PRODUCTS

NONOXYNOL

IUPAC name: 26-(4-Nonylphenoxy)-3,6,9,12,15,18,21,24-nonaoxahexacosan-1-o
CAS Number: 26027-38-3
Chemical formula: C33H60O10
Molar mass: 616.833 g
EC Number: 247-816-5

Nonoxynol, sometimes abbreviated as N-9, is an organic compound that is used as a surfactant.
Nonoxynolis a member of the nonoxynol family of nonionic surfactants.
N-9 and related compounds are ingredients in various cleaning and cosmetic products.
Nonoxynolis 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.

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%.

Condoms
Many models of condoms are lubricated with solutions containing nonoxynol.
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 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 are limited by the shelf-life of the spermicide.

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.
Nonoxynoleffectively helps to break up the oil urushiol that causes the rash.

Side effects of Nonoxynol
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 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.

Nonoxynol (N-9) is a typical surfactant used as a vaginal spermicide.
Spermicides are locally acting non-hormonal contraceptives.
When present in the vagina during intercourse, they immobilize/inactivate/damage and/or kill sperms without eliciting systemic effects.

N-9 has been in use for more than 30 years as an over-the-counter (OTC) drug in creams, gels, foams and condom lubricants.
Nonoxynolis the most commonly used spermicidal contraceptive in the UK and the USA.
In several European countries, spermicides are no longer on the market.

Nonoxynol is a surfactant spermicide used for contraception in spermicidal creams, jellies, foams, gel, and lubricants.
Nonoxynolis also used in conjuction with other methods of contraception, including condoms, cervical caps and diaphragms.

Nonoxynol interacts with the lipids in the membranes of the acrosome and the midpiece of the sperm.
The sperm membranes are lysed; the acrosome, neck and midpiece of the spermatozoa are loosened and then detached which results in their immobilization and death.

The major drawback of nonoxynol is its detergent-type action on epithelial cells and the normal vaginal flora.
Detergent-type spermicides alter the vaginal flora, possibly leading to an increased risk of opportunistic infections.

These are known to enhance the susceptibility of the epithelium of the lower genital tract to HIV and human papillomavirus infection.
N-9 can cause vaginal irritation and allergic vaginitis as well as genital irritation in male partners.

Flash Point: 197 °C
Boiling Point: 250 °C
Melting Point: 6 °C

XLogP3-AA: 4.6
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 10
Rotatable Bond Count: 35

Exact Mass: 616.41864811
Monoisotopic Mass: 616.41864811
Topological Polar Surface Area: 103 Å²
Heavy Atom Count: 43

Complexity: 520
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0

Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Nonoxynol is a spermicide.
Nonoxynolis used for birth control to prevent pregnancy.
Some formulas of this birth control can be used along with condoms, the cervical cap, or a diaphragm; read the label of the product you have chosen.

This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

How should I use Nonoxynol
To prevent pregnancy, it is very important that this product be used properly.
These products are used in the vagina and must be applied before sexual contact begins.
Do not use in the rectum.
Make sure you carefully read and follow the instructions that come with the product.
Reapply prior to each episode of sexual intercourse.

If you are using nonoxynol containing products with latex cervical caps, condoms, or diaphragms, make sure the product is labeled as safe for use with latex products.
If not, this may cause the cervical cap, condom, or diaphragm to weaken or even break.
If leakage or breakage occurs during intercourse, additional spermicide may be inserted into the vagina.

Other products that can weaken latex include hand, face, or body cream; petroleum jelly; cooking oils or shortenings; and baby oil.
These are oil-based products and should not be used as lubricants.
Instead, use a water-based lubricant that is safe for use with cervical caps, condoms, or diaphragms.

This product may not work as well to prevent pregnancy if you use other vaginal products at the same time.
Talk with your doctor or pharmacist before using the products together.

This list may not describe all possible interactions.
Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use.
Also tell them if you smoke, drink alcohol, or use illegal drugs.
Some items may interact with your medicine.

Where should I Nonoxynol
Keep out of the reach of children.

Store at room temperature between 15 and 30 degrees C.
Follow the directions on the product label.
Throw away any unused medicine after the expiration date.

NONOXYNOL belongs to the class of medicines called spermicidal contraceptives used to prevent pregnancy.
Pregnancy is the period in which the foetus develops inside a womb or uterus of a woman.
Nonoxynoloccurs when a sperm fertilizes an egg.

NONOXYNOL contains Nonoxynol-9 that breaks the outer covering of sperms and kills them.
Thereby, it prevents pregnancy.

Use NONOXYNOL as advised by your doctor.
In some cases, you may experience vaginal irritation, burning, bad-smelling vaginal discharge or difficulty in urination.
Most of these side effects of NONOXYNOL do not require medical attention and gradually resolve over time.
However, if the side effects persist or worsen, please consult your doctor.

If you are allergic to NONOXYNOL or any other medicines, please tell your doctor.
NONOXYNOL is not recommended for pregnant women.
If you are breastfeeding, consult a doctor before taking NONOXYNOL.
If you are at risk of getting HIV (AIDS) or any other sexually transmitted disease, it is advised to use a latex condom to prevent the spread of sexually transmitted diseases.

Products containing nonoxynol have been used as spermicidal contraceptives for many years, but limited data have been published describing the long-term effects of nonoxynol-9 use on the vaginal microbial ecosystem.
This longitudinal study was conducted to examine the effects of nonoxynol-9 on the vaginal ecology.

Vaginal swabs were obtained from 235 women enrolled in a randomized clinical trial before initiation of use of 1 of 5 different formulations of nonoxynol for contraception, and up to 3 more samples were gathered over 7 months of use.
The swab samples were evaluated in a single laboratory.

The prevalence of several constituents of the normal vaginal flora was evaluated.
The associations between nonoxynol-9 dosage, formulation, average product use per week, and number of sex acts per week were calculated.
The changes in prevalence of vaginal microbes after nonoxynol-9 use were minimal for each of the different nonoxynol-9 formulations.

However, when both nonoxynol-9 concentration and number of product uses are taken into account, nonoxynol-9 did have dose-dependant effects on the increased prevalence of anaerobic gram-negative rods, H2O2-negative lactobacilli, and bacterial vaginosis.
This study demonstrated that most nonoxynol-9 users experienced minimal disruptions in their vaginal ecology.

There were no differences between the different formulations evaluated with respect to changes in vaginal microflora.
However, independent of the nonoxynol-9 formulation, there was a dose-dependent effect with increased exposure to nonoxynol-9 on the risk of bacterial vaginosis and its associated flora

Uses of Nonoxynol

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.

Condoms
Many models of condoms are lubricated with solutions containing nonoxynol-9.
In this role, it has been promoted as a backup method for pregnancy and STI prevention 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 STIs 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.

Additionally, the WHO statement suggests that N-9 should not be used rectally under any circumstances.

Cervical barriers
Almost all brands of diaphragm jelly contain nonoxynol-9 as the active ingredient.
This jelly may also be used for cervical caps and Lea's shields.
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 it's Foamy products, but has discontinued the practice.

Sports Cream
Nonoxynol-9 is also found in Bengay Vanishing Scent as an inactive ingredient.

Side effects
Nonoxynol-9's ability to kill microbes in vitro was initially taken as evidence that it might be effective at preventing STI transmission.
However, more recent findings indicate that it may actually increase a person's risk of contracting STIs, especially if used frequently.
This is because the chemical causes tiny abrasions inside the sensitive vaginal and anal walls.
These abrasions may make transmission more likely especially if condoms are not used.

From 1996 to 2000, a UN-sponsored study carried out in several locations in Africa followed nearly 1000 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.

Regular use of nonoxynol-9 likely increases the risk of infection with sexually transmitted human papillomaviruses (HPVs) that can cause cervical cancer.
While 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."

Nonoxynol-9 based products (including condoms containing the spermicide) should not be used for prevention of HIV or STDs or for contraception between non-monogamous partners because of the increased risk of infection by HIV or sexually transmitted infections.
However, non-spermicide condoms are available and are still highly successful at preventing both pregnancy and STD transmission.

Frequent use of nonoxynol-9 is linked to higher risk of urinary tract infections (UTIs).
Some people have reported allergic reactions to Nonoxynol-9; however, it is possible to test it oneself on the lymph nodes on the upper thigh by the groin to see if one is hypersensitive.
If so, the skin usually turns red and causes a burning sensation. Recovery from an allergic reaction usually takes about 6-8 hours.

Alternatives
Chemically speaking, there are two alternatives to nonoxynol-9 spermicide:

Menfegol: Available as a foaming tablet in Europe.
Benzalkonium chloride: Benzalkonium chloride is the active ingredient in one brand of contraceptive sponge, available only in France.
For use with a cervical barrier such as a diaphragm, a jelly containing lactic acid may work as a substitute. Lactic acid is known to immobilize sperm, also. But in contrast with nonoxynol-9, this immobilization seems to be reversible and is for that reason less reliable.

Nonoxynol-9 is a product widely used in spermicides found on condoms and other contraceptive devices. Until recently, Nonoxynolhas been thought to reduce the risk of HIV and other STD transmission.

What’s the problem?

Recent studies have indicated that nonoxynol-9 is not only ineffective in preventing HIV infection, but may actually increase a woman’s chances of becoming HIV positive.

How can this be?

Nonoxynol-9 has been likened to an extremely potent detergent.
Nonoxynolseems that it may damage vaginal walls during intercourse, creating a site infection point through which STDs could enter the blood stream.
The vagina produces a number of secretions that form a natural protective barrier.
Stripping these secretions from the vagina and causing open abrasions is potentially very dangerous.

A recent study by UNAIDS in Africa revealed that women (HIV negative sex trade workers) who used the N-9 spermicide gel had become infected with HIV at approximately a 50% higher rate than women who used a placebo gel.
In addition, the more frequently women used only the N-9 gel (without a condom) to protect themselves, the higher their risk for contracting the HIV virus.
So, in this high-risk group, N-9 gel may have facilitated the transmission of the HIV virus.

How do I know if a specific contraceptive device contains Nonoxynol?

Products that have been sold in Canada that contain N-9 spermicides include:
Trojan Ribbed Condom with N-9 spermicide
Gynol II Contraceptive Jelly with N-9
Lifestyles Spermicidally Lubricated Condom
Hardcover Ultra Condom with Nonoxynol-9
Advantage 24 (Vaginal Contraceptive Gel)
Delfen Foam Spermicide

Other names:
14409-72-4
Delfen
Tergitol NP-9
PEG-9 Nonyl phenyl ether
26571-11-9
Nonoxynol9
Tergitol NP9
Nonaethylene glycol nonylphenyl ether
Nonylphenol octa(oxyethylene) ethanol
Nonaethylene glycol mono(nonylphenyl) ether
NONOXINOL-9
Nonylphenoxypolyethoxyethanol
Polyoxyethylene (9) nonyl phenyl ether
26-(4-nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
26-(Nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
CHEBI:53775
NSC-758941
p-Nonylphenyl polyethylene glycol ether
Nonoxynol, n=9
N-9
Conceptrol
Intercept
Semicid
3,6,9,12,15,18,21,24-Octaoxahexacosan-1-ol, 26-(4-nonylphenoxy)-
2-[2-[2-[2-[2-[2-[2-[2-[2-(4-nonylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-ethoxy]ethoxy]ethoxy]ethoxy]ethanol
Nonoxinolum 9
HSDB 8094
Gynol II
C-Film
Norfox np-9
Tergitol TP-9
Nonoxynol-9.5
EINECS 247-816-5
Conco NI-90
K-Y plus nonoxynol-9
Spectrum2_001247
Spectrum3_001946
ALOSETRONHYDROCHLORIDE
CHEMBL1410
SCHEMBL36844
BSPBio_003546
SPECTRUM1505292
SPBio_001154
Dowfax 9N9, Neutronyx 611
CO-630SP
KBio3_002833
DTXSID00858720
HMS2093O22
Pharmakon1600-01505292
ZINC8214629
3,6,9,12,15,18,21,24-Octaoxahexacosan-1-ol, 26-(nonylphenoxy)-
BDBM50442874
CCG-39124
NSC758941
AKOS015910808
DB06804
NSC 758941
NCGC00095907-02
NCGC00095907-03
N 9
SBI-0206761.P001
Polyethylene glycol 450 nonyl phenyl ether
AB01563056_01
Q420039
SR-05000001885
J-016227
Q-201490
SR-05000001885-1
BRD-K88625236-001-01-8
1-(4-nonylphenyl)-1,4,7,10,13,16,19,22,25-nonaoxaheptacosan-27-ol
N9
Poly(oxy-1,2-ethanediyl), α-(4-nonylphenyl)-ω-hydroxy-
Glycols, polyethylene, mono(p-nonylphenyl) ether
Phenol, p-nonyl-, monoether with polyethylene glycol
α-(p-Nonylphenyl)-ω-hydroxypoly(oxyethylene)
Polyethylene glycol p-nonylphenyl ether
Polyethylene glycol mono(p-nonylphenyl) ether
Tetra(oxyethylene), α-(4-nonylphenyl)-ω-hydroxy-
p-Nonylphenol-polyethylene glycol adduct
Ethoxylated p-nonyl phenol
Polyethylene glycol mono(4-nonylphenyl) ether
Nonoxynol
p-Nonylphenol polyethylene glycol ether
Rokafenol NX 8
Nonoxynol 13
Nonoxynol 6
Nonoxynol 14
Nonoxynol 10
Rokafenol N 25
Rokafenol N
Rokafenol N 10
Rokafenol N 8
Rokafenol N 4
Rokafenol N 5
Rokafenol N 14
Rokafenol N 6
Rexol 25/6
Polyethylene glycol 4-nonylphenyl monoether
Newcol 565
Bion NE 9
Nonoxynol 9
Rokafenol N 2
Rokafenol N 45
Delfen
Conceptrol
Encare oval
NOP 8
NOP 17
Egyptol
Koromex
Prevocell W-ON 100
Rokafenol N 3
Praewozell W-ON 100
N 100
Polyoxyethylene p-nonylphenyl ether
Gynol II
Iconol NP 100
Akyporox NP 150
Liponox NCY
PEG p-nonylphenyl ether
W-ON 100
Polyethylene glycol-10 p-nonylphenol ether
p-Nonylphenyl polyoxyethylene ether
Pannox 16
Pannox 18
Pannox 110
Pannox 111
Pannox 116
Pannox 140
Pannox 150
NP 8.5
Polyoxyethylene mono-p-nonylphenyl ether
Poly(oxyethylene)-4-nonylphenyl ether
Nonoxynol 8.5
Imbetin N 7A
APSA 80
Amway All Purpose Spray Adjuvant
Amway APSA 80
Hyoxyd X 400
Nonoxynol 15
Monopol NP 1013
Monopol NP 1060
p-Nonylphenol decaethylene glycol ether
Decaethylene glycol mono(p-nonylphenyl) ether
4-Nonylphenol decaglycol ether
Decaethylene glycol p-nonylphenyl ether
Advantage 24
PONPE 7.5
Rexol 25/1
Prevocell N 9
PONPE 10
PONPE 15
PONPE 20
Cremophor NP 10
Cremophor NP 14
Polyethylene glycol p-nonylphenyl monoether
Emulan 30
Emulan 40
Rokafenol N 705
Hyoxyd X 200
Hyoxyd X 100
K-Y Plus
Nonoxynol 100
Nonoxynol 12
C-Film
Intercept
Today Sponge
Semicid
Staycept
Conco NI 90
Neutronyx 611
Encare
Findet 9Q21.5
COL 1492
Nonal 204
Nonal 202
Nonal 106
Rokafenol N 9
Emulsogen ELN
Rokafenol N 7
4-Nonylphenol polyethoxylate
Rokafenol N 22
NP 1060
Polyoxyethylene mono(4-nonylphenyl) ether
IKD
Tergitol NP 50
Coulter Dispersant IC
Sympatens NP 090
NP 40
APEO 7
APEO 10
2-[2-[2-[2-[2-[2-[2-[2-[2-(4-nonylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol
26-(4-nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
26-(nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
Nonoxynol 9
14409-72-4
Delfen
Tergitol NP-9
PEG-9 Nonyl phenyl ether
26571-11-9
Nonoxynol9
Tergitol NP9