| Size | Price | Stock | Qty |
|---|---|---|---|
| 1g |
|
||
| 10g |
|
||
| Other Sizes |
| Targets |
Nonoxynol-9 targets the lipid membranes of sperm cells. It interacts with the lipids in the membranes of the acrosome and midpiece of the sperm, causing lysis of sperm membranes. The acrosome, neck, and midpiece of the spermatozoa are loosened and then detached, resulting in immobilization and death of the sperm. This membrane-disrupting mechanism prevents sperm from reaching and fertilizing the egg. It may also have antimicrobial activity against bacteria, fungi, and viruses through similar membrane disruption mechanisms, though it does not exhibit antiviral benefit for HIV prevention.
|
|---|---|
| ln Vitro |
In vitro, nonoxynol-9 demonstrates spermicidal activity by immobilizing sperm and disrupting acrosomal membranes. It also exhibits antimicrobial activity against a broad spectrum of microorganisms, including bacteria, fungi, and viruses. Its membrane-disrupting mechanism has been characterized in various in vitro systems, showing concentration-dependent activity. However, it does not exhibit antiviral benefit against HIV. Its in vitro activity is used to evaluate the efficacy of spermicidal products and to assess potential microbicidal applications.
|
| ln Vivo |
In vivo, nonoxynol-9 is used as a vaginal spermicide, where it is locally active in the vagina during intercourse. It immobilizes, inactivates, damages, and/or kills sperm without eliciting systemic effects. Its efficacy depends on proper application and concentration. It has been extensively studied for contraceptive and microbicide applications, though its use as a microbicide has been limited due to lack of antiviral benefit against HIV. It remains a widely used over-the-counter contraceptive agent.
|
| Enzyme Assay |
In vitro enzyme/receptor binding studies are not applicable to nonoxynol-9, as its mechanism is physicochemical rather than receptor-mediated. Its activity is based on surfactant properties that disrupt lipid membranes rather than binding to specific proteins. Standard assays for spermicidal activity involve mixing sperm samples with various concentrations of nonoxynol-9 and assessing sperm motility and viability microscopically. Membrane disruption may be evaluated using fluorescent dyes or electron microscopy.
|
| Cell Assay |
In vitro cellular assays for nonoxynol-9 involve incubating sperm cells with serial dilutions of the compound and assessing motility, viability, and membrane integrity. Sperm motility is assessed microscopically, and viability is measured using vital dyes such as eosin-nigrosin or Hoechst staining. Membrane integrity may be assessed using fluorescent probes such as propidium iodide or SYBR-14. For antimicrobial activity, bacteria or fungi are cultured in the presence of nonoxynol-9, and growth inhibition is assessed by optical density or colony counting. Cytotoxicity in vaginal epithelial cells may be evaluated using MTT or LDH release assays.
|
| Animal Protocol |
In vivo animal studies for nonoxynol-9 are limited, as the compound is used topically in humans rather than systemically. Preclinical safety studies may involve vaginal irritation and toxicity assessments in animal models such as rabbits or rodents. Standard protocols involve daily vaginal administration of nonoxynol-9 for a specified period, followed by histological examination of vaginal tissues for irritation, inflammation, or epithelial damage. Efficacy studies in animal models of contraception or infection are less common due to species differences in reproductive physiology.
|
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
In in vitro skin penetration studies using cadaver skin (rinse and residence protocols), nonoxynol-2, -4, and -9 showed total skin penetration of less than 1% over 48 hours. Pharmacokinetic properties of nonoxynol-9 indicate that it is minimally absorbed through the vaginal mucosa when used as a spermicide. It acts locally and does not produce significant systemic concentrations, which is consistent with its use as a non-hormonal, locally acting contraceptive. Its lack of systemic absorption contributes to its favorable safety profile, as systemic side effects are rare. It is a surfactant with a molecular weight of approximately 616.82 g/mol for the n=9 variant. |
| Toxicity/Toxicokinetics |
Non-Human Toxicity Values
Mouse intraperitoneal injection LD50: 150 mg/kg Toxicological data for nonoxynol-9 indicate that it is generally safe for use as a vaginal spermicide. Common side effects include local irritation, burning, or itching in some users. Frequent use may increase the risk of vaginal irritation and disruption of normal vaginal flora. It does not protect against sexually transmitted infections and may actually increase the risk of HIV transmission with frequent use due to mucosal irritation. It is not recommended for use as a microbicide. In high concentrations, it can cause epithelial damage. It is contraindicated in individuals with known hypersensitivity. |
| Additional Infomation |
Tergitol is a polyethylene glycol derivative whose structure involves converting a terminal hydroxyl group of polyethylene glycol into the corresponding p-nonylphenyl ether. It is a nonionic surfactant. It is both a polyethylene glycol derivative and a hydroxyl polyether. The number of repeating ethoxy (oxy-1,2-ethylene glycol) groups in a mixture of nonionic surfactants varies. They can be used as detergents, emulsifiers, wetting agents, defoamers, etc. Nonoxynol-9 is a compound containing nine repeating ethoxy groups; it is a spermicide and is mainly formulated as an ingredient in vaginal foams and creams. See also: Nonoxynol-10 (note moved to); C11-15 secondary alcohols, ethoxylated (note moved to)... See more...
Nonoxynol-9 is the most widely used spermicide worldwide and is available in various over-the-counter contraceptive products including creams, gels, foams, suppositories, and condoms. It is marketed under brand names including Conceptrol, Gynol II, Today Sponge, and VCF Contraceptive. It is a non-hormonal contraceptive option that provides local contraception without systemic hormonal effects. However, it does not protect against sexually transmitted infections. Its use has declined in some regions due to availability of more effective contraceptive methods, but it remains an important option for women who cannot use hormonal contraceptives. |
| Molecular Formula |
C17H28O2
|
|---|---|
| Molecular Weight |
264.41
|
| Exact Mass |
514.351
|
| CAS # |
26027-38-3
|
| Related CAS # |
26027-38-3
|
| PubChem CID |
7700
|
| Appearance |
Lower adducts (n<15) yellow to almost colorless liquid; higher adducts (n>20) pale yellow to off-white pastes or waxes
|
| Density |
1.06
|
| Boiling Point |
250ºC
|
| Melting Point |
57-58ºC
|
| Flash Point |
94ºC
|
| Index of Refraction |
1.4950-1.4990
|
| LogP |
3.871
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
11
|
| Heavy Atom Count |
19
|
| Complexity |
186
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CCCCCCCCCC1=CC=C(OCCO)C=C1.[n]
|
| InChi Key |
KUXGUCNZFCVULO-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C17H28O2/c1-2-3-4-5-6-7-8-9-16-10-12-17(13-11-16)19-15-14-18/h10-13,18H,2-9,14-15H2,1H3
|
| Chemical Name |
2-(4-nonylphenoxy)ethanol
|
| Synonyms |
Delfen; Conceptrol; Nonoxynols
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
Ethanol : ~50 mg/mL
DMSO : ≥ 45 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (Infinity mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (Infinity mM) (saturation unknown) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (Infinity mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.7820 mL | 18.9100 mL | 37.8201 mL | |
| 5 mM | 0.7564 mL | 3.7820 mL | 7.5640 mL | |
| 10 mM | 0.3782 mL | 1.8910 mL | 3.7820 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
