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GroupsApproved, Withdrawn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
26-(Nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
Nonaethylene glycol mono(nonylphenyl) ether
Nonaethylene glycol nonylphenyl ether
Nonoxynol 9
Nonylphenol octa(oxyethylene) ethanol
P-Nonylphenyl polyethylene glycol ether
PEG-9 nonyl phenyl ether
Polyoxyethylene (9) nonyl phenyl ether
Tergitol NP-9
Tergitol NP9
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Conceptrol OptionsGel4 g/100gVaginalCaldwell Consumer Health Llc2011-05-01Not applicableUs
EncareInsert100 mg/1VaginalBlairex Laboratories, Inc.1999-09-01Not applicableUs
Gynol II Extra StrengthGel3 g/100gVaginalCaldwell Consumer Health Llc2011-05-01Not applicableUs
Today Vaginal ContraceptiveSponge1000 mg/1VaginalMayer Laboratories, Inc.1983-04-01Not applicableUs
VCF ContraceptiveFilm, soluble280 mg/1VaginalApothecus Pharmaceutical Corp.1988-06-01Not applicableUs
VCF ContraceptiveAerosol, foam125 mg/gVaginalApothecus Pharmaceutical Corp.1997-06-01Not applicableUs
VCF Contraceptive Pre-filled ApplicatorsGel, metered4 g/100gVaginalApothecus Pharmaceutical Corp.2014-06-01Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
Advantage 24Lake Pharmaceuticals
GynollOrtho Options
TodayBliss Pharmaceuticals
VCFApothecus Pharmaceuticals
Brand mixturesNot Available
Categories
UNII48Q180SH9T
CAS number26027-38-3
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
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.

Structured Indications Not Available
PharmacodynamicsNot 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.

Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot 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 organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Iyer V, Poddar SS: Update on nonoxynol-9 as vaginal spermicide. Eur J Contracept Reprod Health Care. 2008 Dec;13(4):339-50. doi: 10.1080/13625180802263515. [PubMed:19117251 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedDiagnosticHuman Immunodeficiency Virus (HIV) Infections1
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedBasic ScienceVaginal Infections / Vaginal Inflammation1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionPregnancy1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
GelVaginal4 g/100g
InsertVaginal100 mg/1
GelVaginal3 g/100g
SpongeVaginal1000 mg/1
Aerosol, foamVaginal125 mg/g
Film, solubleVaginal280 mg/1
Gel, meteredVaginal4 g/100g
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.877
CYP450 2D6 inhibitorNon-inhibitor0.9161
CYP450 2C19 inhibitorNon-inhibitor0.7044
CYP450 3A4 inhibitorInhibitor0.5899
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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as polyethylene glycols. These are oligomers or polymers of ethylene oxide, with the general formula (C2H4O)n (with n>=3).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPolyethylene glycols
Alternative ParentsPhenoxy compounds / Phenol ethers / Alkyl aryl ethers / Primary alcohols / Hydrocarbon derivatives
SubstituentsPolyethylene glycol / Phenoxy compound / Phenol ether / Alkyl aryl ether / Benzenoid / Monocyclic benzene moiety / Hydrocarbon derivative / Primary alcohol / Alcohol / Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorstergitol (CHEBI:53775 )

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Uniprot Name:
Prostaglandin G/H synthase 2
Molecular Weight:
68995.625 Da
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.x. Epub 2011 Jan 18. [PubMed:21241401 ]
Drug created on September 14, 2010 10:21 / Updated on August 02, 2017 17:11