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| Names | |
|---|---|
| Preferred IUPAC name 26-(4-Nonylphenoxy)-3,6,9,12,15,18,21,24-nonaoxahexacosan-1-ol[1] | |
| Other names 1-(4-Nonylphenyl)-1,4,7,10,13,16,19,22,25-nonaoxaheptacosan-27-ol[citation needed] | |
| Identifiers | |
3D model (JSmol) | |
| 2031786 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| DrugBank |
|
| ECHA InfoCard | 100.043.454 |
| EC Number |
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| KEGG |
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| MeSH | Nonoxynol |
| UNII | |
| |
| |
| Properties | |
| C33H60O10 | |
| Molar mass | 616.833 g·mol−1 |
| logP | 4.02 |
| Pharmacology | |
| Topical | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Nonoxynol-9, sometimes abbreviated asN-9, is anorganic compound that is used as asurfactant. It is a member of thenonoxynol family of nonionic surfactants. N-9 and related compounds are ingredients in various cleaning and cosmetic products. It is widely used incontraceptives for its spermicidal properties.
As aspermicide, it attacks theacrosomal membranes of thesperm, causing the sperm to be immobilized.Nonoxynol-9 is the active ingredient in most spermicidal creams, jellies, foams, gel, film, andsuppositories.[citation needed]
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, thetypical-use failure rates for five nonoxynol-9vaginal contraceptives (film, suppository, and gels at three different concentrations) ranged from 10% to 20%.[2]
Many models ofcondoms arelubricated with solutions containing nonoxynol-9. In this role, it has been promoted as a backup method for avoiding pregnancy and amicrobicide for sexually transmitted diseases in the event of condom failure. However, the 2001WHO /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.[3]
Compared to regular lubricated condoms, condoms containing nonoxynol-9 present another disadvantage — they are limited by the shelf-life of thespermicide.[4]
Almost all brands ofdiaphragm jelly contain nonoxynol-9 as the active ingredient. This jelly may also be used for acervical cap. Mostcontraceptive sponges contain nonoxynol-9 as an active ingredient.
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.
Nonoxynol-9 is also found inBengay Vanishing Scent as an inactive ingredient.
Nonoxynol-9 is also found in Zanfel poison ivy cream. It effectively helps to break up the oilurushiol that causes the rash.
From 1996 to 2000, aUN-sponsored study conducted in several locations inAfrica followed nearly 1,000 sex workers who used nonoxynol-9 gels or aplacebo. TheHIV 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 ofvaginallesions, 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 theWorld 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 againstsexually transmitted infections such asgonorrhoea,chlamydia."[3] A 2006 study of a nonoxynol-9 vaginal gel in female sex workers inAfrica concluded that it did not prevent genitalhuman papillomavirus (HPV) infection and could increase the virus's ability to infect or persist.[5]
