chlorhexidine

CHEBI:3614 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A bisbiguanide compound with a structure consisting of two (p-chlorophenyl)guanide units linked by a hexamethylene bridge. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

disinfecting agents and antisepticsARO:3005386

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:53662 CHEBI:53662
CHEBI:83403 CHEBI:83403
ARO:3005386 ARO:3005386

Chemical structure

Computed structure properties
Molecular formula	C22H30Cl2N10
Charge	0
Average mass	505.458 Da
Monoisotopic mass	504.2032 Da
Source	ChEBI
InChIKey	GHXZTYHSJHQHIJ-UHFFFAOYSA-N

SMILES

N=C(NCCCCCCNC(=N)NC(=N)Nc1ccc(Cl)cc1)NC(=N)Nc1ccc(Cl)cc1

InChI

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)

Also called

N',N'''''-hexane-1,6-diylbis[N-(4-chlorophenyl)(imidodicarbonimidic diamide)] (EXACT_SYNONYM)— chebi
1,1'-Hexamethylene bis(5-(p-chlorophenyl)biguanide) (EXACT_SYNONYM)— chebi
Chlorhexidine (EXACT_SYNONYM)— chebi
N,N'-Bis(4-chlorophenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide (EXACT_SYNONYM)— chebi
chlorhexidine acetate (EXACT_SYNONYM)— aro
chlorhexidine digluconate (EXACT_SYNONYM)— aro
chlorhexidine gluconate (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3007039
cas:55-56-1
drugbank:DB00878
drugcentral:597
kegg.compound:C06902
kegg.drug:D07668
lincs.smallmolecule:LSM-5633
reaxys:2826432
vsdb:1779
wikipedia.en:Chlorhexidine
chembl:CHEMBL790
pubchem.compound:9552079

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33282 CHEBI:33282

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3007039`	chlorhexidine	`antibioticmech:aro-0a95fd2950`	2026-08-30
CHEBI	`CHEBI:3614`	chlorhexidine	`antibioticmech:chebi-0773f08e3a`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

Acetyltransferase, GNAT family PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Bacillus anthracis NCBITaxon:1392

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	1.4e+4 nM	Eis Ban Inhibition Assay Briefly, reactions (200 μL) contained compounds 1−3 dissolved in Tris-HCl buffer (50 mM, pH 8.0, 10% DMSO) with a 5-fold serial dilution, Eis_Ban enzyme (0.25 μM), and NEO (100 μM), AcCoA (0.5 mM), and DTNB (2 mM). Reagents were added in a stepwise manner, allowing the enzyme to incubate with the inhibitor and NEO, and the reactions were initiated with the AcCoA in solution with DTNB. The reactions were monitored as described for the kinetic analysis.	`RSID 293339` `assay 6801_1` `monomer 152706`	`PMID:25928210`

Organism-specific examples
Protein	Gene	Organism	Entry
Acetyltransferase, GNAT family `UniProtKB:A0A3P1UAV8`	—	Bacillus anthracis	UNREVIEWED

PMID:25928210 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Resistance mechanisms

4 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_EFFLUX 4

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Acinetobacter baumannii AbuO	ARO:3004578	not organism-specific	—	ARO:3004578 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007039 (chlorhexidine); database assertion, not a primary citation.)
Klebsiella pneumoniae KpnEF	ARO:3004585	not organism-specific	—	ARO:3004585 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007039 (chlorhexidine); database assertion, not a primary citation.)
PmpM	ARO:3004077	not organism-specific	—	ARO:3004077 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007039 (chlorhexidine); database assertion, not a primary citation.)
aadT	ARO:3007669	not organism-specific	—	ARO:3007669 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007039 (chlorhexidine); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.