Nonoxynol-9

Identification

Name
Nonoxynol-9
Accession Number
DB06804
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.

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Thumb
Weight
Average: 616.8235
Monoisotopic: 616.41864814
Chemical Formula
C33H60O10
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

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.

Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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
Adverse Effects
Learn about our commercial Adverse Effects data.
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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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetazolamideThe metabolism of Nonoxynol-9 can be increased when combined with Acetazolamide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Nonoxynol-9.
AmobarbitalThe metabolism of Nonoxynol-9 can be increased when combined with Amobarbital.
AprepitantThe serum concentration of Nonoxynol-9 can be decreased when it is combined with Aprepitant.
BrexanoloneThe metabolism of Nonoxynol-9 can be increased when combined with Brexanolone.
BrivaracetamThe metabolism of Nonoxynol-9 can be increased when combined with Brivaracetam.
ButalbitalThe metabolism of Nonoxynol-9 can be increased when combined with Butalbital.
CannabidiolThe metabolism of Nonoxynol-9 can be increased when combined with Cannabidiol.
CarbamazepineThe metabolism of Nonoxynol-9 can be increased when combined with Carbamazepine.
CenobamateThe metabolism of Nonoxynol-9 can be increased when combined with Cenobamate.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

International/Other Brands
Advantage 24 (Lake Pharmaceuticals) / Gynoll (Ortho Options) / Today (Bliss Pharmaceuticals) / VCF (Apothecus Pharmaceuticals)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Conceptrol OptionsGel4.0 g/100gVaginalCaldwell Consumer Health Llc2011-05-01Not applicableUs
ContraSeedSuppository100 mg/1VaginalInternational Trading Pharmaceutical Laboratories, Inc2015-02-262017-03-31Us
EncareInsert100 mg/1VaginalBlairex Laboratories, Inc.1999-09-012020-01-01Us
Gynol II Extra StrengthGel3.0 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/1gVaginalAPOTHECUS PHARMACEUTICAL CORP1997-06-01Not applicableUs
Vcf Contraceptive Pre-filled ApplicatorsGel, metered4 g/100gVaginalAPOTHECUS PHARMACEUTICAL CORP2014-06-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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).
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Ethers
Direct Parent
Polyethylene glycols
Alternative Parents
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Primary alcohols / Hydrocarbon derivatives
Substituents
Alcohol / Alkyl aryl ether / Aromatic homomonocyclic compound / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Phenol ether / Phenoxy compound / Polyethylene glycol / Primary alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tergitol (CHEBI:53775)

Chemical Identifiers

UNII
48Q180SH9T
CAS number
26027-38-3
InChI Key
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
IUPAC Name
26-(4-nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
SMILES
CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1

References

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]
Human Metabolome Database
HMDB0015680
KEGG Drug
D06490
PubChem Compound
72385
PubChem Substance
99443296
ChemSpider
65319
BindingDB
50442874
RxNav
53750
ChEBI
53775
ChEMBL
CHEMBL1410
ZINC
ZINC000008214629
PharmGKB
PA450648
Wikipedia
Nonoxynol-9

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionPregnancy1
2CompletedBasic ScienceVaginal Infections / Vaginal Inflammation1
2CompletedPreventionHealthy Volunteers1
2, 3CompletedPreventionContraception1
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
0CompletedDiagnosticHuman Immunodeficiency Virus (HIV) Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
GelVaginal4.0 g/100g
SuppositoryVaginal100 mg/1
InsertVaginal100 mg/1
GelVaginal3.0 g/100g
SpongeVaginal1000 mg/1
Aerosol, foamVaginal125 mg/1g
Film, solubleVaginal280 mg/1
Gel, meteredVaginal4 g/100g
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Enzymes

Kind
Protein
Organism
Humans
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...
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 June 12, 2020 10:52

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