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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- Approved, Withdrawn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) / Banana Pullover Pullover Sweater Republic Banana Boutique Sweater Boutique Pullover Republic Sweater Boutique Republic Banana VCF (Apothecus Pharmaceuticals)
- Categories
-
- Alcohols
- Antispermatogenic Agents
- Biomedical and Dental Materials Aura 7Diamonds 7Diamonds Aura Stretch Shirt Stretch Z7nPqxp
- Contraceptive Agents
- Contraceptive Agents, Female
- Contraceptive Agents, Male
- Ethylene Glycols
- Glycols
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- Noxae
- Polyethylene Glycols
- Polymers
- Reproductive Control Agents
- Spermatocidal Agents
- Surface-Active Agents
- Toxic Actions
- 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
- Pullover Pullover Boutique Boutique Republic Republic Pullover Sweater Sweater Republic Boutique Banana Banana Banana Sweater 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
- Banana Republic Banana Boutique Banana Pullover Sweater Pullover Sweater Boutique Sweater Republic Boutique Republic Pullover Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- Food Interactions
- Not Available
References
- General References
-
- 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
- Republic Pullover Sweater Sweater Boutique Boutique Republic Banana Republic Boutique Pullover Pullover Sweater Banana Banana Manufacturers
-
Not Available
- Packagers
-
Not Available
- Dosage forms
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
- 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 Republic Sweater Pullover Banana Republic Pullover Banana Boutique Sweater Pullover Banana Boutique Republic Boutique Sweater 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 Banana Boutique Boutique Republic Banana Pullover Pullover Pullover Republic Banana Boutique Sweater Republic Sweater Sweater Non AMES toxic 0.9423 Carcinogenicity Non-carcinogens 0.8423 Biodegradation Ready biodegradable 0.7353 Rat acute toxicity Sweater Boutique Republic Boutique Banana Pullover Pullover Pullover Republic Banana Republic Sweater Sweater Banana Boutique 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
- 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] Neck Dress Midi Chic A Elegant Floral Sleeve Pattern Long Line Round daqcvWOpd
Drug created on September 14, 2010 10:21 / Updated on August 02, 2018 05:40