Bromhexine

Identification

Name
Bromhexine
Accession Number
DB09019
Type
Small Molecule
Groups
Approved
Description

Bromhexine is an expectorant/mucolytic agent. Bromhexine is not available in the United States. It is marketed under the trade name Bisolvon(R) in Germany, England, Belgium, France, Italy, Netherlands, Norway, Sweden, Australia, and South Africa.

Structure
Thumb
Synonyms
  • 3,5-Dibromo-N(alpha)-cyclohexyl-N(alpha)-methyltoluene-alpha-2-diamine
  • Bromexina
  • Bromhexina
  • Bromhexinum
  • Fluibron
  • N-Cyclohexyl-N-methyl-(2-amino-3,5-dibrombenzyl)amine
  • Tauglicolo
External IDs
NA 274
Product Ingredients
IngredientUNIICASInChI Key
Bromhexine HydrochlorideYC2ZOM3Z8V611-75-6UCDKONUHZNTQPY-UHFFFAOYSA-N
International/Other Brands
Amiorel (Boehringer Ingelheim) / Bisolmed (Boehringer Ingelheim) / Bisolvon (Boehringer Ingelheim) / Bisolvon Chesty (Boehringer Ingelheim)
Categories
UNII
Q1J152VB1P
CAS number
3572-43-8
Weight
Average: 376.13
Monoisotopic: 373.999323944
Chemical Formula
C14H20Br2N2
InChI Key
OJGDCBLYJGHCIH-UHFFFAOYSA-N
InChI
InChI=1S/C14H20Br2N2/c1-18(12-5-3-2-4-6-12)9-10-7-11(15)8-13(16)14(10)17/h7-8,12H,2-6,9,17H2,1H3
IUPAC Name
2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline
SMILES
CN(CC1=CC(Br)=CC(Br)=C1N)C1CCCCC1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,336,308.

General References
Not Available
External Links
KEGG Drug
D07542
PubChem Compound
2442
PubChem Substance
310264976
ChemSpider
2348
ChEBI
77032
ChEMBL
CHEMBL253376
Drugs.com
Drugs.com Drug Page
Wikipedia
Bromhexine
ATC Codes
R05CB02 — Bromhexine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)232-235U.S. Patent 3,336,308.
Predicted Properties
PropertyValueSource
Water Solubility0.00362 mg/mLALOGPS
logP4.08ALOGPS
logP4.42ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)19.89ChemAxon
pKa (Strongest Basic)9.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.26 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.56 m3·mol-1ChemAxon
Polarizability32.98 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0095000000-2c4f15e31beb22fd1178
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0090000000-4d3be1605bfa79609959
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0090000000-428c05c13a2a9e326945
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0390000000-b0ece5d5d6f8b78af198

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylmethylamines
Direct Parent
Phenylmethylamines
Alternative Parents
Benzylamines / 2-bromoanilines / Cyclohexylamines / Bromobenzenes / Aralkylamines / Aryl bromides / Trialkylamines / Primary amines / Organopnictogen compounds / Organobromides
show 1 more
Substituents
Benzylamine / Phenylmethylamine / 2-bromoaniline / Aniline or substituted anilines / Bromobenzene / Cyclohexylamine / Halobenzene / Aralkylamine / Aryl bromide / Aryl halide
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organobromine compound, tertiary amino compound, substituted aniline (CHEBI:77032)

Drug created on June 24, 2014 10:22 / Updated on November 02, 2018 08:46