You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameNonoxynol-9
Accession NumberDB06804
Typesmall molecule
Groupsapproved, withdrawn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
Thumb
SynonymsNot Available
SaltsNot Available
Brand names
NameCompany
Advantage 24Lake Pharmaceuticals
GynollOrtho Options
TodayBliss Pharmaceuticals
VCFApothecus Pharmaceuticals
Brand mixturesNot Available
Categories
CAS number26571-11-9
WeightAverage: 616.8235
Monoisotopic: 616.41864814
Chemical FormulaC33H60O10
InChI KeyFBWNMEQMRUMQSO-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
IUPAC Name
1-(4-nonylphenyl)-1,4,7,10,13,16,19,22,25-nonaoxaheptacosan-27-ol
SMILES
CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenol Ethers
Direct parentPhenol Ethers
Alternative parentsAlkyl Aryl Ethers; Polyamines; Primary Alcohols
Substituentsalkyl aryl ether; polyamine; primary alcohol; ether; alcohol
Classification descriptionThis compound belongs to the phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Pharmacology
IndicationNonoxynol 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.
PharmacodynamicsNot Available
Mechanism of actionNonoxynol-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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityThe 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 organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9932
Blood Brain Barrier + 0.8118
Caco-2 permeable + 0.661
P-glycoprotein substrate Substrate 0.721
P-glycoprotein inhibitor I Non-inhibitor 0.6742
P-glycoprotein inhibitor II Non-inhibitor 0.7359
Renal organic cation transporter Non-inhibitor 0.7701
CYP450 2C9 substrate Non-substrate 0.7821
CYP450 2D6 substrate Non-substrate 0.7658
CYP450 3A4 substrate Non-substrate 0.5396
CYP450 1A2 substrate Non-inhibitor 0.7665
CYP450 2C9 substrate Non-inhibitor 0.877
CYP450 2D6 substrate Non-inhibitor 0.9161
CYP450 2C19 substrate Non-inhibitor 0.7044
CYP450 3A4 substrate Inhibitor 0.5899
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9084
Ames test Non AMES toxic 0.9423
Carcinogenicity Non-carcinogens 0.8423
Biodegradation Ready biodegradable 0.7353
Rat acute toxicity 2.2394 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.6776
hERG inhibition (predictor II) Inhibitor 0.5489
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility2.14e-04 g/lALOGPS
logP3.49ALOGPS
logP4.82ChemAxon
logS-6.5ALOGPS
pKa (strongest acidic)15.12ChemAxon
pKa (strongest basic)-2.7ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count10ChemAxon
hydrogen donor count1ChemAxon
polar surface area103.3ChemAxon
rotatable bond count35ChemAxon
refractivity169.01ChemAxon
polarizability77.07ChemAxon
number of rings1ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. 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
ResourceLink
PubChem Compound72385
PubChem Substance99443296
ChemSpider65319
ChEBI445872
ChEMBLCHEMBL1410
WikipediaNonoxynol-9
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

1. Prostaglandin G/H synthase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

References:

  1. 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
comments powered by Disqus
Drug created on September 14, 2010 10:21 / Updated on September 16, 2013 18:04