U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H32NO2.Br
Molecular Weight 362.3457
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANISOTROPINE METHYLBROMIDE

SMILES

CCCC(CCC)C(=O)O[C@]1([H])C[C@]2([H])CC[C@]([H])(C1)[N+]2(C)C.[Br-]

InChI

InChIKey=QSFKGMJOKUZAJM-CNKDKAJDSA-M
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/t14-,15+,16+;

HIDE SMILES / InChI

Molecular Formula C17H32NO2
Molecular Weight 282.4421
Charge 1
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula BrH
Molecular Weight 80.9115
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Methyl anisotropinium (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 Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents.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. Methyl anisotropinium inhibits 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. It is used 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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Valpin

Approved Use

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.

Launch Date

-2.24294404E11
Doses

Doses

DosePopulationAdverse events​
120 mg single, oral
Highest studied dose
Dose: 120 mg
Route: oral
Route: single
Dose: 120 mg
Sources:
healthy, 21-45 years
n = 12
Health Status: healthy
Age Group: 21-45 years
Sex: M
Population Size: 12
Sources:
Other AEs: Blurred vision, Sleepy...
Other AEs:
Blurred vision (3 patients)
Sleepy (1 patient)
Dry mouth (5 patients)
Chest pain (1 patient)
Sneezing (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Chest pain 1 patient
120 mg single, oral
Highest studied dose
Dose: 120 mg
Route: oral
Route: single
Dose: 120 mg
Sources:
healthy, 21-45 years
n = 12
Health Status: healthy
Age Group: 21-45 years
Sex: M
Population Size: 12
Sources:
Sleepy 1 patient
120 mg single, oral
Highest studied dose
Dose: 120 mg
Route: oral
Route: single
Dose: 120 mg
Sources:
healthy, 21-45 years
n = 12
Health Status: healthy
Age Group: 21-45 years
Sex: M
Population Size: 12
Sources:
Sneezing 1 patient
120 mg single, oral
Highest studied dose
Dose: 120 mg
Route: oral
Route: single
Dose: 120 mg
Sources:
healthy, 21-45 years
n = 12
Health Status: healthy
Age Group: 21-45 years
Sex: M
Population Size: 12
Sources:
Blurred vision 3 patients
120 mg single, oral
Highest studied dose
Dose: 120 mg
Route: oral
Route: single
Dose: 120 mg
Sources:
healthy, 21-45 years
n = 12
Health Status: healthy
Age Group: 21-45 years
Sex: M
Population Size: 12
Sources:
Dry mouth 5 patients
120 mg single, oral
Highest studied dose
Dose: 120 mg
Route: oral
Route: single
Dose: 120 mg
Sources:
healthy, 21-45 years
n = 12
Health Status: healthy
Age Group: 21-45 years
Sex: M
Population Size: 12
Sources:
PubMed

PubMed

TitleDatePubMed
Clinical evaluation of anisotropine methyl bromide (valpin), an anticholinergic drug.
1972 Jun
Diazepam and octatropine-methyl-bromide interaction: protecting activity in experimental gastric-mucosal damage.
1980 Apr
[Effectiveness of octatropine methylbromide (OMB) in the treatment of gastritis, duodenal ulcer and spastic colon--a double blind study].
1982 Sep 30
Octatropine-methyl-bromide and sulglycotide salt in the short-term treatment of active duodenal ulcer. A double blind endoscopic study of 40 outpatients.
1989
Patents

Sample Use Guides

Oral route a) As an adjunct in the treatment of PEPTIC ULCER DISEASE, the recommended oral dose of anisotropine methylbromide is 50 milligrams 3 times daily; the dose should be adjusted according to therapeutic response (Prod Info Valpin 50(R), 1993). b) In the treatment of VISCERAL SPASMS the oral dose of anisotropine methylbromide is 10 milligrams 3 to 4 times daily
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 04:43:37 UTC 2021
Edited
by admin
on Sat Jun 26 04:43:37 UTC 2021
Record UNII
62M960DHIL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANISOTROPINE METHYLBROMIDE
HSDB   MI   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
8-METHYLTROPINIUM BROMIDE 2-PROPYLPENTANOATE
Common Name English
METHYLOCTATROPINE BROMIDE
JAN  
Common Name English
OCTATROPINE METHYLBROMIDE [INN]
Common Name English
VALPIN 50
Brand Name English
VALPIN
Brand Name English
ANISOTROPINE METHYLBROMIDE [HSDB]
Common Name English
3.ALPHA.-HYDROXY-8-METHYL-1.ALPHA.H,5.ALPHA.H-TROPANIUM BROMIDE 2-PROPYLVALERATE
Common Name English
ANISOTROPINE METHYLBROMIDE [ORANGE BOOK]
Common Name English
8-AZONIABICYCLO(3.2.1)OCTANE, 8,8-DIMETHYL-3-((1-OXO-2-PROPYLPENTYL)OXY)-, BROMIDE, ENDO-
Common Name English
OCTATROPINE METHYLBROMIDE
INN   MART.   WHO-DD  
INN  
Official Name English
OCTATROPINE METHYLBROMIDE [WHO-DD]
Common Name English
ANISOTROPINE METHYLBROMIDE [USAN]
Common Name English
OCTOTROPINE METHYLBROMIDE
Common Name English
METHYLOCTATROPINE BROMIDE [JAN]
Common Name English
OCTATROPINE METHYLBROMIDE [MART.]
Common Name English
ANISOTROPINE METHYLBROMIDE [MI]
Common Name English
ANISOTROPINE METHYLBROMIDE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
Code System Code Type Description
INN
913
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL1186610
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
EVMPD
SUB09408MIG
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
RXCUI
17945
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
223
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
FDA UNII
62M960DHIL
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
HSDB
3010
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
WIKIPEDIA
OCTATROPINE METHYLBROMIDE
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
DRUG BANK
DB00517
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-285-6
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
CAS
80-50-2
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
MERCK INDEX
M1010
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY Merck Index
EPA CompTox
80-50-2
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
NCI_THESAURUS
C65237
Created by admin on Sat Jun 26 04:43:37 UTC 2021 , Edited by admin on Sat Jun 26 04:43:37 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY