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Groups	vet_approved approved withdrawn
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 Chlorhexidinum Cloresidina 1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide) Chlorhexidine hydrochloride Chlorhexidine N,N'-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide Chlorhexidine acetate Chlorhexidin Chlorhexidine gluconate
Brand Names	Bactoshield CHG Chlorhexidine Gluconate Solution Wart removal Bioprep Hibitane Skin Cleanser Pre and Post Sx Pouch PMS-chlorhexidine NuSurgePak Surgical Prep/CarePak Chloraprep Swabsticks Scrub Care 3M Avagard Disinfectant Spray(Speedy effect type) Loris I.V. Pro - Sponge KleerSight Pre-moistened Towelette Tai Yu Ling Antibacterial Sprays 10mL Provon Antimicrobial Foam Handwash Q2 Oral Care Kit with CHG Sanital Antibacterial Hand Soap Chlorhexidine Baxedin 2% - 70% Steri-stat Liq 20% Prevantics swabstick Dr. Luke Molluscum Wart Remover Foster and Thrive Scrub-stat IV 4% Calgon Vestal 4% Chg Antimicrob.skin Cleans. Mlk F4-C Hibistat Pro-dentx Chlorhexidene Oral Rinse Wart Remover Ointment. Smart Sense Antiseptic Skin Cleanser Periogard Aplicare Chlorhexidine Gluconate 2% Solution Avidene Surgical Scrub Provon Antiseptic Lotion Soap With 2% Chg Chlorhexidine Gluconate Applicator (Qiqing) Chlorhexidine Gluconate Alcohol Disinfectant Antiseptic Cleanser Solution Chlorhexidine Gluconate Solution USP 20% PS2 Aciurgy Pack Eyewash Station Additive Concentrate Chlorhexidine Liq 0.05% Chlorhexidine Gluconante Hibiclens Antiseptic/antimicrobial Skin Cleanser Hibitane Skin Cleanser Liq 4% Seaqua X E-Z Scrub 747 4% Dyural LM- C ChloraPrep Swabstick PMS-chlorhexidine Without Alcohol QCare Rx Oral Cleansing and Suctioning System, Q2 Scrub Care Surgical Scrub Brush/nail Cleaner With Exidine 4 Hygenipak 2% Chg Foaming Skin Cleanser Laura Line Antibacterial Cream Soap 2% Germi Stat Gel 2% Anti Mucedine Feminine Wash Soluprep Swab Stanhexidine 4% With Isopropyl Alcohol 4% Denti-Care Denti-Rinse Chlorhexidine Gluconate Oral Rinse Hibiclens Gum Paroex Rougier Vap-chlorhexidine Gluconate 2% W/V Dermsafe Pc Bioprep Liq ChloraPrep One-Step Scrub, Scrub-Stat QCare Rx Oral Cleansing and Suctioning System Antiseptic Foam Handwash Loris I.V. Pro - Swabstick Hibidil Paroex Soluprep Qd Wipe Antiseptic Skin Cleanser CliniClean NUPRO Chlorhexidine Gluconate Soluprep AQ Prevantics Swabstick Surgical Continuum System Baxedin Liq 20% Dexlido M-C Spray On Plastic Bandage Non-aerosol Rouhex G 20% DermacinRx Surgical ComboPak Soluprep AQ Sponge Dyural 80 LM-C Baxedin Pre-OP B-good Hand and Skin Disinfecting Agent PerioChip Dexidin 2 Solution Dyna-hex 2 KIMVENT ORAL CARE Q4 Kit WITH CHG Germi-stat Prep Gel Soluprep AQ Wipe Halyard Chlorhexidine Gluconate Akilspray Hand Sanitizer SAITENM Health Wet wipes Peridex Chlorhexidine Gluconate Endure 400 Scrub-Stat 4 Skin antisepsis, oral cleansing, nasal antisepsis Cida-stat Liq Oral Cleansing and Suctioning System, q2 Loris - I.V. Zedoary Oils Feminine Antibacterial Gels HYDROGEL ESSENCE Antimicrobial Virginal Gel. WhyteDerm SurgiPak Dyna-Hex 2 Hygienipak 4% Chg Skin Cleanser Soft Care 2% Chg Antimicrobial Skin Cleanser Foaming Hand Antiseptic With Chg 2% Perioselect Antimicrobial Sol 0.12% Antiseptic Skin Cleanser Exidine-2 CHG Dr. Dean Loris 2% Chg Solution Hand Sanitizer BD E-Z Scrub E-Z Scrub 107 Alcohol Antibacterial Wipes Betasept Wart Removal Pen Hand Sanitizer Biokaab Chlorhexidine Gluconate Solution 0.75% Antiseptic Plant Herb Based Bacteriostatic Feminine Wash SANIDEP Advanced Sanitizer with Organic Extracts Scrub, Scrub-Stat, Foam Safe, Micro-Guard Chlorhexidine gluconate Selpak Antibacterial Wet Wipes Oro-clense Sterixin 0.05% Flamazine C Soluprep AQ Swab Cardinal Health Antiseptic Skin Cleanser BD E-Z Scrub 107 Steri-stat Liq 4.0% Bactoshield Chg 4% Major Oral Rinse Gelato Chlorohexidine QCare Rx Oral Cleansing and Suctioning System, Q4 Zappy Ultimate Antiseptic Wipes Acclean Chlorhexidine Gluconate 0.12% Oral Rinse Hand wipes DASH Chlorhexidine Gluconate 0.12% Oral Rinse CleanCare Chlorhexidine Gluconate 0.12% Oral Rinse Antiseptic Cleansing Wipes 3M SoluPrep S PS1 Aciurgy Pack Dermawerx Surgical PrePak Antiseptic Body Cleanser Medifresh Hand Skin Antiseptic Disinfectant Wet Wipes LARA MED Antibacterial Wet Wipes Instillagel Soluprep Antiseptic Skin Cleanser Preoperative Kit Scrub Care Exidine-2 CHG Maxiclens Chlorhexidine Gluconate Liquid Solution, 4% Sunberry Rinse free Hand Sanitizer Chlorhexidine Gluconate, 0.12% Oral Rinse JIANLIANG Antibacterial Sprays 10mL Chlorhexidine Gluconate, 0.12% Oral Rinse Solution Soft Care Antiseptic Hand Soap Solunet C Brosse 4% Foam Safe Rougier Clean Derm Disinfectant Fabric Wash Ostar Antimicrobial Hand Soap 2% - Liquid Chlorhexidine Gluconate 0.12% Oral Rinse Surgical and healthcare personnel hand antiseptic with moisturizers Stanhexidine Aqueous 2% With 4% Isopropyl Alcohol Dexidin 2 Detergent HandSoap Bactigras Purmist Chlorhexidine Alcohol Free Bei Ling Tong Bao Er Zheng Yuan Antibacterial Creams Chlorhexidine Gluconate Oral Rinse Microban Medical Bactoshield Dyna-hex 4 Pre-Scrub II Surgical Hand Scrub Soluprep Antiseptic Skin Cleanser Sponge Hygienium ICEKING Skin Expert Refreshing Body Roller Savlodil Dermawerx Surgical Plus Pak Savlon Hospital Concentrate Foaming Hand Wash Germi Stat Gel 4% Kimvent Oral Care Q2 Kit with CHG Prevantics Swab Chlorhexseptic-liq 0.5mg/ml Quick-drying rinse-free hand skin disinfectant Stat Touch 2 Antimicrobial Skin Cleanser Salvesept Crm Betalido-C Soluprep Stanhexidine 2% With Isopropyl Alcohol 4% Anti-bac Hand Oro Clear Hexifoam-skin Disinfectant Aer 1% DermacinRx Surgical PharmaPak Peridex Oral Rinse Septi-san Rugby Antiseptic Skin Cleanser Bactoshield CHG Chlorhexidine Gluconate Scrub Care Exidine -4 CHG Hexicinide Oronine H Ointment 1% Hexirex Antiseptic Skin Cleanser Purell CS Foam Handwash 2% CHG Dr. Zheng s acteriostatic gel Bactoshield Chg 2% Chloraprep Chlorhexidine Solution Spectro Gram 2 Skin Cleanser Scrub-Stat Dyna-Hex 4 Steri-stat Liq 2.0% Foaming Chlorhexidine Gluconate Laura Line Chlorhexidine Antiseptic Soap Motherwort Herb Feminine Antibacterial Gels Oral Cleansing and Suctioning System, q4 Hygenipak 2% Chg Skin Cleanser Ezy-TM Chlora-cleanze Quick-Drying Hand Sanitizer Chlorhexidine and Isopropyl Alcohol Prep Pads Chlorhexidine Gluconate 0.12% Oral Rinse, USP Purell Antimicrobial Foam Handwash 2% Chg X-pur Chlorhexidine Antimicrobial Foam Handwash Soluprep Applicator Maxiclens Chlorhexidine gluconate Liquid Solution, 4% Soluprep Wipe Spray On Plastic Bandage Aerosol Skinvisible Chlorhexidine Formula Hand Sanitizer Lotion Soluprep Qd Swab Chlorhexidine Gluconate Solution 0.05% Steri-stat Tincture (tinted) Antis Prep Gel Baxedin Chlorhexidine 4% Antiseptic Hand Wash Chlorhexidine and Isopropyl Alcohol Swabsticks Dermsafe Chlorhexidine Gluconate Hand Sanitizer Lotion QCare Rx Petite Oral Cleansing and Suctioning System Scrub Stat 4 Foam Liq Antiseptic Lotion Soap 2% Jisberry Hand Sanitizer Loris 2% Chg Wipe/serviette Aplicare Antiseptic Chlorhexidine Gluconate Prevantics Maxi Swabstick Calgon Vestal 2% Chg Antimicrob.skin Cleans. Disinfectant Wet Tissues Noble 75% Alcohol Wipes Alcohol Disinfectant Wipes Soluprep Ld Sponge Scrub Stanhexidine 20% Ultrastat Freeman Packing Alcohol Wipe Periogard Alcohol Free Hibiclens for Georgia Pacific DermacinRx Clorhexacin Chloraprep Liq 0.5% Euro-chlorhexidine Antiseptic First Aid Spray Burn O Sol Spray Periogard (Chlorhexidine Gluconate) Hospicare 40R Adult Body Wipes Hand Wipes Endure 420 Cida-Stat Dr. Luke Wart Remover E-Z Scrub Antimicrobial Foam Solution Containing 4% Chg Spectro Tar Antiseptic Shampoo Rouhex G Liq 2% Cida-stat Foam 3M SoluPrep Antimicrobial Skin Cleanser Bacti-stat Chg DEQGEL Advanced Hand Sanitizer Antibacterial Protective Hand Sky Oral Rinse PhysiciansCare Eyewash Station Additive Concentrate Dexidin 20 Peridex Oral Rinse 0.12% Hands-free skin sanitizer 3m Soluprep Sponge Smart San CHG Chlorhexidine 0.5% Liq Soluprep AQ Applicator Germi-stat 2% Foaming Liquid Loris I.V. Pro - Prefilled Applicator With Solution Oris Chx Skin Antisepsis, Oral Cleansing and Nasal Antisepsis System Denticare Chlorhexidine Gluconate Oral Rinse 0.12% Antiseptic Solution CLIP Liquid Sanitizer Loris 2% Chg Body Cleanser/nettoyant Pour Le Corps Steri-clean Soluprep Qd Solution Henry Schein Antimicrobial Skin Cleanser Sterigel Plus Prevora Stage 1 Stanhexidine Red Tincture 0.5% ReadyPrep CHG Avagard Chg Dyna-Hex 75 Hibistat Germicidal Hand Rinse Ic-gel (Fruli) Quick-Dry Disposable Hand Sanitizer Dexidin Liq 4% Hygienipak 4% Chg Foaming Skin Cleanser Germi-stat 0.5% Antiseptic Prep Gel Purell Antimicrobial Foam Bactoshield CHG Chlorhexidine 2% Antiseptic Hand Wash Hand Sanitizer Gel Biokaab Yu Ding Antibacterial Sprays 10mL Hibitane Skin Cleanser 4% Dexidin 0.5 Solution Akilgeld Hand Sanitizer Liquivida Hydration Chlorhexidine-cetrimide Soltn Conc Rouhex G 4% Liszt Hand sanitizer without washing First Aid Antiseptic Skin Cleanser Hibitane Skin Cleanser 2% Cardinal Health Protective Hand Serdaen Foam Care Chg Surgical Hand Scrub Chinese Herb Essence Bacteriostatic Feminine Wash
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 A01AB53 S01AX09 D08AC02 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
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