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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GroupsApproved, Withdrawn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
Synonyms
SynonymLanguageCode
26-(Nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-olNot AvailableNot Available
Nonaethylene glycol mono(nonylphenyl) etherNot AvailableNot Available
Nonaethylene glycol nonylphenyl etherNot AvailableNot Available
Nonoxynol 9Not AvailableNot Available
Nonylphenol octa(oxyethylene) ethanolNot AvailableNot Available
P-Nonylphenyl polyethylene glycol etherNot AvailableNot Available
PEG-9 nonyl phenyl etherNot AvailableNot Available
Polyoxyethylene (9) nonyl phenyl etherNot AvailableNot Available
Tergitol NP9Not AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Today Vaginal Contraceptivesponge1000 mgvaginalMayer Laboratories, Inc.1983-04-01Not AvailableUs
Encareinsert100 mgvaginalBlairex Laboratories, Inc.1999-09-01Not AvailableUs
Vcf Contraceptive Pre-filled Applicatorsgel, metered4 g/100gvaginalAPOTHECUS PHARMACEUTICAL CORP2014-06-01Not AvailableUs
International Brands
NameCompany
Advantage 24Lake Pharmaceuticals
GynollOrtho Options
TodayBliss Pharmaceuticals
VCFApothecus Pharmaceuticals
Brand mixturesNot Available
SaltsNot 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
26-(4-nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
SMILES
CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as polyethylene glycols. These are oligomers or polymers of ethylene oxide, with the general formula (C2H4O)n (with n>=3).
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassEthers
Sub ClassDialkyl ethers
Direct ParentPolyethylene glycols
Alternative Parents
Substituents
  • Polyethylene glycol
  • Phenol ether
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+0.9932
Blood Brain Barrier+0.8118
Caco-2 permeable+0.661
P-glycoprotein substrateSubstrate0.721
P-glycoprotein inhibitor INon-inhibitor0.6742
P-glycoprotein inhibitor IINon-inhibitor0.7359
Renal organic cation transporterNon-inhibitor0.7701
CYP450 2C9 substrateNon-substrate0.7821
CYP450 2D6 substrateNon-substrate0.7658
CYP450 3A4 substrateNon-substrate0.5396
CYP450 1A2 substrateNon-inhibitor0.7665
CYP450 2C9 substrateNon-inhibitor0.877
CYP450 2D6 substrateNon-inhibitor0.9161
CYP450 2C19 substrateNon-inhibitor0.7044
CYP450 3A4 substrateInhibitor0.5899
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9084
Ames testNon AMES toxic0.9423
CarcinogenicityNon-carcinogens0.8423
BiodegradationReady biodegradable0.7353
Rat acute toxicity2.2394 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6776
hERG inhibition (predictor II)Inhibitor0.5489
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Gel, meteredvaginal4 g/100g
Insertvaginal100 mg
Spongevaginal1000 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000214 mg/mLALOGPS
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 Area103.3 Å2ChemAxon
Rotatable Bond Count35ChemAxon
Refractivity169.01 m3·mol-1ChemAxon
Polarizability77.07 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
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

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Drug created on September 14, 2010 10:21 / Updated on September 16, 2013 18:04