Nonoxynol-9

Nonoxynol-9

Names
IUPAC name 2-[2-[2-[2-[2-[2-[2-[2-[2-(4-Nonylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy] ethoxy]ethoxy]ethoxy]ethoxy]ethanol
Systematic IUPAC name 1-(4-Nonylphenyl)-1,4,7,10,13,16,19,22,25-nonaoxaheptacosan-27-ol
Other names 26-(4-Nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
Identifiers
CAS Number	26571-11-9 Y
Beilstein Reference	2031786
ChEBI	CHEBI:53775 Y
ChEMBL	ChEMBL1410 Y
ChemSpider	65319 Y
DrugBank	DB06804 Y
EC Number	247-816-5
Jmol 3D model	Interactive image Interactive image Interactive image
KEGG	D06490 N
MeSH	Nonoxynol
PubChem	72385
UNII	48Q180SH9T Y
InChI 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 Y Key: FBWNMEQMRUMQSO-UHFFFAOYSA-N Y InChI=1/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 Key: FBWNMEQMRUMQSO-UHFFFAOYAL
SMILES CCCCCCCCCc1ccc(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)cc1 CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 O(c1ccc(cc1)CCCCCCCCC)CCOCCOCCOCCOCCOCCOCCOCCOCCO
Properties
Chemical formula	C33H60O10
Molar mass	616.83 g·mol−1
log P	4.02
Pharmacology
Routes of administration	Topical
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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

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.

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%.

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.

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

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 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." 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.

External links

• Safety of Nonoxynol-9 when used for contraception World Health Organization (October 2001)
• Vaginal Spermicide: Nonoxynol Family Practice Notebook.com
• Docs: 'Nonoxynol-9 Doesn't Work' Wired News: Lite, Jordan (May 13, 2002)
• Info on microbicides
• ChemSub Online: Nonoxynol-9
• Record in the Household Products Database of NLM