View source for Nonoxynol-9

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461741978
| ImageFile = Nonoxynol-9.svg
| ImageClass = skin-invert
| ImageFile2 = Nonoxynol-9-spacefill.png
| ImageName = Partially condensed skeletal formula of nonoxynol-9
| ImageName2 = Ball-and-stick model of a nonoxynol-9 molecule.
| PIN = 26-(4-Nonylphenoxy)-3,6,9,12,15,18,21,24-nonaoxahexacosan-1-ol<ref>{{BlueBook2013|rec=51.4.1}}</ref>
| OtherNames = 1-(4-Nonylphenyl)-1,4,7,10,13,16,19,22,25-nonaoxaheptacosan-27-ol{{citation needed|date = March 2011}}

| Section1 = {{Chembox Identifiers
  | CASNo = 26027-38-3
  | CASNo_Ref = {{cascite|correct|CAS}}
  | PubChem = 72385
  | ChemSpiderID = 65319
  | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
  | EINECS = 247-816-5
  | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
  | DrugBank = DB06804
  | KEGG = D06490
  | KEGG_Ref = {{keggcite|changed|kegg}}
  | MeSHName = Nonoxynol
  | ChEBI_Ref = {{ebicite|correct|EBI}}
  | ChEBI = 53775
  | ChEMBL = 1410
  | ChEMBL_Ref = {{ebicite|correct|EBI}}
  | Beilstein = 2031786
  | UNII_Ref = {{fdacite|correct|FDA}}
  | UNII = 48Q180SH9T
  | SMILES = CCCCCCCCCc1ccc(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)cc1
  | SMILES1 = CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1
  | SMILES2 = O(c1ccc(cc1)CCCCCCCCC)CCOCCOCCOCCOCCOCCOCCOCCOCCO
  | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
  | StdInChI = 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
  | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
  | StdInChIKey = FBWNMEQMRUMQSO-UHFFFAOYSA-N
  }}

| Section2 = {{Chembox Properties
  | C=33 | H=60 | O=10 
  | LogP = 4.02
  }}

| 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  [[Nonoxynols|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.

==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}}

===Lubricant===
Nonoxynol-9 is a common ingredient of most vaginal and anal lubricants due to its spermicidal properties.

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="Raymond 2004">{{cite journal|last1=Raymond|first1=Elizabeth G.|last2=Lien Chen|first2=Pai|last3=Luoto|first3=Joanne|author4=for the Spermicide Trial Group|date=March 2004|title=Contraceptive effectiveness and safety of five nonoxynol-9 spermicides: a randomized trial|journal=Obstetrics & Gynecology|volume=103|issue=3|pages=430–439|doi=10.1097/01.AOG.0000113620.18395.0b|pmid=14990402|s2cid=31754199}}</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 avoiding pregnancy and a [[Microbicides for sexually transmitted diseases|microbicide for sexually transmitted diseases]] in the event of condom failure. However, the 2001 [[World Health Organization|WHO]] / [[CONRAD (organization)|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.''<ref name="Siegfried 2003">{{cite web|last=Siegfried|first=Nandi|date=September 25, 2003|title=Nonoxynol-9 for preventing vaginal acquisition of HIV infection by women from men|work=Reproductive Health Library|location=Geneva|publisher=World Health Organization|url=http://apps.who.int/rhl/hiv_aids/nscom1/en/index.html|archive-url=https://web.archive.org/web/20090522232257/http://apps.who.int/rhl/hiv_aids/nscom1/en/index.html|url-status=dead|archive-date=May 22, 2009|accessdate=February 21, 2010}}</ref>

Compared to regular lubricated condoms, condoms containing nonoxynol-9 present another disadvantage — they are limited by the shelf-life of the
spermicide. <ref>{{Cite web |date=28 June 2022 |title=The Male Latex Condom 10 Condom Programming Fact Sheets |url=https://data.unaids.org/publications/irc-pub01/jc003-malecondom-factsheets_en.pdf |url-status=live |archive-url=https://web.archive.org/web/20220625073514/https://data.unaids.org/publications/irc-pub01/jc003-malecondom-factsheets_en.pdf |archive-date=25 June 2022 |access-date=28 June 2022 |website=UNAIDS.org |page=11 |format=PDF}}</ref>

===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 1,000 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 [[vagina]]l [[lesion]]s, 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 led the [[World Health Organization]] to recommend that it no longer be used by those 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="Siegfried 2003"/> A 2006 study of a nonoxynol-9 vaginal gel in female sex workers in [[Africa]] concluded that it did not prevent genital [[human papillomavirus]] (HPV) infection and could increase the virus's ability to infect or persist.<ref name="Marais 2006">{{cite journal|last1=Marais|first1=Dianne|last2=Carrara|first2=Henri|last3=Kay|first3=Patti|last4=Ramjee|first4=Gita|last5=Allan|first5=Bruce|last6=Williamson|first6=Anna-Lise|date=November 2006|title=The impact of the use of COL-1492, a nonoxynol-9 vaginal gel, on the presence of cervical human papillomavirus in female sex workers|journal=Virus Research|volume=121|issue=2|pages=220–222|doi=10.1016/j.virusres.2006.04.009|pmid=16860426}}</ref>

==References==
{{Reflist}}

==External links==
* [http://whqlibdoc.who.int/hq/2003/WHO_RHR_03.08.pdf Safety of Nonoxynol-9 when used for contraception] [[World Health Organization]] (October 2001)
* [https://web.archive.org/web/20031005023708/http://www.fpnotebook.com/GYN16.htm Vaginal Spermicide: Nonoxynol] Family Practice Notebook.com
* [https://www.wired.com/news/medtech/0,1286,52481,00.html Docs: 'Nonoxynol-9 Doesn't Work'] Wired News: Lite, Jordan (May 13, 2002)
* [https://web.archive.org/web/20050205192624/http://mas-health.org/microbicides.htm Info on microbicides]
* [http://chemsub.online.fr/name/nonoxynol-9.html ChemSub Online: Nonoxynol-9]
* {{CPID|id=2786}}

{{Microbicides for sexually transmitted diseases}}
{{Birth control methods}}

[[Category:Phenol ethers]]
[[Category:Glycol ethers]]
[[Category:Primary alcohols]]
[[Category:Spermicide]]
[[Category:Non-ionic surfactants]]
[[Category:Drugs acting on the genito-urinary system]]
[[Category:Microbicides]]