DrugBank: Nonoxynol-9 (DB06804)

enzymes (1)

Identification

Name

Nonoxynol-9

Accession Number

DB06804

Type

small molecule

Groups

approved, withdrawn

Description

Nonoxynol-9 (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. It is the most commonly used spermicidal contraceptive in the UK and the USA. In several European countries, spermicides are no longer on the market.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

N-9

Salts

Not Available

Brand names

Name	Company
Advantage 24	Lake Pharmaceuticals
Gynoll	Ortho Options
Today	Bliss Pharmaceuticals
VCF	Apothecus Pharmaceuticals

Brand mixtures

Not Available

Categories

Contraceptives

CAS number

26571-11-9

Weight

Average: 616.8235
Monoisotopic: 616.41864814

Chemical Formula

C₃₃H₆₀O₁₀

InChI Key

InChIKey=FBWNMEQMRUMQSO-UHFFFAOYSA-N

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

Plain Text

IUPAC Name

1-(4-nonylphenyl)-1,4,7,10,13,16,19,22,25-nonaoxaheptacosan-27-ol

SMILES

CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Nonoxynol 9 is a surfactant spermicide used for contraception in spermicidal creams, jellies, foams, gel, and lubricants. It is also used in conjuction with other methods of contraception, including condoms, cervical caps and diaphragms.

Pharmacodynamics

Not Available

Mechanism of action

Nonoxynol-9 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.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

The major drawback of nonoxynol-9 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.

Affected organisms

Not Available

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	2.14e-04 g/l	ALOGPS
logP	3.49	ALOGPS
logP	4.82	ChemAxon
logS	-6.5	ALOGPS
pKa (strongest acidic)	15.12	ChemAxon
pKa (strongest basic)	-2.7	ChemAxon
physiological charge	0	ChemAxon
hydrogen acceptor count	10	ChemAxon
hydrogen donor count	1	ChemAxon
polar surface area	103.3	ChemAxon
rotatable bond count	35	ChemAxon
refractivity	169.01	ChemAxon
polarizability	77.07	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Iyer V, Poddar SS: Update on nonoxynol-9 as vaginal spermicide. Eur J Contracept Reprod Health Care. 2008 Dec;13(4):339-50. Pubmed

External Links

Resource	Link
PubChem Compound	72385
PubChem Substance	99443296
ChemSpider	65319
ChEBI	445872
ChEMBL	445872
Wikipedia	http://en.wikipedia.org/wiki/Nonoxynol-9

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Enzymes
1. Prostaglandin G/H synthase 2 Actions: inducer May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity UniProt ID: P35354 Gene: PTGS2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Zalenskaya IA, Cerocchi OG, Joseph T, Donaghay MA, Schriver SD, Doncel GF: Increased COX-2 expression in human vaginal epithelial cells exposed to nonoxynol-9, a vaginal contraceptive microbicide that failed to protect women from HIV-1 infection. Am J Reprod Immunol. 2011 Jun;65(6):569-77. doi: 10.1111/j.1600-0897.2010.00964.×. Epub 2011 Jan 18. Pubmed

Enzymes

1. Prostaglandin G/H synthase 2

Actions: inducer

May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

UniProt ID: P35354 Link_out

Gene: PTGS2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Zalenskaya IA, Cerocchi OG, Joseph T, Donaghay MA, Schriver SD, Doncel GF: Increased COX-2 expression in human vaginal epithelial cells exposed to nonoxynol-9, a vaginal contraceptive microbicide that failed to protect women from HIV-1 infection. Am J Reprod Immunol. 2011 Jun;65(6):569-77. doi: 10.1111/j.1600-0897.2010.00964.×. Epub 2011 Jan 18. Pubmed

Comments

Drug created on September 14, 2010 10:21 / Updated on February 08, 2013 16:24