levomenthol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
934 89-78-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • menthol
  • hexahydrothymol
  • menthacamphor
  • menthomenthol
  • thymomenthol
  • levomenthol
  • (-)-menthol
A monoterpene cyclohexanol produced from mint oils.
  • Molecular weight: 156.27
  • Formula: C10H20O
  • CLOGP: 3.23
  • LIPINSKI: 0
  • HAC: 1
  • HDO: 1
  • TPSA: 20.23
  • ALOGS: -2.45
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
None FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 813.35 38.30 282 2029 46361 2309413
Toxicity to various agents 471.93 38.30 173 2138 32581 2323193
Cardiac arrest 396.16 38.30 125 2186 14805 2340969
Methaemoglobinaemia 385.93 38.30 62 2249 277 2355497
Drug ineffective 362.75 38.30 202 2109 101422 2254352
Anaphylactic reaction 276.64 38.30 86 2225 9619 2346155
Lagophthalmos 260.90 38.30 37 2274 51 2355723
Toxic anterior segment syndrome 223.29 38.30 38 2273 255 2355519
Generalised tonic-clonic seizure 219.77 38.30 63 2248 5309 2350465
Hypotension 215.97 38.30 99 2212 32337 2323437
Anaesthetic complication 200.15 38.30 37 2274 418 2355356
Seizure 176.28 38.30 79 2232 24387 2331387
Anaphylactic shock 174.02 38.30 50 2261 4236 2351538
Bradycardia 166.00 38.30 59 2252 9922 2345852
Incorrect route of product administration 150.52 38.30 47 2264 5289 2350485
Overdose 142.35 38.30 64 2247 19843 2335931
Cyanosis 133.00 38.30 38 2273 3147 2352627
Dyspnoea 127.43 38.30 96 2215 78637 2277137
Unresponsive to stimuli 125.24 38.30 40 2271 4836 2350938
Maternal exposure during pregnancy 113.24 38.30 50 2261 14813 2340961
Pulseless electrical activity 110.65 38.30 26 2285 989 2354785
Exposure during pregnancy 104.77 38.30 56 2255 25163 2330611
Respiratory arrest 104.40 38.30 37 2274 6141 2349633
Product adhesion issue 95.21 38.30 24 2287 1228 2354546
Loss of consciousness 93.19 38.30 47 2264 18720 2337054
Tachycardia 90.07 38.30 44 2267 16365 2339409
Ophthalmoplegia 83.37 38.30 16 2295 223 2355551
Dizziness 82.54 38.30 66 2245 58599 2297175
Product quality issue 81.02 38.30 36 2275 10793 2344981
Pulse absent 81.00 38.30 20 2291 939 2354835
Cardio-respiratory arrest 80.17 38.30 34 2277 9112 2346662
Ventricular tachycardia 78.49 38.30 25 2286 2986 2352788
Confusional state 76.38 38.30 45 2266 24299 2331475
Drug interaction 71.36 38.30 46 2265 29117 2326657
Anaphylactoid reaction 71.12 38.30 18 2293 935 2354839
Pruritus 70.09 38.30 53 2258 43287 2312487
Myopathy toxic 69.76 38.30 12 2299 86 2355688
Oxygen saturation decreased 69.13 38.30 29 2282 7557 2348217
Ventricular fibrillation 68.79 38.30 21 2290 2180 2353594
Drug abuse 68.20 38.30 33 2278 11993 2343781
Muscular weakness 67.20 38.30 35 2276 14862 2340912
Neurotoxicity 65.20 38.30 20 2291 2110 2353664
Rash 65.15 38.30 58 2253 59500 2296274
Hypoaesthesia 65.04 38.30 38 2273 20177 2335597
Mydriasis 64.39 38.30 20 2291 2199 2353575
Coma 64.19 38.30 29 2282 9027 2346747
Hypertension 64.08 38.30 42 2269 27319 2328455
Urticaria 63.63 38.30 40 2271 24221 2331553
Product use in unapproved indication 61.29 38.30 30 2281 11170 2344604
Hypoxia 60.76 38.30 25 2286 6202 2349572
Local anaesthetic systemic toxicity 60.05 38.30 8 2303 4 2355770
Parophthalmia 58.08 38.30 10 2301 72 2355702
Nausea 57.64 38.30 73 2238 112116 2243658
Blood pressure decreased 57.40 38.30 27 2284 9209 2346565
Peripheral nerve injury 57.15 38.30 10 2301 80 2355694
Accidental overdose 56.63 38.30 21 2290 3951 2351823
Agitation 55.72 38.30 28 2283 11023 2344751
Syncope 55.00 38.30 32 2279 16843 2338931
Spinal epidural haemorrhage 54.50 38.30 8 2303 16 2355758
Delirium 54.47 38.30 22 2289 5201 2350573
Pain 53.69 38.30 53 2258 61804 2293970
Mental status changes 53.06 38.30 22 2289 5560 2350214
Heart rate increased 52.67 38.30 27 2284 11078 2344696
Maternal exposure during delivery 50.40 38.30 10 2301 167 2355607
Hypersensitivity 49.87 38.30 34 2277 23559 2332215
Horner's syndrome 49.82 38.30 9 2302 88 2355686
Sensory loss 49.28 38.30 14 2297 1130 2354644
Sinus tachycardia 48.94 38.30 18 2293 3307 2352467
Respiratory failure 47.67 38.30 27 2284 13501 2342273
Blood pressure increased 47.01 38.30 29 2282 16957 2338817
Circulatory collapse 46.98 38.30 18 2293 3702 2352072
Apnoea 46.38 38.30 14 2297 1397 2354377
Status epilepticus 46.25 38.30 16 2295 2462 2353312
Paraesthesia 44.71 38.30 31 2280 22057 2333717
Angioedema 44.46 38.30 22 2289 8374 2347400
Swollen tongue 43.93 38.30 19 2292 5324 2350450
Airway peak pressure increased 42.67 38.30 7 2304 36 2355738
Product use issue 42.09 38.30 24 2287 12145 2343629
Stress cardiomyopathy 41.67 38.30 13 2298 1448 2354326
Pneumocephalus 40.83 38.30 7 2304 49 2355725
Heart rate decreased 40.11 38.30 16 2295 3660 2352114
Post procedural complication 39.84 38.30 15 2296 2939 2352835
Foetal heart rate abnormal 39.75 38.30 8 2303 144 2355630
Arthritis bacterial 39.74 38.30 11 2300 807 2354967
Respiratory acidosis 39.70 38.30 11 2300 810 2354964
Spinal anaesthesia 38.90 38.30 6 2305 19 2355755
Erythema 38.88 38.30 30 2281 25129 2330645
Somnolence 38.48 38.30 29 2282 23456 2332318
Treatment failure 38.41 38.30 19 2292 7220 2348554
Septic arthritis staphylococcal 38.33 38.30 7 2304 73 2355701
Medication error 38.31 38.30 18 2293 6113 2349661

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxicity to various agents 568.50 42.62 199 1425 28942 1716215
Methaemoglobinaemia 330.73 42.62 56 1568 308 1744849
Drug ineffective 300.55 42.62 160 1464 63641 1681516
Hypotension 262.29 42.62 115 1509 29539 1715618
Cardiac arrest 244.68 42.62 92 1532 15838 1729319
Overdose 233.24 42.62 90 1534 16611 1728546
Anaphylactic reaction 219.79 42.62 67 1557 6046 1739111
Anaesthetic complication 167.40 42.62 30 1594 238 1744919
Generalised tonic-clonic seizure 165.30 42.62 49 1575 3997 1741160
Seizure 150.37 42.62 70 1554 20371 1724786
Lagophthalmos 147.55 42.62 21 1603 23 1745134
Ventricular tachycardia 137.82 42.62 42 1582 3756 1741401
Respiratory arrest 135.66 42.62 46 1578 5793 1739364
Unresponsive to stimuli 129.64 42.62 42 1582 4587 1740570
Accidental overdose 125.69 42.62 40 1584 4124 1741033
Drug hypersensitivity 117.87 42.62 54 1570 15081 1730076
Drug abuse 116.60 42.62 52 1572 13637 1731520
Respiratory depression 108.40 42.62 31 1593 2216 1742941
Loss of consciousness 106.23 42.62 50 1574 14825 1730332
Anaphylactic shock 100.60 42.62 31 1593 2868 1742289
Coma 100.35 42.62 39 1585 7223 1737934
Bradycardia 99.28 42.62 43 1581 10491 1734666
Electrocardiogram QRS complex prolonged 92.61 42.62 22 1602 753 1744404
Tachycardia 91.81 42.62 43 1581 12585 1732572
Dizziness 81.23 42.62 56 1568 34305 1710852
Blood pressure increased 79.30 42.62 37 1587 10716 1734441
Sinus tachycardia 79.12 42.62 25 1599 2507 1742650
Cardiotoxicity 75.95 42.62 19 1605 809 1744348
Depressed level of consciousness 75.70 42.62 31 1593 6561 1738596
Pulmonary oedema 72.33 42.62 30 1594 6556 1738601
Pallor 71.80 42.62 25 1599 3386 1741771
Neurotoxicity 71.69 42.62 22 1602 2002 1743155
Product adhesion issue 68.93 42.62 15 1609 343 1744814
Ventricular fibrillation 65.01 42.62 22 1602 2734 1742423
Circulatory collapse 63.80 42.62 23 1601 3444 1741713
Drug interaction 62.30 42.62 44 1580 27914 1717243
Oxygen saturation decreased 59.43 42.62 25 1599 5650 1739507
Substance abuse 58.17 42.62 16 1608 987 1744170
Cyanosis 57.81 42.62 20 1604 2654 1742503
Brain oedema 57.63 42.62 19 1605 2177 1742980
Ophthalmoplegia 57.34 42.62 12 1612 226 1744931
Arthritis infective 55.72 42.62 13 1611 410 1744747
Confusional state 55.67 42.62 37 1587 21241 1723916
Metabolic acidosis 53.90 42.62 23 1601 5379 1739778
Mydriasis 53.78 42.62 16 1608 1308 1743849
Cardio-respiratory arrest 53.45 42.62 27 1597 9266 1735891
Bronchospasm 50.59 42.62 17 1607 2065 1743092
Embolia cutis medicamentosa 49.56 42.62 9 1615 77 1745080
Drug level increased 49.50 42.62 18 1606 2759 1742398
Toxic anterior segment syndrome 48.16 42.62 10 1614 181 1744976
Apnoea 48.12 42.62 15 1609 1434 1743723
Rash 47.65 42.62 43 1581 38650 1706507
Dyspnoea 47.45 42.62 49 1575 52010 1693147
Angioedema 46.74 42.62 25 1599 9639 1735518
Myopathy toxic 46.64 42.62 9 1615 110 1745047
Hypersensitivity 44.92 42.62 25 1599 10419 1734738
Dysarthria 44.68 42.62 20 1604 5239 1739918
Lethargy 44.62 42.62 22 1602 7162 1737995
Pulse absent 44.57 42.62 13 1611 991 1744166
Post procedural complication 44.56 42.62 16 1608 2364 1742793
Hyperhidrosis 43.34 42.62 26 1598 12462 1732695

Pharmacologic Action:

SourceCodeDescription
CHEBI has role CHEBI:51177 antitussive
CHEBI has role CHEBI:53784 antispasmodic drug
CHEBI has role CHEBI:59683 antipruritic drug
MeSH PA D000982 Antipruritics
MeSH PA D003879 Dermatologic Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Seborrheic dermatitis indication 50563003 DOID:8741
Pityriasis versicolor indication 56454009 DOID:9060
Diaper rash indication 91487003
Backache indication 161891005
Pityriasis simplex indication 200767005
Skin irritation indication 367466007
Local anesthesia indication 386761002
Itching of skin indication 418363000
Mouth Irritation indication
Minor Skin Wound Pain indication
Suppression of the Gag Reflex indication
Sprains and Strains indication
Arthritic Pain indication
Gastritis contraindication 4556007 DOID:4029
Bacterial septicemia contraindication 10001005 DOID:0040085
Primary hyperoxaluria contraindication 17901006 DOID:2977
Hypocupremia contraindication 19577007
Infection of skin AND/OR subcutaneous tissue contraindication 19824006
Shock contraindication 27942005
Methemoglobinemia contraindication 38959009 DOID:10783
Gastrointestinal ulcer contraindication 40845000
Distinctive exudative discoid AND lichenoid chronic dermatosis of Sulzberger and Garbe contraindication 41580004
Body fluid retention contraindication 43498006
Conduction disorder of the heart contraindication 44808001
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Hepatic failure contraindication 59927004
Blood coagulation disorder contraindication 64779008 DOID:1247
Diabetes mellitus contraindication 73211009 DOID:9351
Factor II deficiency contraindication 73975000
Gastrointestinal hemorrhage contraindication 74474003
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Decreased respiratory function contraindication 80954004
Kidney disease contraindication 90708001 DOID:557
Thyrotoxicosis contraindication 90739004 DOID:7997
Hemophilia contraindication 90935002
Disorder of skin contraindication 95320005 DOID:37
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Deficiency of cytochrome-b>5< reductase contraindication 124184009
Open wound contraindication 125643001
Hb SS disease contraindication 127040003 DOID:10923
Seizure disorder contraindication 128613002
Heart block contraindication 233916004
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Condyloma acuminatum contraindication 240542006 DOID:11168
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Hemochromatosis contraindication 399187006 DOID:2352
Peripheral vascular disease contraindication 400047006
Breastfeeding (mother) contraindication 413712001
Blister contraindication 417237009
Denuded skin contraindication 418242004
Inflammatory dermatosis contraindication 703938007

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Transient receptor potential cation channel subfamily M member 8 Ion channel ACTIVATOR EC50 4.60 IUPHAR SCIENTIFIC LITERATURE
Transient receptor potential cation channel subfamily A member 1 Ion channel ACTIVATOR EC50 4.50 IUPHAR
Transient receptor potential cation channel subfamily A member 1 Unclassified GATING INHIBITOR IC50 4.20 IUPHAR
Transient receptor potential cation channel subfamily M member 8 Unclassified ACTIVATOR EC50 4.20 IUPHAR
Transient receptor potential cation channel subfamily M member 8 Unclassified ACTIVATOR EC50 5.40 IUPHAR

External reference:

IDSource
4018868 VUID
N0000147167 NUI
C0025368 UMLSCUI
D04918 KEGG_DRUG
423685001 SNOMEDCT_US
236388 RXNORM
421208001 SNOMEDCT_US
005811 NDDF
BZ1R15MTK7 UNII
6725 INN_ID
2216-51-5 SECONDARY_CAS_RN
16666 PUBCHEM_CID
CHEBI:15409 CHEBI
CHEMBL256087 ChEMBL_ID
DB00825 DRUGBANK_ID
CHEMBL470670 ChEMBL_ID
2430 IUPHAR_LIGAND_ID
D008610 MESH_DESCRIPTOR_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Theragesic Creme HUMAN OTC DRUG LABEL 2 0178-0320 GEL 10 mg TOPICAL OTC monograph not final 16 sections
Theragesic Plus HUMAN OTC DRUG LABEL 2 0178-0350 GEL 40 mg TOPICAL OTC monograph not final 15 sections
Humphreys Bendito Alcoholado HUMAN OTC DRUG LABEL 1 0219-0203 LIQUID 12.50 mg TOPICAL OTC monograph not final 12 sections
Mineral Ice HUMAN OTC DRUG LABEL 1 0316-0226 GEL 20 mg TOPICAL OTC monograph not final 15 sections
Studio 35 Medicated Body HUMAN OTC DRUG LABEL 1 0363-0043 POWDER 1.50 mg TOPICAL OTC monograph not final 13 sections
Tartar Control Plus HUMAN OTC DRUG LABEL 4 0363-0045 MOUTHWASH 0.42 mg ORAL OTC monograph not final 15 sections
Antispetic HUMAN OTC DRUG LABEL 4 0363-0080 MOUTHWASH 0.42 mg ORAL OTC monograph not final 12 sections
WALGREENS COOL AND HEAT MUSCLE AND JOINT RELIEF HUMAN OTC DRUG LABEL 2 0363-0147 CREAM 10 g TOPICAL OTC monograph not final 11 sections
WALGREENS MEDICATED PAIN RELIEVING HUMAN OTC DRUG LABEL 3 0363-0149 PATCH 33 mg TOPICAL OTC monograph not final 14 sections
Cool n Heat Patch for Arm, Neck and Leg HUMAN OTC DRUG LABEL 1 0363-0150 PATCH 0.05 mg TOPICAL OTC monograph not final 11 sections
Pain Relieving Patch HUMAN OTC DRUG LABEL 1 0363-0151 PATCH 0.05 mg TOPICAL OTC monograph not final 13 sections
Cool n Heat Patch for Back HUMAN OTC DRUG LABEL 1 0363-0152 PATCH 0.05 mg TOPICAL OTC monograph not final 11 sections
Rinse HUMAN OTC DRUG LABEL 4 0363-0318 MOUTHWASH 0.42 mg ORAL OTC monograph not final 14 sections
Tartar control plus HUMAN OTC DRUG LABEL 4 0363-0434 MOUTHWASH 0.42 mg ORAL OTC monograph not final 13 sections
Body HUMAN OTC DRUG LABEL 2 0363-0551 POWDER 1.50 mg TOPICAL OTC monograph not final 13 sections
Studio 35 External Analgesic Medicated Body HUMAN OTC DRUG LABEL 2 0363-0552 POWDER 1.50 mg TOPICAL OTC monograph not final 12 sections
Antispetic HUMAN OTC DRUG LABEL 4 0363-0664 MOUTHWASH 0.42 mg ORAL OTC monograph not final 13 sections
Tartar control plus HUMAN OTC DRUG LABEL 4 0363-0855 MOUTHWASH 0.42 mg ORAL OTC monograph not final 13 sections
Walgreens Cold Pain Relief HUMAN OTC DRUG LABEL 1 0363-0864 GEL 40 mg TOPICAL OTC monograph not final 8 sections
Walgreens Cold Pain Relief HUMAN OTC DRUG LABEL 1 0363-0874 GEL 40 mg TOPICAL OTC monograph not final 8 sections
Pain Relief Patches HUMAN OTC DRUG LABEL 3 0363-0907 PATCH 6 g TOPICAL OTC monograph not final 9 sections
Menthol Cough Drop HUMAN OTC DRUG LABEL 1 0363-1070 LOZENGE 5.40 mg ORAL OTC monograph final 12 sections
Cherry Cough Drop HUMAN OTC DRUG LABEL 1 0363-1071 LOZENGE 5.80 mg ORAL OTC monograph final 12 sections
Honey Lemon Cough Drop HUMAN OTC DRUG LABEL 1 0363-1072 LOZENGE 7.50 mg ORAL OTC monograph final 12 sections
Strawberry Cough Drop HUMAN OTC DRUG LABEL 1 0363-1073 LOZENGE 2.70 mg ORAL OTC monograph final 12 sections
SF Honey Lemon Cough Drop HUMAN OTC DRUG LABEL 1 0363-1077 LOZENGE 7.60 mg ORAL OTC monograph final 12 sections
Cherry Sore Throat Lozenge HUMAN OTC DRUG LABEL 2 0363-1079 LOZENGE 3.60 mg ORAL OTC monograph not final 13 sections
Menthol Cough Drop HUMAN OTC DRUG LABEL 1 0363-1084 LOZENGE 5.40 mg ORAL OTC monograph final 12 sections
SF Menthol Cough Drop HUMAN OTC DRUG LABEL 1 0363-1085 LOZENGE 5.80 mg ORAL OTC monograph final 12 sections
Cherry Cough Drops HUMAN OTC DRUG LABEL 1 0363-1086 LOZENGE 5.80 mg ORAL OTC monograph final 12 sections