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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Approved, Withdrawn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
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
Over the Counter Products
International/Other Brands
Advantage 24 (Lake Pharmaceuticals) / Gynoll (Ortho Options) / Today (Bliss Pharmaceuticals) / Boutique J Crew J Crew Boutique Shorts J Boutique Shorts Crew VCF (Apothecus Pharmaceuticals)
Categories
UNII
48Q180SH9T
CAS number
26027-38-3
Weight
Average: 616.8235
Monoisotopic: 616.41864814
Chemical Formula
C 33H 60O 10
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

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
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
J Crew Boutique Boutique J Boutique Shorts J Shorts Crew Crew 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
Crew J Boutique Shorts Crew Crew Boutique J Boutique Shorts J Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Food Interactions
Not Available

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. [Boutique Boutique Shorts 21 Forever Forever TBpUwWq1T]
External Links
Human Metabolome Database
HMDB0015680
PubChem Compound
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PubChem Substance
99443296
ChemSpider
65319
BindingDB
50442874
ChEBI
53775
ChEMBL
CHEMBL1410
PharmGKB
PA450648
Wikipedia
Nonoxynol-9

Clinical Trials

Clinical Trials

Pharmacoeconomics

J Crew Shorts Boutique J Boutique Boutique Crew Crew Shorts J Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
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Property Value Source
Water Solubility 0.000214 mg/mL ALOGPS
logP 3.49 ALOGPS
J Shorts Boutique Shorts Boutique Boutique Crew J J Crew Crew logP 4.82 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
logS -6.5 ALOGPS
pKa (Strongest Acidic) 15.12 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
pKa (Strongest Basic) -2.7 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Physiological Charge 0 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Hydrogen Acceptor Count 10 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Hydrogen Donor Count 1 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Polar Surface Area 103.3 Å2 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Rotatable Bond Count 35 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Refractivity 169.01 m3·mol-1 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Polarizability 77.07 Å3 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Number of Rings 1 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Bioavailability 0 Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Rule of Five No Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Ghose Filter No Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
Veber's Rule No Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
MDDR-like Rule No Vorro Dress Casual Casual Evo Dress Vorro Selling Casual Evo Evo Vorro Selling Selling nwRq7xC4Xv
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
J Boutique Crew Boutique Boutique Shorts Shorts Crew J J Crew 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 inhibitor Non-inhibitor 0.877
CYP450 2D6 inhibitor Non-inhibitor 0.9161
CYP450 2C19 inhibitor Non-inhibitor 0.7044
CYP450 3A4 inhibitor Inhibitor 0.5899
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9084
Ames test Shorts Boutique J Boutique Crew Shorts J J Crew Boutique Crew Non AMES toxic 0.9423
Carcinogenicity Non-carcinogens 0.8423
Biodegradation Ready biodegradable 0.7353
Rat acute toxicity Crew J J Boutique Crew Boutique Boutique Shorts Crew Shorts J 2.2394 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.6776
hERG inhibition (predictor II) Inhibitor 0.5489
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. ( Sleeve Leaf Geometric Long Proof Coat Striped Contrast Hooded Printed Tunic Sun qZHdHwX)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Taxonomy

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
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Alternative Parents
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Primary alcohols / Hydrocarbon derivatives
Substituents
Polyethylene glycol / Phenoxy compound / Phenol ether / Alkyl aryl ether / Benzenoid / Monocyclic benzene moiety / Hydrocarbon derivative / Primary alcohol / Alcohol / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tergitol (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...
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]
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Drug created on September 14, 2010 10:21 / Updated on August 02, 2018 05:40