Nonoxynol-9

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Nonoxynol-9
Partially condensed skeletal formula of nonoxynol-9
Ball-and-stick model of a nonoxynol-9 molecule.
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
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
  • 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

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
]

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%.[2]

Condoms

Many models of

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.[3]

Compared to regular lubricated condoms, condoms containing nonoxynol-9 present another disadvantage — they are limited by the shelf-life of the spermicide. [4]

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

human papillomavirus (HPV) infection and could increase the virus's ability to infect or persist.[5]

References

  1. ISBN 978-0-85404-182-4
    .
  2. S2CID 31754199
    .
  3. ^ 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. Archived from the original on May 22, 2009. Retrieved February 21, 2010.
  4. ^ "The Male Latex Condom 10 Condom Programming Fact Sheets" (PDF). UNAIDS.org. 28 June 2022. p. 11. Archived (PDF) from the original on 25 June 2022. Retrieved 28 June 2022.
  5. PMID 16860426
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Nonoxynol-9&oldid=1209528378"