XC9

1-[6-[azanylidene-[[azanylidene-[[(4-chlorophenyl)amino]methyl]-$l^{4}-azanyl]methyl]-$l^{4}-azanyl]hexyl]-3-[~{N}-(4-chlorophenyl)carbamimidoyl]guanidine

Created: 2022-11-11
Last modified:  2023-02-08

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Chemical Details

Formal Charge0
Atom Count64
Chiral Atom Count0
Bond Count65
Aromatic Bond Count12
2D diagram of XC9

Chemical Component Summary

Name1-[6-[azanylidene-[[azanylidene-[[(4-chlorophenyl)amino]methyl]-$l^{4}-azanyl]methyl]-$l^{4}-azanyl]hexyl]-3-[~{N}-(4-chlorophenyl)carbamimidoyl]guanidine
Systematic Name (OpenEye OEToolkits)1-(4-chlorophenyl)-3-[~{N}-[6-[[~{N}-[~{N}-(4-chlorophenyl)carbamimidoyl]carbamimidoyl]amino]hexyl]carbamimidoyl]guanidine
FormulaC22 H30 Cl2 N10
Molecular Weight505.447
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Clc1ccc(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(Cl)cc2)cc1
SMILESCACTVS3.385Clc1ccc(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(Cl)cc2)cc1
SMILESOpenEye OEToolkits2.0.7c1cc(ccc1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(cc2)Cl)Cl
Canonical SMILESCACTVS3.385 Clc1ccc(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(Cl)cc2)cc1
Canonical SMILESOpenEye OEToolkits2.0.7 [H]/N=C(\NCCCCCCNC(=N)NC(=N)Nc1ccc(cc1)Cl)/N/C(=N\[H])/Nc2ccc(cc2)Cl
InChIInChI1.06 InChI=1S/C22H30Cl2N10/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34)
InChIKeyInChI1.06 GHXZTYHSJHQHIJ-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00878 
NameChlorhexidine
Groups
  • approved
  • withdrawn
  • vet_approved
DescriptionChlorhexidine is a broad-spectrum antimicrobial biguanide used as a topical antiseptic and in dental practice for the treatment of inflammatory dental conditions caused by microorganisms.[L11512] It is one of the most common skin and mucous membrane antiseptic agents in use today.[A190417] The molecule itself is a cationic bis-guanide consisting of two 4-chlorophenyl rings and two biguanide groups joined by a central hexamethylene chain.[A190453] Topical chlorhexidine for disinfection, as well as oral rinses for dental use, carries activity against a broad range of pathogens including bacteria, yeasts, and viruses.[L11518,L11512,A190453] Chlorhexidine was developed in the UK by Imperial Chemical Industries in the early 1950s[A190474] and was introduced to the US in the 1970s.[L11572] The FDA withdrew its approval for the use of chlorhexidine gluconate topical tincture 0.5%, due to a significant number of reports concerning chemical and thermal burns associated with the use of this product.[L43942,L44027] Other formulations of chlorhexidine continue to be available.
Synonyms
  • N,N'-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide
  • Chlorhexidinum
  • Chlorhexidin
  • Chlorhexidine gluconate
  • Cloresidina
Brand Names
  • Steri-stat Tincture (tinted) Antis Prep Gel
  • Ic-gel
  • Pre and Post Sx Pouch
  • Calgon Vestal 2% Chg Antimicrob.skin Cleans.
  • Soluprep AQ Swab
IndicationChlorhexidine is available over-the-counter in various formulations (e.g. solution, sponge, cloth, swab) as a topical antiseptic to sanitize prior to surgeries and/or medical procedures.[L11518,L11521,L11527,L11533] Dental formulations, available by prescription only, include an oral rinse indicated for the treatment of gingivitis[L11512] and a slow-release "chip" which is inserted into periodontal pockets and is indicated for the reduction of pocket depth in adult patients with periodontitis as an adjunct therapy to dental scaling and root planing procedures.[L11536]
Categories
  • Alimentary Tract and Metabolism
  • Amidines
  • Anti-Infective Agents
  • Anti-Infective Agents, Local
  • Antiinfectives and Antiseptics for Local Oral Treatment
ATC-Code
  • R02AA05
  • S03AA04
  • D08AC52
  • D08AC02
  • S01AX09
CAS number55-56-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Bacterial outer membrane-unknownincorporation into and destabilization
Serum albuminMKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL790
PubChem 88536661, 5353524, 5360566, 2713, 9552079
ChEMBL CHEMBL790
ChEBI CHEBI:3614
CCDC/CSD RUMPUN, AMASIS, WODGIG