Nonoxynol-9 387807 224805505 2008-07-10T14:23:30Z Sardanaphalus 427947 updating link using [[Project:AutoWikiBrowser|AWB]] {{drugbox |IUPAC_name = 2-[2-[2-[2-[2-[2-[2-[2-[2-(4-nonylphenoxy)<br>ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]<br>ethoxy]ethoxy]ethanol |image = Nonoxynol-9.png |image2= Nonoxynol-9-3d-sticks.png |CAS_number = 26571-11-9 |ATC_prefix = |ATC_suffix = |PubChem = 72385 |DrugBank = |C=33 | H=60 | O=10 |molecular_weight = 616.823 g/mol |synonyms = 26-(Nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol |bioavailability = |protein_bound = |metabolism = |elimination_half-life = |excretion = not applicable |pregnancy_category = |legal_status = legal |routes_of_administration = topical }} '''Nonoxynol-9''', sometimes abbreviated as '''N-9''', is a non-ionic [[nonoxynol]] [[surfactant]] that is used as an ingredient in various cleaning and cosmetic products, but is also widely used in [[contraceptive]]s for its spermicidal properties. Although it was at one time widely promoted as a protection against [[sexually transmitted infection]]s including [[HIV]], subsequent studies have shown that it can in fact ''increase'' the risk of infection by damaging the physical barriers of the rectum or vagina.<ref name="WHO">[[World Health Organization]]: Microbicides. [http://www.who.int/hiv/topics/microbicides/microbicides/en/ available online]</ref> ==Uses== ===Spermicide=== As a [[spermicide]], it attacks the [[acrosome|acrosomal]] membranes of the [[spermatozoon|sperm]] causing the sperm to be immobilized. Nonoxynol-9 is the active ingredient in most spermicidal creams, jellies, foams, gel, film, and [[suppositories]]. A 2004 study found that over a six-month period, the [[efficacy|typical-use]] failure rates for five nonoxynol-9 vaginal contraceptives (film, suppository, and gels at three different concentrations) ranged from 10% to 20%.<ref name="greenjournal">Elizabeth G. Raymond, MD, MPH, Pai Lien Chen, PhD and Joanne Luoto, MD for the Spermicide Trial Group.Contraceptive Effectiveness and Safety of Five Nonoxynol-9 Spermicides: A Randomized Trial. ''Obstetrics & Gynecology.'' 2004;103:430-439. [http://www.greenjournal.org/cgi/content/full/103/3/430 available online]</ref> ===Condoms=== Many models of [[condoms]] are [[personal lubricant|lubricated]] with solutions containing nonoxynol-9. In this role, it has been promoted as a backup method for pregnancy and STI prevention in the event of condom failure. However, the 2001 [[World Health Organization|WHO]]/CONRAD Technical Consultation on Nonoxynol-9 concluded that: ''There is no published scientific evidence that N-9-lubricated condoms provide any additional protection against pregnancy or STDs compared with condoms lubricated with other products. Since adverse effects due to the addition of N-9 to condoms cannot be excluded, such condoms should no longer be promoted. However, it is better to use N-9-lubricated condoms than no condoms.'' Additionally, the WHO statement suggests that N-9 should not be used rectally under any circumstances. ===Cervical barriers=== Almost all brands of [[diaphragm (contraceptive)|diaphragm]] jelly contain nonoxynol-9 as the active ingredient. This jelly may also be used for a [[cervical cap]]. Most [[contraceptive sponge]]s contain nonoxynol-9 as an active ingredient. ===Shaving cream=== Nonoxynol-9 is sometimes included in shaving creams for its properties as a nonionic surfactant; it helps break down skin oils that normally protect hair from moisture, so that they become wet and, hence, softer and easier to shave. [[Global Gillette|Gillette]] formerly used nonoxynol-9 for this purpose in its Foamy products, but has discontinued the practice.<ref name="thestraightdope">The Straight Dope: "Why is spermicide in my shaving cream?" [http://www.straightdope.com/columns/060929.html available online]</ref> ===Sports cream=== Nonoxynol-9 is also found in [[Bengay]] Vanishing Scent as an inactive ingredient. ==Side effects== Nonoxynol-9's ability to kill microbes ''[[in vitro]]'' was initially taken as evidence that it might be effective at preventing STI transmission. However, more recent findings indicate that it may actually increase a person's risk of contracting STIs, especially if used frequently. This is because the chemical causes tiny abrasions inside the sensitive [[vagina]]l and [[anus|anal]] walls. These abrasions may make transmission more likely especially if condoms are not used. From 1996 to 2000, a [[United Nations|UN]]-sponsored study carried out in several locations in [[Africa]] followed nearly 1000 sex workers who used nonoxynol-9 gels or a placebo. The HIV infection rate among those using nonoxynol-9 was about 50% higher than those who used the placebo; those using nonoxynol-9 also had a higher incidence of vaginal lesions, which may have contributed to this increased risk. While these results may not be directly applicable to lower-frequency use, these findings combined with lack of any demonstrated HIV-prevention benefit from nonoxynol-9 use have led most major health agencies to recommend that it no longer be used by women at high risk of HIV infection. The WHO further notes that "Nonoxynol-9 offers no protection against sexually transmitted infections such as [[gonorrhoea]], [[Chlamydia infection|chlamydia]]."<ref name="WHO"/> Nonoxynol-9 based products (including condoms containing the spermicide) should not be used for prevention of HIV or STDs or for contraception between non-monogamous partners because of the increased risk of infection by HIV or sexually transmitted infections. However, non-spermicide condoms are available and are still highly successful at preventing both pregnancy and STD transmission. Regular use of nonoxynol-9 likely increases the risk of infection with sexually transmitted [[human papillomavirus]]es (HPVs) that can cause [[cervical cancer]].<ref name="MaraisD">Marais D, Carrara H, Kay P, Ramjee G, Allan B, Williamson AL. The impact of the use of COL-1492, a nonoxynol-9 vaginal gel, on the presence of cervical human papillomavirus in female sex workers. ''Virus Res.'' 2006 Nov;121(2):220-2. Epub 2006 Jul 24. PMID 16860426</ref><ref>{{Cite journal |doi = 10.1038/nm1598 |issn = 1078-8956 |volume = 13 |issue = 7 |pages=857–861 |last=Roberts |first=Jeffrey N |coauthors = Christopher B Buck, Cynthia D Thompson, Rhonda Kines, Marcelino Bernardo, Peter L Choyke, Douglas R Lowy, John T Schiller |title=Genital transmission of HPV in a mouse model is potentiated by nonoxynol-9 and inhibited by carrageenan |journal = Nat Med |accessdate=2007-09-05 |year=2007 |month = July |quote = A widely used vaginal spermicide, nonoxynol-9 (N-9), greatly increased susceptibility to infection. ... As expected, the CMC-based gel containing N-9 rendered the mucosa susceptible to significant HPV pseudovirus infection (P = 0.03), while the carrageenan-based gel prevented detectable infection. ... Overall, these results raised the possibility that use of over-the-counter N-9-containing vaginal contraceptives is a risk factor for genital HPV infection in women. }}</ref> In one of the studies, researchers at the National Cancer Institute also reported that the increased likelihood of HPV infection caused by N-9 was mitigated through the use of [[carrageenan]]-based lubricants mixed 1:1 with N-9. Two consumer products containing carrageenan, [[Divine No. 9]] and BIOglide, prevented detectable HPV infection in the study. Frequent use of nonoxynol-9 is linked to higher risk of [[urinary tract infection]]s (UTIs). Some people have reported [[allergic]] reactions to Nonoxynol-9; however, it is possible to test it oneself on the [[lymph nodes]] on the upper thigh by the groin to see if one is hypersensitive. If so, the skin usually turns red and causes a burning sensation. Recovery from an allergic reaction usually takes about 6-8 hours. ==Alternatives== Chemically speaking, there are two alternatives to nonoxynol-9 spermicide: * Menfegol: Available as a foaming tablet in Europe. * [[Benzalkonium chloride]]: Benzalkonium chloride is the active ingredient in one brand of [[contraceptive sponge]], available only in France. For use with a cervical barrier such as a [[diaphragm (contraceptive)|diaphragm]], a jelly containing [[lactic acid]] may work as a substitute. Lactic acid is known to immobilize sperm, also. But in contrast with nonoxynol-9, this immobilization seems to be reversible and is for that reason less reliable. ==References== {{reflist}} ==External links== *[http://www.who.int/reproductive-health/stis/nonoxynol9.html Safety of Nonoxynol-9 when used for contraception] [[World Health Organization]] (October 2001) *[http://www.fpnotebook.com/GYN16.htm Vaginal Spermicide: Nonoxynol] Family Practice Notebook.com *[http://www.wired.com/news/medtech/0,1286,52481,00.html Docs: 'Nonoxynol-9 Doesn't Work'] Wired News: Lite, Jordan (May 13, 2002) *[http://www.femprotect.com Femprotect] alternative to nonoxynol-9 *[http://www.mas-health.org/microbicides.htm Info on microbicides] *[http://householdproducts.nlm.nih.gov/cgi-bin/household/brands?tbl=chem&id=2786 Household Products Database: Nonoxynol-9] listing of other household products containing Nonoxynol-9 {{Birth control methods}} [[Category:Aromatic compounds]] [[Category:Ethers]] [[Category:Alcohols]] [[Category:Chemical contraception]] [[Category:Surfactants]] <!-- The below are interlanguage links. --> [[de:Nonoxinol-9]] [[ru:Ноноксинол-9]]