Nonoxynol-9

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Nonoxynol-9
Partially condensed, Kekulé, skeletal formula of nonoxynol-9
Identifiers
CAS number 26571-11-9 YesY
PubChem 72385
ChemSpider 65319 YesY
UNII 48Q180SH9T YesY
EC number 247-816-5
DrugBank DB06804
KEGG D06490 N
MeSH Nonoxynol
ChEBI CHEBI:53775 YesY
ChEMBL CHEMBL1410 YesY
Beilstein Reference 2031786
Jmol-3D images Image 1
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Properties
Molecular formula C33H60O10
Molar mass 616.82 g mol−1
log P 4.02
Pharmacology
Routes of
administration
Topical
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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[edit]

Spermicide[edit]

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]

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%.[1]

Condoms[edit]

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.[2]

Compared to regular lubricated condoms, condoms containing nonoxynol-9 present another disadvantage — they have a shorter shelf life.

Cervical barriers[edit]

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[edit]

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[edit]

Nonoxynol-9 is also found in Bengay Vanishing Scent as an inactive ingredient.

Poison ivy creams[edit]

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[edit]

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 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."[2] 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.[3]

References[edit]

  1. ^ Raymond, Elizabeth G.; Lien Chen, Pai; Luoto, Joanne; for the Spermicide Trial Group (March 2004). "Contraceptive effectiveness and safety of five nonoxynol-9 spermicides: a randomized trial". Obstetrics & Gynecology 103 (3): 430–439. doi:10.1097/01.AOG.0000113620.18395.0b. PMID 14990402. 
  2. ^ a b Siegfried, Nandi (September 25, 2003). "Nonoxynol-9 for preventing vaginal acquisition of HIV infection by women from men". Reproductive Health Library. Geneva: World Health Organization. Retrieved February 21, 2010. 
  3. ^ Marais, Dianne; Carrara, Henri; Kay, Patti; Ramjee, Gita; Allan, Bruce; Williamson, Anna-Lise (November 2006). "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 Research 121 (2): 220–222. doi:10.1016/j.virusres.2006.04.009. PMID 16860426. 

External links[edit]