Clove oil

Identification

Generic Name
Clove oil
DrugBank Accession Number
DB11338
Background

Clove oil is obtained by extraction from the dried flower buds of the clove plant. Traditionally, it has been used as a flavouring spice in foods, or as a fragrance. It is also found in topical analgesics. Clove oil has shown to exert some antimicrobial activities. The antioxidant and antimicrobial activity of clove is higher than that of many fruits, vegetables, and other spices 2.

Clove is native of Indonesia but is now cultured in several parts of the world, including Brazil in the state of Bahia. This plant represents one of the richest source of phenolic compounds such as eugenol, eugenol acetate and gallic acid and has great potential for pharmaceutical, cosmetic, food and agricultural applications 2.

Interestingly, clove oil has been studied for its potential benefit in treating neuropathic pain, as well as vaginal candidiasis with promising results 4, 5.

The FDA categorizes clove oil as generally recognized as safe (GRAS) for use in dental cement or as a food additive 13.

Type
Biotech
Groups
Approved, Nutraceutical
Synonyms
  • Caryophylii floris aetheroleum
  • Caryophyllus aromaticus bud oil
  • Clove bud oil
  • Clove volatile oil
  • Ding xiang bud oil
  • Eugenia aromatica bud oil
  • Eugenia caryophyllata bud oil
  • Eugenia caryophyllus (clove) bud oil
  • Eugenia caryophyllus (clove) flower oil
  • Nelken oel
  • Syzygium aromaticum bud oil
  • Syzygium aromaticum oil
External IDs
  • Fema no. 2323

Pharmacology

Indication

Clove oil is primarily indicated in conditions like colic, flatulence, and toothache 9.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Clove (Eugenia caryophyllata Thunb. [Myrtaceae]) essential oil (CEO) has been demonstrated to possess antimicrobial, antifungal, antiviral, antioxidant, anti-inflammatory, anti-histamine, and anticancer properties. However, few studies have focused on its topical use 2, 10.

Clove essential oil, used as an antiseptic in oral infections, inhibits gram-negative and gram-positive bacteria as well as yeast 1.

Mechanism of action

The chief constituent present in clove oil is the phenol "eugenol" which is present in amounts up to 85%. Clove oil acts as a germicide 9 to Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa 1.

Clove oil is thought to inhibit prostaglandin synthesis, thereby reducing painful symptoms 6.

Eugenol, the main constituent of clove oil is purported to have anticancer action. In one study, eugenol-treated HL-60 cells showed features of apoptosis including DNA fragmentation and formation of DNA ladders in agarose gel electrophoresis. It was observed that eugenol transduced the apoptotic signal via reactive oxygen species (ROS) generation, inducing mitochondrial permeability transition (MPT), decreasing anti-apoptotic protein bcl-2 level, inducing cytochrome c release to the cytosol, and subsequent apoptotic cell death. When taken together, the study showed that ROS plays a critical role in eugenol-induced apoptosis in HL-60, and this is the first report on the mechanism of the anticancer effect of eugenol 7.

TargetActionsOrganism
UVascular cell adhesion protein 1
antagonist
Humans
UC-X-C motif chemokine 10Not AvailableHumans
UCollagen alpha-1(I) chainNot AvailableHumans
UGranulocyte-macrophage colony-stimulating factor receptor subunit alphaNot AvailableHumans
Absorption

Clove oil is rapidly absorbed through the skin and is used in patented systems for dermal drug delivery to enhance drug uptake from skin patch delivery systems 13.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

In the rat, 20-30% of eugenol is metabolized to homovanillic acid and 4-hydroxy-3-methoxymandelic acid 10.

In a pharmacokinetic study in man, 95% of the ingested eugenol dose was recovered in the urine, most of which (greater than 99%) consisted of phenolic conjugates; 50% of the conjugated metabolites were eugenol-glucuronide and sulfate. Other metabolic routes observed were the epoxide-diol pathway, synthesis of a thiophenol and of a substituted propionic acid, allylic oxidation, and migration of the double bond 8.

Route of elimination

In a pharmacokinetic study, the metabolism of eugenol (the primary constituent of clove oil) was investigated in healthy male and female volunteers. It was quickly absorbed and metabolized after oral administration and was almost completely excreted in the urine within 24 hours of ingestion 8.

Half-life

In a pharmacokinetic study, average half-life values of eugenol in plasma and blood were long (14.0 and 18.3 h, respectively), suggesting a potential accumulation of the drug following repeated administrations 4.

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Acute oral toxicity (LD50): 2650 mg/kg [Rat] MSDS.

Clove oil is considered safe in small quantities (< 1,500 ppm) as a food additive 13. The lethal oral dose is 3.75 g per kg body weight in humans 13.

Contact with skin or soft tissue may cause transient irritation, contact dermatitis, inflammation of the lips, and inflammation or ulceration of the mouth. The eugenol present in clove oil may act as an irritant to skin and mucous membranes; it may also cause hypersensitivity and is reported to inhibit prostaglandin synthesis. Patients may become sensitive to clove oil 10.

After oral administration of 5-10 ml of clove oil in children below 2 years of age, life-threatening conditions were observed. Adverse effects included coma, acidosis, a generalized seizure, disordered blood clotting, and acute liver damage 13.

Overdose may lead to CNS depression, urinary abnormalities, anion-gap acidosis, deterioration of liver function, coma, seizure and low blood glucose levels. Treatment should be supportive and symptomatic; there have been reports in the literature that N-acetylcysteine has been successfully used as an antidote 10.

There are no epidemiological studies of potential adverse human health effects related to exposure to clove leave oil or eugenol from any human exposure scenarios. Nor are there any studies of agricultural use, either in workers or those with bystander exposure or other applications. There are no occupational exposure standards for clove leaf oil or eugenol including OSHA PEL (Permissible Exposure Limit) or AGIHA TLVs (Threshold Limit Value) in air 13.

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
AbacavirAbacavir may decrease the excretion rate of Clove oil which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Clove oil which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Clove oil which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Clove oil which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Clove oil which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Clove oil which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Clove oil which could result in a higher serum level.
AcrivastineAcrivastine may decrease the excretion rate of Clove oil which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Clove oil which could result in a higher serum level.
Adefovir dipivoxilAdefovir dipivoxil may decrease the excretion rate of Clove oil which could result in a higher serum level.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Clove OilLiquidDentalD.C. Labs Limited1951-12-312003-07-11Canada flag
Clove OilLiquid100 %DentalStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1965-12-312002-07-31Canada flag
WILISAN CLOVE OIL PREPARATIONOilBuccalCHONG PARK PHARMACEUTICAL SDN BHD2020-09-082020-12-18Malaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AmolClove oil (0.1 %) + Cinnamon oil (0.24 %) + Lavender oil (0.24 %) + Peppermint oil (1.963 %)LiquidOralAmol Pharma Gmbh1999-11-012010-03-09Canada flag
Arhtri PlusClove oil (0.25 g/100g) + Eucalyptus oil (0.72 g/100g) + Levomenthol (2.5 g/100g)SprayTopicalDistributions Ar?Mes D`espagne Enr2014-10-30Not applicableUS flag
Dentalgar LiqClove oil (1.98 mL / 30 mL) + Benzocaine (54 mg / 30 mL) + Camphor (1.98 g / 30 mL) + Guaiacol (1.98 g / 30 mL) + Levomenthol (54 mg / 30 mL)LiquidDentalProduits Marc O (1987) Inc., Division Of Technilab Inc.1982-05-311999-09-17Canada flag
Denture Orajel GelClove oil (0.2 %) + Benzocaine (7.5 %) + Benzyl alcohol (1 %)GelBuccal; TopicalCommerce Pharmaceutics Inc.1997-12-172004-07-20Canada flag
DİŞİNOL 1G + 0,5G + 3,5G/10 ML ÇÖZELTİClove oil (350 mg/10ml) + Chlorobutanol (200 mg/10ml) + Phenol (50 mg/10ml)SolutionOralKOÇAK FARMA İLAÇ VE KİMYA SAN. A.Ş.2020-08-14Not applicableTurkey flag
Dso DressingClove oil (63.4 mL / 100 mL) + Chlorobutanol (38.3 g / 100 mL) + Cinnamaldehyde (5 mL / 100 mL) + Cinnamon oil (5 mL / 100 mL) + Methyl salicylate (2.5 mL / 100 mL)LiquidDentalGermiphene Corporation1963-12-312014-07-24Canada flag
Gouttes DentairesClove oil (6.6 mL / 100 mL) + Benzocaine (180 mg / 100 mL) + Camphor (6.6 g / 100 mL) + Guaiacol (6.6 g / 100 mL) + Levomenthol (180 mg / 100 mL)LiquidDentalLab Valmo EnregistrÉ, Division Of Technilab Inc.1983-12-312000-08-24Canada flag
Minyak Merah Cap LabuClove oil (6 %) + Camphor (10 %) + Methyl salicylate (60 %)LinimentTopicalKIMIPACK MEDICAL INDUSTRIES SDN BHD2020-09-08Not applicableMalaysia flag
Minyak Panas Merah Cap Kuda HitamClove oil (6 %) + Camphor (10 %) + Methyl salicylate (60 %)LinimentTopicalMastura Enterprise2020-09-08Not applicableMalaysia flag
New Skin Clear Liquid BandageClove oil (.8 %) + Oxyquinoline (1 %)LiquidTopicalMedtech Laboratories, Inc.1969-12-311998-07-08Canada flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
578389D6D0
CAS number
8000-34-8

References

General References
  1. Nunez L, Aquino MD: Microbicide activity of clove essential oil (Eugenia caryophyllata). Braz J Microbiol. 2012 Oct;43(4):1255-60. doi: 10.1590/S1517-83822012000400003. Epub 2012 Jun 1. [Article]
  2. Cortes-Rojas DF, de Souza CR, Oliveira WP: Clove (Syzygium aromaticum): a precious spice. Asian Pac J Trop Biomed. 2014 Feb;4(2):90-6. doi: 10.1016/S2221-1691(14)60215-X. [Article]
  3. Han X, Parker TL: Anti-inflammatory activity of clove (Eugenia caryophyllata) essential oil in human dermal fibroblasts. Pharm Biol. 2017 Dec;55(1):1619-1622. doi: 10.1080/13880209.2017.1314513. [Article]
  4. Guenette SA, Ross A, Marier JF, Beaudry F, Vachon P: Pharmacokinetics of eugenol and its effects on thermal hypersensitivity in rats. Eur J Pharmacol. 2007 May 7;562(1-2):60-7. doi: 10.1016/j.ejphar.2007.01.044. Epub 2007 Feb 1. [Article]
  5. Ahmad N, Alam MK, Shehbaz A, Khan A, Mannan A, Hakim SR, Bisht D, Owais M: Antimicrobial activity of clove oil and its potential in the treatment of vaginal candidiasis. J Drug Target. 2005 Dec;13(10):555-61. doi: 10.1080/10611860500422958 . [Article]
  6. Pongprayoon U, Baeckstrom P, Jacobsson U, Lindstrom M, Bohlin L: Compounds inhibiting prostaglandin synthesis isolated from Ipomoea pes-caprae. Planta Med. 1991 Dec;57(6):515-8. doi: 10.1055/s-2006-960196. [Article]
  7. Yoo CB, Han KT, Cho KS, Ha J, Park HJ, Nam JH, Kil UH, Lee KT: Eugenol isolated from the essential oil of Eugenia caryophyllata induces a reactive oxygen species-mediated apoptosis in HL-60 human promyelocytic leukemia cells. Cancer Lett. 2005 Jul 8;225(1):41-52. doi: 10.1016/j.canlet.2004.11.018. Epub 2004 Dec 15. [Article]
  8. Fischer IU, von Unruh GE, Dengler HJ: The metabolism of eugenol in man. Xenobiotica. 1990 Feb;20(2):209-22. [Article]
  9. Drug Infosys: Clove Oil [Link]
  10. Medicines UK Document, Clove Oil [Link]
  11. Eugenol Overview [Link]
  12. Clove oil, FDA Document [File]
  13. Chapter 6- Eugenol [File]
PubChem Substance
347911190
RxNav
7624
ChEMBL
CHEMBL2108247
Wikipedia
Oil_of_clove
MSDS
Download (47.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidOral
SprayTopical
LiquidDental
LiquidDental100 %
GelBuccal; Topical
SolutionOral
LinimentTopical
LiquidTopical
AerosolTopical
OilTopical
Ointment
CapsuleOral
OilBuccal
LiquidDental
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
boiling point (°C)250MSDS

Targets

Drugtargets2
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insights and accelerate drug research.
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Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Primary amine oxidase activity
Specific Function
Important in cell-cell recognition. Appears to function in leukocyte-endothelial cell adhesion. Interacts with integrin alpha-4/beta-1 (ITGA4/ITGB1) on leukocytes, and mediates both adhesion and si...
Gene Name
VCAM1
Uniprot ID
P19320
Uniprot Name
Vascular cell adhesion protein 1
Molecular Weight
81275.43 Da
References
  1. Han X, Parker TL: Anti-inflammatory activity of clove (Eugenia caryophyllata) essential oil in human dermal fibroblasts. Pharm Biol. 2017 Dec;55(1):1619-1622. doi: 10.1080/13880209.2017.1314513. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
Gene Name
CXCL10
Uniprot ID
P02778
Uniprot Name
C-X-C motif chemokine 10
Molecular Weight
10880.915 Da
References
  1. Han X, Parker TL: Anti-inflammatory activity of clove (Eugenia caryophyllata) essential oil in human dermal fibroblasts. Pharm Biol. 2017 Dec;55(1):1619-1622. doi: 10.1080/13880209.2017.1314513. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Platelet-derived growth factor binding
Specific Function
Type I collagen is a member of group I collagen (fibrillar forming collagen).
Gene Name
COL1A1
Uniprot ID
P02452
Uniprot Name
Collagen alpha-1(I) chain
Molecular Weight
138941.105 Da
References
  1. Han X, Parker TL: Anti-inflammatory activity of clove (Eugenia caryophyllata) essential oil in human dermal fibroblasts. Pharm Biol. 2017 Dec;55(1):1619-1622. doi: 10.1080/13880209.2017.1314513. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Receptor activity
Specific Function
Low affinity receptor for granulocyte-macrophage colony-stimulating factor. Transduces a signal that results in the proliferation, differentiation, and functional activation of hematopoietic cells.
Gene Name
CSF2RA
Uniprot ID
P15509
Uniprot Name
Granulocyte-macrophage colony-stimulating factor receptor subunit alpha
Molecular Weight
46206.185 Da
References
  1. Han X, Parker TL: Anti-inflammatory activity of clove (Eugenia caryophyllata) essential oil in human dermal fibroblasts. Pharm Biol. 2017 Dec;55(1):1619-1622. doi: 10.1080/13880209.2017.1314513. [Article]

Drug created on December 03, 2015 16:52 / Updated on September 28, 2021 21:54