Nonoxinol 9

Structural formula
	Mixture with variable chain length ; (Figure: structural formula with nine ethoxy units)
General
Non-proprietary name	Nonoxinol 9
other names	2- {2- [2- (2- {2- [2- (2- {2- [2- (4-nonylphenoxy) ethoxy] ethoxy} ethoxy) ethoxy] ethoxy} ethoxy) ethoxy] ethoxy} ethanol ( IUPAC ) (Structure example); Nonoxynol 9;
Molecular formula	C 33 H 60 O 10 (structural example)
Brief description	clear, colorless to light yellow, viscous liquid
External identifiers / databases
EC number	247-816-5
ECHA InfoCard	100.043.454
PubChem	72385
ChemSpider	65319
DrugBank	DB06804
Wikidata	Q420039
Drug information
ATC code	G02 BB02
Drug class	Spermicide
properties
Molar mass	616.82 g mol −1
solubility	miscible with water, ethanol and vegetable oils
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302-315-317-318-335
	P: 280-301 + 312 + 330-305 + 351 + 338 + 310
Toxicological data	1410 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nonoxinol 9 , also Nonoxynol 9 , is a nonionic surfactant from the group of nonylphenol ethoxylates . Because of its spermicidal effect, it is used as an active ingredient in topical contraceptives .

effect

Spermicidal effect

Due to its surface-active properties, nonoxinol 9 attacks the cell membrane of the sperm . If the membrane is destroyed, the sperm are unable to move. Nonoxinol 9 is contained in many creams, gels, contraceptive suppositories and foams.

Antiviral and antimicrobial effects

Laboratory tests showed that nonoxinol 9 attacks the membrane of the HI virus . However, there is no protective effect against HIV infections in vivo , since a vaginal mucosa damaged by Nonoxinol 9 is at the same time much more permeable to all types of viruses.

Certain sexually transmitted germs (such as Chlamydia trachomatis , Neisseria gonorrhoeae , Treponema pallidum , Trichomonas vaginalis ) are also partially inhibited in vitro by nonoxinol 9. With regular use, Nonoxinol 9 can impair the vaginal flora .

unwanted effects

Nonoxinol 9 can irritate and injure the vaginal lining. In some cases, inflammation, wounds and even ulcers were found in women who regularly used products containing nonoxinol 9. In an American study from 1993, women who used a vaginal suppository with nonoxinol 9 once a day for two weeks already showed clear disorders of the mucous membrane. Irritation was found mainly on the vagina and cervix .

Allergic reactions also rarely occur.

use

Nonoxinol 9 is used in the sliding coating of some condoms as well as in vaginal gels, suppositories and foams, which are also used in connection with a diaphragm for contraception.

Furthermore, nonoxinol 9 is used as a pharmaceutical excipient because of its surface-active properties.

Alternatives

Other surface-active ingredients are:
- Octoxinol 9 : A few gels containing Octoxinol 9 are available in the United States.
- Benzalkonium chloride : Benzalkonium chloride is found in spermicidal gels that are on the market in Canada and some European countries (Hungary, France).
For use in conjunction with a diaphragm, cervical cap or LEA contraceptivum , gels with lactic acid or citric acid as active ingredients can be used as an alternative . According to current knowledge, these acids make sperm immobile. More comprehensive studies are not available.

chemistry

The synthesis is carried out by reacting 4-nonylphenol with 9 molar equivalents of ethylene oxide . A mixture of polyethylene glycol ethers of 4-nonylphenol is produced, the chain length being approximately 4 to 16 ethylene oxide units and a mean of approximately 9.

Trade names

Monopreparations

Patentex Oval (D, A, except sales)

Combination preparations

a-gen 53 (D, except sales)

Individual evidence

↑ ^a ^b ^c data sheet NONOXINOL 9 CRS (PDF) at EDQM , accessed on October 27, 2008.
↑ ^a ^b Data sheet Nonoxinol 9, European Pharmacopoeia (EP) Reference Standard from Sigma-Aldrich , accessed on October 31, 2016 ( PDF ).
↑ ^a ^b ^c K. Hardtke et al. (Ed.): Commentary on the European Pharmacopoeia Ph. Eur. 6.0, Nonoxinol 9. Loose-leaf collection, 30. Delivery 2008, Wissenschaftliche Verlagsgesellschaft Stuttgart.
↑ Ronald E. Roddy: Effect of Nonoxynol-9 Gel on Urogenital Gonorrhea and Chlamydial Infection (Subtitle: A Randomized Controlled Trial). In: JAMA. 287, 2002, p. 1117, doi : 10.1001 / jama.287.9.1117 .
^ JA McGroarty, G. Reid, AW Bruce: The influence of nonoxynol-9-containing spermicides on urogenital infection. In: The Journal of Urology . 152, 1994, pp. 831-833. PMID 8051730 .

[Ph._Eur.-1] ta sheet NONOXINOL 9 CRS (PDF) at EDQM , accessed on October 27, 2008.

[Sigma-2] Data sheet Nonoxinol 9, European Pharmacopoeia (EP) Reference Standard from Sigma-Aldrich , accessed on October 31, 2016 ( PDF ).

[ABKomm-3] K. Hardtke et al. (Ed.): Commentary on the European Pharmacopoeia Ph. Eur. 6.0, Nonoxinol 9. Loose-leaf collection, 30. Delivery 2008, Wissenschaftliche Verlagsgesellschaft Stuttgart.

[DOI10.1001/jama.287.9.1117-4] Ronald E. Roddy: Effect of Nonoxynol-9 Gel on Urogenital Gonorrhea and Chlamydial Infection (Subtitle: A Randomized Controlled Trial). In: JAMA. 287, 2002, p. 1117, doi : 10.1001 / jama.287.9.1117 .

[5] JA McGroarty, G. Reid, AW Bruce: The influence of nonoxynol-9-containing spermicides on urogenital infection. In: The Journal of Urology . 152, 1994, pp. 831-833. PMID 8051730 .