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Chemistry

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Also known as: Anisotropine methobromide, Anisotropine methyl bromide, 80-50-2, 8-methyltropinium bromide 2-propylvalerate, Anisotropine (methobromide), [(1r,5s)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl] 2-propylpentanoate;bromide
Molecular Formula
C17H32BrNO2
Molecular Weight
362.3  g/mol
InChI Key
QSFKGMJOKUZAJM-UHFFFAOYSA-M

SCHEMBL892570
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 Its use as treatment adjunct in peptic ulcer has been replaced by the use of more effective agents.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.
1 2D Structure

SCHEMBL892570

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl) 2-propylpentanoate;bromide
2.1.2 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
2.1.3 InChI Key
QSFKGMJOKUZAJM-UHFFFAOYSA-M
2.1.4 Canonical SMILES
CCCC(CCC)C(=O)OC1CC2CCC(C1)[N+]2(C)C.[Br-]
2.2 Synonyms
2.2.1 Depositor-Supplied Synonyms

1. Anisotropine Methobromide

2. Anisotropine Methyl Bromide

3. 80-50-2

4. 8-methyltropinium Bromide 2-propylvalerate

5. Anisotropine (methobromide)

6. [(1r,5s)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl] 2-propylpentanoate;bromide

7. Endovalpin

8. Anisotropine Methylbromide; Lytispasm; Octatropine Methylbromide; Valpin; Valpin 50; Vapin

9. Endo-8,8-dimethyl-3-((1-oxo-2-propylpentyl)oxy)-8-azoniabicyclo(3.2.1)octane Bromide

10. Octatropini Methylbromidum

11. 8-methyltropinium Bromide 2-propylpentanoate

12. Methylbromure D'octatropine

13. Metilbromuro De Octatropina

14. Schembl892570

15. Chebi:2739

16. Hms3261a20

17. Hms3371o22

18. Tox21_500409

19. Ccg-221713

20. Db00517

21. Lp00409

22. Ncgc00261094-01

23. Ft-0772217

24. 8,8-dimethyl-3-[(2-propylpentanoyl)oxy]-8-azoniabicyclo[3.2.1]octane Bromide

2.3 Create Date
2007-12-05
3 Chemical and Physical Properties
Molecular Weight 362.3 g/mol
Molecular Formula C17H32BrNO2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count7
Exact Mass361.16164 g/mol
Monoisotopic Mass361.16164 g/mol
Topological Polar Surface Area26.3 Ų
Heavy Atom Count21
Formal Charge0
Complexity318
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Parasympatholytics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


...ANTIMUSCARINIC DRUG. IT APPEARS TO BE RELATIVELY SELECTIVE FOR GI TRACT... IT IS USED IN TREATMENT OF MUCOUS COLITIS & IRRITABLE COLON, SPASTIC COLITIS, SPLENIC FLEXURE SYNDROME, BILIARY DYSKINESIA, CHOLELITHIASIS, PYLOROSPASM, GASTRITIS, DUODENITIS, ENTEROCOLITIS, & PEPTIC ULCER.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 849


VALPIN 50-PB INDICATED FOR USE AS ADJUNCTIVE THERAPY IN PEPTIC ULCER; IRRITABLE BOWEL SYNDROME (IRRITABLE COLON, SPASTIC COLON, MUCOUS COLITIS, ACUTE ENTEROCOLITIS, & FUNCTIONAL GI DISORDERS).

PDR; 33RD EDITION, 1979, MEDICAL ECONOMICS CO, LITTON INDUST, ORADELL, NJ 07649, 871-872


VALPIN 50-PB EFFECTIVELY PRODUCES VISCERAL SMOOTH MUSCLE RELAXATION. CONTROLS SMOOTH MUSCLE SPASM SEEN IN MOTILITY DISORDERS OF GI TRACT, SUCH AS SPASTIC COLON & FUNCTIONAL GI DISORDERS.

PDR; 33RD EDITION, 1979. MEDICAL ECONOMICS CO, LITTON INDUST, ORADELL, NJ 07649, 871-872


For more Therapeutic Uses (Complete) data for ANISOTROPINE METHYLBROMIDE (11 total), please visit the HSDB record page.


4.2 Drug Warning

ALTHOUGH INCIDENCE & INTENSITY OF SIDE EFFECTS IS LESS THAN THOSE OF METHANTHELINE BROMIDE, THEY ARE QUALITATIVELY SAME.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 849


...NO DRUG OF THIS CLASS HAS YET BEEN SHOWN TO PRODUCE ADEQUATE CONTROL OF GASTRIC SECRETION OR GI MOTILITY @ DOSES THAT ARE DEVOID OF SIGNIFICANT SIDE EFFECTS DUE TO MUSCARINIC BLOCKADE @ OTHER SITES. /QUATERNARY AMMONIUM CMPD/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 158


...USED WITH GREAT CAUTION, & IN SOME CASES MAY BE CONTRAINDICATED, IN PATIENTS WITH REFLUX ESOPHAGITIS, ACHALASIA, PARTIAL GASTRIC OUTLET OBSTRUCTION, PARALYTIC ILEUS, INTESTINAL OBSTRUCTION, NARROW ANGLE GLAUCOMA, & PROSTATISM. /ANTISPASMODICS/

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 1041


ANTICHOLINERGIC ANTISPASMODICS SHOULD BE USED WITH CAUTION IN PATIENTS WITH PROSTATIC HYPERTROPHY, PYLORIC OBSTRUCTION, OBSTRUCTION OF BLADDER NECK, CONGESTIVE HEART FAILURE WITH TACHYCARDIA, & ACHALASIA (CARDIOSPASM). /ANTICHOLINERGIC AGENTS/

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 935


For more Drug Warnings (Complete) data for ANISOTROPINE METHYLBROMIDE (11 total), please visit the HSDB record page.


4.3 Drug 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.


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 Absorption, Distribution and Excretion

Absorption

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


...POORLY & UNRELIABLY ABSORBED AFTER ORAL ADMIN... PENETRATION OF CONJUNCTIVA IS ALSO POOR, SO THAT...CMPD ARE OF LITTLE VALUE IN OPHTHALMOLOGY. CENTRAL EFFECTS ARE GENERALLY LACKING, BECAUSE THESE AGENTS DO NOT READILY PASS BLOOD-BRAIN BARRIER. ...LITTLE...KNOWN OF FATE & EXCRETION... /QUATERNARY AMMONIUM CMPD/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 158


WHOLE-BODY AUTORADIOGRAPHY OF MICE GIVEN SC, ORAL, OR IP DOSES OF ANTISPASMODIC, [(14)C]ANISOTROPINE METHBROMIDE SHOWED THAT PARENTERAL DOSES WERE DISTRIBUTED MAINLY IN EXCRETORY ORGANS (KIDNEYS, LIVER, SALIVARY GLANDS, & INTESTINES).

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 123


SOME (14)C /ANISOTROPINE METHBROMIDE/ WAS...PRESENT IN STOMACH MUCOSA, PANCREAS, OVIDUCTS, UTERUS, & SPERMATIC DUCTS /AFTER ADMIN TO MICE/. CATION WOULD NOT BE EXPECTED TO DIFFUSE EASILY ACROSS BIOLOGICAL MEMBRANES...DID NOT APPEAR READILY TO CROSS BLOOD-BRAIN OR PLACENTAL BARRIERS, OR GASTROINTESTINAL EPITHELIUM.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 123


5.3 Metabolism/Metabolites

Hepatic, by enzymatic hydrolysis.


5.4 Biological Half-Life

Not Known


5.5 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.


THERE IS CLINICAL IMPRESSION THAT QUATERNARY AMMONIUM CMPD HAVE RELATIVELY GREATER EFFECT ON GASTROINTESTINAL ACTIVITY & THAT DOSES NECESSARY TO TREAT GASTROINTESTINAL DISORDERS ARE, CONSEQUENTLY...MORE READILY TOLERATED; THIS HAS BEEN ATTRIBUTED TO ADDITIONAL ELEMENT OF GANGLIONIC BLOCK. /QUATERNARY AMMONIUM CMPD/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 158-9


RATIO OF GANGLIONIC BLOCKING TO ANTIMUSCARINIC ACTIVITY IS GREATER FOR CMPD WITH QUATERNARY AMMONIUM STRUCTURE BECAUSE OF THEIR GREATER POTENCY AT NICOTINIC RECEPTORS; SOME OF SIDE EFFECTS SEEN AFTER HIGH DOSES ARE DUE TO GANGLIONIC BLOCKADE. /QUATERNARY AMMONIUM CMPD/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 159


ANTISPASMODICS ARE COMPETITIVE ANTAGONISTS OF ACETYLCHOLINE, WHICH IS RELEASED @ ENDINGS OF PARASYMPATHETIC NERVES SUPPLYING GI TRACT. ...THESE DRUGS CAUSE MEAN REDUCTION OF BASAL ACID OUTPUT OF ABOUT 50%. THEY ALSO REDUCE MAXIMAL ACID OUTPUT BY 15 TO 50%. /ANTISPASMODICS/

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 1039


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API | Excipient name

SCHEMBL892570

Synonyms

Anisotropine methobromide, Anisotropine methyl bromide, 80-50-2, 8-methyltropinium bromide 2-propylvalerate, Anisotropine (methobromide), [(1r,5s)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl] 2-propylpentanoate;bromide

Cas Number

80-50-2

About SCHEMBL892570

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.

SCHEMBL892570 Manufacturers

A SCHEMBL892570 manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of SCHEMBL892570, including repackagers and relabelers. The FDA regulates SCHEMBL892570 manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. SCHEMBL892570 API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

SCHEMBL892570 Suppliers

A SCHEMBL892570 supplier is an individual or a company that provides SCHEMBL892570 active pharmaceutical ingredient (API) or SCHEMBL892570 finished formulations upon request. The SCHEMBL892570 suppliers may include SCHEMBL892570 API manufacturers, exporters, distributors and traders.

SCHEMBL892570 GMP

SCHEMBL892570 Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of SCHEMBL892570 GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right SCHEMBL892570 GMP manufacturer or SCHEMBL892570 GMP API supplier for your needs.

SCHEMBL892570 CoA

A SCHEMBL892570 CoA (Certificate of Analysis) is a formal document that attests to SCHEMBL892570's compliance with SCHEMBL892570 specifications and serves as a tool for batch-level quality control.

SCHEMBL892570 CoA mostly includes findings from lab analyses of a specific batch. For each SCHEMBL892570 CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

SCHEMBL892570 may be tested according to a variety of international standards, such as European Pharmacopoeia (SCHEMBL892570 EP), SCHEMBL892570 JP (Japanese Pharmacopeia) and the US Pharmacopoeia (SCHEMBL892570 USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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