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Home > Encyclopedia > Anisotropine methylbromide

Anisotropine methylbromide

pharmaceutical raw materials
Anisotropine methylbromide structure

Anisotropine methylbromide 

structure
  • CAS No:

    80-50-2

  • Formula:

    C17H32NO2.Br

  • Chemical Name:

    Anisotropine methylbromide

  • Synonyms:

    8-Azoniabicyclo[3.2.1]octane,8,8-dimethyl-3-[(1-oxo-2-propylpentyl)oxy]-,bromide,(3-endo)-;1αH,5αH-Tropanium,3α-hydroxy-8-methyl-,bromide,2-propylvalerate;8-Azoniabicyclo[3.2.1]octane,8,8-dimethyl-3-[(1-oxo-2-propylpentyl)oxy]-,bromide,endo-;8-Methyltropinium bromide,2-propylvalerate;8-Methyltropinium bromide 2-propylpentanoate;Octatropine methylbromide;Valpin;Anisotropine methobromide;Anisotropine methylbromide;8-Methyl-3-(2-propylpentanoyloxy)tropinium bromide;Lytispasm;Vapin;Valpin 50

  • Categories:

    Natural Products  >  Alkaloids

Description

ChEBI: A quaternary ammonium salt resulting from the reaction of the amino group of anisotropine with methyl bromide.

Anisotropine methylbromide Basic Attributes

362.35

525.29400

201-285-6

DTXSID8022612

CRYSTALS FROM ACETONE|WHITE, GLISTENING POWDER OR PLATES

Characteristics

174.31000

329 °C

>54.4 [ug/mL]

2-8°C

PROBABLY ODORLESS

BITTER TASTE

Safety Information

UN30779/PG3

3

20/21/22-50/53

36-61-60

YM3710000

Xn,N

STABILITY BOTH TO ACID & ALKALINE HYDROLYSIS MIMIMIZES INACTIVATION.

P273-P280

H302-H312-H332-H400

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P391, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

RATE OF ABSORPTION OF ANISOTROPINE METHYL BROMIDE IS REDUCED BY FOOD IN RAT, & THERE IS EVIDENCE OF SATURABLE PROCESS, INFLUENCING INTESTINAL ABSORPTION OF THIS CMPD.|...ANTICHOLINERGIC AGENTS, SUCH AS ANISOTROPINE...WOULD BE EXPECTED TO INTERACT WITH DIGOXIN.../MAY CAUSE INCR SERUM DIGOXIN LEVELS/. /ANISOTROPINE/|DIAZEPAM & OCTATROPINE METHYLBROMIDE INTERACTED POS IN REDUCING SPONTANEOUS & STIMULATED GI MOTILITY IN ISOLATED RABBIT JEJUNUM & IN VIVO IN RABBIT COLON & DOG GASTRIC POUCH.|Urinary excretion of anticholinergics may be delayed by the alkalinization of the urine, /with the use of urinary alkalizers such as: calcium- and/or magnesium-containing antacids, carbonic anhydrase inhibitors, citrates, sodium bicarbonate/ thus potentiating the anticholinergics' therapeutic and/or side effects. /Anticholinergics, antispasmodics/|For more Interactions (Complete) data for ANISOTROPINE METHYLBROMIDE (13 total), please visit the HSDB record page.

Drug Information

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

ALTHOUGH INCIDENCE & INTENSITY OF SIDE EFFECTS IS LESS THAN THOSE OF METHANTHELINE BROMIDE, THEY ARE QUALITATIVELY SAME.|...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/|...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/|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/|For more Drug Warnings (Complete) data for ANISOTROPINE METHYLBROMIDE (11 total), please visit the HSDB record page.

...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/|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).|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.

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/|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/|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/

...SOME OF SIDE EFFECTS SEEN AFTER HIGH DOSES ARE DUE TO GANGLIONIC BLOCKADE. ... TOXIC DOSES...PRODUCE...USUAL MANIFESTATIONS OF ANTIMUSCARINIC POISONING WITH ADDNL EFFECTS OF GANGLIONIC & RARELY, NEUROMUSCULAR BLOCK, BUT USUALLY WITHOUT SIGNIFICANT CNS INVOLVEMENT. /QUATERNARY AMMONIUM CMPD/|TOXIC DOSES MAY PRODUCE...BURNING SENSATION /OF MOUTH/, DYSPHAGIA, THIRST... FLUSHING IN THE BLUSH AREA, FEVER, LEUKOCYTOSIS, RASH, NAUSEA, VOMITING, TACHYCARDIA, HYPOTENSION OR HYPERTENSION. ILEUS OR TOXIC MEGACOLON HAS BEEN REPORTED WHEN...USED IN SOME PATIENTS WITH SEVERE FORMS OF INFLAMMATORY ISCHEMIC OR AMEBIC BOWEL DISORDERS. /ANTICHOLINERGIC AGENTS/|...UNTOWARD EFFECTS ASSOC WITH USE OF ANTICHOLINERGIC...ANHIDROSIS, MYDRIASIS, CYCLOPLEGIA, TACHYCARDIA...DYSURIA, & ACUTE URINARY RETENTION... DERMATOLOGIC REACTIONS... TOLERANCE DEVELOPS TO MANY OF THESE REACTIONS...BUT THIS ADJUSTMENT MAY BE ACCOMPANIED BY DECR...EFFECTIVENESS. /ANTICHOLINERGIC AGENTS/|ANTICHOLINERGIC/ANTISPASMODIC DRUGS MAY PRODUCE ALLERGIC REACTION OR DRUG IDIOSYNCRASIES INCL ANAPHYLAXIS & URTICARIA; SOME DEGREE OF MENTAL CONFUSION &/OR EXCITEMENT ESP IN ELDERLY PERSONS. DECR SWEATING IS ANOTHER ADVERSE REACTION.|For more Human Toxicity Excerpts (Complete) data for ANISOTROPINE METHYLBROMIDE (9 total), please visit the HSDB record page.

Anisotropine methylbromide Use and Manufacturing

Methods of Manufacturing

ESTERIFICATION OF TROPINE WITH 2-PROPYLVALERYL CHLORIDE, THEN QUATERNIZATION OF THE RESULTING ESTER WITH METHYL BROMIDE.|Weiner, Gordon, US Patent 2,962,499 (1960 to Endo Labs)

Uses

Anisotropine Methylbromide is a antichloindergic agent and has been used for relief of gastrointestinal spasm and for the suppression of gastric acid secretion. Anisotropine Methylbromide was found to be potentially useful in the treatment of duodenal ulcer disease.

Production

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS

ESSENTIALLY 100% AS AN ANTICHOLINERGIC

TABLETS: 10 MG; ELIXIR: 2 MG/ML, 10 MG.|VALPIN (TRADEMARK) 50-PB (ANISOTROPINE METHYLBROMIDE 50 MG WITH PHENOBARBITAL 15 MG).

ANISOTROPINE METHYLBROMIDE, DIFFERS CHEMICALLY FROM ATROPINE & MOST OTHER ANTICHOLINERGICS/ANTISPASMODICS IN SUBSTITUTION OF ALIPHATIC FOR AROMATIC SIDE CHAIN IN ACID MOIETY OF ESTER.

Computed Properties

Molecular Weight:362.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:7
Exact Mass:361.16164
Monoisotopic Mass:361.16164
Topological Polar Surface Area:26.3
Heavy Atom Count:21
Complexity:318
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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