Triclosan: Difference between revisions

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{{Chembox new
{{DrugProjectFormSinglePage
|ImageFile=Triclosan.svg
|authorTag={{Ammu}}
|ImageSize=
|OTC=Yes
|genericName=triclosan
|aOrAn=an
|drugClass=[[antiseptic]]
|indicationType=treatment
|indication=for hand washing to decrease [[bacteria]] on [[skin]]
|adverseReactions=[[hypersensitivity]]
|blackBoxWarningTitle=<span style="color:#FF0000;">ConditionName: </span>
|blackBoxWarningBody=<i><span style="color:#FF0000;">ConditionName: </span></i>
 
 
<!--Adult Indications and Dosage-->
 
<!--FDA-Labeled Indications and Dosage (Adult)-->
|fdaLIADAdult=* For hand washing to decrease bacteria on [[skin]]
* Recommended for repeated use
<!--Guideline-Supported Use (Adult)-->
|offLabelAdultGuideSupport=There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.
 
<!--Non–Guideline-Supported Use (Adult)-->
|offLabelAdultNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.
 
<!--Pediatric Indications and Dosage-->
 
<!--FDA-Labeled Indications and Dosage (Pediatric)-->
|fdaLIADPed=* For hand washing to decrease bacteria on [[skin]]
* Recommended for repeated use
 
 
<!--Off-Label Use and Dosage (Pediatric)-->
 
<!--Guideline-Supported Use (Pediatric)-->
|offLabelPedGuideSupport=There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.
 
<!--Non–Guideline-Supported Use (Pediatric)-->
|offLabelPedNoGuideSupport=There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.
 
<!--Contraindications-->
|warnings=* For external use only.
* When using this product avoid contact with [[eyes]]. In case of [[eye]] contact, flush eyes with water.
* Stop use and ask a doctor if irritation or redness develops, or if condition persists for more than 72 hours.
* Keep out of reach of children.
* If swallowed, get medical help or contact a Poison Control Center right away.
|clinicalTrials=There is limited information regarding <i>Clinical Trial Experience</i> of {{PAGENAME}} in the drug label.
|postmarketing=There is limited information regarding <i>Postmarketing Experience</i> of {{PAGENAME}} in the drug label.
 
<!--Drug Interactions-->
|drugInteractions=<!--Use in Specific Populations-->
|useInPregnancyFDA=* '''Pregnancy Category'''
|useInPregnancyAUS=* '''Australian Drug Evaluation Committee (ADEC) Pregnancy Category'''
 
There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of {{PAGENAME}} in women who are pregnant.
|useInLaborDelivery=There is no FDA guidance on use of {{PAGENAME}} during labor and delivery.
|useInNursing=There is no FDA guidance on the use of {{PAGENAME}} with respect to nursing mothers.
|useInPed=There is no FDA guidance on the use of {{PAGENAME}} with respect to pediatric patients.
|useInGeri=There is no FDA guidance on the use of {{PAGENAME}} with respect to geriatric patients.
|useInGender=There is no FDA guidance on the use of {{PAGENAME}} with respect to specific gender populations.
|useInRace=There is no FDA guidance on the use of {{PAGENAME}} with respect to specific racial populations.
|useInRenalImpair=There is no FDA guidance on the use of {{PAGENAME}} in patients with renal impairment.
|useInHepaticImpair=There is no FDA guidance on the use of {{PAGENAME}} in patients with hepatic impairment.
|useInReproPotential=There is no FDA guidance on the use of {{PAGENAME}} in women of reproductive potentials and males.
|useInImmunocomp=There is no FDA guidance one the use of {{PAGENAME}} in patients who are immunocompromised.
 
<!--Administration and Monitoring-->
|administration=* [[Topical]]
|monitoring=There is limited information regarding <i>Monitoring</i> of {{PAGENAME}} in the drug label.
|IVCompat=There is limited information regarding <i>IV Compatibility</i> of {{PAGENAME}} in the drug label.
 
<!--Overdosage-->
|overdose=There is limited information regarding <i>Chronic Overdose</i> of {{PAGENAME}} in the drug label.
 
<!--Pharmacology-->
 
<!--Drug box 2-->
|drugBox={{chembox2
| Watchedfields = changed
| verifiedrevid = 470613750
|ImageFile=Triclosan22.png
|ImageSize=200
|ImageFile1=Triclosan22.png
|IUPACName=5-chloro-2-(2,4-dichlorophenoxy)phenol
|IUPACName=5-chloro-2-(2,4-dichlorophenoxy)phenol
|OtherNames=
|OtherNames= 2,4,4'-trichloro-2'-hydroxydiphenyl ether, 5-chloro-(2,4-dichlorophenoxy)phenol, trichloro-2'-hydroxydiphenyl ether, CH-3565, Lexol 300, Irgasan DP 300
|Section1= {{Chembox Identifiers
|Section1= {{Chembox Identifiers
|  CASNo=3380-34-5
|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| PubChem=5564
| ChemSpiderID = 5363
| SMILES=C1=CC(=C(C=C1Cl)O)OC2=C(C=C(C=C2)Cl)Cl
| UNII_Ref = {{fdacite|correct|FDA}}
  }}
| UNII = 4NM5039Y5X
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D06226
| InChI = 1/C12H7Cl3O2/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6,16H
| InChIKey = XEFQLINVKFYRCS-UHFFFAOYAS
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 849
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H7Cl3O2/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6,16H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XEFQLINVKFYRCS-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=3380-34-5
| PubChem=5564
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 164200
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB08604
| SMILES = Clc2cc(Cl)ccc2Oc1ccc(Cl)cc1O
| ATCCode_prefix = D08
| ATCCode_suffix = AE04
| ATC_Supplemental = <br />{{ATC|D09|AA06}} (medicated dressing)
}}
|Section2= {{Chembox Properties
|Section2= {{Chembox Properties
|  Formula=C<sub>12</sub>H<sub>7</sub>Cl<sub>3</sub>O<sub>2</sub>
|  C=12|H=7|Cl=3|O=2
|  MolarMass=289.541
|  Appearance=White solid
|  Appearance=
|  Density=1.49 g/cm<sup>3</sup>
|  Density=
|  MeltingPtC=55-57
|  MeltingPt=55-57°C
|  BoilingPtC=120
|  BoilingPt=120 °C
|  Solubility=
|  Solubility=
   }}
   }}
|Section3= {{Chembox Hazards
|Section3= {{Chembox Hazards
| ExternalMSDS = [http://www.glenmartinlimited.com/MSDS/gmmsds1154.pdf MSDS]
|  MainHazards=
|  MainHazards=
|  FlashPt=
|  FlashPtC = 162.2
|  Autoignition=
|  AutoignitionC =
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
   }}
   }}
}}
}}
{{SI}}
|mechAction=* At high concentrations, triclosan acts as a biocide with multiple cytoplasmic and membrane targets.<ref name="pmid15073159.">{{cite journal| author=Russell AD| title=Whither triclosan? | journal=J Antimicrob Chemother | year= 2004 | volume= 53 | issue= 5 | pages= 693-5 | pmid=15073159. | doi=10.1093/jac/dkh171 | pmc= | url=http://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&tool=sumsearch.org/cite&retmode=ref&cmd=prlinks&id=15073159  }} </ref> However, at the lower concentrations seen in commercial products, triclosan appears bacteriostatic, and it targets bacteria primarily by inhibiting fatty acid synthesis.
{{EH}}
* Triclosan binds to bacterial enoyl-acyl carrier protein reductase (ENR) enzyme, which is encoded by the gene FabI. This binding increases the enzyme's affinity for nicotinamide adenine dinucleotide (NAD+). This results in the formation of a stable, ternary complex of ENR-NAD+-triclosan, which is unable to participate in fatty acid synthesis. Fatty acids are necessary for building and reproducing cell membranes. Humans do not have an ENR enzyme and thus are not affected.


==Overview==
<!--Structure-->
'''Triclosan''' (chemically 5-chloro-2-(2,4-dichlorophenoxy)phenol) is a potent wide spectrum [[antibiotic|antibacterial]] and [[fungus|antifungal]] agent.
|PD=There is limited information regarding <i>Pharmacodynamics</i> of {{PAGENAME}} in the drug label.


==Chemical structure and properties==
<!--Pharmacokinetics-->
This [[organic compound]] is a white powdered [[solid]] with a slight aromatic/phenolic odor.  It is a [[chlorine|chlorinated]] [[aromatic compound]] which has [[functional group]]s representative of both [[ethers]] and [[phenols]]. Phenols often show anti-bacterial properties.  Triclosan is slightly soluble in water, but soluble in [[ethanol]], [[diethyl ether]], and stronger [[basic (chemistry)|basic]] [[solution]]s such as 1 [[Concentration#Molarity|M]] [[sodium hydroxide]], like many other phenols.
|PK=There is limited information regarding <i>Pharmacokinetics</i> of {{PAGENAME}} in the drug label.


Synonyms: 2,4,4'-trichloro-2'-hydroxydiphenyl ether, 5-chloro-(2,4-dichlorophenoxy)phenol, trichloro-2'-hydroxydiphenyl ether, CH-3565, Lexol 300, Irgasan DP 200
<!--Nonclinical Toxicology-->
|nonClinToxic=There is limited information regarding <i>Nonclinical Toxicology</i> of {{PAGENAME}} in the drug label.


==Uses==
<!--Clinical Studies-->
Triclosan is found in [[soap]]s, [[deodorant]]s, [[toothpaste]]s, mouthwashes, and cleaning supplies and is infused in an increasing number of consumer products, such as kitchen utensils, toys, bedding, socks, and trash bags, sometimes as the proprietary Microban treatment. It has been shown to be effective in reducing and controlling bacterial contamination on the hands and on treated products. More recently, showering or bathing with 2% triclosan has become a recommended regime for the decolonization of patients whose skin is carrying [[methicillin]] resistant ''Staphylococcus aureus'' ([[MRSA]])<ref name="pmid16581155">{{cite journal |author=Coia JE, Duckworth GJ, Edwards DI, ''et al'' |title=Guidelines for the control and prevention of meticillin-resistant Staphylococcus aureus (MRSA) in healthcare facilities |journal=J. Hosp. Infect. |volume=63 Suppl 1 |issue= |pages=S1-44 |year=2006 |pmid=16581155 |doi=10.1016/j.jhin.2006.01.001}}</ref> following the successful control of MRSA outbreaks in several clinical settings.<ref name="pmid2255283">{{cite journal |author=Brady LM, Thomson M, Palmer MA, Harkness JL |title=Successful control of endemic MRSA in a cardiothoracic surgical unit |journal=Med. J. Aust. |volume=152 |issue=5 |pages=240-5 |year=1990 |pmid=2255283 |doi=}}</ref><ref name="pmid7677266">{{cite journal |author=Zafar AB, Butler RC, Reese DJ, Gaydos LA, Mennonna PA |title=Use of 0.3% triclosan (Bacti-Stat) to eradicate an outbreak of methicillin-resistant Staphylococcus aureus in a neonatal nursery |journal=American journal of infection control |volume=23 |issue=3 |pages=200-8 |year=1995 |pmid=7677266 |doi=}}</ref>
|clinicalStudies=There is limited information regarding <i>Clinical Studies</i> of {{PAGENAME}} in the drug label.


Triclosan is regulated by both the U.S. [[Food and Drug Administration]] and by the European Union.  During wastewater treatment, a portion of triclosan is degraded while the remaining adsorbs to sewage sludge or exits the plant in wastewater effluent.<ref name="pmid12523412">{{cite journal |author=Singer H, Muller S, Tixier C, Pillonel L. |title=Triclosan: occurrence and fate of a widely used biocide in the aquatic environment: field measurements in wastewater treatment plants, surface waters, and lake sediments. |journal=Environ Sci Technol. |volume=36 |issue=23 |pages=4998-5004 |year=2002 |pmid=12523412 |doi=}}</ref><ref name="pmid16766013">{{cite journal |author=Heidler J, Halden RU. |title=Mass balance assessment of triclosan removal during conventional sewage treatment.|journal=Chemosphere |volume=66 |issue=2 |pages=362-369 |year=2007 |pmid=16766013 |doi=}}</ref> In the environment, triclosan may be degraded by microorganisms or react with sunlight forming other compounds which may include chlorophenols and [[dioxin]], or it may adsorb to particles that settle out of the water column and form sediment.<ref name="pmid12523412">{{cite journal |author=Singer H, Muller S, Tixier C, Pillonel L. |title=Triclosan: occurrence and fate of a widely used biocide in the aquatic environment: field measurements in wastewater treatment plants, surface waters, and lake sediments. |journal=Environ Sci Technol. |volume=36 |issue=23 |pages=4998-5004 |year=2002 |pmid=12523412 |doi=}}</ref><ref name="pmid15779749">{{cite journal |author=Latch DE, Packer JL, Stender BL, VanOverbeke J, Arnold WA, McNeill K |title=Aqueous photochemistry of triclosan: formation of 2,4-dichlorophenol, 2,8-dichlorodibenzo-p-dioxin, and oligomerization products |journal=Environ. Toxicol. Chem. |volume=24 |issue=3 |pages=517-25 |year=2005 |pmid=15779749 |doi=}}</ref>. Triclosan was found in Lake Greifensee sediment that was over 30 years old suggesting that triclosan is degraded or removed slowly in sediment.<ref name="pmid12523412">{{cite journal |author=Singer H, Muller S, Tixier C, Pillonel L. |title=Triclosan: occurrence and fate of a widely used biocide in the aquatic environment: field measurements in wastewater treatment plants, surface waters, and lake sediments. |journal=Environ Sci Technol. |volume=36 |issue=23 |pages=4998-5004 |year=2002 |pmid=12523412 |doi=}}</ref>
<!--How Supplied-->
|packLabel=[[File:Triclosan 01.jpg|thumb|none|400px|This image is provided by the National Library of Medicine.]]
[[File:Triclosan 02.png|thumb|none|400px|This image is provided by the National Library of Medicine.]]
|fdaPatientInfo=There is limited information regarding <i>Patient Counseling Information</i> of {{PAGENAME}} in the drug label.


==Mechanism of action==
<!--Precautions with Alcohol-->
At in-use concentrations triclosan acts as a [[biocide]], with multiple cytoplasmic and membrane targets.<ref name="pmid15073159">{{cite journal |author=Russell AD |title=Whither triclosan? |journal=J. Antimicrob. Chemother. |volume=53 |issue=5 |pages=693-5 |year=2004 |pmid=15073159 |doi=10.1093/jac/dkh171}}</ref> At lower concentrations, however, triclosan appears [[bacteriostatic]] and is seen to target bacteria mainly by inhibiting [[Fatty acid metabolism#Synthesis|fatty acid synthesis]].  Triclosan binds to bacterial [[enoyl-acyl carrier protein reductase]] enzyme (ENR), which is encoded by the gene FabI.  This binding increases the enzyme's affinity for [[nicotinamide adenine dinucleotide]] (NAD<sup>+</sup>).  This results in the formation of a stable ternary complex of ENR-NAD<sup>+</sup>-triclosan, which is unable to participate in fatty acid synthesis.  Fatty acid is necessary for reproducing and building cell membranes.  Humans do not have an ENR enzyme, and thus are not affected.  Some bacterial species can develop low-level resistance to triclosan due to FabI mutations which decrease triclosan's effect on ENR-NAD<sup>+</sup> binding, as shown in ''[[Escherichia coli]]'' and ''[[Staphylococcus aureus]]''.  <ref name="pmid10196195">{{cite journal |author=Heath RJ, Rubin JR, Holland DR, Zhang E, Snow ME, Rock CO |title=Mechanism of triclosan inhibition of bacterial fatty acid synthesis |journal=J. Biol. Chem. |volume=274 |issue=16 |pages=11110-4 |year=1999 |pmid=10196195 |doi=}}</ref><ref name="pmid12384334">{{cite journal |author=Fan F, Yan K, Wallis NG, ''et al'' |title=Defining and combating the mechanisms of triclosan resistance in clinical isolates of Staphylococcus aureus |journal=Antimicrob. Agents Chemother. |volume=46 |issue=11 |pages=3343-7 |year=2002 |pmid=12384334 |doi=}}</ref>  Another way for these bacteria to gain low-level resistance to triclosan is to [[overexpress]] ''FabI''.<ref name="pmid11418506">{{cite journal |author=Slater-Radosti C, Van Aller G, Greenwood R, ''et al'' |title=Biochemical and genetic characterization of the action of triclosan on Staphylococcus aureus |journal=J. Antimicrob. Chemother. |volume=48 |issue=1 |pages=1-6 |year=2001 |pmid=11418506 |doi=}}</ref> Some bacteria have innate resistance to triclosan, such as ''[[Pseudomonas aeruginosa]]'', which possesses multi-drug efflux pumps that 'pump' triclosan out of the cell.<ref name="pmid12665747">{{cite journal |author=Chuanchuen R, Karkhoff-Schweizer RR, Schweizer HP |title=High-level triclosan resistance in Pseudomonas aeruginosa is solely a result of efflux |journal=American journal of infection control |volume=31 |issue=2 |pages=124-7 |year=2003 |pmid=12665747 |doi=}}</ref> Other bacteria, such as some of the ''[[Bacillus]]'' genus, have alternative ''FabI'' genes (''FabK'') to which triclosan does not bind and hence are less susceptible.
|alcohol=* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.


==Resistance concerns==
<!--Brand Names-->
An article coauthored by Dr. Stuart Levy in the August 6, 1998 issue of ''[[Nature (journal)|Nature]]''<ref name="pmid9707111">{{cite journal |author=McMurry LM, Oethinger M, Levy SB |title=Triclosan targets lipid synthesis |journal=Nature |volume=394 |issue=6693 |pages=531-2 |year=1998 |pmid=9707111 |doi=10.1038/28970}}</ref> warned that its overuse could cause resistant strains of [[bacterium|bacteria]] to develop, in much the same way that [[Antibiotic resistance|antibiotic-resistant]] bacterial strains are emerging, based on speculation that triclosan behaved like an antibiotic.  Based on this speculation, in 2003, the Sunday Herald newspaper [http://ww1.sundayherald.com/37782 reported] that some UK supermarkets and other retailers were considering phasing out products containing triclosan.
|brandNames=* ANTIBACTERIAL SPRAY®<ref>{{Cite web | title =ANTIBACTERIAL SPRAY - triclosan liquid  | url = http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a7b2119e-5f3b-42e6-9cea-4a881532b5ef }}</ref>


It has since been shown that the laboratory method used by Dr. Levy was not effective in predicting bacterial resistance for [[biocide]]s like triclosan, based on work by Dr. Peter Gilbert in the UK, whose research is supported by Procter & Gamble [http://pubs.acs.org/subscribe/journals/esthag-w/2003/nov/science/rr_triclosan.html].<ref name="pmid12957932">{{cite journal |author=McBain AJ, Bartolo RG, Catrenich CE, ''et al'' |title=Exposure of sink drain microcosms to triclosan: population dynamics and antimicrobial susceptibility |journal=Appl. Environ. Microbiol. |volume=69 |issue=9 |pages=5433-42 |year=2003 |pmid=12957932 |doi=}}</ref>  At least seven peer-reviewed and published studies have been conducted demonstrating that triclosan is not significantly associated with bacterial resistance over the short term, including one study coauthored by Dr. Levy, published in August of 2004 in ''Antimicrobial Agents and Chemotherapy''.<ref name="pmid15273108">{{cite journal |author=Aiello AE, Marshall B, Levy SB, Della-Latta P, Larson E |title=Relationship between triclosan and susceptibilities of bacteria isolated from hands in the community |journal=Antimicrob. Agents Chemother. |volume=48 |issue=8 |pages=2973-9 |year=2004 |pmid=15273108 |doi=10.1128/AAC.48.8.2973-2979.2004}}</ref>
<!--Look-Alike Drug Names-->
|lookAlike=<!--Drug Shortage Status-->
|drugShortage=
}}
<!--Pill Image-->


Some level of triclosan resistance can occur in some microorganisms, but the larger concern is with the potential for cross-resistance or co-resistance to other antimicrobials. Studies investigating this possibility have been limited.<ref name="pmid16922622">{{cite journal |author=Yazdankhah SP, Scheie AA, Høiby EA, ''et al'' |title=Triclosan and antimicrobial resistance in bacteria: an overview |journal=Microb. Drug Resist. |volume=12 |issue=2 |pages=83-90 |year=2006 |pmid=16922622 |doi=10.1089/mdr.2006.12.83}}</ref>


==Health concerns==
Reports have suggested that triclosan can combine with [[chlorine]] in tap water to form [[chloroform]] gas,<ref name="pmid15926568">{{cite journal |author=Rule KL, Ebbett VR, Vikesland PJ |title=Formation of chloroform and chlorinated organics by free-chlorine-mediated oxidation of triclosan |journal=Environ. Sci. Technol. |volume=39 |issue=9 |pages=3176-85 |year=2005 |pmid=15926568 |doi=}}</ref> which the United States Environmental Protection Agency classifies as a probable human [[carcinogen]]. As a result, triclosan was the target of a UK cancer alert, even though the study showed that the amount of chloroform generated was less than amounts often present in chlorinated drinking waters.


Triclosan reacts with the free chlorine in tap water to also produce lesser amounts of other compounds, like 2,4-dichlorophenol.<ref name="pmid15926568">{{cite journal |author=Rule KL, Ebbett VR, Vikesland PJ |title=Formation of chloroform and chlorinated organics by free-chlorine-mediated oxidation of triclosan |journal=Environ. Sci. Technol. |volume=39 |issue=9 |pages=3176-85 |year=2005 |pmid=15926568 |doi=}}</ref> Most of these intermediates convert into [[dioxin]]s upon exposure to [[UV]] radiation (from the sun or other sources). Although small amounts of dioxins are produced, there is a great deal of concern over this effect because dioxins are extremely toxic and are very potent [[endocrine disruptor]]s. They are also chemically very stable, so that they are eliminated from the body very slowly (they can [[bioaccumulate]] to dangerous levels), and they persist in the environment for a very long time.
<!--Label Display Image-->


Triclosan is chemically somewhat similar to the dioxin class of compounds. Its production leads to small amounts of residual polychlorinated dioxins, and polychlorinated [[furan]]s which are contained in small amounts, in the products that are using it.


A 2006 study concluded that low doses of triclosan act as an [[endocrine disruptor]] in the North American bullfrog.<ref>{{cite journal
| author = Nik Veldhoen, Rachel C. Skirrow, Heather Osachoff, Heidi Wigmore, David J. Clapson, Mark P. Gunderson, Graham Van Aggelen and Caren C. Helbing
| year = 2006
| month = December
| title = The bactericidal agent triclosan modulates thyroid hormone-associated gene expression and disrupts postembryonic anuran development
| journal = Aquatic Toxicology
| volume = 80
| issue = 3
| pages = 217&ndash;227
| url = http://www.sciencedirect.com/science/article/B6T4G-4M0S2Y9-1/2/1607f34b5f4663b9c487f0481cab2162
}}</ref> The hypothesis proposed is that triclosan blocks the metabolism of thyroid hormone, because it chemically mimics thyroid hormone, and binds to the hormone receptor sites, blocking them, so that normal hormones cannot be utilized. Triclosan has also been found in both the bile of fish living down stream from waste water processing plants and in human breast milk.<ref>{{cite journal
| author = Adolfsson-Erici M, Pettersson M, Parkkonen J, Sturve J.
| year = 2002
| month = March
| title = Triclosan, a commonly used bactericide found in human milk and in the aquatic environment in Sweden
| journal = Chemosphere
| volume = 46
| issue = 9&ndash;10
| pages = 1485&ndash;1489
| url = http://dx.doi.org/10.1016/S0045-6535(01)00255-7
}}</ref> The negative effects of Triclosan on the environment and its questionable benefits in toothpastes <ref>{{cite journal
| author = Edvardsson S, Burman. L G, Adolfsson­Erici. M, Bäckman. N.
| year = 2005
| month = August
| title = Risker och nytta med triklosan i tandkräm
| journal = Tandläkartidningen
| volume = 97
| issue = 10
| pages = 58&ndash;64
| url = http://www.socialstyrelsen.se/NR/rdonlyres/712300A4-7273-4388-9E64-1F55CAF02B0D/4285/Triklosan_text.pdf
}}</ref> has led to the Swedish Naturskyddsföreningen to recommend not using Triclosan in toothpaste. <ref>http://www.snf.se/pdf/rap-triclosan.pdf</ref>


Triclosan is used in many common household products including [[Clearasil]] Daily Face Wash, Dentyl mouthwash, Dawn, the Colgate Total range, Softsoap,  Dial, Right Guard deodorant, Sensodyne Total Care, Old Spice and Mentadent.


At this time, in the United States, manufacturers of products containing triclosan must say so somewhere on the label.


==Alternatives==
<!--Category-->
Although frequently used as an additive to [[soap]], triclosan is not actually necessary in soap to kill bacteria. Soap is itself an effective microbicide due to the fact that soap breaks down oils. All bacterial cell walls are based on lipid chains, which are oil-based. The simple act of applying soap to the hands and rubbing vigorously will cause the cell walls of any bacteria on the hands to be ripped apart by the soap, disintegrating and killing any bacteria present.  A comprehensive analysis from the U-M School of Public Health indicated that plain soaps are just as effective as consumer-grade anti-bacterial soaps with triclosan in preventing illness and reducing bacteria on the hands.<ref>{{cite web |url=http://www.physorg.com/news106418144.html |title=Plain soap as effective as antibacterial but without the risk |accessdate=2007-08-17 |format= |work=}}</ref>


Soap can damage the cell walls of all animal cells and can also kill / disintegrate human cells, but the thick layer of dead cells in the epidermis of the skin generally protects humans from the potentially damaging effects of soap. Repeated frequent scrubbing with soap can remove the skin oils impregnating the layer of dead skin cells, leading to dryness and flaking of the dead cell layer.
[[Category:Drug]]
 
The addition of triclosan to hand soap can be seen as a convenience. The breakdown of waxes and oils with pure soap takes time, and a very quick application and wash-off of pure soap may be insufficient to break down bacteria protected by thick waxes. A popular instruction for hand-washing with pure soap is that it should take about as long to scrub and rub the hands and brush under the fingernails as it does to sing the nursery rhyme Twinkle Twinkle Little Star. Triclosan is useful in that it is retained on the hands following washing as a residual skin coating, and continues to kill bacteria.<ref>{{cite web |url=http://www.statenews.com/article.phtml?pk=34523 |title=The State News - www.statenews.com |accessdate=2007-08-17 |format= |work=}}</ref><ref>{{cite web |url=http://fcs.tamu.edu/Health/Health_Education_Rural_Outreach/Health_Hints/2006/october06/staph.php |title=Antibiotic-Resistant "Staph" Infection in Our Communities | HealthHints |accessdate=2007-08-17 |format= |work=}}</ref>
 
==References==
{{Reflist|2}}
 
==See also==
*[[Chlorine]]
*[[Chloroform]]
*[[Chloroxylenol]]
*[[Dioxin]]
*[[Furan]]
 
==External links==
'''Positive/neutral/official'''
*[http://www.cibasc.com/ind-pc-triclosan.htm ''Triclosan Information'' from Ciba Specialty Chemicals] &ndash; manufacturer information pages.
'''Primary source (research)'''
*[http://www.quantexlabs.com/AboutTriclosan/ABOUTTRICLOSAN.htm.htm ''Triclosan and Its Impurities'']
'''Negative'''
*[http://www.beyondpesticides.org/pesticides/factsheets/Triclosan%20cited.pdf The Ubiquitous Triclosan: An Antibacterial Agent Exposed ]by Aviva Glaser, Beyond Pesticides
*[http://www.worldwatch.org/pubs/goodstuff/soap/ ''Antibacterials? Here's the Rub''] &ndash; campaign site.
*[http://www.thisislondon.co.uk/news/articles/17956139?source=Evening%20Standard&ct=5 ''Toothpaste cancer alert''] &ndash; Newspaper story.
*[http://pubs.acs.org/subscribe/journals/esthag-w/2005/apr/science/kb_chlorine.html ''When chlorine + antimicrobials = unintended consequences''] &ndash; summary of research paper.
*[http://www.cbc.ca/marketplace/2007/01/triclosan.html ''CBC Marketplace investigation into Triclosan''] &ndash; Investigative News story.
 
{{Antiseptics and disinfectants}}
{{Medicated dressings}}
[[Category:Antibiotics]]
[[Category:Antibiotics]]
[[Category:Antifungals]]
[[Category:Antifungals]]
[[Category:Ethers]]
[[Category:Organochlorides]]
[[Category:Organochlorides]]
[[Category:Phenols]]
[[Category:Phenol ethers]]
 
{{SIB}}
 
{{WH}}
{{WS}}

Latest revision as of 14:26, 10 March 2015

Triclosan
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Ammu Susheela, M.D. [2]

Disclaimer

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NOTE: Most over the counter (OTC) are not reviewed and approved by the FDA. However, they may be marketed if they comply with applicable regulations and policies. FDA has not evaluated whether this product complies.

Overview

Triclosan is an antiseptic that is FDA approved for the treatment of for hand washing to decrease bacteria on skin. Common adverse reactions include hypersensitivity.

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

  • For hand washing to decrease bacteria on skin
  • Recommended for repeated use

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Triclosan in adult patients.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Triclosan in adult patients.

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

  • For hand washing to decrease bacteria on skin
  • Recommended for repeated use

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

There is limited information regarding Off-Label Guideline-Supported Use of Triclosan in pediatric patients.

Non–Guideline-Supported Use

There is limited information regarding Off-Label Non–Guideline-Supported Use of Triclosan in pediatric patients.

Contraindications

There is limited information regarding Triclosan Contraindications in the drug label.

Warnings

  • For external use only.
  • When using this product avoid contact with eyes. In case of eye contact, flush eyes with water.
  • Stop use and ask a doctor if irritation or redness develops, or if condition persists for more than 72 hours.
  • Keep out of reach of children.
  • If swallowed, get medical help or contact a Poison Control Center right away.

Adverse Reactions

Clinical Trials Experience

There is limited information regarding Clinical Trial Experience of Triclosan in the drug label.

Postmarketing Experience

There is limited information regarding Postmarketing Experience of Triclosan in the drug label.

Drug Interactions

There is limited information regarding Triclosan Drug Interactions in the drug label.

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA):

  • Pregnancy Category


Pregnancy Category (AUS):

  • Australian Drug Evaluation Committee (ADEC) Pregnancy Category

There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Triclosan in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Triclosan during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Triclosan with respect to nursing mothers.

Pediatric Use

There is no FDA guidance on the use of Triclosan with respect to pediatric patients.

Geriatic Use

There is no FDA guidance on the use of Triclosan with respect to geriatric patients.

Gender

There is no FDA guidance on the use of Triclosan with respect to specific gender populations.

Race

There is no FDA guidance on the use of Triclosan with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Triclosan in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Triclosan in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Triclosan in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Triclosan in patients who are immunocompromised.

Administration and Monitoring

Administration

Monitoring

There is limited information regarding Monitoring of Triclosan in the drug label.

IV Compatibility

There is limited information regarding IV Compatibility of Triclosan in the drug label.

Overdosage

There is limited information regarding Chronic Overdose of Triclosan in the drug label.

Pharmacology

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Template:Chembox header2 | Triclosan
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
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KEGG
UNII
Properties
C12H7Cl3O2
Molar mass 289.54 g·mol−1
Hazards
Template:Chembox header2 | Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Mechanism of Action

  • At high concentrations, triclosan acts as a biocide with multiple cytoplasmic and membrane targets.[1] However, at the lower concentrations seen in commercial products, triclosan appears bacteriostatic, and it targets bacteria primarily by inhibiting fatty acid synthesis.
  • Triclosan binds to bacterial enoyl-acyl carrier protein reductase (ENR) enzyme, which is encoded by the gene FabI. This binding increases the enzyme's affinity for nicotinamide adenine dinucleotide (NAD+). This results in the formation of a stable, ternary complex of ENR-NAD+-triclosan, which is unable to participate in fatty acid synthesis. Fatty acids are necessary for building and reproducing cell membranes. Humans do not have an ENR enzyme and thus are not affected.

Structure

There is limited information regarding Triclosan Structure in the drug label.

Pharmacodynamics

There is limited information regarding Pharmacodynamics of Triclosan in the drug label.

Pharmacokinetics

There is limited information regarding Pharmacokinetics of Triclosan in the drug label.

Nonclinical Toxicology

There is limited information regarding Nonclinical Toxicology of Triclosan in the drug label.

Clinical Studies

There is limited information regarding Clinical Studies of Triclosan in the drug label.

How Supplied

There is limited information regarding Triclosan How Supplied in the drug label.

Storage

There is limited information regarding Triclosan Storage in the drug label.

Images

Drug Images

{{#ask: Page Name::Triclosan |?Pill Name |?Drug Name |?Pill Ingred |?Pill Imprint |?Pill Dosage |?Pill Color |?Pill Shape |?Pill Size (mm) |?Pill Scoring |?NDC |?Drug Author |format=template |template=DrugPageImages |mainlabel=- |sort=Pill Name }}

Package and Label Display Panel

This image is provided by the National Library of Medicine.
This image is provided by the National Library of Medicine.

{{#ask: Label Page::Triclosan |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Patient Counseling Information of Triclosan in the drug label.

Precautions with Alcohol

  • Alcohol-Triclosan interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

  • ANTIBACTERIAL SPRAY®[2]

Look-Alike Drug Names

There is limited information regarding Triclosan Look-Alike Drug Names in the drug label.

Drug Shortage Status

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

  1. ↑ Russell AD (2004). "Whither triclosan?". J Antimicrob Chemother. 53 (5): 693–5. doi:10.1093/jac/dkh171. PMID 15073159. Check |pmid= value (help).
  2. ↑ "ANTIBACTERIAL SPRAY - triclosan liquid".
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