Camphor

Identification

Summary

Camphor is a compound used topically to help relieve pain and also as a topical antiseptic. May also be used in vaporizers to help suppress coughing. This medication should not be swallowed.

Brand Names
Fast Freeze
Generic Name
Camphor
DrugBank Accession Number
DB01744
Background

Camphor is a bicyclic monoterpene ketone found widely in plants, especially Cinnamomum camphora. It is used topically as a skin antipruritic and as an anti-infective agent. When ingested, camphor has a rapid onset of toxic effects, and camphorated oil is the product most often responsible for its toxicity. The FDA ruled that camphorated oil could not be marketed in the United States and that no product could contain a concentration higher than 11%. It appears in the list of drug products withdrawn or removed from the market for safety or effectiveness.1,2 However, camphor can be found in several nonprescription medications at lower concentrations.1

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Weight
Average: 152.2334
Monoisotopic: 152.120115134
Chemical Formula
C10H16O
Synonyms
  • (+)-bornan-2-one
  • (+)-Camphor
  • (1R,4R)-camphor
  • (1R)-(+)-camphor
  • (R)-(+)-camphor
  • (R)-camphor
  • Camphor (natural)
  • Camphor D-form
  • Camphor oil
  • Camphor(D)
  • Camphora
  • D-Camphor
  • Dextrocamphor
  • Natural camphor
External IDs
  • FEMA NO. 2230

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofArthritis••• •••
Symptomatic treatment ofBackache••• •••
Symptomatic treatment ofBruises••• •••
Symptomatic treatment ofCommon cold••• •••
Used in combination to treatInflammatory reaction caused by insect bitesCombination Product in combination with: Eucalyptus oil (DB11114)••• •••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ATransient receptor potential cation channel subfamily V member 1
agonist
activator
Humans
ATransient receptor potential cation channel subfamily V member 3
agonist
activator
Humans
ATransient receptor potential cation channel subfamily A member 1
inhibitor
Humans
ATransient receptor potential cation channel subfamily M member 8
activator
Humans
UCamphor 5-monooxygenase
substrate
Pseudomonas putida
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

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
No interactions found.

Products

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
365 Medicated Lip BalmStick0.0578 g/4.25gTopicalWhole Foods Market, Inc.2019-06-13Not applicableUS flag
amoray premium Vaporizing InhalerLiquid13 mg/1NasalNingbo Pulisi Daily Chemical Products2016-03-31Not applicableUS flag
ArthroNEOSpray0.5 g/100gTopicalHakimian Global LLC2021-10-27Not applicableUS flag
ArthroNEOSpray0.5 g/100gTopicalLikasso LTD2021-10-27Not applicableUS flag
Band-aid Brand Anti-itch GelGel0.50 %TopicalJohnson & Johnson2001-06-012009-08-06Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Aching Head RubCamphor (3.09 g/100g) + Menthol (2.55 g/100g)OintmentTopicalLittle Moon Essentials2016-09-26Not applicableUS flag
After Bite NaturalCamphor (10 mg/1g) + Colloidal oatmeal (100 mg/1g)SalveTopicalAdventure Ready Brands2022-04-01Not applicableUS flag
AIM Muscle Pain Relief CreamCamphor (2.5 g/100g) + Menthol (1.5 g/100g) + Methyl salicylate (10 g/100g)CreamTopicalLaboratorios Bremer, S.A.2018-01-042019-12-19US flag
Air SalonpasCamphor (3.00 mg/100mL) + Menthol (3.20 mg/100mL) + Methyl salicylate (1.75 mg/100mL)Aerosol, sprayPercutaneous; Topical; TransdermalHisamitsu Pharmaceutical Co., Inc.1997-09-032014-04-30US flag
Amoray Care Chest RubCamphor (4.7 g/113g) + Eucalyptus oil (1 g/113g) + Menthol (2 g/113g)GelTopicalMY IMPORT USA INC2010-03-102017-02-10US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AMULDY SPORTS gelCamphor (0.05 g/100mL) + Menthol (2.5 g/100mL) + Methyl salicylate (0.3 g/100mL) + Salicylic acid (0.03 g/100mL)LiquidTopicalLydia Co., Ltd.2020-04-24Not applicableUS flag
CamphomexCamphor (3.6 mg/1mL) + Histamine (0.03 mg/1mL) + Menthol (12 mg/1mL)SprayTopical1st Class Pharmaceuticals2014-03-242016-01-15US flag
Chun Gi SoCamphor (1 g/100g) + Menthol (1 g/100g)CreamTopicalCHO WELL GF2019-11-17Not applicableUS flag
DdsgenCamphor (1 g/100g) + Menthol (1 g/100g)CreamTopicalThe Times Co., Ltd.2019-05-11Not applicableUS flag
Kaydia PatchCamphor (3 g/100g) + Cannabidiol (0.15 g/100g) + Levomenthol (1 g/100g)PatchTopicalStrong Current Enterprises Limited2020-05-02Not applicableUS flag

Categories

ATC Codes
C01EB02 — Camphora
Drug Categories
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:15396)
Affected organisms
Not Available

Chemical Identifiers

UNII
N20HL7Q941
CAS number
464-49-3
InChI Key
DSSYKIVIOFKYAU-XCBNKYQSSA-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+/m1/s1
IUPAC Name
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
SMILES
[H][C@@]12CC[C@@](C)(C(=O)C1)C2(C)C

References

Synthesis Reference

Gerard Lang, Serge Forestier, Alain LaGrange, "Derivatives of 3-benzylidene camphor, process for their preparation and their use as protective agents against UV rays and as medicaments." U.S. Patent US4710584, issued January, 1984.

US4710584
General References
  1. Love JN, Sammon M, Smereck J: Are one or two dangerous? Camphor exposure in toddlers. J Emerg Med. 2004 Jul;27(1):49-54. doi: 10.1016/j.jemermed.2004.02.010. [Article]
  2. Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
Human Metabolome Database
HMDB0059838
KEGG Drug
D06392
KEGG Compound
C00808
PubChem Compound
159055
PubChem Substance
46508429
ChemSpider
139902
BindingDB
36263
RxNav
1298738
ChEBI
15396
ChEMBL
CHEMBL504760
ZINC
ZINC000000967520
PharmGKB
PA448759
PDBe Ligand
CAM
Drugs.com
Drugs.com Drug Page
Wikipedia
Camphor
PDB Entries
1akd / 1dz4 / 1dz6 / 1dz8 / 1dz9 / 1geb / 1iwi / 1iwj / 1o76 / 1t85
show 64 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentCough1
1CompletedTreatmentCommon Cold1
Not AvailableCompletedDiagnosticDermatitis, Photocontact1
Not AvailableCompletedTreatmentHypopituitarism1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • DSHealthcare Inc.
Dosage Forms
FormRouteStrength
StickTopical0.0578 g/4.25g
OintmentNasal
Aerosol, sprayPercutaneous; Topical; Transdermal
Drug delivery systemCutaneous
LiquidNasal13 mg/1
LiquidBuccal
LiquidOral
SprayTopical0.5 g/100g
Solution / dropsAuricular (otic)
LiquidRespiratory (inhalation)6 %
GelTopical0.50 %
SolutionTopical0.5 %
OilPercutaneous; Topical; Transdermal
OintmentTopical12.4 mg/1g
OintmentRespiratory (inhalation); Topical
GelTopical
CreamTopical0.15 g/100g
OintmentTopical10 g/100g
LiquidOral; Topical10 %
LiquidTopical10 g / 100 mL
LiquidTopical10 %
LiquidTopical100 mg / mL
LiquidTopical20 %
LiquidTopical200 mg / g
LiquidTopical200 g / 1 kg
OintmentTopical20 %
TinctureOral
LinimentTopical
SolutionTopical10 %
SolutionTopical
SolutionCutaneous
CreamTopical3 g/100g
CreamTopical5 g/100g
OilTopical3 g/100mL
StickTopical
PlasterTopical1 g/100g
PatchTopical13.875 mg/1h
JellyTopical
Oil
PatchTopical
OintmentTopical2 % w/w
CreamTopical2 g/100mL
PlasterTransdermal
OilTopical1.1 g/100g
OintmentTopical2.576 g/60mL
LiquidIntramuscular
SuppositoryRectal
CreamTopical3 g/100mL
LotionTopical
LotionTopical0.005 g/1mL
LiquidTopical7.79 g/100mL
Aerosol, sprayTopical
PatchCutaneous
KitTopical
LiquidRespiratory (inhalation)1 %w/v
SwabTopical0.15 mg/1g
OintmentTopical3.0 g/100g
SprayTopical3.1 g/100mL
CreamTopical0.5 g/100mL
LotionCutaneous
LotionTopical32 g/1000g
CreamTopical30 mg / g
PatchTopical22.5 mg/1
GelTopical4 g/100mL
OintmentTopical
LiquidRespiratory (inhalation)
GelTopical50 mg/1mL
LotionTopical0.7 g/100mL
CreamTopical30 mg/1000mg
AerosolTopical
SalveTopical
InhalantNasal
OilTopical6 g/4576mL
LinimentPercutaneous; Transdermal1 g/3500mL
LinimentPercutaneous; Transdermal
Solution
OilTopical3 mL/100mL
CreamTopical1.5 g/50g
SprayTopical3 g/100mL
LiquidTopical3.1 g/100g
LiquidTopical3.1 g/100mL
SolutionTopical
TabletOral
LiquidTopical.0225 g/.75mL
CreamTopical1 g/100g
Aerosol, sprayTopical1.5 g/100mL
LotionTopical1.5 g/100g
PatchTopical280 mg/1
GelTopical1.5 g/100g
LinimentTopical3.5 g/100mL
PlasterTopical
CreamTopical3.3 g/100g
Kit; patchTopical
CreamTopical2 g/100g
LiquidTopical100 mg/1mL
OilTopical
CreamTopical
SprayCutaneous
OintmentTopical1 g/100g
CreamTopical13 g/100g
SolutionTopical2.8 % w/w
SprayTopical1 mL/30mL
LiquidOral; Topical10 g / 100 mL
LiquidTopical
Plaster
PowderTopical
LiquidTopical1 mg/1mL
PatchTopical0.1 g/100g
OintmentTopical1.344 g/28g
PatchTransdermal
SprayTopical
PlasterCutaneous
Ointment
PoulticeTransdermal
LiquidRespiratory (inhalation)62 mg/1mL
OintmentCutaneous
SolutionIntrasinal; Respiratory (inhalation)
SolutionNasal
StickNasal
OintmentTopical5 %
LiquidOphthalmic
PlasterTransdermal3.1 g/1
LiquidDental
SolutionOral
EmulsionTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)180 °CPhysProp
boiling point (°C)204 °CPhysProp
water solubility1600 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP2.38DAYLIGHT (1999)
Predicted Properties
PropertyValueSource
Water Solubility0.88 mg/mLALOGPS
logP2.85ALOGPS
logP2.55Chemaxon
logS-2.2ALOGPS
pKa (Strongest Basic)-7.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area17.07 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity44.49 m3·mol-1Chemaxon
Polarizability17.74 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier+0.9836
Caco-2 permeable+0.8084
P-glycoprotein substrateNon-substrate0.5868
P-glycoprotein inhibitor INon-inhibitor0.639
P-glycoprotein inhibitor IINon-inhibitor0.9104
Renal organic cation transporterNon-inhibitor0.8103
CYP450 2C9 substrateNon-substrate0.823
CYP450 2D6 substrateNon-substrate0.8379
CYP450 3A4 substrateSubstrate0.6692
CYP450 1A2 substrateNon-inhibitor0.8876
CYP450 2C9 inhibitorNon-inhibitor0.9088
CYP450 2D6 inhibitorNon-inhibitor0.9696
CYP450 2C19 inhibitorNon-inhibitor0.9313
CYP450 3A4 inhibitorNon-inhibitor0.9583
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.978
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8235
BiodegradationNot ready biodegradable0.6872
Rat acute toxicity1.6328 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.913
hERG inhibition (predictor II)Non-inhibitor0.8076
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4r-5900000000-f1efb31da7c673a3dbe9
GC-MS Spectrum - EI-BGC-MSsplash10-05nb-9200000000-1b9d8eae41ec7b1ad819
GC-MS Spectrum - EI-BGC-MSsplash10-05o1-9300000000-f5c5e5805061cef08d31
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-5128b8f555a7e82225a7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-2900000000-d1f2122565c9f9eae861
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-f988c217c33c41bd9884
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-a77c45fae32da597897d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-9300000000-b84a02be1ab328f87f8f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-bcc7bae1dc5deb7796d7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-131.1976868
predicted
DarkChem Lite v0.1.0
[M-H]-131.2102868
predicted
DarkChem Lite v0.1.0
[M-H]-131.3263868
predicted
DarkChem Lite v0.1.0
[M-H]-131.1880868
predicted
DarkChem Lite v0.1.0
[M-H]-140.105
predicted
DeepCCS 1.0 (2019)
[M+H]+131.6908868
predicted
DarkChem Lite v0.1.0
[M+H]+131.4797868
predicted
DarkChem Lite v0.1.0
[M+H]+131.5289868
predicted
DarkChem Lite v0.1.0
[M+H]+131.5985868
predicted
DarkChem Lite v0.1.0
[M+H]+142.23589
predicted
DeepCCS 1.0 (2019)
[M+Na]+131.4667868
predicted
DarkChem Lite v0.1.0
[M+Na]+131.4058868
predicted
DarkChem Lite v0.1.0
[M+Na]+131.4706868
predicted
DarkChem Lite v0.1.0
[M+Na]+131.4826868
predicted
DarkChem Lite v0.1.0
[M+Na]+148.1484
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
Activator
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
  1. 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
Agonist
Activator
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. 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]
  2. 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
  1. 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
  1. 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]
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
Actions
Substrate
General Function
Iron ion binding
Specific Function
Involved in a camphor oxidation system.
Gene Name
camC
Uniprot ID
P00183
Uniprot Name
Camphor 5-monooxygenase
Molecular Weight
46668.8 Da
References
  1. Balaraman P, Plettner E: Chemotaxis by Pseudomonas putida (ATCC 17453) towards camphor involves cytochrome P450cam (CYP101A1). Biochim Biophys Acta Gen Subj. 2019 Feb;1863(2):304-312. doi: 10.1016/j.bbagen.2018.10.018. Epub 2018 Nov 1. [Article]
  2. Kammoonah S, Prasad B, Balaraman P, Mundhada H, Schwaneberg U, Plettner E: Selecting of a cytochrome P450cam SeSaM library with 3-chloroindole and endosulfan - Identification of mutants that dehalogenate 3-chloroindole. Biochim Biophys Acta Proteins Proteom. 2018 Jan;1866(1):68-79. doi: 10.1016/j.bbapap.2017.09.006. Epub 2017 Sep 18. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48