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ChemicalBook--->CAS DataBase List--->34552-83-5

34552-83-5

34552-83-5 Structure

34552-83-5 Structure
IdentificationMore
[Name]

Loperamide hydrochloride
[CAS]

34552-83-5
[Synonyms]

4-(4-CHLOROPHENYL)-4-HYDROXY-N,N-DIMETHYL-ALPHA,ALPHA-DIPHENYL-1-PIPERIDINBUTYRAMIDE HYDROCHLORIDE
4-(4-CHLOROPHENYL)-4-HYDROXY-N,N-DIMETHYL-ALPHA,ALPHA-DIPHENYL-1-PIPERIDINEBUTANAMIDE HYDROCHLORIDE
4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenylpiperidine-1-butyramide monohydrochloride
4-[P-CHLOROPHENYL]-4-HYDROXY-N,N-DIMETHYL-ALPHA,ALPHA-DIPHENYL-1-PIPERIDINEBUTYRAMIDE HYDROCHLORIDE
LABOTEST-BB LT00134703
LOPERAMIDE HCL
LOPERAMIDE HYDROCHLORIDE
LOSERAMIN
4-(4-(p-chlorophenyl)-4-hydroxy-1-piperidyl)-n,n-dimethyl-2,2-diphenylbutyra
4-(p-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-1-piperidine
blox
butyramidehcl
dissenten
fortasec
imodium
imosec
lopemid
lopemin
loperyl
pj185
[EINECS(EC#)]

252-082-4
[Molecular Formula]

C29H34Cl2N2O2
[MDL Number]

MFCD00058581
[Molecular Weight]

513.5
[MOL File]

34552-83-5.mol
Chemical PropertiesBack Directory
[Appearance]

White Solid
[Melting point ]

223-225°C
[density ]

1.1905 (rough estimate)
[refractive index ]

1.6100 (estimate)
[storage temp. ]

2-8°C
[solubility ]

Slightly soluble in water, freely soluble in ethanol (96 per cent) and in methanol.
[form ]

neat
[pka]

8.66(at 25℃)
[color ]

White to Almost white
[Usage]

Labeled Loperamide, which is used as an antidiarrheal
[Merck ]

5571
[CAS DataBase Reference]

34552-83-5(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

R25:Toxic if swallowed.
[Safety Statements ]

S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

TM4960000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29333990
[Toxicity]

LD50 in mice (mg/kg): 75 s.c.; 28 i.p.; 105 orally; in rats (mg/kg): 185 orally (Niemegeers)
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Originator]

Imodium,Janssen,UK,1975
[Uses]

Ca channel blocker
[Uses]

Labeled Loperamide, which is used as an antidiarrheal
[Uses]

Loperamide hydrochloride is a Ca2+ channel protein inhibitor and MOR activator.
[Definition]

ChEBI: A hydrochloride obtained by combining loperamide with one equivalent of hydrochloric acid. Used for treatment of diarrhoea resulting from gastroenteritis or inflammatory bowel disease.
[Indications]

Loperamide hydrochloride (Imodium) structurally resembles both haloperidol and meperidine. In equal doses, loperamide protects against diarrhea longer than does diphenoxylate. It reduces the daily fecal volume and decreases intestinal fluid and electrolyte loss. Loperamide produces rapid and sustained inhibition of the peristaltic reflex through depression of longitudinal and circular muscle activity.The drug also possesses antisecretory activity, presumably through an effect on intestinal opioid receptors.
[Manufacturing Process]

23.6 parts of 2-oxo-3,3-diphenyl-tetrahydrofuranare melted at 100°C in an oil-bath and gaseous hydrogen bromide is introduced into it during 3 hours. The reaction mixture is cooled and triturated in benzene. The product is filtered off, washed with petroleum ether and dried in an exsiccator, yielding 4-bromo-2,2-diphenylbutyric acid; MP 127.5%.
To a stirred suspension of 16 parts of 4-bromo-2,2-diphenylbutyric acid in 150 parts of chloroform are added dropwise 16 parts of thionyl chloride and the whole is stirred and refluxed for 2 hours. The reaction mixture is evaporated,yielding 4-bromo-2,2-diphenyl-butyrylchloride as a residue.
60 parts of 4-bromo-2,2-diphenylbutyrylchloride are dissolved in 400 parts of toluene and gaseous dimethylamine is introduced slowly into the solution while cooling (temperature is kept at about 0°C). The introduction is ceased when dimethylamine escapes from the cooler, and stirring is continued for 2 hours at ordinary temperature. The precipitated product is filtered off and dissolved in a minimum quantity of water. The product is extracted with chloroform. The extract is dried and evaporated. The residue solidifies on triturating in 4-methyl-2-pentanone. The solid is filtered off and dried, yielding dimethyl -(tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide; MP 169° to 171.5°C.
A mixture of 6.33 parts of 4-(p-chlorophenyl)-4-piperidinol, 8 parts of sodium carbonate, 0.2 part of potassium iodide and 240 parts of 4-methyl-2- pentanone is distilled azeotropically. Then there are added 12.12 parts of dimethyl-(tetrahydro-3,3-diphenyl-2-furylidene)ammonium bromide (from the preceding step) and the whole is stirred and refluxed for about 15 hours. The reaction mixture is filtered hot and the filtrate is evaporated.
The oily residue is dissolved in 2-propanol and to this solution is added an excess of 2-propanol previously saturated with gaseous hydrogen chloride. The whole is evaporated and the oily residue is warmed in diluted hydrochloric acid solution. Upon the addition of toluene, the salt is precipitated. It is filtered off, boiled in acetone, and filtered off again after cooling, yielding 4- (p-chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenylpiperidine-1-butyramide hydrochloride; MP 222.1°C.
[Brand name]

Imodium (Janssen); Imodium (McNeil).
[Therapeutic Function]

Antidiarrheal
[General Description]

Loperamide is an antidiarrheal agent used in controlling acute nonspecific diarrhea and chronic diarrhea associated with inflammatory bowel diseases.
[Biological Activity]

High affinity μ -opioid receptor agonist with peripheral selectivity (K i values are 2, 48 and 1156 nM for μ -, δ - and κ -opioid receptors respectively). Antidiarrhoeal and antihyperalgesic agent. Also a Ca 2+ channel blocker; at low micromolar concentrations it blocks broad spectrum neuronal HVA Ca 2+ channels and at higher concentrations it reduces Ca 2+ flux through NMDA receptor operated channels.
[Biochem/physiol Actions]

Loperamide hydrochloride (HCl) is a non-selective Ca2+ channel blocker. At nanomolar concentrations, it binds to μ-opioid receptors. Loperamide HCl does not cross the blood-brain barrier.
[Mechanism of action]

Loperamide also is a potent inhibitor of intestinal CYP3A4, increasing the intestinal absorption of other CYP3A4 substrates. The clinically significant drug interactions of loperamide with coadministered CYP3A4 and CYP2C8 substrates or inhibitors would be limited, however, because of its two metabolic pathways.
[Pharmacokinetics]

Loperamide is marketed as capsules (2 mg) and liquid (1 mg/5 mL) preparations. The recommended dose is 4 mg initially and an additional 2 mg following each diarrheal stool. The dose should not exceed 16 mg/day. It is too lipophilic to dissolve in water for an intravenous dosage form, a property that limits its abuse potential. The compound is highly lipophilic and undergoes slow dissolution, thus limiting the bioavailability of the agent to approximately 40% of the dose. Its low oral bioavailability also can be attributed to first-pass metabolism by both CYP2C8 and CYP3A4 to its primary N-demethyl metabolite. Peak plasma levels are reached in approximately 5 hours, with an elimination half-life of approximately 11 hours. Approximately 1% of the dose is excreted into the urine unchanged.
[Clinical Use]

Loperamide is effective against a wide range of secretory stimuli and can be used in the control and symptomatic relief of acute diarrhea that is not secondary to bacterial infection.
[Side effects]

Adverse effects associated with its use include abdominal pain and distention, constipation, dry mouth, hypersensitivity, and nausea and vomiting.
[storage]

Room temperature
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

34552-83-5(sigmaaldrich)
[TCI AMERICA]

Loperamide Hydrochloride,>98.0%(LC)(T)(34552-83-5)
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