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Identification
NameAnisotropine Methylbromide
Accession NumberDB00517  (APRD00800)
TypeSmall Molecule
GroupsApproved
DescriptionAnisotropine methylbromide is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion.
Structure
Thumb
Synonyms
8-Methyl-3-(2-propylpentanoyloxy)tropinium bromide
8-Methyltropinium bromide 2-propylpentanoate
8-Methyltropinium bromide 2-propylvalerate
Anisotropine methobromide
Anisotropine methylbromide
Endo-8,8-dimethyl-3-((1-oxo-2-propylpentyl)oxy)-8-azoniabicyclo(3.2.1)octane bromide
Methylbromure d'octatropine
Methyloctatropine bromide
Metilbromuro de octatropina
Octatropine methylbromide
Octatropini methylbromidum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EndovalpinNot Available
LytispasmNot Available
ValpinEndo
Brand mixturesNot Available
SaltsNot Available
Categories
UNII62M960DHIL
CAS number80-50-2
WeightAverage: 362.345
Monoisotopic: 361.16164192
Chemical FormulaC17H32BrNO2
InChI KeyQSFKGMJOKUZAJM-UHFFFAOYSA-M
InChI
InChI=1S/C17H32NO2.BrH/c1-5-7-13(8-6-2)17(19)20-16-11-14-9-10-15(12-16)18(14,3)4;/h13-16H,5-12H2,1-4H3;1H/q+1;/p-1
IUPAC Name
8,8-dimethyl-3-[(2-propylpentanoyl)oxy]-8-azabicyclo[3.2.1]octan-8-ium bromide
SMILES
[Br-].CCCC(CCC)C(=O)O[[email protected]]1CC2CCC(C1)[N+]2(C)C
Pharmacology
IndicationFor use in conjunction with antacids or histamine H2-receptor antagonists in the treatment of peptic ulcer, to reduce further gastric acid secretion and delay gastric emptying.
Structured Indications Not Available
PharmacodynamicsAnisotropine methylbromide is a quaternary ammonium compound. Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents. Depending on the dose, anisotropine methylbromide may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder. In general, smaller doses of anisotropine methylbromide inhibit salivary and bronchial secretions, sweating, and accommodation; cause dilatation of the pupil; and increase the heart rate. Larger doses are required to decrease motility of the gastrointestinal and urinary tracts and to inhibit gastric acid secretion.
Mechanism of actionQuaternary ammonium compounds such as anisotropine methylbromide inhibit the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves as well as on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These postganglionic receptor sites are present in the autonomic effector cells of the smooth muscle, cardiac muscle, sinoatrial and atrioventricular nodes, and exocrine glands.
TargetKindPharmacological actionActionsOrganismUniProt ID
Muscarinic acetylcholine receptor M1Proteinyes
antagonist
HumanP11229 details
Muscarinic acetylcholine receptor M2Proteinyes
antagonist
HumanP08172 details
Muscarinic acetylcholine receptor M3Proteinyes
antagonist
HumanP20309 details
Related Articles
AbsorptionGastrointestinal absorption is poor and irregular. Total absorption after an oral dose is about 10 to 25%.
Volume of distributionNot Available
Protein bindingNot Known
Metabolism

Hepatic, by enzymatic hydrolysis.

Route of eliminationNot Available
Half lifeNot Known
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with 1,10-Phenanthroline.Experimental
AclidiniumAclidinium may increase the anticholinergic activities of Anisotropine Methylbromide.Approved
AlfentanilThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Alfentanil.Approved, Illicit
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Alphacetylmethadol.Experimental, Illicit
AmbenoniumThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Ambenonium.Approved
Atracurium besylateThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Atracurium besylate.Approved
AtropineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Atropine.Approved, Vet Approved
BenactyzineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Benactyzine.Withdrawn
BendroflumethiazideThe serum concentration of Bendroflumethiazide can be increased when it is combined with Anisotropine Methylbromide.Approved
BenzatropineThe risk or severity of adverse effects can be increased when Benzatropine is combined with Anisotropine Methylbromide.Approved
BezitramideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Bezitramide.Experimental, Illicit, Withdrawn
BiperidenThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Biperiden.Approved
Botulinum Toxin Type AAnisotropine Methylbromide may increase the anticholinergic activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BAnisotropine Methylbromide may increase the anticholinergic activities of Botulinum Toxin Type B.Approved
BuprenorphineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
ButorphanolThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Butorphanol.Approved, Illicit, Vet Approved
CarfentanilThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Carfentanil.Illicit, Vet Approved
ChlorothiazideThe serum concentration of Chlorothiazide can be increased when it is combined with Anisotropine Methylbromide.Approved, Vet Approved
ChlorphenoxamineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Chlorphenoxamine.Withdrawn
ChlorthalidoneThe serum concentration of Chlorthalidone can be increased when it is combined with Anisotropine Methylbromide.Approved
CimetropiumAnisotropine Methylbromide may increase the anticholinergic activities of Cimetropium.Experimental
CodeineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Codeine.Approved, Illicit
CoumaphosThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Coumaphos.Vet Approved
CyclopentolateThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Cyclopentolate.Approved
DarifenacinThe risk or severity of adverse effects can be increased when Darifenacin is combined with Anisotropine Methylbromide.Approved, Investigational
DecamethoniumThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Decamethonium.Approved
DemecariumThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Demecarium.Approved
DesloratadineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Desloratadine.Approved, Investigational
DexetimideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Dexetimide.Withdrawn
DextromoramideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Dextromoramide.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Dextropropoxyphene.Approved, Illicit, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Dezocine.Approved
DichlorvosThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Dichlorvos.Vet Approved
DicyclomineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Dicyclomine.Approved
DihydrocodeineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Dihydrocodeine.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Dihydroetorphine.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Dihydromorphine.Experimental, Illicit
DiphenoxylateThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Diphenoxylate.Approved, Illicit
DonepezilThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Donepezil.Approved
DPDPEThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with DPDPE.Investigational
DronabinolAnisotropine Methylbromide may increase the tachycardic activities of Dronabinol.Approved, Illicit
EchothiophateThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Echothiophate.Approved
EdrophoniumThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Edrophonium.Approved
EluxadolineAnisotropine Methylbromide may increase the constipating activities of Eluxadoline.Approved
EthopropazineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Anisotropine Methylbromide.Approved
EthylmorphineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Ethylmorphine.Approved, Illicit
EtorphineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Etorphine.Illicit, Vet Approved
FentanylThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FenthionThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Fenthion.Vet Approved
FesoterodineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Fesoterodine.Approved
GalantamineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Galantamine.Approved
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Anisotropine Methylbromide.Approved
Ginkgo bilobaThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Ginkgo biloba.Approved, Nutraceutical
Glucagon recombinantThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Glucagon recombinant.Approved
GlycopyrroniumAnisotropine Methylbromide may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational, Vet Approved
HeroinThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Heroin.Approved, Illicit
HexamethoniumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Hexamethonium.Experimental
HomatropineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Homatropine.Approved
Huperzine AThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Huperzine A.Investigational
HydrochlorothiazideThe serum concentration of Hydrochlorothiazide can be increased when it is combined with Anisotropine Methylbromide.Approved, Vet Approved
HydrocodoneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Hydrocodone.Approved, Illicit
HydroflumethiazideThe serum concentration of Hydroflumethiazide can be increased when it is combined with Anisotropine Methylbromide.Approved
HydromorphoneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Hydromorphone.Approved, Illicit
HyoscyamineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Anisotropine Methylbromide.Approved
IndapamideThe serum concentration of Indapamide can be increased when it is combined with Anisotropine Methylbromide.Approved
Ipratropium bromideThe risk or severity of adverse effects can be increased when Ipratropium bromide is combined with Anisotropine Methylbromide.Approved
IsoflurophateThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Isoflurophate.Approved, Withdrawn
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Anisotropine Methylbromide.Investigational
KetobemidoneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Ketobemidone.Approved
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Levomethadyl Acetate.Approved
LevorphanolThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Levorphanol.Approved
LofentanilThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Lofentanil.Illicit
MalathionThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Malathion.Approved, Investigational
MecamylamineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Mecamylamine.Approved
MefloquineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Mefloquine.Approved
MemantineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Memantine.Approved, Investigational
MethadoneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Methadone.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Methadyl Acetate.Approved, Illicit
Methanesulfonyl FluorideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Methanesulfonyl Fluoride.Investigational
MethanthelineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Methantheline.Approved
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Anisotropine Methylbromide.Approved
MetixeneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Metixene.Approved
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Anisotropine Methylbromide.Approved
MianserinMianserin may increase the anticholinergic activities of Anisotropine Methylbromide.Approved
MinaprineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Minaprine.Approved
MirabegronThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Mirabegron.Approved
MorphineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Morphine.Approved, Investigational
N-butylscopolammonium bromideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with N-butylscopolammonium bromide.Vet Approved
NabiloneAnisotropine Methylbromide may increase the tachycardic activities of Nabilone.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Nalbuphine.Approved
NeostigmineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Neostigmine.Approved, Vet Approved
NormethadoneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Normethadone.Approved, Illicit
NVA237The risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with NVA237.Investigational
OpiumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Opium.Approved, Illicit
OrphenadrineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Orphenadrine.Approved
OxybutyninThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Oxybutynin.Approved, Investigational
OxycodoneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Oxycodone.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Oxymorphone.Approved, Investigational, Vet Approved
OxyphenoniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Anisotropine Methylbromide.Approved
PancuroniumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Pancuronium.Approved
PentazocineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Pentazocine.Approved, Vet Approved
PentoliniumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Pentolinium.Approved
PethidineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Pethidine.Approved
PhysostigmineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Physostigmine.Approved
PipecuroniumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Pipecuronium.Approved
PirenzepineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Pirenzepine.Approved
PiritramideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Piritramide.Investigational
PolythiazideThe serum concentration of Polythiazide can be increased when it is combined with Anisotropine Methylbromide.Approved
Potassium ChlorideAnisotropine Methylbromide may increase the ulcerogenic activities of Potassium Chloride.Approved, Withdrawn
PramlintidePramlintide may increase the anticholinergic activities of Anisotropine Methylbromide.Approved, Investigational
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Anisotropine Methylbromide.Approved
PropanthelineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Propantheline.Approved
PropiverineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Propiverine.Investigational
PyridostigmineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Pyridostigmine.Approved
QuinethazoneThe serum concentration of Quinethazone can be increased when it is combined with Anisotropine Methylbromide.Approved
QuinidineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Quinidine.Approved
RamosetronAnisotropine Methylbromide may increase the constipating activities of Ramosetron.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Remifentanil.Approved
RivastigmineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Rivastigmine.Approved, Investigational
ScopolamineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Scopolamine.Approved
Scopolamine butylbromideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Scopolamine butylbromide.Approved
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Anisotropine Methylbromide.Approved, Investigational
SolifenacinThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Solifenacin.Approved
SufentanilThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Sufentanil.Approved, Investigational
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Anisotropine Methylbromide.Approved
TacrineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Tacrine.Withdrawn
TapentadolThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Tapentadol.Approved
TiotropiumAnisotropine Methylbromide may increase the anticholinergic activities of Tiotropium.Approved
TolterodineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Tolterodine.Approved, Investigational
TopiramateThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Topiramate.Approved
TramadolThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Tramadol.Approved, Investigational
TrichlorfonThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Trichlorfon.Vet Approved
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Anisotropine Methylbromide.Approved, Vet Approved
TrihexyphenidylThe risk or severity of adverse effects can be increased when Trihexyphenidyl is combined with Anisotropine Methylbromide.Approved
TrimethaphanThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Trimethaphan.Approved
TropicamideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Tropicamide.Approved
TrospiumThe risk or severity of adverse effects can be increased when Trospium is combined with Anisotropine Methylbromide.Approved
TubocurarineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Tubocurarine.Approved
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Anisotropine Methylbromide.Approved
VecuroniumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Vecuronium.Approved
Food InteractionsNot Available
References
Synthesis Reference

Weiner, N. and Gordon, S.M.; US. Patent 2,962,499; November 29,1960; assigned to Endo
Laboratories, Inc.

General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7332
Blood Brain Barrier+0.9683
Caco-2 permeable+0.602
P-glycoprotein substrateNon-substrate0.5078
P-glycoprotein inhibitor INon-inhibitor0.6258
P-glycoprotein inhibitor IINon-inhibitor0.8571
Renal organic cation transporterNon-inhibitor0.5586
CYP450 2C9 substrateNon-substrate0.8222
CYP450 2D6 substrateNon-substrate0.7474
CYP450 3A4 substrateSubstrate0.6949
CYP450 1A2 substrateNon-inhibitor0.7455
CYP450 2C9 inhibitorNon-inhibitor0.8657
CYP450 2D6 inhibitorNon-inhibitor0.7622
CYP450 2C19 inhibitorNon-inhibitor0.8572
CYP450 3A4 inhibitorNon-inhibitor0.937
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9752
Ames testNon AMES toxic0.7025
CarcinogenicityNon-carcinogens0.8765
BiodegradationReady biodegradable0.8093
Rat acute toxicity2.6936 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9113
hERG inhibition (predictor II)Non-inhibitor0.7206
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Watson laboratories inc
  • Endo pharmaceuticals inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point329 °CWeiner, N. and Gordon, S.M.; US. Patent 2,962,499; November 29,1960; assigned to Endo Laboratories, Inc.
water solubility1600 mg/LNot Available
logP0.60Not Available
Predicted Properties
PropertyValueSource
Water Solubility9.67e-05 mg/mLALOGPS
logP-0.4ALOGPS
logP-0.67ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity93.26 m3·mol-1ChemAxon
Polarizability34.09 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound 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
  • Fatty acid ester
  • Fatty acyl
  • N-alkylpyrrolidine
  • Piperidine
  • Quaternary ammonium salt
  • Pyrrolidine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic bromide salt
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Bachrach WH: Clinical evaluation of anisotropine methyl bromide (valpin), an anticholinergic drug. Am J Dig Dis. 1972 Jun;17(6):505-12. [PubMed:4555460 ]
  4. Tittor W, Lechmann R, Herrmann HJ, Dincer T, Weckesser G: [Effectiveness of octatropine methylbromide (OMB) in the treatment of gastritis, duodenal ulcer and spastic colon--a double blind study]. ZFA (Stuttgart). 1982 Sep 30;58(27):1481-4. [PubMed:6897316 ]
  5. Pace F, Maurano A, Ciacci C, Savarino V, Attili A, Iaquinto G, Magni E, Porro GB: Octatropine methyl bromide and diazepam combination (Valpinax) in patients with irritable bowel syndrome: a multicentre, randomized, placebo-controlled trial. Eur Rev Med Pharmacol Sci. 2010 Mar;14(3):155-62. [PubMed:20391952 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Bachrach WH: Clinical evaluation of anisotropine methyl bromide (valpin), an anticholinergic drug. Am J Dig Dis. 1972 Jun;17(6):505-12. [PubMed:4555460 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Bachrach WH: Clinical evaluation of anisotropine methyl bromide (valpin), an anticholinergic drug. Am J Dig Dis. 1972 Jun;17(6):505-12. [PubMed:4555460 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23