Hexamidine
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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
- Weight
- Average: 354.446
Monoisotopic: 354.205576096 - Chemical Formula
- C20H26N4O2
- Synonyms
- hexamidina
- Hexamidine
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Dermatomycoses Combination Product in combination with: Clotrimazole (DB00257) •••••••••••• ••••• Used in combination to treat Superficial skin infections Combination Product in combination with: Clotrimazole (DB00257) •••••••••••• ••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UHTH-type transcriptional regulator QacR Not Available Staphylococcus aureus UHTH-type transcriptional regulator QacR Not Available Staphylococcus 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Hexamidine diisethionate 023XA5Z50L 659-40-5 NBVZMBLJRHUOJR-UHFFFAOYSA-N - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cabral Ids Shampoo 0.1 % Topical Vivier Canada Incorporated 2002-11-20 2004-01-15 Canada DESOMEDINE EYE DROPS 1 mg/ml Solution 100 mg/100ml Ophthalmic BAUSCH & LOMB (SINGAPORE) PRIVATE LIMITED 1990-03-05 Not applicable Singapore Hexam Ids Gel 0.1 % Topical Vivier Canada Incorporated 2002-12-01 2004-01-15 Canada Lexxel Ids Cream 0.1 % Topical Vivier Canada Incorporated 2002-12-01 2004-05-14 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Imazol duo 10 mg/g + 2,5 mg/g Creme Hexamidine diisethionate (2.5 mg/g) + Clotrimazole (10 mg/g) Cream Topical Laboratoires Bailleul S.A. 2008-07-02 Not applicable Austria Lexxel Ids Hexamidine diisethionate (0.1 %) + Aluminum chloride (23 %) Gel Topical Vivier Canada Incorporated Not applicable Not applicable Canada
Categories
- ATC Codes
- S03AA05 — Hexamidine
- S03AA — Antiinfectives
- S03A — ANTIINFECTIVES
- S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
- S — SENSORY ORGANS
- D08AC — Biguanides and amidines
- D08A — ANTISEPTICS AND DISINFECTANTS
- D08 — ANTISEPTICS AND DISINFECTANTS
- D — DERMATOLOGICALS
- R01AX — Other nasal preparations
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- 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
- External Links
- PubChem Compound
- 65130
- PubChem Substance
- 46505102
- ChemSpider
- 58639
- BindingDB
- 50015234
- 26849
- ChEBI
- 87184
- ChEMBL
- CHEMBL25105
- ZINC
- ZINC000001705403
- PDBe Ligand
- DID
- Wikipedia
- Hexamidine
- PDB Entries
- 1rpw
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Shampoo Topical 0.1 % Solution Ophthalmic 100 mg/100ml Gel Topical 0.1 % Cream Topical Cream Topical 0.1 % Gel Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0142 mg/mL ALOGPS logP 1.77 ALOGPS logP 2.77 Chemaxon logS -4.4 ALOGPS pKa (Strongest Basic) 12.13 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 118.2 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 125.13 m3·mol-1 Chemaxon Polarizability 40.85 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9416 Blood Brain Barrier + 0.9133 Caco-2 permeable - 0.8957 P-glycoprotein substrate Non-substrate 0.5352 P-glycoprotein inhibitor I Non-inhibitor 0.8571 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Inhibitor 0.6653 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Non-substrate 0.7339 CYP450 1A2 substrate Non-inhibitor 0.5272 CYP450 2C9 inhibitor Non-inhibitor 0.7439 CYP450 2D6 inhibitor Non-inhibitor 0.7676 CYP450 2C19 inhibitor Non-inhibitor 0.6581 CYP450 3A4 inhibitor Non-inhibitor 0.8661 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5621 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.8395 Biodegradation Not ready biodegradable 0.9818 Rat acute toxicity 2.2925 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7428 hERG inhibition (predictor II) Non-inhibitor 0.7711
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-000i-0921000000-e1defb75714a63dcce8c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4r-0019000000-b9708cef953d01e397e4 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0129000000-50fccb9323d68ecb9adc Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0419000000-1fc68ca063fd01ac5c1d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9827000000-e4e705ecca2a1c3174e8 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0901000000-f90b1ccdd690daf7fa27 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9100000000-6db5ac167de5c2560fc8 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 203.545584 predictedDarkChem Lite v0.1.0 [M-H]- 188.25829 predictedDeepCCS 1.0 (2019) [M+H]+ 203.937884 predictedDarkChem Lite v0.1.0 [M+H]+ 190.80959 predictedDeepCCS 1.0 (2019) [M+Na]+ 203.802584 predictedDarkChem Lite v0.1.0 [M+Na]+ 199.22058 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsHTH-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
- 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]
2. DetailsHTH-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
Drug created at June 13, 2005 13:24 / Updated at June 08, 2021 11:32