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    Chemistry

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    Also known as: Nonoxynol 9, 14409-72-4, Delfen, Nonoxynol, n=9, 26571-11-9, Tergitol np-9
    Molecular Formula
    C33H60O10
    Molecular Weight
    616.8  g/mol
    InChI Key
    FBWNMEQMRUMQSO-UHFFFAOYSA-N
    NONOXYNOL-9
    Nonionic surfactant mixtures varying in the number of repeating ethoxy (oxy-1,2-ethanediyl) groups. They are used as detergents, emulsifiers, wetting agents, defoaming agents, etc. Nonoxynol-9, the compound with 9 repeating ethoxy groups, is a spermatocide, formulated primarily as a component of vaginal foams and creams.
    1 2D Structure

    NONOXYNOL-9

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[2-[2-[2-[2-[2-[2-[2-[2-(4-nonylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol
    2.1.2 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
    2.1.3 InChI Key
    FBWNMEQMRUMQSO-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCCCCCCC1=CC=C(C=C1)OCCOCCOCCOCCOCCOCCOCCOCCOCCO
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Advantage S

    2. Advantage-s

    3. Delfen Cream

    4. Delfen Creams

    5. Emulgen 911

    6. Emulgin 913

    7. Nonoxinol

    8. Nonoxinols

    9. Nonoxynol

    10. Nonoxynol 9

    11. Nonoxynol, 1(4)-sulfate, Sodium Salt

    12. Nonoxynol, 4-sulfate, Ammonium Salt

    13. Nonoxynols

    14. Nonylphenoxypolyethoxyethanol

    15. Nonylphenoxypolyethoxyethanols

    16. Oval, Patentex

    17. Patentex Oval

    2.2.2 Depositor-Supplied Synonyms

    1. Nonoxynol 9

    2. 14409-72-4

    3. Delfen

    4. Nonoxynol, N=9

    5. 26571-11-9

    6. Tergitol Np-9

    7. Peg-9 Nonyl Phenyl Ether

    8. Nonoxynol9

    9. Tergitol Np9

    10. Nonaethylene Glycol Nonylphenyl Ether

    11. Nonylphenol Octa(oxyethylene) Ethanol

    12. Nonaethylene Glycol Mono(nonylphenyl) Ether

    13. Nonoxinol-9

    14. 2-[2-[2-[2-[2-[2-[2-[2-[2-(4-nonylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol

    15. Nonylphenoxypolyethoxyethanol

    16. Polyoxyethylene (9) Nonyl Phenyl Ether

    17. 26-(4-nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol

    18. 26-(nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol

    19. Chebi:53775

    20. Nsc-758941

    21. P-nonylphenyl Polyethylene Glycol Ether

    22. N-9

    23. Conceptrol

    24. Intercept

    25. Semicid

    26. 3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol, 26-(4-nonylphenoxy)-

    27. 2-[2-[2-[2-[2-[2-[2-[2-[2-(4-nonylphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]-ethoxy]ethoxy]ethoxy]ethoxy]ethanol

    28. Staycept

    29. Emko

    30. Today Sponge

    31. Nonoxinolum 9

    32. Hsdb 8094

    33. Gynol Ii

    34. C-film

    35. Norfox Np-9

    36. Tergitol Tp-9

    37. Nonoxynol-9.5

    38. Einecs 247-816-5

    39. Conco Ni-90

    40. K-y Plus Nonoxynol-9

    41. Spectrum2_001247

    42. Spectrum3_001946

    43. Alosetronhydrochloride

    44. Chembl1410

    45. Schembl36844

    46. Bspbio_003546

    47. Spectrum1505292

    48. Spbio_001154

    49. Dowfax 9n9, Neutronyx 611

    50. Co-630sp

    51. Kbio3_002833

    52. Dtxsid00858720

    53. Hms2093o22

    54. Pharmakon1600-01505292

    55. Zinc8214629

    56. 3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol, 26-(nonylphenoxy)-

    57. Bdbm50442874

    58. Ccg-39124

    59. Nsc758941

    60. Akos015910808

    61. Db06804

    62. Nsc 758941

    63. Ncgc00095907-02

    64. Ncgc00095907-03

    65. N 9

    66. Sbi-0206761.p001

    67. Polyethylene Glycol 450 Nonyl Phenyl Ether

    68. Ab01563056_01

    69. Q420039

    70. Sr-05000001885

    71. J-016227

    72. Q-201490

    73. Sr-05000001885-1

    74. Brd-k88625236-001-01-8

    75. 1-(4-nonylphenyl)-1,4,7,10,13,16,19,22,25-nonaoxaheptacosan-27-ol

    76. N9

    2.3 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 616.8 g/mol
    Molecular Formula C33H60O10
    XLogP34.6
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count35
    Exact Mass616.41864811 g/mol
    Monoisotopic Mass616.41864811 g/mol
    Topological Polar Surface Area103 Ų
    Heavy Atom Count43
    Formal Charge0
    Complexity520
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameToday
    PubMed HealthNonoxynol 9 (Vaginal)
    Drug ClassesContraceptive, Local
    Active IngredientNonoxynol-9
    Dosage FormSponge
    RouteVaginal
    Strength1gm
    Market StatusOver the Counter
    CompanyMayer Labs

    2 of 2  
    Drug NameToday
    PubMed HealthNonoxynol 9 (Vaginal)
    Drug ClassesContraceptive, Local
    Active IngredientNonoxynol-9
    Dosage FormSponge
    RouteVaginal
    Strength1gm
    Market StatusOver the Counter
    CompanyMayer Labs

    4.2 Drug Warning

    In January, 2003, FDA proposed new warning statements and other labeling information for these products after results from a major clinical study in Africa and Thailand showed that women using a contraceptive gel product containing N9 were not protected against HIV and other STDs and were, in fact, at higher risk for HIV infection than women using a placebo gel. Because these and other studies have shown that use of products containing N9 cause vaginal and rectal irritation that can heighten the chance of becoming infected with HIV from an infected partner, FDA believes the warning will empower consumers to make better informed decisions about the use of these products, and better protect the public health.

    DHHS/FDA; For Consumers: New Warning for Nonoxynol 9 OTC Contraceptive Products re: STDS and HIV/AIDS (June18, 2009). Available from, as of October 16, 2012: https://www.fda.gov/ForConsumers/ByAudience/ForPatientAdvocates/HIVandAIDSActivities/ucm124023.htm

    The FDA issued a final rule on December 18, 2007 requiring manufacturers of over-the-counter (OTC) stand-alone vaginal contraceptive and spermicidal products containing the chemical ingredient nonoxynol 9 (N9) include a warning stating that the chemical N9 does not provide protection against infection from HIV (the virus that causes AIDS) or other sexually transmitted diseases (STDs). Stand-alone spermicides include gels, foams, films, or inserts containing N9 that are used by themselves for contraception. Consumers can protect themselves from the transmission of STDs and HIV by practicing abstinence, being in a monogamous relationship where neither partner is infected, and using condoms consistently and correctly. FDA is issuing the rule in an effort to correct misconceptions that N9 protects against sexually transmitted diseases, including HIV infection.

    DHHS/FDA; For Consumers: New Warning for Nonoxynol 9 OTC Contraceptive Products re: STDS and HIV/AIDS (June18, 2009). Available from, as of October 16, 2012: https://www.fda.gov/ForConsumers/ByAudience/ForPatientAdvocates/HIVandAIDSActivities/ucm124023.htm

    Sexually transmitted diseases (STDs) alert: This product does not protect against HIV/AIDS or other STDs and may increase the risk of getting HIV from an infected partner.

    DHHS/FDA; For Consumers: New Warning for Nonoxynol 9 OTC Contraceptive Products re: STDS and HIV/AIDS (June18, 2009). Available from, as of October 16, 2012: https://www.fda.gov/ForConsumers/ByAudience/ForPatientAdvocates/HIVandAIDSActivities/ucm124023.htm

    Do not use if you or your sex partner has HIV/AIDS. If you do not know if you or your sex partner is infected, choose another form of birth control.

    DHHS/FDA; For Consumers: New Warning for Nonoxynol 9 OTC Contraceptive Products re: STDS and HIV/AIDS (June18, 2009). Available from, as of October 16, 2012: https://www.fda.gov/ForConsumers/ByAudience/ForPatientAdvocates/HIVandAIDSActivities/ucm124023.htm

    For more Drug Warnings (Complete) data for Nonoxynol-9 (7 total), please visit the HSDB record page.

    4.3 Drug 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.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Surface-Active Agents

    Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics. (See all compounds classified as Surface-Active Agents.)

    Spermatocidal Agents

    Chemical substances that are destructive to spermatozoa used as topically administered vaginal contraceptives. (See all compounds classified as Spermatocidal Agents.)

    5.2 Absorption, Distribution and Excretion

    In mice intravenously injected with (14)C-Nonoxynol-9, the highest amounts of radioactivity were reported for the small and large intestines. (14)C radioactivity was excreted mainly in the urine and feces. An HPLC analysis of the urine and bile indicated that no intact Nonoxynol-9 was present in the bile or urine, and that Nonoxynol-9 was metabolized to highly polar species.

    Alan AF ed.; Cosmetic Ingredient Review: Amended final report on the safety assessment of Nonoxynol -1, -2, -3, -4, -5, -6, -7 and -8. Int J Toxicol 18 (Suppl 1):11-31 (1999)

    In in vitro skin penetration studies using cadaver skin (rinse off and leave-on protocols), the total skin penetration of Nonoxynol-2, -4, and -9 was less than 1 % over a period of 48 hours.

    Alan AF ed.; Cosmetic Ingredient Review: Amended final report on the safety assessment of Nonoxynol -1, -2, -3, -4, -5, -6, -7 and -8. Int J Toxicol 18 (Suppl 1):11-31 (1999)

    The disposition of nonoxynol-9 labeled with (14)C at the ethylene oxide units was studied following an iv or vaginal administration to female Sprague-Dawley rats. The results from the vaginal administration studies indicate 12.8% absorption of (14)C radioactivity in 6.0 hr and 37.7% in 24.0 hr. Tissue distribution studies showed that the small and large intestines, including their contents, had the highest (14)C activity by either route of administration. Radiomonitored HPLC of bile collected at 6.0 hr and urine at 6.0, 24.0, and 48.0 hr following an iv injection of (14)C nonoxynol-9 showed that the compound was completely metabolized in the body of the rat. The metabolites were primarily excreted in the feces and secondarily in the urine. Analysis of urinary metabolites containing the (14)C label, 6.0 hr following an iv dose, indicated the presence of highly polar neutral (53.27%) and acidic (39.23%) species.

    PMID:2848334 Walter BA et al; Toxicol Appl Pharmacol 96 (2): 258-68 (1988)

    5.3 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.

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