View source for Nonoxynol-9

{{Chembox
| Watchedfields = changed
|  verifiedrevid = 302630926
|  ImageFile = NonylPhenolBranched.png
|   ImageName = 1-[4-(3,5-Dimethylheptan-2-yl)phenyl]-1,4,7,10,13,16,19,22,25-nonaoxaheptacosan-27-ol
|  PIN = 2-[2-[2-[2-[2-[2-[2-[2-[2-(4-Nonylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]<br />
ethoxy]ethoxy]ethoxy]ethoxy]ethanol
|  SystematicName = 1-(4-Nonylphenyl)-1,4,7,10,13,16,19,22,25-nonaoxaheptacosan-27-ol
|  OtherNames = 26-(4-Nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
| Section1 = {{Chembox Identifiers
|  CASNo = 26571-11-9
|   CASNo_Ref = {{cascite}}
|  PubChem = 72385
|   PubChem_Ref = {{Pubchemcite}}
|  ChemSpiderID = 65319
|   ChemSpiderID_Ref = {{Chemspidercite}}
|  EINECS = 247-816-5
|  ChEBI = 445872
|  MeSHName = Nonoxynol
|  SMILES = CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1
|  InChI = 1S/C33H60O10/c1-2-3-4-5-6-7-8-9-32-10-12-33(13-11-32)43-31-30-42-29-28-41-27-26-40-25-24-39-23-22-38-21-20-37-19-18-36-17-16-35-15-14-34/h10-13,34H,2-9,14-31H2,1H3
|  InChIKey = FBWNMEQMRUMQSO-UHFFFAOYSA-N}}
| Section2 = {{Chembox Properties
|  C=33
|   H=60
|   O=10
|  ExactMass = 616.418648140 g mol<sup>-1</sup>}}
| Section3 = {{Chembox Pharmacology
|  AdminRoutes = Topical}}
}}

'''Nonoxynol-9''', sometimes abbreviated as '''N-9''', is an [[organic compound]] that is used as a [[surfactant]].  It is a member of the  [[nonoxynol]] family of nonionic surfactants.  N-9 and related compounds are ingredients in various cleaning and cosmetic products.  It is widely-used in [[contraceptive]]s for its spermicidal properties. However, its use in STI prevention is controversial.

==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]].{{Citation needed|date=May 2010}}

A 2004 study found that over a six-month period, the [[effectiveness|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, Pai Lien Chen, Joanne Luoto, 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 STD prevention in the event of condom failure. However, the 2001 [[World Health Organization|WHO]]/CONRAD Technical Consultation on Nonoxynol-9 concluded:<ref name="WHO">http://apps.who.int/rhl/hiv_aids/nscom1/en/index.html</ref>
:''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.'' Compared to regular lubricated condoms, condoms containing nonoxynol-9 present another disadvantage—they have a shorter expiration date.

===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. [[Gillette (brand)|Gillette]] formerly used nonoxynol-9 for this purpose in its Foamy products, but has discontinued the practice.

===Sports cream===
Nonoxynol-9 is also found in [[Bengay]] Vanishing Scent as an inactive ingredient.

===Poison ivy creams===
Nonoxynol-9 is also found in Zanfel poison ivy cream.  It effectively helps to break up the oil urushiol that causes the rash.

==Side effects==
From 1996 to 2000, a [[United Nations|UN]]-sponsored study conducted 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. Whereas 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"/>

Regular use of nonoxynol-9 appears also to increase 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.
|pmid = 17603495}}</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 9]] and BIOglide, prevented detectable HPV infection in the study.

==Alternatives==
Three alternatives to nonoxynol-9 spermicide are:{{Citation needed|date=May 2010}}
* ContraGel Green: Manufactured by DeltaMed GmbH in Germany and approved for use in Europe with the CE0124 mark.
* Menfegol:  Available as a foaming tablet in Europe.
* [[Benzalkonium chloride]]: The active ingredient in one brand of [[contraceptive sponge]], available only in France.

==References==
{{Reflist}}

==External links==
* [http://who.int/reproductive-health/publications/nonoxynol9/nonoxynol9.pdf 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://contragel.co.uk/about.php ContraGel Green] alternative to nonoxynol-9
* [http://www.mas-health.org/microbicides.htm Info on microbicides]
* [http://www.condomjungle.com/Spermicidal_Nonoxynol_9_Lubricated_Condoms_s/61.htm Condoms containing nonoxynol-9], present a risk to users.
* [http://chemsub.online.fr/name/nonoxynol-9.html ChemSub Online: Nonoxynol-9]
* {{HPD|2786}}

{{Birth control methods}}

[[Category:Aromatic compounds]]
[[Category:Ethers]]
[[Category:Alcohols]]
[[Category:Spermicide]]
[[Category:Non-ionic surfactants]]
[[Category:Drugs acting on the genito-urinary system]]

<!-- The below are interlanguage links. -->
[[cs:Nonoxynol-9]]
[[de:Nonoxinol 9]]
[[es:Nonoxinol-9]]
[[pl:Nonoksynol-9]]
[[ru:Ноноксинол-9]]
[[Category:2Fix]]