: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{{BlueBook2013|rec=51.4.1}}
| 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 nonoxynol family of nonionic surfactants. N-9 and related compounds are ingredients in various cleaning and cosmetic products. It is widely used in contraceptives for its spermicidal properties.
Uses
=Spermicide=
As a spermicide, it attacks the acrosomal membranes of the 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 typical-use failure rates for five nonoxynol-9 vaginal contraceptives (film, suppository, and gels at three different concentrations) ranged from 10% to 20%.{{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}}
=Condoms=
Many models of condoms are lubricated with solutions containing nonoxynol-9. In this role, it has been promoted as a backup method for avoiding pregnancy and a microbicide for sexually transmitted diseases in the event of condom failure. However, the 2001 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.{{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}}
Compared to regular lubricated condoms, condoms containing nonoxynol-9 present another disadvantage — they are limited by the shelf-life of the
=Cervical barriers=
Almost all brands of diaphragm jelly contain nonoxynol-9 as the active ingredient. This jelly may also be used for a cervical cap. Most contraceptive sponges 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 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 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 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 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." 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.{{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}}
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:Non-ionic surfactants