permethrin

[PER- + (res)methrin, a pyrethroid (resm-, of unknown origin + (PYR)ETHRIN).]

Brand names: A-200® Lice Control Spray, Acticin®, Elimite®, Nix® Cream Rinse

Chemical formula:

Drug Forms:
• Permethrin Topical cream (below)
• Permethrin lotion
• Permethrin skin cream
• Permethrin Topical lotion

Español:
• Permetrina, Crema tópica
• Loción de permetrina
• Crema de permetrina para la piel
• Permetrina, Loción tópica

Permethrin Topical cream

What is this medicine?

PERMETHRIN skin cream is used to treat scabies.

This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
• asthma
• an unusual or allergic reaction to permethrin, veterinary or household insecticides, other medicines, chrysanthemums, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I use this medicine?

This medicine is for external use only. Do not take by mouth. Follow the directions on the prescription label. A bath or shower is NOT recommended before applying this medicine. Thoroughly rub the cream into all skin surfaces, from your head to the soles of your feet. It is important to apply it everywhere on your body, not just where the rash is. Apply the cream between fingers and toe creases, in the folds of the wrist and waistline, in the cleft of the buttocks, on the genitals, and in the belly button. Use a toothpick to apply the cream beneath your fingernails and toenails. Nails should be cut short. If you have little or no hair, or you are applying the cream to an infant or young child, make sure you rub the cream into the neck, scalp, hairline, temples, and forehead. Leave it on for 8 to 14 hours, then remove it by bathing and shampooing. If you are applying this medicine to another person, wear plastic or disposable gloves to protect yourself from infestation. Do not get this medicine in your eyes. If you do, rinse out with plenty of cool tap water.

Talk to your pediatrician regarding the use of this medicine in children. While this drug may be prescribed for children as young as 2 months of age for selected conditions, precautions do apply.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

Interactions are not expected. Do not use any other skin products on the affected area without telling your doctor or health care professional.

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

It is not unusual for itching and rash to continue for as long as 2 to 4 weeks after treatment. These symptoms may be a temporary reaction to the remains of the mites. This does not mean this cream did not work or that it needs to be reapplied. If you feel that the itching and rash is intense or if it continues beyond 4 weeks, talk to your doctor or health care professional right away.

Scabies is spread by direct skin contact with an infected person. Family members and sexual partners may require treatment with this medicine. You should discuss this with your doctor or health care professional.

Using a normal washing cycle, you should wash all clothing, towels and bed linen that has touched your skin. You do not need to rewash clean clothing that has not yet been worn. Coats, furniture, rugs, floors, and walls do not need to be cleaned in any special manner.

What side effects may I notice from receiving this medicine?

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
• itching
• numbness
• rash
• redness or mild swelling of the skin
• stinging or burning
• tingling sensation

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature away from heat and direct light. Do not refrigerate or freeze. Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

A third-generation synthetic pyrethroid widely used in the control of ectoparasites. It is very stable and lasts for several weeks.

Permethrin
IUPAC name	3-Phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate
Identifiers
CAS number	52645-53-1 Y
ATC code	P03AC04,QP53AC04
SMILES	c3ccccc3Oc(c2)cccc2COC(=O) C1C(C1(C)C)C=C(Cl)Cl
Properties
Molecular formula	C21H20Cl2O3
Molar mass	391.28 g/mol
Appearance	colourless crystals
Density	1.19 g/cm³, solid
Melting point	34 °C, 307 K, 93 °F
Boiling point	200 °C, 473 K, 392 °F
Solubility in water	Insoluble (5.5 x 10-3 ppm)
Hazards
MSDS	External MSDS
Main hazards	Irritating to skin and eyes, damaging to lungs
Related compounds
Related pyrethroids	Bifenthrin Deltamethrin
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Permethrin is a common synthetic chemical, widely used as an insecticide, acaricide, and insect repellent. It belongs to the family of synthetic chemicals called pyrethroids and functions as a neurotoxin, affecting neuron membranes by prolonging sodium channel activation. It is not known to rapidly harm most mammals or birds, but is highly toxic to cats.^[1][2] It generally has a low mammalian toxicity and is poorly absorbed by skin. Permethrin has recently been linked to poisoning dogs as a flea/tick repellent.^{[citation needed]}

Contents 1 Uses 2 Stereochemistry 3 Toxicology and safety 4 See also 5 References 6 External links

Uses

In agriculture, permethrin is mainly used on cotton, wheat, maize, and alfalfa crops, and is also used to kill parasites on chickens and other poultry. It is also extensively used in Europe as a timber treatment against wood boring beetle (woodworm). Its use is controversial since, as a broad-spectrum chemical, it kills indiscriminately; as well as the intended pests, it can harm beneficial insects including honey bees, aquatic life,^[3] and small mammals such as mice.

Recently, in South Africa, residues of permethrin were found in breast milk, together with DDT, in an area that experienced DDT treatment for malaria control, as well as the use of pyrethroids in small-scale agriculture.^[4]

Permethrin is toxic to cats and many cats die after being given flea treatments intended for dogs, or by contact with dogs who have recently been treated with permethrin.^[5]

Permethrin is also used in healthcare, to eradicate parasites such as head lice and mites responsible for scabies, and in industrial and domestic settings to control pests such as ants and termites. However, the British National Formulary states that permethrin has low efficiency in eradicating head lice.

Permethrin kills ticks on contact with treated clothing. A method of reducing deer tick populations in terms of rodent vectors involves utilizing biodegradable cardboard tubes stuffed with permethrin treated cotton. Mice collect the cotton for lining their nests. Permethrin on the cotton instantly kills any immature ticks that are feeding on the mice. It is important to put the tubes where mice will find them, such as in dense, dark brush, or at the base of a log; mice are unlikely to gather cotton from an open lawn. According to the Connecticut Department of Public Health, permethrin "has low mammalian toxicity, is poorly absorbed through the skin and is rapidly inactivated by the body. Skin reactions have been uncommon."^[6] Permethrin is also used on humans for lice or scabies; the common prescription is Permethrin with 5% concentration for scabies, and OTC (over the counter) treatment for head lice/crabs is usually permethrin with 1% concentration.

Permethrin is used in tropical areas to prevent mosquito-borne disease such as dengue fever and malaria. Mosquito nets used to cover beds may be treated with a solution of permethrin. This increases the effectiveness of the bed net by killing parasitic insects before they are able to find gaps or holes in the net. Malaria kills 1-3 million people per year. Military personnel training in malaria-endemic areas may be instructed to treat their uniforms with permethrin as well. An application should last several washes.

Stereochemistry

Permethrin has four stereoisomers (two enantiomeric pairs), arising from the two stereocentres in the cyclopropane ring. The trans enantiomeric pair is known as transpermethrin.

(1R)-trans-acid moiety, known as biopermethrin

(1S)-trans-acid moiety

one cis enantiomer

the other cis enantiomer

Toxicology and safety

Permethrin is extremely toxic to fish. Extreme care must be taken when using products containing permethrin near water sources. Permethrin is also highly toxic to cats.^[7] Flea and tick repellent formulas intended (and labeled) for dogs may contain permethrin and cause feline permethrin toxicosis in cats.

Permethrin is classified by the US EPA a likely human carcinogen, based on reproducible studies in which mice fed permethrin developed liver and lung tumors.^[8] Carcinogenic action in nasal mucosal cells for inhalation exposure is suspected due to observed genotoxicity in human tissue samples, and in rat livers the evidence of increased preneoplastic lesions lends concern over oral exposure.^[9][10]

Recent studies have linked permethrin exposure to Parkinson's disease, including very small (per kg.) exposures. ^[11][12]

The use of the substance has been restricted by the US government, although such restriction is outdated now ^[13]

See also

• Insect repellents from natural sources
• Methoprene

References

1. ^ "PERMETHRIN HAZARDS FOR CATS". ASPCA NATIONAL ANIMAL POISON CONTROL CENTER. http://www.vetprof.com/clientinfo/permethrincats.html. 
2. ^ Franny Syufy. "Cat Flea Control Products Warning". About.com. http://cats.about.com/cs/healthissues/a/permethrin.htm. 
3. ^ R. H. Ian (1989). "Aquatic organisms and pyrethroids". Pesticide Science 27 (4): 429–457. doi:10.1002/ps.2780270408. 
4. ^ Bouwman, H; Sereda, B; Meinhardt, HM (2006). "Simultaneous presence of DDT and pyrethroid residues in human breast milk from a malaria endemic area in South Africa". Environmental Pollution 144 (3): 902–917. doi:10.1016/j.envpol.2006.02.002. PMID 16564119. 
5. ^ Linnett, PJ (2008). "Permethrin toxicosis in cats". Australian Veterinary Journal 86 (1-2): 32–35. doi:10.1111/j.1751-0813.2007.00198.x. PMID 18271821. 
6. ^ Kirby C. Stafford III (February 1999). "Tick Bite Prevention". Connecticut Department of Public Health. http://www.dph.state.ct.us/BCH/infectiousdise/tickborne/tick.htm#Permethrin. 
7. ^ BBC NEWS | UK | Cats 'killed by flea treatment'
8. ^ Permethrin Facts, US EPA, June 2006.
9. ^ M. Tisch, P. Schmezer, M. Faulde, A. Groh and H. Maier (2002). "Genotoxicity studies on permethrin, DEET and diazinon in primary human nasal mucosal cells". European Archives of Oto-Rhino-Laryngology 259 (3): 150–153. doi:10.1007/s004050100406. 
10. ^ K. Hakoi, R. Cabral, T. Hoshiya, R. Hasegawa, T. Shirai and N. Ito (1992). "Analysis of carcinogenic activity of some pesticides in a medium-term liver bioassay in the rat". Teratogenesis, Carcinogenesis, and Mutagenesis 12 (6): 269–276. doi:10.1002/tcm.1770120605. 
11. ^ [1]BBC News, March 2006.
12. ^ [2]Virginia Tech, March 2003.
13. ^ Environmental Protection Agency. "Restricted Use Products (RUP) Report: Six Month Summary List". http://www.epa.gov/opprd001/rup/rup6mols.htm. Retrieved 1 December 2009. 

External links

• Pesticide link to Parkinson Disease
• Permethrin Fact Sheet - National Pesticide Information Center
• Permethrin-treated Clothing Hot Topic - National Pesticide Information Center
• Permethrin Pesticide Information Profile - Extension Toxicology Network
• Permethrin chemical data
• Example of permethrin river poisoning (broken link)

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