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

• ChemBase ID: 4481
• Molecular Formular: C33H60O10
• Molecular Mass: 616.8235
• Monoisotopic Mass: 616.41864812
• SMILES: CCCCCCCCCc1ccc(cc1)OCCOCCOCCOCCOCCOCCOCCOCCOCCO
• Canonical SMILES: CCCCCCCCCc1ccc(cc1)OCCOCCOCCOCCOCCOCCOCCOCCOCCO
• 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
• InChIKey: FBWNMEQMRUMQSO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-nonylphenyl)-1,4,7,10,13,16,19,22,25-nonaoxaheptacosan-27-ol
• IUPAC Traditional name: nonoxynol 9
• Brand Name: Advantage 24; Conceptrol; Delfen; Semicid; VCF; Gynoll; Today
• Synonyms: N-9; Nonoxynol-9

Database IDs

• CAS Number: 26571-11-9
• PubChem SID: 99443296; 160967913
• PubChem CID: 72385

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.121156
• H Acceptors: 10
• H Donor: 1
• LogD (pH = 5.5): 4.819639
• LogD (pH = 7.4): 4.819639
• Log P: 4.819639
• Molar Refractivity: 169.0107 cm^3
• Polarizability: 66.84011 Å^3
• Polar Surface Area: 103.3 Å^2
• Rotatable Bonds: 35
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.49
• LOG S: -6.46
• Solubility (Water): 2.14e-04 g/l

DETAILS

DrugBank - DB06804

• Drug Groups: approved; withdrawn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.
• 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.
• 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.
• References: Iyer V, Poddar SS: Update on nonoxynol-9 as vaginal spermicide. Eur J Contracept Reprod Health Care. 2008 Dec;13(4):339-50. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Iyer V, Poddar SS: Update on nonoxynol-9 as vaginal spermicide. Eur J Contracept Reprod Health Care. 2008 Dec;13(4):339-50. Pubmed