Identification

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Name
Levomenthol
Commonly known or available as Menthol
Accession Number
DB00825  (APRD01604)
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
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
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
0 Degrees Pain RelievingGel5 g/100mLTopicalRlabs, Llc2016-04-012016-08-11Us
4JointzCream1.5 g/100gTopicalArp(usa) Pty Ltd2017-01-31Not applicableUs
A.C.C Fresh and Cooling Scalp MistLiquid0.3 g/100mLTopicalNature4 Co., Ltd.2017-07-26Not applicableUs
AbsorbineGel100 mg/1gTopicalW.F. Young, Inc.2011-01-102013-01-31Us
Absorbine BackPatch5000 mg/8hTransdermalDSE Healthcare Solutions, LLC2013-10-152013-10-01Us
Absorbine BACK Therapeutic Pain ReliefPatch5 g/100gTopicalTeh Seng Pharmaceutical Mfg. Co., Ltd.2013-10-102021-04-30Us
Absorbine JrCream2.5 g/100gTopicalDse Healthcare Solutions, Llc.2013-11-01Not applicableUs
Absorbine JrCream2.5 g/100gTopicalW.F. Young, Inc.2012-04-302015-06-30Us
Absorbine JrCream2.5 g/100gTopicalClarion Brands, Llc2015-08-15Not applicableUs
Absorbine JrPatch5000 mg/1hTopicalClarion Brands, Llc2018-02-15Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
1st Medxpatch With Lidocaine 4%Levomenthol (5 g/1) + Capsaicin (0.025 g/1) + Lidocaine (4 g/1) + Methyl salicylate (20 g/1)PatchTopical1ST MEDX LLC2018-03-15Not applicableUs
1st RELIEF TOPICALLevomenthol (10 mg/1mL) + Lidocaine (40 mg/1mL)SprayTopical1st Class Pharmaceuticals2014-12-02Not applicableUs
4125 First Aid KitLevomenthol (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4204 First Aid KitLevomenthol (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)KitOralHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4210 First Aid KitLevomenthol (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)KitOralHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4221 First Aid KitLevomenthol (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4230 First Aid KitLevomenthol (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4232 First Aid KitLevomenthol (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4240 First Aid KitLevomenthol (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)KitOralHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4241 First Aid KitLevomenthol (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
1st Medxpatch With Lidocaine 4%-rxLevomenthol (5 1/1) + Capsaicin (0.0375 1/1) + Lidocaine (4 1/1) + Methyl salicylate (20 1/1)PatchTopical1ST MEDX LLC2018-03-15Not applicableUs
4125 First Aid KitLevomenthol (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4204 First Aid KitLevomenthol (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)KitOralHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4210 First Aid KitLevomenthol (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)KitOralHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4221 First Aid KitLevomenthol (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4230 First Aid KitLevomenthol (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4232 First Aid KitLevomenthol (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4240 First Aid KitLevomenthol (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)KitOralHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4241 First Aid KitLevomenthol (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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4242 First Aid KitLevomenthol (0.33 g/100g) + 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)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
Categories
UNII
BZ1R15MTK7
CAS number
2216-51-5
Weight
Average: 156.2652
Monoisotopic: 156.151415262
Chemical Formula
C10H20O
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

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.

Associated Conditions
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.

TargetActionsOrganism
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
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

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

Affected organisms
  • Humans and other mammals
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
AbexinostatThe risk or severity of QTc prolongation can be increased when Levomenthol is combined with Abexinostat.
AcebutololThe risk or severity of QTc prolongation can be increased when Levomenthol is combined with Acebutolol.
AceclofenacThe risk or severity of hyperkalemia can be increased when Levomenthol is combined with Aceclofenac.
AcemetacinThe risk or severity of hyperkalemia can be increased when Levomenthol is combined with Acemetacin.
AceprometazineThe risk or severity of QTc prolongation can be increased when Levomenthol is combined with Aceprometazine.
AcetyldigoxinThe risk or severity of QTc prolongation can be increased when Levomenthol is combined with Acetyldigoxin.
Acetylsalicylic acidThe risk or severity of hyperkalemia can be increased when Levomenthol is combined with Acetylsalicylic acid.
AcrivastineThe risk or severity of QTc prolongation can be increased when Levomenthol is combined with Acrivastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Levomenthol is combined with Adenosine.
AgmatineThe risk or severity of hyperkalemia can be increased when Levomenthol is combined with Agmatine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

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
ChEBI
15409
ChEMBL
CHEMBL470670
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
Download (73.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedHealth Services ResearchNicotine Dependence1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedOtherArterial Stiffness1
1CompletedOtherBioequivalence / Healthy Volunteers1
1CompletedOtherPain3
1CompletedTreatmentPain1
1CompletedTreatmentAcute Rhinitis1
1, 2RecruitingTreatmentDiabetic Peripheral Neuropathy (DPN)1
2RecruitingDiagnosticBowel Diseases1
2WithdrawnTreatmentPain, Acute1
2, 3RecruitingPreventionHigh Blood Pressure (Hypertension) / Prehypertension1
2, 3WithdrawnTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Immune Reconstitution Inflammatory Syndrome / Immune Reconstitution Syndrome / Tuberculosis Infection1
3CompletedDiagnosticPatients Undergoing Gastrointestinal Endoscopy1
3CompletedTreatmentColon Nos Polypectomy Tubular Adenoma / Gastric Adenoma / Malignant Neoplasm of Stomach1
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentIncontinence Associated Dermatitis1
3CompletedTreatmentMalignant Neoplasm of Stomach1
3CompletedTreatmentPain1
3CompletedTreatmentPatients Undergoing Gastric Endoscopy1
3CompletedTreatmentStomach Diseases1
3CompletedTreatmentThroat Pain2
3TerminatedDiagnosticColorectal Polyps / Malignant Neoplasm of Colon1
3Unknown StatusTreatmentCoughing1
3WithdrawnTreatmentKnee Osteoarthritis (Knee OA)1
4Active Not RecruitingTreatmentBack Pain Lower Back Chronic1
4CompletedTreatmentBack Pain Lower Back Chronic1
4CompletedTreatmentCessation, Smoking / Smoking1
4CompletedTreatmentSub-acute Back Pain1
4Not Yet RecruitingPreventionBiofilms / Oils, Essential / Periodontitis1
4Not Yet RecruitingPreventionBiofilms / Oils, Essential / Substantivity1
4Not Yet RecruitingTreatmentAmbu ACTion / Cesarean Section / Infusion Catheter, Wound / Lidopatch / Medication Assisted Treatment / Opioid Abuse / Opioid Dependence / Opioid-use Disorder / Opioids Use / Pregnancy Related1
4RecruitingPreventionDental Plaque / Oral Biofilm / Periodontitis1
4RecruitingTreatmentActinic Keratosis (AK)1
4RecruitingTreatmentBack Pain Lower Back Chronic1
4RecruitingTreatmentDiaper Dermatitis1
4TerminatedTreatmentKnee Osteoarthritis (Knee OA)1
4Unknown StatusBasic ScienceGingival Inflammation / Oral Biofilm / Periodontitis1
Not AvailableCompletedNot AvailableArthritis / Gouty Arthritis / Headache / Migraine / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis1
Not AvailableCompletedBasic ScienceHealth Behavior1
Not AvailableCompletedOtherNicotine Dependence1
Not AvailableCompletedTreatmentHeadache / Migraine1
Not AvailableCompletedTreatmentHypopituitarism1
Not AvailableCompletedTreatmentNeck Pain1
Not AvailableCompletedTreatmentShoulder Pain1
Not AvailableRecruitingBasic ScienceDermatology/Skin - Other / Pain / Pain, Neuropathic / Pruritus1
Not AvailableRecruitingBasic ScienceOSAS (Obstructive Sleep Apneas Syndrome)1
Not AvailableRecruitingTreatmentArthritis / Back Pain, Unspecified1
Not AvailableRecruitingTreatmentPeriodontitis / Type 2 Diabetes Mellitus1
Not AvailableUnknown StatusTreatmentPain Relief1
Not AvailableUnknown StatusTreatmentInduction of Uterine contractions1

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
FormRouteStrength
KitOphthalmic
LiquidTopical0.3 g/100mL
GelTopical100 mg/1g
PatchTopical5000 mg/1h
LiquidTopical1.27 g/100mL
PatchTopical6500 mg/1h
PatchTopical6500 mg/8h
PatchTopical5000 mg/8h
PatchTransdermal5000 mg/8h
LiquidTopical40 mg/1mL
LiquidTopical0.0127 g/1mL
LiquidTopical4 g/100mL
LotionTopical8.5 mg/88mL
PatchTransdermal6500 mg/8h
CreamTopical28 g/90mL
GelTopical12 mg/1mL
CreamTopical70 mg/1mL
GelTopical80 g/1000g
SprayTopical80 g/1000g
StickTopical0.05138 g/1g
SolutionTopical35 mg/1mL
CreamTopical35 mg/1mL
LozengeOral7.6 1/1
LozengeOral8.6 1/1
TapeTopical
Aerosol, sprayPercutaneous; Topical; Transdermal
Aerosol, sprayCutaneous; Topical; Transdermal
PatchTopical30 mg/1
PatchTopical2.5 mg/100mg
OintmentTopical0.31 g/100g
LiquidDental
GelTopical70 mg/1L
SprayTopical70 mg/1L
SprayTopical700 mL/1L
OintmentEnteral
LiquidBuccal
SprayTopical5 mL/100mL
LotionTopical0.15 g/100g
RinseOral
MouthwashOral
SprayTopical5 g/100mL
SprayTopical10 g/100mL
GelTopical3.2 g/100mL
GelTopical3 g/100mL
LiquidTopical3 g/100mL
GelTopical2.5 g/100mL
GelTopical3.969 g/113.4g
GelTopical3.969 g/90g
CreamTopical3.7 g/100g
CreamTopical12.5 mg/1g
CreamTopical1.4125 g/113g
CreamTopical8.5 mg/85g
GelTopical10 g/100mL
LozengeOral2.8 mg/1
PatchTopical5 mg/100mg
GelTopical1.25 g/100g
PowderTopical0.15 g/100g
StickTopical1.34 g/57g
Gel, dentifriceTopical10 mg/1g
CreamTopical10 g/100g
MouthwashBuccal
SolutionTopical100 mg/1mL
PatchTopical; Transdermal
CreamTopical4 g/100g
SprayTopical9 g/100g
StickTopical2.6 mg/1g
CreamTopical25 mg/1mL
PatchTopical4.62 g/100g
OintmentNasal
LinimentTopical3.7 g/100mL
GelTopical3 g/120mL
GelTopical2.4 mg/120mL
GelTopical3 mg/120mL
GelTopical1.5 g/60mL
OilPercutaneous; Topical; Transdermal
GelTopical50 mg/1g
Tablet, chewableOral
GelTopical4.5 g/100g
GelTopical5.085 g/113g
SprayTopical11.8 g/118mL
LozengeOral7.6 mg/1
LozengeOral7.5 mg/1
LozengeOral9.1 mg/1
LozengeOral5.4 mg/1
LiquidTopical4.2 mL/60mL
LotionTopical5.11 g/113g
GelTopical30 mg/1g
GelTopical2.1 g/60mL
GelTopical4.0 g/100mL
GelTopical0.03 g/1g
GelTopical35 mg/1mL
GelTopical105 mg/1mL
SprayTopical105 mg/1mL
SprayTopical590 mg/1mL
PatchTopical0.156 g/1
PatchTopical0.348 g/1
SalveTopical1 g/100g
SalveTopical1.1 g/100g
SoapTopical1 g/100mL
GelTopical2.0 g/100g
GelTopical.02 g/1g
PowderTopical1.5 mg/1g
PowderTopical10 mg/1g
LiquidTopical70 mg/1mL
CreamTopical100 mg/1mL
CreamTopical170 g/90mL
OintmentRespiratory (inhalation); Topical
SyrupOral
GelTopical0.025 g/1g
OintmentRespiratory (inhalation)
OintmentTopical
LiquidTopical5 mg/1mL
CreamTopical0.5 g/100g
CreamTopical40 mg/1g
PatchTopical0.05 mg/1
PatchTopical.05 mg/1
OilTopical0.08 kg/1kg
CreamTopical1.25 g/100mL
CreamTopical1.5 g/100g
LiquidTransdermal
ShampooTopical0.3 g/100mL
OilTopical1.5 g/50g
LozengeOral4.5 mg/1
SalveTopical27.6 mg/1g
LozengeOral
GelTopical2 g/100g
GelTopical
GelTopical0.1 mg/1mL
CreamTopical20 mg/1g
LiquidNasal
SprayTopical16 g/100mL
PatchTopical240 mg/1
PatchTopical50 mg/1
PatchTopical500 mg/1
PatchTopical875 mg/1
PatchTopical400 mg/1
PatchTopical205.5 mg/1
LiquidTopical16 g/100mL
PatchTopical5 g/100g
LipstickTopical
Aerosol, sprayTopical6 mL/60mL
GelTopical0.46 L/3.8L
OintmentTopical13 mL/90mL
SwabTopical.96 mL/8mL
GelTopical4 g/100g
PatchTopical1.14 g/100g
PatchTopical100 mg/5mg
Granule, for solutionOral490 mg/5g
Kit
SprayTopical16 g/100g
MouthwashBuccal; Oral
GelTransdermal
LozengeOral16.0 mg/1
LozengeOral15.3 mg/1
Granule, for solutionTopical11.7 mg/1mL
PatchTopical0.75 g/1
PatchTopical5 mg/1g
LozengeOral7.2 mg/7.2mg
TabletOral7.5 mg/7.5mg
TabletOral5.8 mg/5.8mg
LotionRespiratory (inhalation)
PatchTopical0.05 g/1g
LiquidTopical160 mg/1mL
LozengeOral20 mg/1
Gel, dentifriceDental
LozengeOral4 mg/1
LotionTopical1 mg/1mL
CreamTopical0.025 g/1g
SolutionTopical60 mg/1mL
Patch, extended releaseTransmucosal2.5 mg/194.85mg
Patch, extended releaseTransmucosal2.5 mg/194.851
CreamTopical1.8 g/100g
LotionTopical1.5 mg/1g
LiquidTopical20 mg/1mL
PatchTopical5 g/1
OilTopical3.5 g/100mL
LiquidTopical30 mg/1mL
SprayTopical
PatchTopical0.5 g/1g
GelTopical3.89 g/100g
GelTopical4.58 g/100g
CreamTopical40 mg/1mL
SolutionTopical
CreamTopical2.625 g/75g
CreamTopical100 mg/1g
PatchCutaneous
LozengeOral8.5 mg/1
LozengeOral8.3 mg/1
CreamTopical50 mg/1mL
LiquidTopical35 mg/1mL
DiscTopical
PatchTopical4 g/1
SprayTopical1000 mg/100mL
SprayTopical1700 mg/100mL
SprayTopical865.4 mg/50mL
CreamTopical60 mg/1mL
LiquidTopical2.5 g/100mL
SprayTopical1.25 g/100mL
StickTopical0.035 g/7g
LiquidTopical16 mg/100mL
SprayTopical4 g/100mL
CreamTopical12.13 mg/1mL
OintmentTopical9.6 mL/60mL
LotionTopical0.1 g/100mL
GelTopical100 mg/1mL
PlasterTopical; Transdermal
LiquidTopical80 mg/1mL
GelTopical2 g/100mL
GelTopical4 g/100mL
StickTopical20 mg/1g
PatchTopical750 mg/1
GelTopical35 mg/1g
SprayTopical100 mg/1g
LotionTopical12.5 mg/1mL
PatchTopical200 mg/1
SwabTopical
SolutionOral
JellyTopical
GelTopical
SprayTopical2.25 g/100mL
GelTopical0.07 g/1g
GelTopical0.16 g/1g
CreamTopical16 g/1
SprayTopical16 g/1
Granule, for solutionOral270 mg/6g
CreamTopical1.25 mg/1mL
LotionTopical13.5 mg/1mL
CreamTopical0.1 g/100mL
OilTopical24 mg/1mL
SprayOropharyngeal
SprayOral; Topical
PatchCutaneous; Topical; Transdermal
OintmentTopical1 g/100g
LotionTopical0.005 g/1g
PowderTopical0.008 g/1g
SprayTopical1 g/100g
LotionTopical0.0015 g/1g
PowderTopical0.0015 g/1g
CreamTopical16 g/100g
LiquidTopical0.16 g/1mL
CreamTopical6.25 g/100g
LotionCutaneous
OilTopical20 mg/500mg
LozengeOral2.6 mg/1
LozengeOral7 mg/1
LozengeOral5.7 mg/1
LozengeOral6.8 mg/1
LozengeOral8.8 mg/1
LozengeOral8.2 mg/1
TabletOral
LozengeOral6.4 mg/1
LozengeOral4.3 mg/1
LozengeOral2.5 mg/1
LozengeOral2.7 mg/1
LozengeOral4.6 mg/1
LozengeOral5.6 mg/1
LozengeOral3.2 mg/1
LozengeOral9.4 mg/1
LozengeOral3.7 mg/1
LozengeOral6.6 mg/1
LozengeOral6.7 mg/1
LozengeOral15 mg/1
LozengeOral3.1 mg/1
LozengeOral18 mg/1
SyrupOral0.1 g/100mL
PoulticeTransdermal280 mg/12g
SprayTopical10.4 g/100g
LotionTopical4 g/100g
CreamTopical7.4 g/100g
MouthwashDental0.2 g/100mL
OintmentRectal
GelTopical8 mg/100mL
LozengeOral4.8 mg/1
LozengeOral5.5 mg/1
LozengeOral1.6 mg/1
LozengeOral6 mg/1
LozengeOral5.5 mg/2.51
LozengeOral9.99 mg/1
LozengeOral3 mg/1
GelTopical4840 mg/1g
LozengeOral3.18 mg/1
LozengeOral7.5 1/1
PastilleOral0.281 mg/1
PastilleOral7.6 mg/1
LozengeOral10 mg/1
LozengeOral3.9 mg/1
LozengeOral8.6 mg/2.5g
CreamTopical12.5 mg/1mL
GelTopical2.27 g/227g
GelTopical0.3 g/100mL
LiquidTopical12.5 mg/1mL
GelTopical34.79 mg/1mL
CreamTopical2 mg/1g
GelTopical2.84 mg/227mg
GelTopical.02 g/100g
CreamTopical30 mg/1g
GelTopical16.95 g/113g
GelTopical55 mg/1mL
PatchTopical336 mg/1
PatchTopical210 mg/1
PatchTopical205.50 mg/1
PatchTopical428.50 mg/1
PatchTopical50.25 mg/1
PatchTopical866.25 mg/1
PatchTopical787.5 mg/1
PatchTopical29.3 mg/1
CreamTopical0.075 g/1g
PatchTopical750.00 mg/1
SprayTopical160 mg/1mL
OilTopical16 g/100mL
LiquidTopical12.5 mg/1g
GelTopical5 mg/5mL
GelTopical1.25 mL/100mL
CreamTopical0.525 g/105g
CreamTopical2.5 g/500g
ShampooTopical0.0025 g/500g
LiquidTopical0.1 g/100mL
CreamTopical2.2 g/100g
SoapTopical4 mg/1mL
LozengeOral5 mg/100mg
CreamTopical50 mg/1g
LotionTopical8.5 g/100mL
LiquidTopical10 g/100mL
ShampooTopical1 mg/1mL
StickTopical
CreamTopical30 mg/1mL
LiquidRespiratory (inhalation)
GelTopical10 g/100g
GelTopical10 mg/1g
LotionTopical3.5 g/100g
PowderTopical1 g/100g
CreamDental
Plaster; swabTopical
PlasterTransdermal3.0 g/100g
OilTopical0.8 mg/50mL
GelTopical12.5 mg/1mL
GelTopical20 mg/1g
SprayTopical0.005 g/1g
LozengeOral5 mg/1
Aerosol, sprayTopical
LozengeOral5.75 mg/1
GelTopical0.23 mg/1mL
GelTopical0.24 mg/1mL
LozengeOral1.0 mg/1
CreamTopical5.6 g/112g
LotionTopical3 g/100g
MouthwashDental; Oral
GelTopical50 mg/1mL
PowderTopical0.1 g/1g
LipstickTopical5 mg/1g
ShampooTopical
LozengeOral8.6 mg/1
GelTopical.07 g/1g
JellyTopical
StickTopical0.9 g/100g
PatchTopical428.5 mg/1
PatchTopical
CreamTopical5 1/85g
PatchTopical20 mg/11.7g
LozengeOral5.8 mg/1
ClothTopical0.05 g/1mL
GelTopical4.54 g/227g
LozengeOral
CreamTopical5 g/100g
OilTopical6 mg/50mL
PatchTopical15 mg/1g
CreamTopical26 mg/1mL
OilTopical0.5 mg/50mL
PowderTopical2.8 g/283g
PowderTopical2.83 g/283g
PatchTopical440 mg/1
LozengeOral5.4 1/1
PastilleOral5.8 mg/1
LozengeOral8.0 mg/1
OintmentTopical27 mg/1g
GelTopical30 mg/1mL
LotionTopical1.3 g/100g
SalveTopical0.5 g/100g
LinimentPercutaneous; Transdermal1 g/3500mL
SalveTopical1 g/1500g
CreamTopical15 mg/1mL
GelTopical0.02 g/1g
GelTopical160 mg/1g
SolutionTopical40 mg/1mL
GelTopical40 mg/1g
CreamTopical0.028 g/28g
CreamTopical0.106 g/106g
CreamTopical0.224 g/224g
LiquidTopical1.8 mL/90mL
CreamTopical3 g/100g
CreamTopical1.5 g/100mL
GelTopical5 g/100g
CreamTopical2.5 g/100g
GelTopical3.5 g/100mL
GelTopical2.5 g/100g
GelTopical25 mg/1g
CreamTopical
CreamTopical1.05 g/42g
SprayTopical100 mg/1mL
CreamTopical5 uL/1mL
CreamTopical20 uL/1mL
PillVaginal0.5 g/100g
LotionTopical60 mg/1mL
KitNot applicable
KitOral
OintmentRectal275 mg/48.2g
MouthwashOral0.3 mg/1mL
LozengeOral1.8 mg/1
LozengeOral2.0 mg/1
LozengeOral3 1/1
LozengeOral1.5 mg/1
LozengeOral3.5 mg/1
LozengeOral1.2 mg/1
GelTopical3 g/100g
LozengeOral2 mg/3g
CreamTopical
GelDental
LozengeOral8 mg/1
Aerosol, foamTopical5 mg/100mg
Aerosol, sprayTopical1 mg/100mg
Aerosol, sprayTopical5 mg/100mg
CreamTopical10 mg/100mg
LiquidTopical10 mg/100mg
SprayTopical0.1 mg/100mg
LinimentTopical
LiquidTopical0.2 g/10mL
Tablet, solubleOral
PowderOral
SprayTopical0.5 g/100mL
OintmentTopical1.25 g/100g
OilTransdermal100 mg/50mL
GelTopical0.33 mg/660mL
GelTopical0.63 g/632.19g
PastilleOral10 mg/1
StripDental
GelOral; Topical
Film, solubleOral
PasteTopical
CreamTopical1.3 g/100g
CreamTopical8 g/100g
GelTopical7 g/100mL
LiquidTopical6 g/100mL
CreamTopical14 g/280g
GranuleTopical1.6 mg/1g
LiquidTopical2.23 mg/1mL
OilTopical12.18 mg/1mL
OilTopical17.62 mg/1mL
CreamTopical6 g/100mL
PatchTopical5 mg/1
SprayTopical10.5 g/100g
PatchTopical160 mg/1mL
TinctureTopical
GelTopical2.4 g/120g
GelTopical4.54 g/1g
PatchTopical0.2 1/1
PatchTopical.05 mg/1g
PatchTopical50 mg/1g
PatchTopical30 mg/1mL
GelTopical85 mg/1mL
CreamTopical35 mg/1g
CreamTopical4.25 g/85g
LotionTopical160 mg/1mL
PatchTopical775 mg/1
PatchTopical5 g/1001
PatchTopical1.22 g/1
PatchTopical350 mg/1
LotionTopical7.5 g/100g
LiquidOral
GelTopical1.0 g/100g
GelTopical31 mg/1mL
SprayTopical104 mg/1mL
PowderTopical
PowderTopical20 mg/2g
GelTopical1 g/100g
Lotion / shampooTopical
CreamTopical20 mg/1mL
ShampooTopical0.1 g/100mL
OintmentTopical13 g/100g
OilTopical15 g/100mL
GelTopical120 mg/1g
GelTopical120 mg/1mL
LiquidTopical140 mg/1mL
GelTopical40 mg/1mL
EmulsionTopical
GelTopical2 mL/100mL
SprayTopical7 g/100mL
SprayTopical10.5 g/10.5mL
CreamCutaneous; Topical
OintmentCutaneous; Topical
GelCutaneous; Topical
SprayTopical8 g/100mL
GelTopical8 g/100mL
LozengeOral2 mg/1
LotionTopical3 g/100mL
PatchTopical0.875 g/100g
CreamTopical1.25 g/100g
GelTopical3.5 mg/1L
LiquidTopical34.86 g/1L
LiquidTopical34.79 g/1L
CreamTopical118.29 mL/100mL
LotionTopical1.5 g/100mL
LotionTopical0.5 g/100mL
LotionTopical1.25 g/100mL
OintmentTopical12.7 mg/1g
LozengeOral6.1 mg/1001
CreamTopical3.0 g/100g
OintmentTopical0.2 g/100g
OintmentTopical937.5 mg/1g
GelTopical27.5 mg/1g
OilTopical7 mg/50mL
PatchTopical50 g/1
GelTopical40 mg/1
GelTopical6.0 g/100g
CreamTopical0.006 g/0.1g
CreamTopical6 mg/100mL
Kit24.03 mg/1mL
SprayTopical4 g/4mL
GelTopical20 mg/1mL
PatchTopical1000 mg/1
PatchTopical600 mg/1
PatchTopical900 mg/1
GelPercutaneous; Topical; Transdermal
PatchPercutaneous; Topical; Transdermal
Aerosol, foamPercutaneous; Topical; Transdermal
OintmentPercutaneous; Topical; Transdermal
PoulticePercutaneous; Topical; Transdermal175 mg/1
GelTopical150 mg/1g
LiquidTopical
GelTopical140 mg/1mL
Paste, dentifriceTopical0.2 g/100g
PastilleOral0.69 mg/1
PlasterTopical
GelTopical12.5 mg/1g
GelTopical12.6 mg/1g
GelTopical2.6 mg/100g
LiquidCutaneous; Topical; Transdermal
PatchTopical0.85 g/17g
CreamOral6 g/100mL
SprayTopical5 mg/1mL
LozengeOral6.5 mg/1
CreamTopical15 mg/1g
GelTopical2.25 g/100g
MouthwashDental
GelTopical.06 g/1g
Solution / dropsTopical
StickTopical
GelTopical0.06 g/1g
GelTopical0.1 g/1g
GelTopical100 g/1mL
GelTopical6 g/100g
SprayTopical60 mg/1mL
GelTopical80 mg/1g
SprayTopical80 mg/1mL
GelTopical0.08 g/1g
OilTopical1 g/93mL
LozengeOral5.8 1/1
LozengeOral6.9 mg/1
LozengeOral4.1 mg/1
LozengeOral5.52 mg/1
LozengeOral1.1 mg/1
LozengeOral2.2 mg/1
OintmentTopical1 mg/1g
LinimentTransdermal3.5 mg/100mL
OilTopical24.56 mg/1mL
OilTopical1.3 mg/50mg
LotionTopical
OintmentTopical8 g/100g
PatchTopical4 g/100g
StickTopical0.6 g/100g
GelTopical3.5 mL/100mL
LozengeOral5.3 mg/1
CreamTopical130 mg/1g
GelTopical60 mg/1mL
GelTopical.04 g/1g
GelTopical3.9 g/100mL
SprayTopical6 g/100mL
PastilleOral2.5 mg/1
PatchTransdermal3 g/1
PatchTransdermal
PlasterTransdermal
CreamTopical0.1 g/100g
LiquidTopical0.002 g/4mL
LiquidTopical0.06 g/120mL
PoulticeTransdermal
LotionTopical0.5 g/100g
GelTopical5.0 g/100mL
SprayTopical10.5 g/100mL
GelTopical4.56 g/114g
GelTopical5 g/100mL
CreamTopical45 mg/1mL
LiquidTopical25 g/100g
SalveTopical
LozengeOral1.7 mg/1
LozengeOral3.3 mg/1
LiquidOral
GelTopical0.1 g/100g
SprayOral2 g/100mL
GelTopical6 g/120g
PatchTopical5 1/1
OilTransdermal
OilTopical
LotionTopical1 g/100mL
CreamTopical0.03 g/1g
Gum, chewingOral
GelTopical3 g/227g
Paste, dentifriceTopical
LinimentPercutaneous; Transdermal3 g/100mL
LinimentPercutaneous; Transdermal
PatchTopical10 mg/1000mg
GelTopical20 g/1L
GelTopical37 mg/1mL
GelTopical37 mg/1g
SprayTopical37 mg/1g
GelTopical70 mg/1g
SprayTopical160 mg/1g
KitTopical
Prices
Unit descriptionCostUnit
Cool & heat patch1.2USD patch
Icy hot medicated 5% patch1.2USD patch
Bengay pain relieving patch1.13USD patch
CVS Pharmacy pain relieving patch1.11USD patch
Cold & hot pain rel patch1.05USD patch
Nuprin muscle & joint patch1.03USD patch
Mentholatum pain patch0.93USD patch
CVS Pharmacy cold & hot medicated patch0.89USD patch
Salonsip aqua-patch0.69USD patch
Menthol crystal0.49USD g
Menthol cough drops0.06USD each
CVS Pharmacy menthol drops0.03USD each
Pv menthol cough drops0.02USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8809615No2014-08-192030-01-03Us
US9233184No2016-01-122027-08-01Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)43 °CPhysProp
boiling point (°C)212 °CPhysProp
water solubility490 mg/L (at 25 °C)CHEM INSPECT TEST INST (1992)
logP3.40GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
Water Solubility0.558 mg/mLALOGPS
logP2.68ALOGPS
logP2.66ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.45 m3·mol-1ChemAxon
Polarizability19.69 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier+0.9408
Caco-2 permeable+0.8127
P-glycoprotein substrateNon-substrate0.569
P-glycoprotein inhibitor INon-inhibitor0.8765
P-glycoprotein inhibitor IINon-inhibitor0.9397
Renal organic cation transporterNon-inhibitor0.8591
CYP450 2C9 substrateNon-substrate0.7798
CYP450 2D6 substrateNon-substrate0.746
CYP450 3A4 substrateSubstrate0.5912
CYP450 1A2 substrateNon-inhibitor0.7188
CYP450 2C9 inhibitorNon-inhibitor0.8484
CYP450 2D6 inhibitorNon-inhibitor0.9451
CYP450 2C19 inhibitorNon-inhibitor0.9185
CYP450 3A4 inhibitorNon-inhibitor0.9458
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9546
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8439
BiodegradationNot ready biodegradable0.7808
Rat acute toxicity1.7142 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8439
hERG inhibition (predictor II)Non-inhibitor0.7727
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (2.96 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0006-1900000000-cc06fe70d7649d059f92
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00ea-9100000000-0be605183591bf5f33a0
GC-MS Spectrum - EI-BGC-MSsplash10-00ea-9100000000-977cf0c036d597693beb
GC-MS Spectrum - GC-MSGC-MSsplash10-0006-1900000000-cc06fe70d7649d059f92
Mass Spectrum (Electron Ionization)MSsplash10-00ea-9100000000-602436010653202a4da9
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-053r-9300000000-d9c35833e73c8655fb23
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0ldl-9000000000-abf2f837df49fbedc53c
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0007-9000000000-adee6385265c6606326d
MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , PositiveLC-MS/MSsplash10-00ea-9100000000-e3f1b7b69a021063fabb
MS/MS Spectrum - EI-B (JEOL JMS-DX-300) , PositiveLC-MS/MSsplash10-00ea-9100000000-d69777874c9615b7e751
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
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Menthane monoterpenoids
Alternative Parents
Monocyclic monoterpenoids / Cyclohexanols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
P-menthane monoterpenoid / Monocyclic monoterpenoid / Cyclohexanol / Cyclic alcohol / Secondary alcohol / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Alcohol / Aliphatic homomonocyclic compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
p-menthan-3-ol (CHEBI:15409) / Menthane monoterpenoids, Cyclic monoterpenes (C00400) / Menthane monoterpenoids (LMPR0102090001)

Targets

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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. Eccles R: Menthol and related cooling compounds. J Pharm Pharmacol. 1994 Aug;46(8):618-30. [PubMed:7529306]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
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
  1. 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]
  2. 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]
  3. 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]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
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
  1. 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]
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
  1. 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]
  2. Taniguchi Y, Deguchi Y, Saita M, Noda K: [Antinociceptive effects of counterirritants]. Nihon Yakurigaku Zasshi. 1994 Dec;104(6):433-46. [PubMed:7851817]
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:
References
  1. 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]
  2. 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

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
  1. 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 07:24 / Updated on November 16, 2019 10:29