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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2 entries where XC9 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	64
Chiral Atom Count	0
Bond Count	65
Aromatic Bond Count	12

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Chemical Component Summary
Name	1-[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
Formula	C₂₂ H₃₀ Cl₂ N₁₀
Molecular Weight	505.447
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	Clc1ccc(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(Cl)cc2)cc1
SMILES	CACTVS	3.385	Clc1ccc(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(Cl)cc2)cc1
SMILES	OpenEye OEToolkits	2.0.7	c1cc(ccc1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(cc2)Cl)Cl
Canonical SMILES	CACTVS	3.385	Clc1ccc(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)Nc2ccc(Cl)cc2)cc1
Canonical SMILES	OpenEye OEToolkits	2.0.7	[H]/N=C(\NCCCCCCNC(=N)NC(=N)Nc1ccc(cc1)Cl)/N/C(=N\[H])/Nc2ccc(cc2)Cl
InChI	InChI	1.06	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)
InChIKey	InChI	1.06	GHXZTYHSJHQHIJ-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB00878
Name	Chlorhexidine
Groups	withdrawn approved vet_approved
Description	Chlorhexidine 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	Clorhexidina Cloresidina Chlorhexidinum Chlorhexidine gluconate Chlorhexidin Chlorhexidine Chlorhexidine acetate 1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide) Chlorhexidine hydrochloride N,N'-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide
Brand Names	DermacinRx Clorhexacin First Aid Antiseptic Skin Cleanser DEQGEL Advanced Hand Sanitizer DermacinRx Surgical PharmaPak Sterixin 0.05% Foaming Chlorhexidine Gluconate Loris I.V. Pro - Prefilled Applicator With Solution Hands-free skin sanitizer Pre-moistened Towelette Sunberry Rinse free Hand Sanitizer Rouhex G Liq 2% Dyna-Hex 4 Seaqua X Soluprep AQ Swab Yu Ding Antibacterial Sprays 10mL Gelato Chlorohexidine Hibistat Chlorhexidine Gluconate Oral Cleansing and Suctioning System, q4 SANIDEP Advanced Sanitizer with Organic Extracts Foster and Thrive Noble 75% Alcohol Wipes E-Z Scrub 747 4% Steri-stat Liq 4.0% Soluprep AQ Wipe Scrub Care Surgical Scrub Brush/nail Cleaner With Exidine 4 Smart Sense Antiseptic Skin Cleanser Rougier Vap-chlorhexidine Gluconate 2% W/V Antiseptic Solution Pre-Scrub II Surgical Hand Scrub Motherwort Herb Feminine Antibacterial Gels Soluprep AQ Chlorhexidine Gluconate 0.12% Oral Rinse Henry Schein Antimicrobial Skin Cleanser B-good Hand and Skin Disinfecting Agent Liquivida Hydration Hibitane Skin Cleanser Laura Line Antibacterial Cream Soap 2% DASH Chlorhexidine Gluconate 0.12% Oral Rinse Acclean Chlorhexidine Gluconate 0.12% Oral Rinse Ultrastat Hygienipak 4% Chg Foaming Skin Cleanser Surgical Continuum System Chloraprep Liq 0.5% Akilgeld Hand Sanitizer Prevora Stage 1 Dermsafe Pc Soluprep Antiseptic Skin Cleanser Preoperative Kit Steri-stat Tincture (tinted) Antis Prep Gel Periogard (Chlorhexidine Gluconate) Instillagel Peridex Oral Rinse 0.12% Purell CS Foam Handwash 2% CHG Antiseptic Lotion Soap 2% Purell Antimicrobial Foam Handwash 2% Chg Hibitane Skin Cleanser Liq 4% Scrub Care Periogard Germi Stat Gel 4% Stanhexidine Aqueous 2% With 4% Isopropyl Alcohol Chlorhexidine 0.5% Liq Scrub Care Exidine -4 CHG Dyna-hex 4 Ic-gel Dexidin 2 Solution Disinfectant Spray(Speedy effect type) Germi Stat Gel 2% Baxedin Liq 20% Alcohol Disinfectant Wipes Hygienium Prevantics swabstick Steri-stat Liq 20% Antiseptic First Aid Spray Q2 Oral Care Kit with CHG Savlon Hospital Concentrate Antiseptic Skin Cleanser Chlorhexidine and Isopropyl Alcohol Prep Pads Aplicare Chlorhexidine Gluconate 2% Solution Hibitane Skin Cleanser 4% Germi-stat 0.5% Antiseptic Prep Gel Chloraprep Swabsticks Hibiclens for Georgia Pacific Chlorhexidine-cetrimide Soltn Conc Calgon Vestal 4% Chg Antimicrob.skin Cleans. Anti Mucedine Feminine Wash Denticare Chlorhexidine Gluconate Oral Rinse 0.12% Bactoshield CHG Scrub Stat 4 Foam Liq Soft Care Antiseptic Hand Soap Calgon Vestal 2% Chg Antimicrob.skin Cleans. Bactoshield CHG Chlorhexidine Gluconate Solution Baxedin 2% - 70% Soluprep AQ Applicator Spray On Plastic Bandage Aerosol Aplicare Antiseptic Chlorhexidine Gluconate Perioselect Antimicrobial Sol 0.12% KleerSight Jisberry Hand Sanitizer Sterigel Plus Hand Sanitizer Biokaab Scrub, Scrub-Stat, Foam Safe, Micro-Guard Bactoshield Chg 4% CLIP Liquid Sanitizer Chlorhexidine gluconate Oral Cleansing and Suctioning System, q2 Wart Remover Ointment. LARA MED Antibacterial Wet Wipes Hand Sanitizer Bioprep Spectro Tar Antiseptic Shampoo Chlorhexidine 2% Antiseptic Hand Wash E-Z Scrub Antimicrobial Foam Solution Containing 4% Chg Rouhex G 20% Stat Touch 2 Antimicrobial Skin Cleanser Pro-dentx Chlorhexidene Oral Rinse BD E-Z Scrub 107 Chlorhexidine Solution (Qiqing) Chlorhexidine Gluconate Alcohol Disinfectant Paroex Perichlor Without Alcohol Savlodil Sky Oral Rinse Oris Chx Skinvisible Chlorhexidine Formula Hand Sanitizer Lotion 3M SoluPrep S Scrub-stat IV 4% Bacti-stat Chg ChloraPrep One-Step Foaming Hand Antiseptic With Chg 2% Hexifoam-skin Disinfectant Aer 1% Loris - I.V. Chlorhexidine QCare Rx Oral Cleansing and Suctioning System, Q4 Hexirex Antiseptic Skin Cleanser Dr. Luke Molluscum Wart Remover Dr. Luke Wart Remover Septi-san Chlorhexidine Alcohol Free Oronine H Ointment 1% Rugby Antiseptic Skin Cleanser Spray On Plastic Bandage Non-aerosol Chlorhexidine Gluconate, 0.12% Oral Rinse Solution Betasept X-pur Chlorhexidine Loris I.V. Pro - Swabstick Sanital Antibacterial Hand Soap Soluprep Wipe Provon Antiseptic Lotion Soap With 2% Chg Bactigras Gum Paroex Soluprep AQ Sponge Denti-Care Denti-Rinse Chlorhexidine Gluconate Oral Rinse Stanhexidine 20% Disinfectant Wet Tissues Chlorhexidine Gluconate Oral Rinse Chlorhexidine Gluconate, 0.12% Oral Rinse Salvesept Crm E-Z Scrub 107 Maxiclens Chlorhexidine gluconate Liquid Solution, 4% Quick-drying rinse-free hand skin disinfectant Antiseptic Foam Handwash Chlorhexidine 4% Antiseptic Hand Wash Dyna-Hex 2 Hygenipak 2% Chg Foaming Skin Cleanser Soluprep Foam Safe Soluprep Qd Swab WhyteDerm SurgiPak Scrub Dr. Dean Loris 2% Chg Solution Dexidin 2 Detergent Provon Antimicrobial Foam Handwash Cardinal Health Dr. Zheng s acteriostatic gel Hand Wipes Hibistat Germicidal Hand Rinse Dexidin 0.5 Solution Oro Clear QCare Rx Petite Oral Cleansing and Suctioning System Antimicrobial Foam Handwash Hygienipak 4% Chg Skin Cleanser Avidene Surgical Scrub Antimicrobial Skin Cleanser Baxedin Pre-OP SAITENM Health Wet wipes Stanhexidine Red Tincture 0.5% CliniClean Burn O Sol Spray Perichlor Spectro Gram 2 Skin Cleanser Alcohol Antibacterial Wipes QCare Rx Oral Cleansing and Suctioning System, Q2 Prevantics Swab PS1 Aciurgy Pack Rouhex G 4% Wart removal Protective Hand Flamazine C Prevantics Swabstick HandSoap Zedoary Oils Feminine Antibacterial Gels ICEKING Skin Expert Refreshing Body Roller JIANLIANG Antibacterial Sprays 10mL Bactoshield CHG Chlorhexidine Gluconate Stanhexidine 2% With Isopropyl Alcohol 4% Hygenipak 2% Chg Skin Cleanser Purell Antimicrobial Foam DermacinRx Surgical ComboPak QCare Rx Oral Cleansing and Suctioning System Chlorhexidine Gluconate Solution 0.75% Antiseptic Purmist Soft Care 2% Chg Antimicrobial Skin Cleanser Chinese Herb Essence Bacteriostatic Feminine Wash Hibiclens Antiseptic/antimicrobial Skin Cleanser Liszt Hand sanitizer without washing Pre and Post Sx Pouch Scrub, Scrub-Stat Bioprep Liq Cardinal Health Antiseptic Skin Cleanser Kimvent Oral Care Q2 Kit with CHG Cida-stat Foam Hand wipes Chlorhexidine Gluconate Solution USP 20% Bactoshield Chg 2% Soluprep Antiseptic Skin Cleanser Sponge Surgical and healthcare personnel hand antiseptic with moisturizers Wart Removal Pen Chlorhexidine Gluconante Soluprep Qd Wipe Soluprep Applicator Chlorhexidine Gluconate 0.12% Oral Rinse, USP Anti-bac Hand Chlorhexidine Liq 0.05% Maxiclens Chlorhexidine Gluconate Liquid Solution, 4% Dermawerx Surgical PrePak Bactoshield Antiseptic Body Cleanser Endure 420 Cida-Stat Peridex Oral Rinse Skin Antisepsis, Oral Cleansing and Nasal Antisepsis System Dyna-hex 2 CleanCare Chlorhexidine Gluconate 0.12% Oral Rinse Chlora-cleanze Dyna-Hex 75 Steri-stat Liq 2.0% Eyewash Station Additive Concentrate Loris 2% Chg Wipe/serviette Dexidin 20 Chloraprep Prevantics Maxi Swabstick NuSurgePak Surgical Prep/CarePak Germi-stat Prep Gel Steri-clean Cida-stat Liq Dermsafe Chlorhexidine Gluconate Hand Sanitizer Lotion Loris I.V. Pro - Sponge Ezy-TM Scrub-Stat Avagard Chg Chlorhexseptic-liq 0.5mg/ml Euro-chlorhexidine Hibitane Skin Cleanser 2% Foaming Hand Wash Periogard Alcohol Free Loris 2% Chg Body Cleanser/nettoyant Pour Le Corps Medifresh Hand Skin Antiseptic Disinfectant Wet Wipes Skin antisepsis, oral cleansing, nasal antisepsis PhysiciansCare Eyewash Station Additive Concentrate Bei Ling Tong Bao Er Zheng Yuan Antibacterial Creams Major Oral Rinse Smart San CHG Antiseptic Skin Cleanser Exidine-2 CHG Chlorhexidine and Isopropyl Alcohol Swabsticks Hibiclens Quick-Drying Hand Sanitizer ReadyPrep CHG Hibidil Chlorhexidine Gluconate Solution 0.05% Antiseptic Cleansing Wipes Oro-clense Hexicinide (Fruli) Quick-Dry Disposable Hand Sanitizer Endure 400 Scrub-Stat 4 Tai Yu Ling Antibacterial Sprays 10mL Antiseptic Cleanser Solution Soluprep Swab Akilspray Hand Sanitizer Serdaen Foam Care Chg Surgical Hand Scrub Rougier Clean Derm Plant Herb Based Bacteriostatic Feminine Wash Soluprep Ld Sponge Disinfectant Fabric Wash Ostar Antimicrobial Hand Soap 2% - Liquid NUPRO Chlorhexidine Gluconate Freeman Packing Alcohol Wipe Hand Sanitizer Gel Biokaab Solunet C Brosse 4% 3M Avagard 3M SoluPrep Stanhexidine 4% With Isopropyl Alcohol 4% PerioChip Chlorhexidine Gluconate Applicator PS2 Aciurgy Pack 3m Soluprep Sponge BD E-Z Scrub KIMVENT ORAL CARE Q4 Kit WITH CHG Microban Medical Dermawerx Surgical Plus Pak Soluprep Qd Solution Baxedin Scrub Care Exidine-2 CHG Antibacterial Protective Hand Dexidin Liq 4% Peridex Laura Line Chlorhexidine Antiseptic Soap Selpak Antibacterial Wet Wipes Germi-stat 2% Foaming Liquid
Indication	Chlorhexidine 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 Antiseptics and Disinfectants Biguanides Biguanides and Amidines Compounds used in a research, industrial, or household setting Decreased Cell Wall Integrity Dental Agents Dermatologicals Disinfectants Guanidines Household Products Irrigating Solutions Medicated Dressings Medicated Dressings With Antiinfectives Miscellaneous Anti-infectives Miscellaneous Local Anti-infectives Mouthwashes Mouthwashes and Gargles Ophthalmological and Otological Preparations Ophthalmologicals Otologicals Sensory Organs Stomatological Preparations Throat Preparations
ATC-Code	R02AA05 S03AA04 D08AC52 D08AC02 S01AX09 D09AA12 B05CA02 A01AB03 S02AA09
CAS number	55-56-1

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Bacterial outer membrane	-	unknown	incorporation into and destabilization
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	substrate

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