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
3D model (Jmol)	Interactive image Interactive image Interactive image
Beilstein Reference	2031786
ChEBI	CHEBI:53775 Y
ChemSpider	65319 Y
DrugBank	DB06804 Y
ECHA InfoCard	100.043.454
EC Number	247-816-5
KEGG	D06490 N
MeSH	Nonoxynol
PubChem CID	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
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  (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.

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%.

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.

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.