Nonoxynol-9

Last updated
Nonoxynol-9
Nonoxynol-9.svg
Nonoxynol-9-spacefill.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 247-816-5
KEGG
MeSH Nonoxynol
PubChem CID
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 Yes check.svgY
    Key: FBWNMEQMRUMQSO-UHFFFAOYSA-N Yes check.svgY
  • 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).
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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.

Contents

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 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. [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 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 those at high risk of HIV infection. The WHO further notes that "Nonoxynol-9 offers no protection against sexually transmitted infections such as gonorrhoea, chlamydia." [3] 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. [5]

Related Research Articles

<span class="mw-page-title-main">Condom</span> Device for birth control and STI prevention

A condom is a sheath-shaped barrier device used during sexual intercourse to reduce the probability of pregnancy or a sexually transmitted infection (STI). There are both male and female condoms. With proper use—and use at every act of intercourse—women whose partners use male condoms experience a 2% per-year pregnancy rate. With typical use, the rate of pregnancy is 18% per-year. Their use greatly decreases the risk of gonorrhea, chlamydia, trichomoniasis, hepatitis B, and HIV/AIDS. To a lesser extent, they also protect against genital herpes, human papillomavirus (HPV), and syphilis.

<span class="mw-page-title-main">Safe sex</span> Ways to reduce the risk of acquiring STDs

Safe sex is sexual activity using methods or contraceptive devices to reduce the risk of transmitting or acquiring sexually transmitted infections (STIs), especially HIV. "Safe sex" is also sometimes referred to as safer sex or protected sex to indicate that some safe sex practices do not eliminate STI risks. It is also sometimes used colloquially to describe methods aimed at preventing pregnancy that may or may not also lower STI risks.

<span class="mw-page-title-main">K-Y Jelly</span> Personal lubricant

K-Y Jelly is a water-based, water-soluble personal lubricant, most commonly used as a lubricant for sexual intercourse and masturbation. A variety of different products and formulas are produced under the K-Y banner, some of which are not water-soluble.

Vaginitis, also known as vulvovaginitis, is inflammation of the vagina and vulva. Symptoms may include itching, burning, pain, discharge, and a bad smell. Certain types of vaginitis may result in complications during pregnancy.

<span class="mw-page-title-main">Diaphragm (birth control)</span> Cervical barrier type of birth control

The diaphragm is a barrier method of birth control. It is moderately effective, with a one-year failure rate of around 12% with typical use. It is placed over the cervix with spermicide before sex and left in place for at least six hours after sex. Fitting by a healthcare provider is generally required.

Spermicide is a contraceptive substance that destroys sperm, inserted vaginally prior to intercourse to prevent pregnancy. As a contraceptive, spermicide may be used alone. However, the pregnancy rate experienced by couples using only spermicide is higher than that of couples using other methods. Usually, spermicides are combined with contraceptive barrier methods such as diaphragms, condoms, cervical caps, and sponges. Combined methods are believed to result in lower pregnancy rates than either method alone.

<span class="mw-page-title-main">Microbicides for sexually transmitted diseases</span> Pharmacologic agents and chemical substances

Microbicides for sexually transmitted diseases are pharmacologic agents and chemical substances that are capable of killing or destroying certain microorganisms that commonly cause human infection.

<span class="mw-page-title-main">Vaginal lubrication</span> Vaginal lubrication

Vaginal lubrication is a naturally produced fluid that lubricates vagina. Vaginal lubrication is always present, but production increases significantly near ovulation and during sexual arousal in anticipation of sexual intercourse. Vaginal dryness is the condition in which this lubrication is insufficient, and sometimes artificial lubricants are used to augment it. Without sufficient lubrication, sexual intercourse can be painful. The vaginal lining has no glands, and therefore the vagina must rely on other methods of lubrication. Plasma from vaginal walls due to vascular engorgement is considered to be the chief lubrication source, and the Bartholin's glands, located slightly below and to the left and right of the introitus, also secrete mucus to augment vaginal-wall secretions. Near ovulation, cervical mucus provides additional lubrication.

<span class="mw-page-title-main">Personal lubricant</span> Substance to reduce friction, usually during sexual acts

Personal lubricants are specialized lubricants used during sexual acts, such as intercourse and masturbation, to reduce friction to or between the penis and vagina, anus or other body parts or applied to sex toys to reduce friction or to ease penetration. Surgical or medical lubricants or gels, which are similar to personal lubricants but not usually referred to or labelled as "personal" lubricants, may be used for medical purposes such as speculum insertion or introduction of a catheter. The primary difference between personal and surgical lubricants is that surgical lubricants are thicker, sterile gels, typically containing a bacteriostatic agent. As of 2015 the personal lubricant market was estimated to be worth at least $400 million.

<span class="mw-page-title-main">Contraceptive sponge</span> Birth control device

The contraceptive sponge combines barrier and spermicidal methods to prevent conception. Sponges work in two ways. First, the sponge is inserted into the vagina, so it can cover the cervix and prevent any sperm from entering the uterus. Secondly, the sponge contains spermicide.

<span class="mw-page-title-main">Comparison of birth control methods</span>

There are many methods of birth control that vary in requirements, side effects, and effectiveness. As technology, education, and awareness about contraception has evolved, new contraception methods have been theorized and put in application. Although no method of birth control is ideal for every user, some methods remain more effective, affordable or intrusive than others. Outlined here are the different types of barrier methods, hormonal methods, various methods including spermicides, emergency contraceptives, and surgical methods and a comparison between them.

Nonoxynols also known as nonaethylene glycol or polyethylene glycol nonyl phenyl ether are mixtures of nonionic surfactants used as detergents, emulsifiers, wetting agents or defoaming agents. The most commonly discussed compound nonoxynol-9 is a spermicide, formulated primarily as a component of vaginal foams and creams. Nonoxynol was found to metabolize into free nonylphenol when administered to lab animals. Arkopal-N60, with on average 6 ethylene glycol units is a related used surfactant.

<span class="mw-page-title-main">Condom effectiveness</span>

Condom effectiveness is how effective condoms are at preventing STDs and pregnancy. Correctly using male condoms and other barriers like female condoms and dental dams, every time, can reduce the risk of sexually transmitted infections (STIs), including human immunodeficiency virus (HIV) and viral hepatitis. They can also provide protection against other diseases that may be transmitted through sex like Zika and Ebola. Using male or female condoms correctly, every time, can also help prevent pregnancy.

Wet Lubricants is a brand of personal lubricants produced by Wet International, part of Trigg Laboratories in Las Vegas. The line includes a variety of water-based and silicone-based lubricants, as well as massage oils and shaving creams.

CAPRISA 004 is the name of a clinical trial conducted by CAPRISA. This particular study was the first to show that a topical gel could reduce a person's risk of contracting HIV. The gel used in the study contained a microbicide.

CONRAD is a non-profit organization scientific research organization that works to improve the reproductive health of women, especially in developing countries. CONRAD was established in 1986 under a cooperative agreement between Eastern Virginia Medical School (EVMS) and the United States Agency for International Development(USAID). CONRAD’s products are developed primarily for women in low-resource settings, in that they are designed to be safe, affordable and user-friendly. CONRAD is led by Scientific and Executive Director Gustavo Doncel, M.D., Ph.D. Primary funding for CONRAD comes from the U.S. President's Emergency Plan for AIDS Relief (PEPFAR) through the U.S. Agency for International Development (USAID), with additional funding from The Bill & Melinda Gates Foundation and the National Institutes of Health (NIH).

A rectal microbicide is a microbicide for rectal use. Most commonly such a product would be a topical gel inserted into the anus so that it make act as protection against the contract of a sexually transmitted infection during anal sex.

A vaginal microbicide is a microbicide for vaginal use. Most commonly such a product would be a topical gel or cream inserted into the vagina so that it may treat some infection in the vagina, such as types of vaginitis.

Sharon Louise Hillier is an American microbiologist. She is the Richard Sweet Endowed Chair in Reproductive Infectious Disease and vice chair of the department of obstetrics, gynecology and reproductive sciences at the University of Pittsburgh Medical Center (UPMC) and Magee-Women's Research Institute.

<span class="mw-page-title-main">Cervical drug delivery</span> Drug delivery methodology

Cervical drug delivery is a route of carrying drugs into the body through the vagina and cervix. This is a form of localized drug delivery that prevents the drugs from impacting unintended areas of the body, which can lower side effects of toxic drugs such as chemotherapeutics. Cervical drug delivery has specific applications for a variety of female health issues: treatment of cervical cancer, pregnancy prevention, STD prevention, and STD treatment. 

References

  1. IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-51.4.1". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPACRSC. ISBN   978-0-85404-182-4.
  2. 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. S2CID   31754199.
  3. 1 2 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. 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.