Anisotropine Methylbromide

Identification

Name
Anisotropine Methylbromide
Accession Number
DB00517  (APRD00800)
Type
Small Molecule
Groups
Approved
Description

Anisotropine 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 Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents.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
International/Other Brands
Endovalpin / Lytispasm / Valpin (Endo)
Categories
UNII
62M960DHIL
CAS number
80-50-2
Weight
Average: 362.345
Monoisotopic: 361.16164192
Chemical Formula
C17H32BrNO2
InChI Key
QSFKGMJOKUZAJM-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

Indication

For 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
Pharmacodynamics

Anisotropine 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 Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents.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 action

Quaternary 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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Human
AMuscarinic acetylcholine receptor M2
antagonist
Human
AMuscarinic acetylcholine receptor M3
antagonist
Human
Absorption

Gastrointestinal absorption is poor and irregular. Total absorption after an oral dose is about 10 to 25%.

Volume of distribution
Not Available
Protein binding

Not Known

Metabolism

Hepatic, by enzymatic hydrolysis.

Route of elimination
Not Available
Half life

Not Known

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not 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
AlcuroniumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Alcuronium.Experimental
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
AlphaprodineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Alphaprodine.Illicit
AmbenoniumThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Ambenonium.Approved
AtracuriumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Atracurium.Experimental
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 Atropine is combined with Anisotropine Methylbromide.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 Biperiden is combined with Anisotropine Methylbromide.Approved
BornaprineThe risk or severity of adverse effects can be increased when Bornaprine is combined with Anisotropine Methylbromide.Experimental
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
CyclopenthiazideThe serum concentration of Cyclopenthiazide can be increased when it is combined with Anisotropine Methylbromide.Experimental
CyclopentolateThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Anisotropine Methylbromide.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 Dexetimide is combined with Anisotropine Methylbromide.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
DistigmineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Distigmine.Experimental
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
EmeproniumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Emepronium.Experimental
EtanautineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Etanautine.Experimental
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
EtybenzatropineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Etybenzatropine.Experimental
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
GallamineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Gallamine.Experimental
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
IpidacrineThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Ipidacrine.Experimental
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
MazaticolThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Mazaticol.Experimental
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
MeptazinolThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Meptazinol.Experimental
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
Methyl salicylateThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Methyl salicylate.Approved, Vet Approved
MetixeneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Metixene.Approved
MetoclopramideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Metoclopramide.Approved, Investigational
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
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
NicomorphineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Nicomorphine.Experimental
NormethadoneThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Normethadone.Approved, Illicit
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 Orphenadrine is combined with Anisotropine Methylbromide.Approved
OtiloniumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Otilonium.Experimental
OxitropiumThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Oxitropium.Investigational
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
ParaoxonThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Paraoxon.Experimental
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
PhenazocineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Phenazocine.Experimental
PhenglutarimideThe risk or severity of adverse effects can be increased when Phenglutarimide is combined with Anisotropine Methylbromide.Experimental
PhenoperidineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Phenoperidine.Experimental
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 Scopolamine is combined with Anisotropine Methylbromide.Approved
Scopolamine butylbromideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Scopolamine butylbromide.Approved, Vet 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
TilidineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Tilidine.Experimental
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
TropatepineThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Tropatepine.Experimental
TropicamideThe risk or severity of adverse effects can be increased when Tropicamide is combined with Anisotropine Methylbromide.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 Interactions
Not Available

References

Synthesis Reference

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

General References
Not Available
External Links
Human Metabolome Database
HMDB14658
KEGG Drug
D00232
KEGG Compound
C06830
PubChem Compound
21867154
PubChem Substance
46504810
ChemSpider
10611962
ChEBI
2739
ChEMBL
CHEMBL1578
Therapeutic Targets Database
DAP000837
PharmGKB
PA164754880
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Watson laboratories inc
  • Endo pharmaceuticals inc
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)329 °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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Tropane alkaloids
Sub Class
Not Available
Direct Parent
Tropane alkaloids
Alternative Parents
Fatty acid esters / Piperidines / N-alkylpyrrolidines / Tetraalkylammonium salts / Carboxylic acid esters / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Organic bromide salts
show 3 more
Substituents
Tropane alkaloid / Fatty acid ester / Piperidine / N-alkylpyrrolidine / Fatty acyl / Pyrrolidine / Tetraalkylammonium salt / Quaternary ammonium salt / Carboxylic acid ester / Carboxylic acid derivative
show 15 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
quaternary ammonium salt, organic bromide salt (CHEBI:2739)

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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
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...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
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...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
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]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:38