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Nonoxynol-9

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Nonoxynol-9
Partially condensed, Kekulé, skeletal formula of 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[citation needed]
Other names
26-(4-Nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
Identifiers
3D model (JSmol)
2031786
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.043.454 Edit this at Wikidata
EC Number
  • 247-816-5
KEGG
MeSH Nonoxynol
UNII
  • 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 checkY
    Key: FBWNMEQMRUMQSO-UHFFFAOYSA-N checkY
  • 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
  • CCCCCCCCCc1ccc(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)cc1
  • CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1
  • O(c1ccc(cc1)CCCCCCCCC)CCOCCOCCOCCOCCOCCOCCOCCOCCO
Properties
C33H60O10
Molar mass 616.833 g·mol−1
log P 4.02
Pharmacology
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 checkY☒N ?)

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]

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

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 [2]

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 have led most major health agencies 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]

Regular use of nonoxynol-9 appears also to increase the risk of infection with sexually transmitted human papillomaviruses (HPVs) that can cause cervical cancer.[3][4] In one of the studies, researchers at the National Cancer Institute also reported that the increased likelihood of HPV infection caused by N-9 was mitigated through the use of carrageenan-based lubricants mixed 1:1 with N-9. Two consumer products containing carrageenan, Divine 9 and BIOglide, prevented detectable HPV infection in the study.

References

  1. ^ Elizabeth G. Raymond, Pai Lien Chen, Joanne Luoto, for the Spermicide Trial Group. "Contraceptive Effectiveness and Safety of Five Nonoxynol-9 Spermicides: A Randomized Trial" Obstetrics & Gynecology. 2004; 103:430-439. available online
  2. ^ a b http://apps.who.int/rhl/hiv_aids/nscom1/en/index.html
  3. ^ Marais D, Carrara H, Kay P, Ramjee G, Allan B, Williamson AL. 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 Res. 2006 Nov;121(2):220-2. Epub 2006 Jul 24. PMID 16860426
  4. ^ Roberts, Jeffrey N (July 2007). "Genital transmission of HPV in a mouse model is potentiated by nonoxynol-9 and inhibited by carrageenan". Nat Med. 13 (7): 857–861. doi:10.1038/nm1598. ISSN 1078-8956. PMID 17603495. A widely used vaginal spermicide, nonoxynol-9 (N-9), greatly increased susceptibility to infection. ... As expected, the CMC-based gel containing N-9 rendered the mucosa susceptible to significant HPV pseudovirus infection (P = 0.03), while the carrageenan-based gel prevented detectable infection. ... Overall, these results raised the possibility that use of over-the-counter N-9-containing vaginal contraceptives is a risk factor for genital HPV infection in women. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
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