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OLANEXIDINE

OLANEXIDINE Structure
OLANEXIDINE
  • CAS No.146510-36-3
  • Chemical Name:OLANEXIDINE
  • CBNumber:CB42451253
  • Molecular Formula:C17H27Cl2N5
  • Formula Weight:372.34
  • MOL File:146510-36-3.mol
OLANEXIDINE Property
  • Boiling point 454.7±55.0 °C(Predicted)
  • Density 1.22±0.1 g/cm3(Predicted)
  • pka 11.92±0.10(Predicted)
  • FDA UNII 92C2328G7P
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal word
  • Hazard statements
  • Precautionary statements

OLANEXIDINE Chemical Properties,Usage,Production

  • Description In July 2015, olanexidine gluconate, a biguanide compound with remarkable antibacterial activity, was approved by the Pharmaceuticals and Medical Devices Agency (PMDA) of Japan for skin antisepsis at surgical sites. The drug was developed and marketed by Otsuka Pharmaceutical in Japan and is available as topical solution (1.5%). Olanexidine gluconate exhibited efficacy against a wide range of bacterial strains, especially Grampositive bacteria. In vitro experiments exploring its mechanism of action indicated that olanexidine interacts with bacterial surface molecules (such as lipopolysaccharides and lipoteichoic acid), disrupting the cell membranes of liposomes. These models suggest that the drug permeates the membranes of both Escherichia coli and Staphylococcus aureus and denatures proteins at relatively high concentrations (>160 g/mL).
  • Uses Olanexidine is an antibacterial agent. Olanexidine is active against a wide range of bacteria, imcluding both Gram-positive and Gram-negative bacteria Olanexidine is also an antiseptic. Olanexidine can be used in the research of infection and inflammation[1][2][3].
  • Definition ChEBI: Olanexidine is a dichlorobenzene.
  • Synthesis The synthesis of olanexidine gluconate is relatively straightforward, involving the linkage of an n-octyl side chain and a dichlorobenzylamine through a bis-guanidyl lynchpin. The synthesis began with the reaction of commercial noctylamine (17) with sodium dicyanamide in the presence of concentrated sulfuric acid in refluxing n-butyl acetate to give rise to 1-cyano-3-octylguanidine (18) in 86% yield . Conditions employed to subsequently secure biguanidine 20 as the HCl salt hemihydrate in 77% yield were nearly identical to those used for the conversion of 17 to 18. Finally, treatment of 20 with sodium hydroxide in the presence of gluconic acid (21) gave rise to olanexidin gluconate (II) in almost quantitative yield.

    Synthesis_146510-36-3

  • in vivo

    Olanexidine (1?-2% in saline, applied to the skin) is active against transient or resident bacterial flora on the skin of male cynomolgus monkeys[4].

    Animal Model:Male cynomolgus monkeys[4]
    Dosage:1?%, 1.5%, 2% in saline
    Administration:Applied to the skin
    Result:Showed the fast-acting and long-lasting bactericidal effects at 1.5% concentration.
  • References [1] Hagi A, et al. Bactericidal Effects and Mechanism of Action of Olanexidine Gluconate, a New Antiseptic. Antimicrob Agents Chemother. 2015 Aug;59(8):4551-9. DOI:10.1128/AAC.05048-14
    [2] Nii T, Yumoto H, Hirota K, Miyake Y. Anti-inflammatory effects of olanexidine gluconate on oral epithelial cells. BMC Oral Health. 2019 Nov 8;19(1):239. DOI:10.1186/s12903-019-0932-0
    [3] Imai K, et al. Disinfection efficacy and mechanism of olanexidine gluconate against norovirus. Am J Infect Control. 2022 Jul;50(7):764-771. DOI:10.1016/j.ajic.2021.11.020
    [4] Nakata H, et al. Effects of olanexidine gluconate on preoperative skin preparation: an experimental study in cynomolgus monkeys. J Med Microbiol. 2017 May;66(5):678-685. DOI:10.1099/jmm.0.000462
OLANEXIDINE Preparation Products And Raw materials
Raw materials
Preparation Products
OLANEXIDINE Suppliers
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OLANEXIDINE Spectrum
146510-36-3, OLANEXIDINERelated Search:
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  • 抑制剂
  • 杂质对照品
  • 对照品-杂质对照品
  • C17H27Cl2N5
  • 奥兰替代尼
  • 奥拉西定
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  • 奥兰西丁(奥兰西丁杂质8)
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  • 奥兰西丁标准品HCL
  • 奥兰西丁
  • 盐酸奥兰西丁
  • 奥拉昔定葡萄糖酸
  • 146510-36-3
  • Imidodicarbonimidicdiamide,N-[(3,4-dichlorophenyl)methyl]-N'-octyl-
  • N''-(3,4-dichlorobenzyl)-N'''-octylimidodicarbonimidic diami...
  • Olanexidine-008
  • Olanexidine-008-HCl
  • Olanexidine Impurity 11
  • 1-[N'-[(3,4-dichlorophenyl)methyl]carbamimidoyl]-2-octylguanidine
  • N''-(3,4-dichlorobenzyl)-N'''-octylimidodicarbonimidic diamide
  • Olanexidine Gluconate
  • N1-(3,4-Dichlorobenzyl)-N5-octylbiguanide
  • N-[(3,4-Dichlorophenyl)methyl]-N'-octylimidodicarbonimidic diamide
  • Olanexidine [inn]
  • Imidodicarbonimidic diamide, N-((3,4-dichlorophenyl)methyl)-N'-octyl
  • OLANEXIDINE

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