical	1 g/100mL
Gel	Topical	2.0 g/100g
Gel	Topical	.02 g/1g
Powder	Topical	1.5 mg/1g
Powder	Topical	10 mg/1g
Liquid	Topical	4.2 g/84g
Liquid	Topical	70 mg/1mL
Cream	Topical	100 mg/1mL
Cream	Topical	170 g/90mL
Ointment	Respiratory (inhalation); Topical
Gel	Topical	0.025 g/1g
Solution	Respiratory (inhalation)
Ointment	Respiratory (inhalation)
Ointment	Topical
Liquid	Topical	5 mg/1mL
Cream	Topical	0.5 g/100g
Cream	Topical	40 mg/1g
Patch	Topical	0.05 mg/1
Lotion	Topical	5 mg/1000mL
Oil	Topical	0.08 kg/1kg
Oil	Topical	8 g/100mL
Cream	Topical	125 mg/1mL
Ointment	Topical	1.25 g/100mL
Cream	Topical	1.25 g/100mL
Cream	Topical	1.5 g/100g
Liquid	Topical	0.25 g/100mL
Liquid	Transdermal
Shampoo	Topical	0.3 g/100mL
Oil	Topical	1.5 g/50g
Lozenge	Oral	4.5 mg/1
Salve	Topical	27.6 mg/1g
Oil
Lozenge	Oral
Gel	Topical	2 g/100g
Gel	Topical
Gel	Topical	1 mg/100mL
Gel	Topical	0.1 mg/1mL
Cream	Topical	20 mg/1g
Liquid	Nasal
Cream	Topical	0.075 g/1g
Spray	Topical	16 g/100mL
Patch	Topical	240 mg/1
Patch	Topical	500 mg/1
Patch	Topical	875 mg/1
Patch	Topical	400 mg/1
Liquid	Topical	16 g/100mL
Patch	Topical	5 g/100g
Lipstick	Topical
Aerosol, spray	Topical	6 mL/60mL
Gel	Topical	0.46 L/3.8L
Ointment	Topical	13 mL/90mL
Swab	Topical	.96 mL/8mL
Gel	Topical	10 g/100mL
Gel	Topical	4 g/100g
Patch	Topical	1.14 g/100g
Patch	Topical	100 mg/5mg
Granule, for solution	Oral	490 mg/5g
Spray	Topical	16 g/100g
Gel	Topical	16 g/100g
Cream	Topical	10 g/100mL
Mouthwash	Buccal; Oral
Gel	Transdermal
Lozenge	Oral	16.0 mg/1
Lozenge	Oral	13.2 mg/1
Lozenge	Oral	15.3 mg/1
Granule, for solution	Topical	11.7 mg/1mL
Patch	Topical	0.75 g/1
Patch	Topical	5 mg/1g
Lozenge	Oral	7.2 mg/7.2mg
Tablet	Oral	7.5 mg/7.5mg
Tablet	Oral	5.8 mg/5.8mg
Tape	Cutaneous; Extracorporeal	0.05 g/1g
Lotion	Respiratory (inhalation)
Patch	Topical	0.05 g/1g
Gel	Topical	36 mg/1mL
Liquid	Topical	160 mg/1mL
Lozenge	Oral	20 mg/1
Gel, dentifrice	Dental
Lozenge	Oral	4 mg/1
Lotion	Topical	1 mg/1mL
Cream	Topical	0.025 g/1g
Solution	Topical	60 mg/1mL
Stick	Topical	10 g/100g
Plaster	Transdermal
Suppository	Rectal
Patch, extended release	Transmucosal	2.5 mg/194.85mg
Patch, extended release	Transmucosal	2.5 mg/194.851
Tablet, extended release	Oral; Topical	2.5 mg/150mg
Kit	Topical
Cream	Topical	1.8 g/100g
Lotion	Topical	1.5 mg/1g
Liquid	Topical	50 mg/1mL
Liquid	Topical	20 mg/1mL
Patch	Topical	5 g/1
Solution / drops	Buccal
Patch	Topical	205.5 mg/1
Oil	Topical	3.5 g/100mL
Liquid	Topical	30 mg/1mL
Aerosol, spray	Topical	3 g/100mL
Spray	Topical
Patch	Topical	0.5 g/1g
Gel	Topical	0.06 g/1g
Gel	Topical	3.89 g/100g
Gel	Topical	4.58 g/100g
Cream	Topical	40 mg/1mL
Spray	Topical	3.7 mg/1g
Solution	Topical
Cream	Topical	2.625 g/75g
Gel	Topical	80 mg/1g
Cream	Topical	100 mg/1g
Patch	Cutaneous
Lozenge	Oral	8.3 mg/1
Lozenge	Oral	8.5 mg/1
Cream	Topical	50 mg/1mL
Liquid	Respiratory (inhalation)	1 %w/v
Liquid	Topical	35 mg/1mL
Disc	Topical
Patch	Topical	4 g/1
Spray	Topical	1000 mg/100mL
Spray	Topical	1700 mg/100mL
Spray	Topical	865.4 mg/50mL
Cream	Topical	60 mg/1mL
Liquid	Topical	2.5 g/100mL
Spray	Topical	1.25 g/100mL
Patch	Topical	0.056 g/1g
Cream	Topical	2.8 g/56g
Solution	Buccal; Oral
Stick	Topical	0.035 g/7g
Liquid	Topical	16 mg/100mL
Gel	Dental
Spray	Topical	4 g/100mL
Syrup	Oral
Cream	Topical	12.13 mg/1mL
Ointment	Topical	9.6 mL/60mL
Lotion	Topical	0.1 g/100mL
Capsule
Liquid	Respiratory (inhalation)
Gel	Topical	100 mg/1mL
Plaster	Topical; Transdermal
Gel	Topical	2 g/100mL
Gel	Topical	4 g/100mL
Stick	Topical	20 mg/1g
Patch	Topical	750 mg/1
Gel	Topical	35 mg/1g
Spray	Topical	100 mg/1g
Gel	Topical	33 mg/1mL
Lotion	Topical	12.5 mg/1mL
Patch	Topical	200 mg/1
Swab	Topical
Solution	Oral
Tablet
Jelly	Topical
Spray	Topical	2.25 g/100mL
Gel	Topical	0.07 g/1g
Gel	Topical	0.16 g/1g
Kit	Oral; Topical
Cream	Topical	16 g/1
Spray	Topical	16 g/1
Granule, for solution	Oral	270 mg/6g
Cream	Topical	1.25 mg/1mL
Crystal	Topical
Lotion	Topical	13.5 mg/1mL
Cream	Topical	0.1 g/100mL
Oil	Topical	24 mg/1mL
Gel	Topical	4.2 mg/100mL
Spray	Oropharyngeal
Gel	Topical	160 mg/1mL
Spray	Oral; Topical
Patch	Cutaneous; Topical; Transdermal
Ointment	Topical	1 g/100g
Solution, concentrate	Oral
Lotion	Topical	0.005 g/1g
Powder	Topical	0.008 g/1g
Powder	Topical	0.8 g/100g
Spray	Topical	1 g/100g
Lotion	Topical	0.0015 g/1g
Powder	Topical	0.0015 g/1g
Cream	Topical	16 g/100g
Cream	Topical	6.25 g/100g
Cream	Topical	62.5 mg/1mL
Lotion	Cutaneous
Oil	Topical	20 mg/500mg
Cream	Topical	5 g/100mL
Liquid	Topical	5 g/100mL
Lozenge	Oral	7 mg/1
Lozenge	Oral	5.7 mg/1
Lozenge	Oral	6.8 mg/1
Lozenge	Oral	1.8 mg/1
Lozenge	Oral	8.8 mg/1
Lozenge	Oral	8.2 mg/1
Tablet	Oral
Lozenge	Oral	6.4 mg/1
Lozenge	Oral	4.3 mg/1
Lozenge	Oral	2.5 mg/1
Lozenge	Oral	2.7 mg/1
Lozenge	Oral	4.6 mg/1
Lozenge	Oral	5.6 mg/1
Lozenge	Oral	3.2 mg/1
Lozenge	Oral	9.4 mg/1
Lozenge	Oral	3.7 mg/1
Lozenge	Oral	6.6 mg/1
Lozenge	Oral	6.7 mg/1
Lozenge	Oral	2.9 mg/1
Lozenge	Oral	15 mg/1
Lozenge	Oral	3.1 mg/1
Lozenge	Oral	18 mg/1
Syrup	Oral	0.1 g/100mL
Gel	Topical	2.0 g/100mL
Poultice	Transdermal	280 mg/12g
Spray	Topical	10.4 g/100g
Lotion	Topical	4 g/100g
Gel	Topical	3402 mg/85.05g
Lotion	Topical	9068 mg/226.7g
Gel	Topical	2832 mg/70.8g
Spray	Topical	8925 mg/85g
Cream	Topical	7.4 g/100g
Mouthwash	Dental	0.2 g/100mL
Mouthwash	Dental	200 mg/100mL
Ointment	Rectal
Cream	Topical	2 mg/100mL
Gel	Topical	8 mg/100mL
Lozenge	Oral	4.8 mg/1
Spray	Topical	0.06 g/1g
Lozenge	Oral	5.5 mg/1
Lozenge	Oral	1.6 mg/1
Lozenge	Oral	6 mg/1
Lozenge	Oral	5.5 mg/2.51
Lozenge	Oral	9.99 mg/1
Lozenge	Oral	3 mg/1
Lozenge	Oral	3.18 mg/1
Lozenge	Oral	7.5 1/1
Pastille	Oral	0.281 mg/1
Pastille	Oral	7.6 mg/1
Lozenge	Oral	3.9 mg/1
Lozenge	Oral	8.6 mg/2.5g
Cream	Topical	12.5 mg/1mL
Gel	Topical	2.27 g/227g
Patch	Topical	285 mg/5700mg
Gel	Topical	0.3 g/100mL
Liquid	Topical	12.5 mg/1mL
Gel	Topical	34.79 mg/1mL
Cream	Topical	2 mg/1g
Gel	Topical	2.84 mg/227mg
Gel	Topical	.02 g/100g
Cream	Topical	30 mg/1g
Gel	Topical	16.95 g/113g
Gel	Topical	55 mg/1mL
Spray	Topical	89 mg/1mL
Patch	Topical	336 mg/1
Patch	Topical	210 mg/1
Patch	Topical	205.50 mg/1
Patch	Topical	428.50 mg/1
Patch	Topical	50.25 mg/1
Patch	Topical	866.25 mg/1
Patch	Topical	787.5 mg/1
Patch	Topical	29.3 mg/1
Liquid	Topical	140.8 mg/1mL
Patch	Topical	750.00 mg/1
Drug delivery system	Topical
Spray	Topical	160 mg/1mL
Oil	Topical	16 g/100mL
Liquid	Topical	12.5 mg/1g
Gel	Topical	5 mg/5mL
Gel	Topical	1.25 mL/100mL
Cream	Topical	0.525 g/105g
Cream	Topical	2.5 g/500g
Shampoo	Topical	0.0025 g/500g
Liquid	Topical	0.1 g/100mL
Cream	Topical	2.2 g/100g
Soap	Topical	4 mg/1mL
Lozenge	Oral	5 mg/100mg
Cream	Topical	1.8 g/100mL
Cream	Topical	50 mg/1g
Lotion	Topical	8.5 g/100mL
Liquid	Topical	10 g/100mL
Shampoo	Topical	1 mg/1mL
Lotion	Topical	4.49 g/100mL
Stick	Topical
Cream	Topical	30 mg/1mL
Gel	Topical	10 g/100g
Gel	Topical	10 mg/1g
Lotion	Topical	8.5 mg/88mL
Lotion	Topical	3.5 g/100g
Powder	Topical	1 g/100g
Cream	Dental
Plaster; swab	Topical
Plaster	Transdermal	3.0 g/100g
Oil	Topical	0.8 mg/50mL
Gel	Topical	12.5 mg/1mL
Gel	Topical	20 mg/1g
Spray	Topical	0.005 g/1g
Lozenge	Oral	7.5 mg/1
Lozenge	Oral	5.4 mg/1
Lozenge	Oral	5 mg/1
Aerosol, spray	Topical
Powder	Topical	2 g/100g
Lozenge	Oral	5.75 mg/1
Gel	Topical	0.23 mg/1mL
Gel	Topical	0.24 mg/1mL
Lozenge	Oral	1.0 mg/1
Lotion	Topical	11.2 g/224g
Cream	Topical	5.6 g/112g
Lotion	Topical	3 g/100g
Mouthwash	Dental; Oral
Gel	Topical	50 mg/1mL
Powder	Topical	0.1 g/1g
Lipstick	Topical	5 mg/1g
Shampoo	Topical
Gel	Topical	.07 g/1g
Powder	Topical	2.26 g/283g
Powder	Topical	0.42 g/283g
Jelly	Topical
Stick	Topical	0.9 g/100g
Patch	Topical	428.5 mg/1
Patch	Topical
Cream	Topical	5 1/85g
Patch	Topical	20 mg/11.7g
Lozenge	Oral	5.8 mg/1
Cloth	Topical	0.05 g/1mL
Gel	Topical	4.54 g/227g
Spray	Topical	105 mg/1g
Cream	Topical	5 g/100g
Oil	Topical	6 mg/50mL
Patch	Topical	15 mg/1g
Cream	Topical	26 mg/1mL
Lozenge	Oral	0.7 g/1g
Lozenge	Oral	0.86 g/1g
Oil	Topical	0.5 mg/50mL
Powder	Topical	2.8 g/283g
Powder	Topical	2.83 g/283g
Spray	Topical	2 g/100mL
Patch	Topical	440 mg/1
Patch	Topical	910 mg/1
Lozenge	Oral	5.4 1/1
Pastille	Oral	5.8 mg/1
Lozenge	Oral	8.0 mg/1
Pastille	Oral	20 mg/1
Ointment	Topical	27 mg/1g
Gel	Topical	30 mg/1mL
Lotion	Topical
Powder	Topical
Powder	Cutaneous
Lotion	Topical	1.3 g/100g
Salve	Topical	0.5 g/100g
Liniment	Percutaneous; Transdermal	1 g/3500mL
Salve	Topical	1 g/1500g
Cream	Topical	4 g/100mL
Cream	Topical	15 mg/1mL
Gel	Topical	0.02 g/1g
Gel	Topical	160 mg/1g
Solution	Topical	40 mg/1mL
Gel	Topical	40 mg/1g
Cream	Topical	0.028 g/28g
Cream	Topical	0.106 g/106g
Cream	Topical	0.224 g/224g
Liquid	Topical	1.8 mL/90mL
Cream	Topical	3 g/100g
Cream	Topical	1.5 g/100mL
Lozenge	Oral	8.6 mg/1
Spray	Oral
Cream	Topical	2.5 g/100g
Gel	Topical	3.5 g/100mL
Gel	Topical	2.5 g/100g
Gel	Topical	25 mg/1g
Cream	Topical
Cream	Topical	1.05 g/42g
Spray	Topical	100 mg/1mL
Cream	Topical	5 uL/1mL
Tape	Topical	10 g/100g
Pill	Vaginal	0.5 g/100g
Lotion	Topical	60 mg/1mL
Ointment	Rectal	275 mg/48.2g
Mouthwash	Oral	0.3 mg/1mL
Lozenge	Oral	3 1/1
Pastille	Oral	0.18 mg/1
Pastille	Oral	4.8 mg/1
Lozenge	Oral	1.5 mg/1
Lozenge	Oral	2.0 mg/1
Lozenge	Oral	3.5 mg/1
Lozenge	Oral	1.2 mg/1
Gel	Topical	3 g/100g
Lozenge	Oral	2 mg/3g
Cream	Topical
Cream	Topical	10 mg/1g
Lotion	Topical	5 mg/1g
Spray	Topical	0.16 g/1g
Pastille	Oral
Lozenge	Oral	8 mg/1
Aerosol, spray	Topical	1 mg/100mg
Aerosol, spray	Topical	5 mg/100mg
Cream	Topical	10 mg/100mg
Liquid	Topical	10 mg/100mg
Spray	Topical	0.1 mg/100mg
Aerosol, foam	Topical	5 mg/100mg
Liniment	Topical
Liquid	Topical	0.2 g/10mL
Tablet, soluble	Oral
Powder	Oral
Spray	Topical	0.5 g/100mL
Kit	Oral
Ointment	Topical	1.25 g/100g
Oil	Transdermal	100 mg/50mL
Gel	Topical	0.33 mg/660mL
Gel	Topical	0.63 g/632.19g
Lozenge	Oral	10 mg/1
Pastille	Oral	10 mg/1
Gel	Topical	85 mg/1mL
Strip	Dental
Gel	Oral; Topical
Film, soluble	Oral
Paste	Topical
Lozenge	Oral	1.9 mg/1
Cream	Topical	1.3 g/100g
Cream	Topical	8 g/100g
Gel	Topical	7 g/100mL
Liquid	Topical	6 g/100mL
Cream	Topical	14 g/280g
Granule	Topical	1.6 mg/1g
Liquid	Topical	2.23 mg/1mL
Oil	Topical	12.18 mg/1mL
Oil	Topical	17.62 mg/1mL
Patch	Topical	105 mg/1
Cream	Topical	17.5 mg/1mL
Cream	Topical	6 g/100mL
Aerosol, spray	Topical	6 g/100mL
Gel	Topical	15 mg/1mL
Gel	Topical	17.5 mg/1mL
Liquid	Topical	0.16 g/1mL
Patch	Topical	5 mg/1
Spray	Topical	10.5 g/100g
Patch	Topical	160 mg/1mL
Tincture	Topical
Gel	Topical	2.4 g/120g
Spray	Topical	7 g/100mL
Gel	Topical	4.54 g/1g
Patch	Topical	0.2 1/1
Patch	Topical	.05 mg/1g
Patch	Topical	50 mg/1g
Patch	Topical	6 g/1
Patch	Topical	30 mg/1mL
Cream	Topical	35 mg/1g
Cream	Topical	4.25 g/85g
Lotion	Topical	160 mg/1mL
Patch	Topical	775 mg/1
Patch	Topical	5 g/1001
Patch	Topical	1.22 g/1
Patch	Topical	350 mg/1
Lotion	Topical	7.5 g/100g
Liquid	Oral
Gel	Topical	1.0 g/100g
Gel	Topical	31 mg/1mL
Spray	Topical	104 mg/1mL
Powder	Topical
Powder	Topical	20 mg/2g
Gel	Topical	1 g/100g
Lotion / shampoo	Topical
Cream	Topical	20 mg/1mL
Shampoo	Topical	0.1 g/100mL
Ointment	Topical	13 g/100g
Oil	Topical	15 g/100mL
Gel	Topical	120 mg/1mL
Gel	Topical	120 mg/1g
Liquid	Topical	140 mg/1mL
Gel	Topical	40 mg/1mL
Gel	Topical	2 mL/100mL
Spray	Topical	10.5 g/10.5mL
Cream	Cutaneous; Topical
Ointment	Cutaneous; Topical
Gel	Cutaneous; Topical
Spray	Topical	8 g/100mL
Gel	Topical	8 g/100mL
Gel	Topical	10.5 g/10.5mL
Ointment	Topical	16 g/16mg
Lozenge	Oral	2 mg/1
Lotion	Topical	3 g/100mL
Patch	Percutaneous; Topical; Transdermal
Liquid	Topical	80 mg/1mL
Patch	Topical	0.875 g/100g
Cream	Topical	1.25 g/100g
Gel	Topical	3.5 mg/1L
Liquid	Topical	34.86 g/1L
Liquid	Topical	34.79 g/1L
Cream	Topical	118.29 mL/100mL
Lotion	Topical	1.5 g/100mL
Lotion	Topical	0.5 g/100mL
Lotion	Topical	1.25 g/100mL
Ointment	Topical	12.7 mg/1g
Lozenge	Oral	6.1 mg/1001
Cream	Topical	3.0 g/100g
Liquid	Topical	1.2 mg/15mL
Ointment	Topical	0.2 g/100g
Ointment	Topical	937.5 mg/1g
Gel	Topical	27.5 mg/1g
Oil	Topical	7 mg/50mL
Cream	Topical	2 g/100g
Patch	Topical	50 g/1
Gel	Topical	40 mg/1
Cream	Topical	0.006 g/0.1g
Cream	Topical	6 mg/100mL
Gel	Topical	6.0 g/100g
Gel	Topical	33.2 g/355mL
Gel	Topical	8.3 g/88.5mL
Kit	Topical	24.03 mg/1mL
Capsule	Oral
Solution	Cutaneous
Cream	Rectal
Spray	Topical	4 g/4mL
Patch	Topical	1000 mg/1
Patch	Topical	600 mg/1
Patch	Topical	900 mg/1
Gel	Percutaneous; Topical; Transdermal
Spray	Cutaneous
Aerosol, foam	Percutaneous; Topical; Transdermal
Ointment	Percutaneous; Topical; Transdermal
Poultice	Percutaneous; Topical; Transdermal	175 mg/1
Gel	Topical	150 mg/1g
Liquid	Topical
Gel	Topical	140 mg/1mL
Paste, dentifrice	Topical	0.2 g/100g
Pastille	Oral	0.69 mg/1
Plaster	Topical
Gel	Topical	12.5 mg/1g
Gel	Topical	12.6 mg/1g
Gel	Topical	2.6 mg/100g
Kit	Topical	10 mg/1g
Stick	Topical	10 mg/1g
Liquid	Cutaneous; Topical; Transdermal
Patch	Topical	0.85 g/17g
Cream	Oral	6 g/100mL
Spray	Topical	5 mg/1mL
Lozenge	Oral	6.5 mg/1
Cream	Topical	15 mg/1g
Gel	Topical	2.25 g/100g
Mouthwash	Dental
Solution / drops	Topical
Stick	Topical
Gel	Topical	2 mg/100mL
Liquid	Topical	4 g/100mL
Tablet	Oral	5.8 mg/1
Gel	Topical	0.1 g/1g
Gel	Topical	100 g/1mL
Liquid	Topical	100 mg/1mL
Gel	Topical	6 g/100g
Spray	Topical	60 mg/1mL
Spray	Topical	80 mg/1mL
Gel	Topical	0.08 g/1g
Oil	Topical	1 g/93mL
Lozenge	Oral	5.8 1/1
Lozenge	Oral	6.9 mg/1
Lozenge	Oral	2.6 mg/1
Lozenge	Oral	4.1 mg/1
Lozenge	Oral	7.6 mg/1
Lozenge	Oral	5.52 mg/1
Lozenge	Oral	1.1 mg/1
Lozenge	Oral	2.2 mg/1
Ointment	Topical	1 mg/1g
Cream	Topical	14 mg/1mL
Liniment	Transdermal	3.5 mg/100mL
Oil	Topical	24.56 mg/1mL
Oil	Topical	1.3 mg/50mg
Ointment	Topical	8 g/100g
Patch	Topical	4 g/100g
Stick	Topical	0.6 g/100g
Gel	Topical	3.5 mg/100mL
Lozenge	Oral	5.3 mg/1
Cream	Topical	130 mg/1g
Gel	Topical	60 mg/1mL
Gel	Topical	.04 g/1g
Gel	Topical	3.9 g/100mL
Spray	Topical	6 g/100mL
Pastille	Oral	2.5 mg/1
Lozenge	Oral	6 mg/4.2g
Patch	Transdermal	3 g/1
Patch	Transdermal
Plaster	Transdermal
Cream	Topical	0.1 g/100g
Liquid	Topical	0.002 g/4mL
Liquid	Topical	0.06 g/120mL
Plaster	Cutaneous
Plaster
Ointment	Topical	24 mg/1g
Poultice	Transdermal
Dressing	Oral
Cream	Topical	1.4 g/100g
Lotion	Topical	0.5 g/100g
Patch	Topical	150 mg/1
Patch	Topical	300 mg/1
Patch	Topical	375 mg/1
Gel	Topical	5.0 g/100mL
Spray	Topical	10.5 g/100mL
Liquid	Topical	5 g/100g
Gel	Topical	8.5 g/100mL
Lotion	Topical	1.35 mg/100mL
Cream	Cutaneous
Gel	Topical	4.56 g/114g
Gel	Topical	5 g/100mL
Gel	Topical	1.25 g/100mL
Cream	Topical	45 mg/1mL
Liquid	Topical	25 g/100g
Salve	Topical
Oil	Topical
Solution	Intrasinal; Respiratory (inhalation)
Lozenge	Oral	1.7 mg/1
Lozenge	Oral	3.3 mg/1
Stick	Nasal
Inhalant	Nasal
Lozenge	Oral	5 mg
Liquid	Oral
Liquid	Topical	0.9 g/100mL
Gel	Topical	0.1 g/100g
Spray	Oral	2 g/100mL
Gel	Topical	6 g/120g
Patch	Topical	5 1/1
Oil	Transdermal
Oil	Topical
Lotion	Topical	1 g/100mL
Solution	Nasal
Cream	Topical	0.03 g/1g
Gum, chewing	Oral
Gel	Topical	3 g/227g
Paste, dentifrice	Topical
Liniment	Percutaneous; Transdermal	3 g/100mL
Liniment	Percutaneous; Transdermal
Patch	Topical	10 mg/1000mg
Gel	Topical	20 g/1L
Gel	Topical	37 mg/1g
Gel	Topical	37 mg/1mL
Spray	Topical	37 mg/1g
Gel	Topical	70 mg/1g
Spray	Topical	160 mg/1g
Spray	Topical	90 mg/1mL
Lozenge	Oral
Ointment
Emulsion	Oral
Suspension	Oral
Pill
Liquid	Dental
Gel	Topical	4 %w/w
Gel	Topical	7 %w/w
Emulsion	Topical

Prices

Unit description	Cost	Unit
Cool & heat patch	1.2USD	patch
Icy hot medicated 5% patch	1.2USD	patch
Bengay pain relieving patch	1.13USD	patch
CVS Pharmacy pain relieving patch	1.11USD	patch
Cold & hot pain rel patch	1.05USD	patch
Nuprin muscle & joint patch	1.03USD	patch
Mentholatum pain patch	0.93USD	patch
CVS Pharmacy cold & hot medicated patch	0.89USD	patch
Salonsip aqua-patch	0.69USD	patch
Menthol crystal	0.49USD	g
Menthol cough drops	0.06USD	each
CVS Pharmacy menthol drops	0.03USD	each
Pv menthol cough drops	0.02USD	each

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8809615	No	2014-08-19	2030-01-03
US9233184	No	2016-01-12	2027-08-01

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	43 °C	PhysProp
boiling point (°C)	212 °C	PhysProp
water solubility	490 mg/L (at 25 °C)	CHEM INSPECT TEST INST (1992)
logP	3.40	GRIFFIN,S ET AL. (1999)

Predicted Properties

Property	Value	Source
Water Solubility	0.558 mg/mL	ALOGPS
logP	2.68	ALOGPS
logP	2.66	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	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	47.45 m³·mol^-1	ChemAxon
Polarizability	19.69 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

Property	Value	Probability
Human Intestinal Absorption	+	0.9944
Blood Brain Barrier	+	0.9408
Caco-2 permeable	+	0.8127
P-glycoprotein substrate	Non-substrate	0.569
P-glycoprotein inhibitor I	Non-inhibitor	0.8765
P-glycoprotein inhibitor II	Non-inhibitor	0.9397
Renal organic cation transporter	Non-inhibitor	0.8591
CYP450 2C9 substrate	Non-substrate	0.7798
CYP450 2D6 substrate	Non-substrate	0.746
CYP450 3A4 substrate	Substrate	0.5912
CYP450 1A2 substrate	Non-inhibitor	0.7188
CYP450 2C9 inhibitor	Non-inhibitor	0.8484
CYP450 2D6 inhibitor	Non-inhibitor	0.9451
CYP450 2C19 inhibitor	Non-inhibitor	0.9185
CYP450 3A4 inhibitor	Non-inhibitor	0.9458
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9546
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.8439
Biodegradation	Not ready biodegradable	0.7808
Rat acute toxicity	1.7142 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8439
hERG inhibition (predictor II)	Non-inhibitor	0.7727

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (2.96 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-MS (1 TMS)	GC-MS	splash10-0006-1900000000-cc06fe70d7649d059f92
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - EI-B	GC-MS	splash10-00ea-9100000000-0be605183591bf5f33a0
GC-MS Spectrum - EI-B	GC-MS	splash10-00ea-9100000000-977cf0c036d597693beb
GC-MS Spectrum - GC-MS	GC-MS	splash10-0006-1900000000-cc06fe70d7649d059f92
Mass Spectrum (Electron Ionization)	MS	splash10-00ea-9100000000-602436010653202a4da9
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	LC-MS/MS	splash10-053r-9300000000-d9c35833e73c8655fb23
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	LC-MS/MS	splash10-0ldl-9000000000-abf2f837df49fbedc53c
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	LC-MS/MS	splash10-0007-9000000000-adee6385265c6606326d
MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	LC-MS/MS	splash10-00ea-9100000000-e3f1b7b69a021063fabb
MS/MS Spectrum - EI-B (JEOL JMS-DX-300) , Positive	LC-MS/MS	splash10-00ea-9100000000-d69777874c9615b7e751
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Targets

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Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	29000	N/A	N/A	17293875
IC 50 (nM)	92000	N/A	N/A	17293875
Kd (nM)	14400	N/A	N/A	17293875

Details1. Transient receptor potential cation channel subfamily M member 8

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inducer

General Function: Calcium channel activity
Specific Function: Receptor-activated non-selective cation channel involved in detection of sensations such as coolness, by being activated by cold temperature below 25 degrees Celsius. Activated by icilin, eucalypto...
Gene Name: TRPM8
Uniprot ID: Q7Z2W7
Uniprot Name: Transient receptor potential cation channel subfamily M member 8
Molecular Weight: 127684.035 Da

References

Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. [PubMed:12654248]
Behrendt HJ, Germann T, Gillen C, Hatt H, Jostock R: 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. Epub 2004 Feb 2. [PubMed:14757700]
Bandell M, Story GM, Hwang SW, Viswanath V, Eid SR, Petrus MJ, Earley TJ, Patapoutian A: Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron. 2004 Mar 25;41(6):849-57. [PubMed:15046718]
Andersson DA, Chase HW, Bevan S: TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH. J Neurosci. 2004 Jun 9;24(23):5364-9. [PubMed:15190109]
Stein RJ, Santos S, Nagatomi J, Hayashi Y, Minnery BS, Xavier M, Patel AS, Nelson JB, Futrell WJ, Yoshimura N, Chancellor MB, De Miguel F: Cool (TRPM8) and hot (TRPV1) receptors in the bladder and male genital tract. J Urol. 2004 Sep;172(3):1175-8. [PubMed:15311065]
Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. [PubMed:7529306]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	28400	N/A	N/A	20356305

Details2. Transient receptor potential cation channel subfamily A member 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inducer

General Function: Temperature-gated cation channel activity
Specific Function: Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in t...
Gene Name: TRPA1
Uniprot ID: O75762
Uniprot Name: Transient receptor potential cation channel subfamily A member 1
Molecular Weight: 127499.88 Da

References

Story GM, Peier AM, Reeve AJ, Eid SR, Mosbacher J, Hricik TR, Earley TJ, Hergarden AC, Andersson DA, Hwang SW, McIntyre P, Jegla T, Bevan S, Patapoutian A: ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures. Cell. 2003 Mar 21;112(6):819-29. [PubMed:12654248]
Namer B, Seifert F, Handwerker HO, Maihofner C: TRPA1 and TRPM8 activation in humans: effects of cinnamaldehyde and menthol. Neuroreport. 2005 Jun 21;16(9):955-9. [PubMed:15931068]
Macpherson LJ, Hwang SW, Miyamoto T, Dubin AE, Patapoutian A, Story GM: More than cool: promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci. 2006 Aug;32(4):335-43. Epub 2006 Jul 7. [PubMed:16829128]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Details3. Transient receptor potential cation channel subfamily V member 3

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inducer

General Function: Calcium channel activity
Specific Function: Putative receptor-activated non-selective calcium permeant cation channel. It is activated by innocuous (warm) temperatures and shows an increased response at noxious temperatures greater than 39 d...
Gene Name: TRPV3
Uniprot ID: Q8NET8
Uniprot Name: Transient receptor potential cation channel subfamily V member 3
Molecular Weight: 90635.115 Da

References

Macpherson LJ, Hwang SW, Miyamoto T, Dubin AE, Patapoutian A, Story GM: More than cool: promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci. 2006 Aug;32(4):335-43. Epub 2006 Jul 7. [PubMed:16829128]

Details4. Kappa-type opioid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Opioid receptor activity
Specific Function: G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name: OPRK1
Uniprot ID: P41145
Uniprot Name: Kappa-type opioid receptor
Molecular Weight: 42644.665 Da

References

Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A, Ghelardini C: Menthol: a natural analgesic compound. Neurosci Lett. 2002 Apr 12;322(3):145-8. [PubMed:11897159]
Taniguchi Y, Deguchi Y, Saita M, Noda K: [Antinociceptive effects of counterirritants]. Nihon Yakurigaku Zasshi. 1994 Dec;104(6):433-46. [PubMed:7851817]

Details5. Voltage-dependent L-type calcium channel (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Voltage-gated calcium channel activity
Specific Function: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...

Components:

Name	UniProt ID
Voltage-dependent L-type calcium channel subunit alpha-1C	Q13936
Voltage-dependent L-type calcium channel subunit alpha-1D	Q01668
Voltage-dependent L-type calcium channel subunit alpha-1F	O60840
Voltage-dependent L-type calcium channel subunit alpha-1S	Q13698
Voltage-dependent L-type calcium channel subunit beta-1	Q02641
Voltage-dependent L-type calcium channel subunit beta-2	Q08289
Voltage-dependent L-type calcium channel subunit beta-3	P54284
Voltage-dependent L-type calcium channel subunit beta-4	O00305
Voltage-dependent P/Q-type calcium channel subunit alpha-1A	O00555

References

Grigoleit HG, Grigoleit P: Pharmacology and preclinical pharmacokinetics of peppermint oil. Phytomedicine. 2005 Aug;12(8):612-6. doi: 10.1016/j.phymed.2004.10.007. [PubMed:16121523]
Hawthorn M, Ferrante J, Luchowski E, Rutledge A, Wei XY, Triggle DJ: The actions of peppermint oil and menthol on calcium channel dependent processes in intestinal, neuronal and cardiac preparations. Aliment Pharmacol Ther. 1988 Apr;2(2):101-18. [PubMed:2856502]

Enzymes

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [PubMed:22039822]

Drug created on June 13, 2005 13:24 / Updated on May 06, 2021 06:19

Menthol

Identification

Structure for Levomenthol (DB00825)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

References

Components:

References

Enzymes

References