Eucalyptus oil

Identification

Name
Eucalyptus oil
Accession Number
DB11114
Type
Small Molecule
Groups
Approved
Description

Eucalyptus oil is a distilled oil derived from the leaves of the tree Eucalyptus. It is shown to be effective in reducing pain, swelling, and inflammation via its modulatory effect on the immune response. It is also shown to exhibit antibacterial activity against some bacterial species and cough suppressant actions. Eucalyptus oil can be applied directly to the skin for pain and swelling of respiratory tract mucous membranes, joint pain, genital herpes, and nasal stuffiness.

Synonyms
Not Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Eucalyptus OilLiquidTopicalDawson Traders Ltd.1977-12-312006-03-22Canada
Eucalyptus OilLiquidRespiratory (inhalation)Regal Pharms, Division Of Bradcan Corporation1983-12-311998-07-29Canada
Eucalyptus OilLiquidOral; Respiratory (inhalation); TopicalStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1972-12-312000-07-27Canada
Eucalyptus Oil Liq 100%Liquid100 %Oral; Respiratory (inhalation); TopicalJedmon Products Ltd.1990-12-312006-03-22Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
4JointzEucalyptus oil (4 g/100g) + Allantoin (0.025 g/100g) + Tannic acid (5 g/100g)CreamTopicalArp(usa) Pty Ltd2017-01-312018-04-05Us
4oz Medicated Chest RubEucalyptus oil (1 g/100g) + Menthol (1 g/100g) + Synthetic Camphor (4.7 g/100g)OintmentTopicalPride Products Corporation2017-12-01Not applicableUs
Allure Vaporizing Chest RubEucalyptus oil (1.0 g/100g) + Menthol (1.0 g/100g) + Synthetic Camphor (4.7 g/100g)GelTopicalUniversal Distribution Center LLC2012-06-30Not applicableUs
Amar Vaporizing Chest RubEucalyptus oil (1.6 g/100g) + Menthol (3.15 g/100g) + Synthetic Camphor (5.25 g/100g)OintmentTopicalAmar Remedies Limited - Mumbai2010-05-01Not applicableUs
Amoray Care Chest RubEucalyptus oil (1 g/113g) + Camphor (4.7 g/113g) + Menthol (2 g/113g)GelTopicalMy Import Inc2010-03-102017-02-10Us
Amrutanjan Relief Cold RubEucalyptus oil (0.012 g/1g) + Menthol (0.026 g/1g) + Synthetic Camphor (0.048 g/1g)OintmentTopicalAmrutanjan Health Care Limited2015-04-16Not applicableUs
Analgesic BalmEucalyptus oil (2.5 %) + Guaiacol (1.25 %) + Menthol (3.12 %) + Methyl salicylate (25 %)OintmentTopicalStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1965-12-312000-07-27Canada
Antiphlogistine Rub A 535 Extra StrengthEucalyptus oil (.5 %) + Camphor (1 %) + Menthol (.75 %) + Methyl salicylate (18 %)OintmentTopicalCarter Products, Division Of Carter Wallace Ns Inc.1983-12-311997-08-14Canada
Antiphlogistine Rub A535Eucalyptus oil (.5 %) + Camphor (1 %) + Menthol (.75 %) + Methyl salicylate (12.5 %)OintmentTopicalCarter Products, Division Of Carter Wallace Ns Inc.1957-12-311997-08-14Canada
Arhtri PlusEucalyptus oil (0.72 g/100g) + Clove oil (0.25 g/100g) + Menthol (2.5 g/100g)SprayTopicalDistributions Ar?Mes D`espagne Enr2014-10-30Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Original Pain Relief CreamEucalyptus oil (38.6 mg/1g) + Tea tree oil (42.5 mg/1g)CreamTopicalUltra Mix (Aust) Pty Ltd2015-02-16Not applicableUs
Categories
UNII
2R04ONI662
CAS number
8000-48-4
Weight
Not Available
Chemical Formula
Not Available
InChI Key
Not Available
InChI
Not Available
IUPAC Name
Not Available
SMILES
Not Available

Pharmacology

Indication

As an active agent, eucalyptus oil has been indicated for relief of the symptoms of catarrhal colds, and/or the relief of the symptoms of minor muscular sprains and cramps [24].

Pharmacodynamics

Lipophilic monoterpene formulations of eucalyptus oil appear to be readily absorbed orally, with a primarily oxidative metabolism that might necessitate induction of the cytochrome P450 enzyme system and subsequent urinary excretion [6]. Gastrointestinal absorption of eucalyptus appears to be rapid and may be enhanced by the intake of lipids and milk. 1,8-cineole (which makes up to as much as 90% of most commonly used cineole-based eucalyptus oils) [4] has also been found in vitro and in animals to possess cytochrome P450 inducing activity [7, 8, 9].

Mechanism of action

The general consensus is that the exact mechanism of action of eucalyptus oil is largely unknown at this time but comprises various hypotheses from various studies.

Cineol containing preparations of eucalyptus oil may contain up to 80% (or more) 1,8-cineole [13] and is one of the most common types of eucalyptus oil formulations used. As an active agent indicated for relieving certain cold symptoms and/or certain muscular sprains and cramps, it is believed that eucalyptus oil may possess some antimicrobial and anti-inflammatory activities.

Some in vitro studies of human blood monocytes suggest a dose-dependent effect of eucalyptus oil to elicit significant inhibition of multiple cytokines, perhaps in the treatment of airway inflammation [14, 15]. Moreover, other studies in animal models discuss the possibility of eucalyptus oil demonstrating anti-inflammatory and anti-nociceptive effects that potentially account for inhibiting the formation of prostaglandins and cytokines by stimulated monocytes in vitro [16, 17].

Furthermore, additional studies have observed eucalyptus oil anti-viral activity against herpes simplex virus (HSV-1, HSV-2) in cell cultures as well as the demonstration of broad antimicrobial activity of eucalyptus medicinal plant extracts against Alicyclobacillus acidoterretris, Bacillus cereus, E. coli, Enterococcus faecalis, MRSA, Propionibacterium acnes, S. aureus, fungus including C. albicans isolates, Trichophyton mentagrophytes, and other Gram-positive bacteria. Specific activity against periodontopathic bacteria, such as Porphyromonas gingivalis, Actinobacillus actinomycetemcomitans, Fusobacterium nucleatum, Streptococcus mutans, and Streptococcus sobrinus has also been observed [18, 19, 20, 21, 22].

Absorption

Common monoterpenoid compound preparations of eucalyptus oil have been observed to be readily absorbed after dermal application, likely due to their lipophilic character [5]. Although maximal plasma levels were demonstrated in as short a time period as 10 minutes even with thicker preparations like eucalyptus oil ointments, like many other topically applied agents, the extent of absorption is also likely largely dependent upon additional factors like the size of treated skin area, patient skin condition(s), concentrations of the applied substance, and time of exposure to the substance [5].

Currently, more data regarding the oral absorption of eucalyptus would be useful, given the relative lack of existing information [5]. Lipophilic monoterpene compound formulations of eucalyptus oil seems to be readily absorbed orally [6]. Regardless, there is some data that suggests that the upper part of the gastrointestinal tract has no particularly significant role in the absorption of cineole based eucalyptus oil [5].

Pulmonary absorption of eucalyptus oil is also possible although little information exists regarding this element at the moment. Nevertheless, 1,8-cineol (which makes up to as much as 90% of most commonly used cineole-based eucalyptus oils) [4] appears to be well absorbed via inhalation with peak plasma levels observed reportedly at 18 minutes [10].

Given the three main constituents from Eucalyptus globulus Labill fruits, the intestinal absorption of macrocarpal A (M-A), macrocarpal B (M-B), and cypellocarpa C (Cy-C) is predominantly via passive diffusion while Cy-C demonstrates some partly ATP-dependent absorption [12].

Volume of distribution

Studies have determined a large terminal volume of distribution for cineole or eucalyptol (which makes up to as much as 90% of most commonly used cineole-based eucalyptus oils) of 27 l/kg in brushtail possum (Trichosurus vulpecula) [4].

Protein binding
Not Available
Metabolism

With in vivo models, eucalyptol or cineole (which make up to as much as 90% of most commonly used cineole-based eucalyptus oils), undergoes oxidation to form hydroxycineole which is excreted as glucuronide [23]. In rats, 2-hydroxycineole, 3-hydroxycineole, and 1,8--dihydroxycineol-9-oic acid were identified as main urinary metabolites [23]. After oral administration to brushtail possums, p-cresol, 9-hydroxycineole, and Cineole-9-oic acid were found in urine [23]. Rabbits given eucalyptol by savage excreted 2-exo- and 2-endo-hydroxycineole in the urine [23].

The monterpene bicyclic ketone verbenone is a known component in eucalyptus globules [11]. In one study, this component was observed to be converted to 10-hydroxyverbenone by rat and human liver microsomal cytochrome P450 enzymes, and indicated that CYP2A6 is a principal enzyme in verbenone hydroxylation in humans [11].

Route of elimination

Studies suggest the route of elimination for cineole or eucalyptol (which makes up to as much as 90% of most commonly used cineole-based eucalyptus oils) in brushtail possum (Trichosurus vulpecula), rats, and rabbit subjects as being in the urine [4].

Half life

Studies have determined a terminal half-life for cineole or eucalyptol (which makes up to as much as 90% of most commonly used cineole-based eucalyptus oils) of approximately 7h in brushtail possum (Trichosurus vulpecula) [4].

Clearance

Studies have determined a high clearance rate for cineole or eucalyptol (which makes up to as much as 90% of most commonly used cineole-based eucalyptus oils) of 43 ml/min/kg in brushtail possum (Trichosurus vulpecula) [4].

Toxicity

Overdose with eucalyptus oil may result in epigastric burning, nausea and vomiting, dizziness, muscular weakness, mitosis, tachycardia, a sensation of suffocation, cyanosis, ataxia, pulmonary damage, delirium, convulsions, CNS depression, coma. Deaths have been recorded from doses as low as 3.5 ml.

The given oral LD50 for rats is 2480 mg/kg [MSDS]

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Eucalyptus oil which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Eucalyptus oil which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Eucalyptus oil which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Eucalyptus oil which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Eucalyptus oil which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Eucalyptus oil which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Eucalyptus oil which could result in a higher serum level.
AcrivastineAcrivastine may decrease the excretion rate of Eucalyptus oil which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Eucalyptus oil which could result in a higher serum level.
AdefovirAdefovir may decrease the excretion rate of Eucalyptus oil which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. Jun YS, Kang P, Min SS, Lee JM, Kim HK, Seol GH: Effect of eucalyptus oil inhalation on pain and inflammatory responses after total knee replacement: a randomized clinical trial. Evid Based Complement Alternat Med. 2013;2013:502727. doi: 10.1155/2013/502727. Epub 2013 Jun 18. [PubMed:23853660]
  2. Serafino A, Sinibaldi Vallebona P, Andreola F, Zonfrillo M, Mercuri L, Federici M, Rasi G, Garaci E, Pierimarchi P: Stimulatory effect of Eucalyptus essential oil on innate cell-mediated immune response. BMC Immunol. 2008 Apr 18;9:17. doi: 10.1186/1471-2172-9-17. [PubMed:18423004]
  3. Bachir RG, Benali M: Antibacterial activity of the essential oils from the leaves of Eucalyptus globulus against Escherichia coli and Staphylococcus aureus. Asian Pac J Trop Biomed. 2012 Sep;2(9):739-42. doi: 10.1016/S2221-1691(12)60220-2. [PubMed:23570005]
  4. McLean S, Boyle RR, Brandon S, Davies NW, Sorensen JS: Pharmacokinetics of 1,8-cineole, a dietary toxin, in the brushtail possum (Trichosurus vulpecula): significance for feeding. Xenobiotica. 2007 Sep;37(9):903-22. doi: 10.1080/00498250701570277. [PubMed:17896321]
  5. Kohlert C, van Rensen I, Marz R, Schindler G, Graefe EU, Veit M: Bioavailability and pharmacokinetics of natural volatile terpenes in animals and humans. Planta Med. 2000 Aug;66(6):495-505. doi: 10.1055/s-2000-8616. [PubMed:10985073]
  6. McLean S, Foley WJ: Metabolism of Eucalyptus terpenes by herbivorous marsupials. Drug Metab Rev. 1997 Feb-May;29(1-2):213-8. [PubMed:9187519]
  7. Jori A, Bianchetti A, Prestini PE, Gerattini S: Effect of eucalyptol (1,8-cineole) on the metabolism of other drugs in rats and in man. Eur J Pharmacol. 1970 Mar;9(3):362-6. [PubMed:5440307]
  8. Pass GJ, McLean S, Stupans I, Davies N: Microsomal metabolism of the terpene 1,8-cineole in the common brushtail possum (Trichosurus vulpecula), koala (Phascolarctos cinereus), rat and human. Xenobiotica. 2001 Apr;31(4):205-21. doi: 10.1080/00498250110043535 . [PubMed:11465406]
  9. Miyazawa M, Shindo M, Shimada T: Oxidation of 1,8-cineole, the monoterpene cyclic ether originated from eucalyptus polybractea, by cytochrome P450 3A enzymes in rat and human liver microsomes. Drug Metab Dispos. 2001 Feb;29(2):200-5. [PubMed:11159812]
  10. Jager W, Nasel B, Nasel C, Binder R, Stimpfl T, Vycudilik W, Buchbauer G: Pharmacokinetic studies of the fragrance compound 1,8-cineol in humans during inhalation. Chem Senses. 1996 Aug;21(4):477-80. [PubMed:8866111]
  11. Miyazawa M, Sugie A, Shimada T: Roles of human CYP2A6 and 2B6 and rat CYP2C11 and 2B1 in the 10-hydroxylation of (-)-verbenone by liver microsomes. Drug Metab Dispos. 2003 Aug;31(8):1049-53. doi: 10.1124/dmd.31.8.1049. [PubMed:12867494]
  12. Yang XW, Guo QM, Wang Y, Xu W, Tian L, Tian XJ: Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model. Bioorg Med Chem Lett. 2007 Feb 15;17(4):1107-11. doi: 10.1016/j.bmcl.2006.11.021. Epub 2006 Nov 10. [PubMed:17118653]
  13. Schnitzler P, Schon K, Reichling J: Antiviral activity of Australian tea tree oil and eucalyptus oil against herpes simplex virus in cell culture. Pharmazie. 2001 Apr;56(4):343-7. [PubMed:11338678]
  14. Juergens UR, Stober M, Vetter H: Inhibition of cytokine production and arachidonic acid metabolism by eucalyptol (1.8-cineole) in human blood monocytes in vitro. Eur J Med Res. 1998 Nov 17;3(11):508-10. [PubMed:9810029]
  15. Juergens UR, Stober M, Schmidt-Schilling L, Kleuver T, Vetter H: Antiinflammatory effects of euclyptol (1.8-cineole) in bronchial asthma: inhibition of arachidonic acid metabolism in human blood monocytes ex vivo. Eur J Med Res. 1998 Sep 17;3(9):407-12. [PubMed:9737886]
  16. Santos FA, Rao VS: Antiinflammatory and antinociceptive effects of 1,8-cineole a terpenoid oxide present in many plant essential oils. Phytother Res. 2000 Jun;14(4):240-4. [PubMed:10861965]
  17. Atta AH, Alkofahi A: Anti-nociceptive and anti-inflammatory effects of some Jordanian medicinal plant extracts. J Ethnopharmacol. 1998 Mar;60(2):117-24. [PubMed:9582001]
  18. Sartorelli P, Marquioreto AD, Amaral-Baroli A, Lima ME, Moreno PR: Chemical composition and antimicrobial activity of the essential oils from two species of Eucalyptus. Phytother Res. 2007 Mar;21(3):231-3. doi: 10.1002/ptr.2051. [PubMed:17154233]
  19. Ahmad I, Beg AZ: Antimicrobial and phytochemical studies on 45 Indian medicinal plants against multi-drug resistant human pathogens. J Ethnopharmacol. 2001 Feb;74(2):113-23. [PubMed:11167029]
  20. Takahashi T, Kokubo R, Sakaino M: Antimicrobial activities of eucalyptus leaf extracts and flavonoids from Eucalyptus maculata. Lett Appl Microbiol. 2004;39(1):60-4. doi: 10.1111/j.1472-765X.2004.01538.x. [PubMed:15189289]
  21. Osawa K, Yasuda H, Morita H, Takeya K, Itokawa H: Macrocarpals H, I, and J from the Leaves of Eucalyptus globulus. J Nat Prod. 1996 Sep;59(9):823-7. doi: 10.1021/np9604994. [PubMed:8864235]
  22. Takarada K, Kimizuka R, Takahashi N, Honma K, Okuda K, Kato T: A comparison of the antibacterial efficacies of essential oils against oral pathogens. Oral Microbiol Immunol. 2004 Feb;19(1):61-4. [PubMed:14678476]
  23. Safety Assessment of Eucalyptus globulus (Eucalyptus) - Derived Ingredients as Used in Cosmetics [Link]
  24. Electronic Medicines Compendium: Eucalyptus Oil BP Monograph [Link]
  25. Sigma-Aldrich: Eucalyptus oil Profile [Link]
External Links
PubChem Substance
347911122
Wikipedia
Eucalyptus_oil
AHFS Codes
  • 48:01.00* — Other Cold and Cough Preparations
MSDS
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Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SprayTopical
OilPercutaneous; Topical; Transdermal
OintmentRespiratory (inhalation); Topical
OintmentRespiratory (inhalation)
MouthwashDental
LozengeOral
LiquidOral; Respiratory (inhalation); Topical
LiquidRespiratory (inhalation)
LiquidTopical
LiquidOral; Respiratory (inhalation); Topical100 %
OilTopical; Transdermal
TabletOral
LiquidRespiratory (inhalation)
JellyTopical
LiquidTopical
StickTopical
OilTopical
PatchCutaneous; Topical; Transdermal
PatchTopical
LotionTopical
GelTopical
CreamTopical
SalveTopical
OintmentTopical
Gum, chewingOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
Not Available
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Drug created on December 03, 2015 09:51 / Updated on November 14, 2018 12:58