Identification
- Generic Name
- (S)-camphor
- DrugBank Accession Number
- DB11345
- Background
(S)-camphor, or L(-)-Camphor, is a stereoisomer of Camphor, a bicyclic monoterpene known to potentiate both heat and cold sensations 2. (S)-camphor is not the naturally-occurring stereoisomer but displays similar TRPV channel affinity and current inhibition 1. Camphor is isolated from the wood of the camphor laurel tree, Cinnamomum camphora, and had a long history of medicinal use. It has been used as a nasal decongestant and cough suppressant, and has been topically applied due to its antipruritic, analgesic, and counterirritant properties 1. Camphor is a major active ingredient in over-the-counter balms and liniments supplied as topical analgesics by causing sensitization to heat and coolness to relieve minor muscle and joint pain 1.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (S)-camphor (DB11345)
- Weight
- Average: 152.2334
Monoisotopic: 152.120115134 - Chemical Formula
- C10H16O
- Synonyms
- (−)-bornan-2-one
- (−)-camphor
- (1S,4S)-camphor
- (1S)-(−)-camphor
- l-camphor
- External IDs
- NSC-26351
Pharmacology
- Indication
Indicated for the temporary symptomatic relief of minor aches and pains of muscles and joints in topical analgesics.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Joint pain ••• ••• Used in combination for symptomatic treatment of Muscle pain ••• ••• - Contraindications & Blackbox Warnings
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Camphor exerts an analgesic action when applied topically by producing a warm sensation. It excites and desensitizes sensory nerves by activating heat-sensitive TRP vanilloid subtype 1 (TRPV1) and TRPV3 receptors. (S)-camphor is reported to exert a weaker action on TRPV1 channels, which is thought to be a result of tachyphylaxis, which is the reduction of the response to multiple stimulations 1.
- Mechanism of action
TRPV3 cation channels are molecular sensors that play a role in nociception and thermosensation by inducing thermal sensation and heat-induced hyperalgesia 3. Camphor interacts with TRPV3 channels via pore-region cysteine residues 3, leading to channel activation and a rise in intracellular calcium levels. Camphor also activates TRPV1 and a TRPV1-like current in dorsal root ganglion (DRG) neurons but inhibits the ankyrin-repeat TRP 1 (TRPA1) channel expressed in most nociceptive DRG neurons, which is responsible for the detection of temperature 1. The precise role of TRPA1 current inhibition on the analgesic properties of camphor is unclear. Repeated stimulation by camphor leads to sensitization of the TRPV1 and TRPV3 channels, resulting in desensitization, or reduced channel response that likely leads to the analgesic effects of camphor 1. Camphor also activates cold-sensitive transient receptor potential melastatin 8 (TRPM8) and sensitizes cold-induced calcium transients, which explains the cooling effect of camphor following dermal application. Additionally, camphor was shown to inhibit the TRPM8 receptor response to menthol 2.
Target Actions Organism ATransient receptor potential cation channel subfamily V member 1 agonistactivatorHumans ATransient receptor potential cation channel subfamily V member 3 agonistactivatorHumans ATransient receptor potential cation channel subfamily A member 1 inhibitorHumans ATransient receptor potential cation channel subfamily M member 8 activatorHumans - Absorption
Absorption of camphor in the mucous membranes and the gastrointestinal tract is rapid, and peak concentration following oral ingestion occurs within 5 to 90 minutes 5.
- Volume of distribution
Volume of distribution of camphor is 2 to 4 L/kg 5. Camphor and its metabolites are relatively fat-soluble thus may accumulate in adipose and other tissues 5. Camphor ingested by mothers was present in amnionic fluid, cord and fetal blood and fetal brain, liver and kidneys 5.
- Protein binding
No pharmacokinetic data available.
- Metabolism
(S)-camphor undergoes rapid oxidation to 5-exo-hydroxyfenchone, which is predominantly mediated by human liver microsomal cytochrome (P450). CYP2A6 is the major enzyme involved in the hydroxylation of (-)-camphor by human liver microsomes 4.
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- Route of elimination
Camphor undergoes renal excretion 5.
- Half-life
Following oral ingestion of 200 mg camphor, the half life was 167 minutes 5.
- Clearance
No pharmacokinetic data available.
- Adverse Effects
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Oral LD50 and intraperitoneal LD50 in mouse were 1310 mg/kg and 3000 mg/kg, respectively 5. Subcutaneous LD50 in rat was 70 mg/kg 5.
The main target organs of camphor are the CNS and kidneys. Camphor is a CNS stimulant that may cause convulsions, depression, apnea, asystole, gastric irritation, colic, nausea, vomiting, diarrhea, anxiety, excitement, delirium, and severe post-convulsive coma 5. Camphor is also irritating to the eyes, skin and mucous membranes following dermal contact of high doses. Gastrointestinal irritation and CNS depression may occur at doses over 10 mg/kg while as little as 1 g has been fatal in infants, and death has been reported with doses of 50 mg/kg or more 5. There is no known antidote for camphor intoxication, thus gastrointestinal decontamination via activated charcoal is generally recommended for oral camphor overdose 5.
- 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.Not Available
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Camphor unknown N20HL7Q941 464-49-3 DSSYKIVIOFKYAU-XCBNKYQSSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antiphlamine (S)-camphor (59 mg/1g) + Levomenthol (8 mg/1g) + Methyl salicylate (46 mg/1g) Patch Topical I World Pharmaceutical Co., Ltd. 2020-09-09 Not applicable US 
Antiphlamine (S)-camphor (59 mg/1g) + Levomenthol (8 mg/1g) + Methyl salicylate (46 mg/1g) Ointment Topical OASIS TRADING 2018-11-15 Not applicable US Antiphlamine (S)-camphor (59 mg/1g) + Levomenthol (8 mg/1g) + Methyl salicylate (46 mg/1g) Lotion Topical Lydia Co., Ltd. 2022-01-02 Not applicable US Balsang Pain Relief (S)-camphor (1.5 mg/100mL) + (+)-menthol (1.5 mg/100mL) + Methyl salicylate (5 mg/100mL) Solution Topical Genuine Drugs 2015-04-20 Not applicable US Bufferin Pain Relief (S)-camphor (40 mg/1g) + (+)-menthol (100 mg/1g) + Methyl salicylate (300 mg/1g) Cream Topical Genomma Lab USA 2023-08-18 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antiphlamine (S)-camphor (59 mg/1g) + Levomenthol (8 mg/1g) + Methyl salicylate (46 mg/1g) Lotion Topical Lydia Co., Ltd. 2022-01-02 Not applicable US
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Monoterpenoids
- Direct Parent
- Bicyclic monoterpenoids
- Alternative Parents
- Ketones / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic homopolycyclic compound / Bicyclic monoterpenoid / Bornane monoterpenoid / Carbonyl group / Hydrocarbon derivative / Ketone / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- camphor (CHEBI:15397)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 213N3S8275
- CAS number
- 464-48-2
- InChI Key
- DSSYKIVIOFKYAU-OIBJUYFYSA-N
- InChI
- InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3/t7-,10+/m0/s1
- IUPAC Name
- (1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
- SMILES
- CC1(C)[C@H]2CC[C@]1(C)C(=O)C2
References
- General References
- Xu H, Blair NT, Clapham DE: Camphor activates and strongly desensitizes the transient receptor potential vanilloid subtype 1 channel in a vanilloid-independent mechanism. J Neurosci. 2005 Sep 28;25(39):8924-37. doi: 10.1523/JNEUROSCI.2574-05.2005. [Article]
- Selescu T, Ciobanu AC, Dobre C, Reid G, Babes A: Camphor activates and sensitizes transient receptor potential melastatin 8 (TRPM8) to cooling and icilin. Chem Senses. 2013 Sep;38(7):563-75. doi: 10.1093/chemse/bjt027. Epub 2013 Jul 4. [Article]
- Sherkheli MA, Vogt-Eisele AK, Weber K, Hatt H: Camphor modulates TRPV3 cation channels activity by interacting with critical pore-region cysteine residues. Pak J Pharm Sci. 2013 May;26(3):431-8. [Article]
- Gyoubu K, Miyazawa M: In vitro metabolism of (-)-camphor using human liver microsomes and CYP2A6. Biol Pharm Bull. 2007 Feb;30(2):230-3. [Article]
- CAMPHOR - National Library of Medicine HSDB Database [Link]
- External Links
- KEGG Compound
- C00809
- ChemSpider
- 392267
- 1648124
- ChEBI
- 15397
- ChEMBL
- CHEMBL2252949
- ZINC
- ZINC000000967521
- MSDS
- Download (48.5 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Lotion Topical Patch Topical Solution Topical Ointment Topical Dressing Cutaneous Gel Topical Cream Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 178-180 MSDS boiling point (°C) 204 MSDS - Predicted Properties
Property Value Source Water Solubility 0.88 mg/mL ALOGPS logP 2.85 ALOGPS logP 2.55 Chemaxon logS -2.2 ALOGPS pKa (Strongest Basic) -7.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 17.07 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 44.49 m3·mol-1 Chemaxon Polarizability 17.73 Å3 Chemaxon Number of Rings 2 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 131.3375868 predictedDarkChem Lite v0.1.0 [M-H]- 131.4022868 predictedDarkChem Lite v0.1.0 [M-H]- 131.4235868 predictedDarkChem Lite v0.1.0 [M-H]- 136.002 predictedDeepCCS 1.0 (2019) [M+H]+ 131.7201868 predictedDarkChem Lite v0.1.0 [M+H]+ 131.5197868 predictedDarkChem Lite v0.1.0 [M+H]+ 131.5664868 predictedDarkChem Lite v0.1.0 [M+H]+ 138.39757 predictedDeepCCS 1.0 (2019) [M+Na]+ 131.6992868 predictedDarkChem Lite v0.1.0 [M+Na]+ 131.6720868 predictedDarkChem Lite v0.1.0 [M+Na]+ 145.04518 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AgonistActivator
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular aci...
- Gene Name
- TRPV1
- Uniprot ID
- Q8NER1
- Uniprot Name
- Transient receptor potential cation channel subfamily V member 1
- Molecular Weight
- 94955.33 Da
References
- Xu H, Blair NT, Clapham DE: Camphor activates and strongly desensitizes the transient receptor potential vanilloid subtype 1 channel in a vanilloid-independent mechanism. J Neurosci. 2005 Sep 28;25(39):8924-37. doi: 10.1523/JNEUROSCI.2574-05.2005. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AgonistActivator
- 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
- Xu H, Blair NT, Clapham DE: Camphor activates and strongly desensitizes the transient receptor potential vanilloid subtype 1 channel in a vanilloid-independent mechanism. J Neurosci. 2005 Sep 28;25(39):8924-37. doi: 10.1523/JNEUROSCI.2574-05.2005. [Article]
- Sherkheli MA, Vogt-Eisele AK, Weber K, Hatt H: Camphor modulates TRPV3 cation channels activity by interacting with critical pore-region cysteine residues. Pak J Pharm Sci. 2013 May;26(3):431-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Xu H, Blair NT, Clapham DE: Camphor activates and strongly desensitizes the transient receptor potential vanilloid subtype 1 channel in a vanilloid-independent mechanism. J Neurosci. 2005 Sep 28;25(39):8924-37. doi: 10.1523/JNEUROSCI.2574-05.2005. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Activator
- 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
- Selescu T, Ciobanu AC, Dobre C, Reid G, Babes A: Camphor activates and sensitizes transient receptor potential melastatin 8 (TRPM8) to cooling and icilin. Chem Senses. 2013 Sep;38(7):563-75. doi: 10.1093/chemse/bjt027. Epub 2013 Jul 4. [Article]
Drug created at December 03, 2015 16:52 / Updated at September 28, 2021 21:54