Ipratropium bromide (CHEM022091)

Record Information
Version1.0
Creation Date2016-05-25 18:19:44 UTC
Update Date2026-08-20 06:37:37 UTC
Accession NumberCHEM022091
Identification
Common NameIpratropium bromide
ClassSmall Molecule
Description
Ipratropium bromide is only found in individuals that have used or taken this drug. It is a muscarinic antagonist structurally related to atropine but often considered safer and more effective for inhalation use. It is used for various bronchial disorders, in rhinitis, and as an antiarrhythmic. [PubChem]Ipratropium bromide is an anticholinergic agent. It blocks muscarinic cholinergic receptors, without specificity for subtypes, resulting in a decrease in the formation of cyclic guanosine monophosphate (cGMP). Most likely due to actions of cGMP on intracellular calcium, this results in decreased contractility of smooth muscle.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(endo,Syn)-(+-)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo[3.2.1]octane bromideHMDB
3alpha-Hydroxy-8-isopropyl-1alphah,5alphah-tropanium bromide (+-)-tropateHMDB
8-Isopropylnoratropine methobromideHMDB
Bromure d'ipratropiumHMDB
Bromuro de ipratropioHMDB
Ipratropii bromidumHMDB
Ipratropium bromide (anhydrous)HMDB
Ipratropium bromide anhydrousHMDB
IpratropiumbromidHMDB
N-Isopropylnoratropinium bromomethylateHMDB
3a-Hydroxy-8-isopropyl-1alphah,5alphah-tropanium bromide (+-)-tropateHMDB
3a-Hydroxy-8-isopropyl-1alphah,5alphah-tropanium bromide (+-)-tropic acidHMDB
3alpha-Hydroxy-8-isopropyl-1alphah,5alphah-tropanium bromide (+-)-tropic acidHMDB
3Α-hydroxy-8-isopropyl-1alphah,5alphah-tropanium bromide (+-)-tropateHMDB
3Α-hydroxy-8-isopropyl-1alphah,5alphah-tropanium bromide (+-)-tropic acidHMDB
N-Isopropylnoratropinium bromomethylic acidHMDB
Ipatropium bromideHMDB
IpratropiumHMDB
N-IsopropylatropineHMDB
Bromide anhydrous, ipratropiumHMDB
Ipratropium bromide, (exo,syn)-isomerHMDB
Anhydrous, ipratropium bromideHMDB
Ipratropium bromide, (endo,anti)-isomerHMDB
Ipratropium bromide, endo-isomerHMDB
ItropHMDB
N IsopropylatropineHMDB
(endo,Syn)-(+-)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo(3.2.1)octaneHMDB
AtroventHMDB
Bromide monohydrate, ipratropiumHMDB
Ipratropium bromide monohydrateHMDB
Monohydrate, ipratropium bromideHMDB
Ipratropium bromideMeSH
Chemical FormulaC20H30BrNO3
Average Molecular Mass412.361 g/mol
Monoisotopic Mass411.141 g/mol
CAS Registry Number60205-81-4
IUPAC Name(1R,5S)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium
Traditional Name(1R,5S)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium
SMILES[Br-].[H][C@]12CC[C@]([H])(C[C@@H](C1)OC(=O)C(CO)C1=CC=CC=C1)[N@+]2(C)C(C)C
InChI IdentifierInChI=1S/C20H30NO3.BrH/c1-14(2)21(3)16-9-10-17(21)12-18(11-16)24-20(23)19(13-22)15-7-5-4-6-8-15;/h4-8,14,16-19,22H,9-13H2,1-3H3;1H/q+1;/p-1/t16-,17+,18+,19?,21+;
InChI KeyLHLMOSXCXGLMMN-VVQPYUEFSA-M
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassTropane alkaloids
Sub ClassNot Available
Direct ParentTropane alkaloids
Alternative Parents
Substituents
  • Tropane alkaloid
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Piperidine
  • N-alkylpyrrolidine
  • Benzenoid
  • Tetraalkylammonium salt
  • Pyrrolidine
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Amine
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alcohol
  • Organic salt
  • Carbonyl group
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP0.89ALOGPS
logP-1.8ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.9 m³·mol⁻¹ChemAxon
Polarizability37.65 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0014476
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIpratropium bromide
Chemspider ID571433
ChEBI ID46659
PubChem Compound ID657309
Kegg Compound IDC07052
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. # Abdine HH, Belala F, and Al-Badra AA. (2003). Ipratropium bromide: Methods of chemical and biochemical synthesis. In H.G. Brittain (Ed.). _Profiles of drug substances, excipients and related methodology_ (pp. 85-99). Amsterdam, Netherlands: Elsevier Academic Press.
2. Yamatake Y, Sasagawa S, Yanaura S, Okamiya Y: [Antiallergic asthma effect of ipatropium bromide (Sch 1000) in dogs (author's transl)]. Nihon Yakurigaku Zasshi. 1977 Oct;73(7):785-91.