NAV

Hexamidine

Identification

Summary

Hexamidine is an antiseptic drug used for dermatomycoses and superficial bacterial infections alone or in combination with clotrimazole.

Generic Name
Hexamidine
DrugBank Accession Number
DB03808
Background

Not Available

Type
Small Molecule
Groups
Approved, Experimental
Structure
3D
Similar Structures
Weight
Average: 354.446
Monoisotopic: 354.205576096
Chemical Formula
C20H26N4O2
Synonyms
  • hexamidina
  • Hexamidine
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatDermatomycosesCombination Product in combination with: Clotrimazole (DB00257)•••••••••••••••••
Used in combination to treatSuperficial skin infectionsCombination Product in combination with: Clotrimazole (DB00257)•••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHTH-type transcriptional regulator QacRNot AvailableStaphylococcus aureus
UHTH-type transcriptional regulator QacRNot AvailableStaphylococcus haemolyticus
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Hexamidine diisethionate023XA5Z50L659-40-5NBVZMBLJRHUOJR-UHFFFAOYSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Cabral IdsShampoo0.1 %TopicalVivier Canada Incorporated2002-11-202004-01-15Canada flag
DESOMEDINE EYE DROPS 1 mg/mlSolution100 mg/100mlOphthalmicBAUSCH & LOMB (SINGAPORE) PRIVATE LIMITED1990-03-05Not applicableSingapore flag
Hexam IdsGel0.1 %TopicalVivier Canada Incorporated2002-12-012004-01-15Canada flag
Lexxel IdsCream0.1 %TopicalVivier Canada Incorporated2002-12-012004-05-14Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Imazol duo 10 mg/g + 2,5 mg/g CremeHexamidine diisethionate (2.5 mg/g) + Clotrimazole (10 mg/g)CreamTopicalLaboratoires Bailleul S.A.2008-07-02Not applicableAustria flag
Lexxel IdsHexamidine diisethionate (0.1 %) + Aluminum chloride (23 %)GelTopicalVivier Canada IncorporatedNot applicableNot applicableCanada flag

Categories

ATC Codes
S03AA05 — HexamidineD08AC04 — HexamidineR02AA18 — HexamidineR01AX07 — HexamidineS01AX08 — Hexamidine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Alkyl aryl ethers / Carboximidamides / Carboxamidines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkyl aryl ether / Amidine / Aromatic homomonocyclic compound / Carboximidamide / Carboxylic acid amidine / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aromatic ether, guanidines, polyether (CHEBI:87184)
Affected organisms
Not Available

Chemical Identifiers

UNII
3483C2H13H
CAS number
3811-75-4
InChI Key
OQLKNTOKMBVBKV-UHFFFAOYSA-N
InChI
InChI=1S/C20H26N4O2/c21-19(22)15-5-9-17(10-6-15)25-13-3-1-2-4-14-26-18-11-7-16(8-12-18)20(23)24/h5-12H,1-4,13-14H2,(H3,21,22)(H3,23,24)
IUPAC Name
4-{[6-(4-carbamimidoylphenoxy)hexyl]oxy}benzene-1-carboximidamide
SMILES
NC(=N)C1=CC=C(OCCCCCCOC2=CC=C(C=C2)C(N)=N)C=C1

References

General References
Not Available
PubChem Compound
65130
PubChem Substance
46505102
ChemSpider
58639
BindingDB
50015234
RxNav
26849
ChEBI
87184
ChEMBL
CHEMBL25105
ZINC
ZINC000001705403
PDBe Ligand
DID
Wikipedia
Hexamidine
PDB Entries
1rpw

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
ShampooTopical0.1 %
SolutionOphthalmic100 mg/100ml
GelTopical0.1 %
CreamTopical
CreamTopical0.1 %
GelTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0142 mg/mLALOGPS
logP1.77ALOGPS
logP2.77Chemaxon
logS-4.4ALOGPS
pKa (Strongest Basic)12.13Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area118.2 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity125.13 m3·mol-1Chemaxon
Polarizability40.85 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9416
Blood Brain Barrier+0.9133
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.5352
P-glycoprotein inhibitor INon-inhibitor0.8571
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterInhibitor0.6653
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateNon-substrate0.7339
CYP450 1A2 substrateNon-inhibitor0.5272
CYP450 2C9 inhibitorNon-inhibitor0.7439
CYP450 2D6 inhibitorNon-inhibitor0.7676
CYP450 2C19 inhibitorNon-inhibitor0.6581
CYP450 3A4 inhibitorNon-inhibitor0.8661
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5621
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8395
BiodegradationNot ready biodegradable0.9818
Rat acute toxicity2.2925 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7428
hERG inhibition (predictor II)Non-inhibitor0.7711
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000i-0921000000-e1defb75714a63dcce8c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0019000000-b9708cef953d01e397e4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0129000000-50fccb9323d68ecb9adc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0419000000-1fc68ca063fd01ac5c1d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9827000000-e4e705ecca2a1c3174e8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0901000000-f90b1ccdd690daf7fa27
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-6db5ac167de5c2560fc8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-203.545584
predicted
DarkChem Lite v0.1.0
[M-H]-188.25829
predicted
DeepCCS 1.0 (2019)
[M+H]+203.937884
predicted
DarkChem Lite v0.1.0
[M+H]+190.80959
predicted
DeepCCS 1.0 (2019)
[M+Na]+203.802584
predicted
DarkChem Lite v0.1.0
[M+Na]+199.22058
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. HTH-type transcriptional regulator QacR
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Transcriptional repressor of qacA. Binds to IR1, an unusually long 28 bp operator, which is located downstream from the qacA promoter and overlaps its transcription start site. QacR is induced from its IR1 site by binding to one of many structurally dissimilar cationic lipophilic compounds, which are also substrates of QacA.
Specific Function
Dna binding
Gene Name
qacR
Uniprot ID
P0A0N4
Uniprot Name
HTH-type transcriptional regulator QacR
Molecular Weight
22174.175 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. HTH-type transcriptional regulator QacR
Kind
Protein
Organism
Staphylococcus haemolyticus
Pharmacological action
Unknown
General Function
Transcription factor activity, sequence-specific dna binding
Specific Function
Transcriptional repressor of qacA. Binds to IR1, an unusually long 28 bp operator, which is located downstream from the qacA promoter and overlaps its transcription start site. QacR is induced from...
Gene Name
qacR
Uniprot ID
P0A0N5
Uniprot Name
HTH-type transcriptional regulator QacR
Molecular Weight
22174.175 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 08, 2021 11:32