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Loperamide hydrochloride

Loperamide hydrochloride
Loperamide hydrochloride structure
CAS No.
34552-83-5
Chemical Name:
Loperamide hydrochloride
Synonyms
blox;pj185;imosec;Imosse;r18553;Clalet;imodium;Imossel;lopemid;lopemin
CBNumber:
CB8758181
Molecular Formula:
C29H34Cl2N2O2
Formula Weight:
513.5
MOL File:
34552-83-5.mol

Loperamide hydrochloride Properties

Melting point:
223-225°C
Density 
1.1905 (rough estimate)
refractive index 
1.6100 (estimate)
storage temp. 
Store at RT
solubility 
Slightly soluble in water, freely soluble in ethanol (96 per cent) and in methanol.
form 
neat
pka
8.66(at 25℃)
Merck 
14,5571
CAS DataBase Reference
34552-83-5(CAS DataBase Reference)
FDA UNII
77TI35393C
NCI Dictionary of Cancer Terms
Imodium; loperamide hydrochloride
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310a-P321-P405-P501a-P301+P310
Hazard Codes  T
Risk Statements  25
Safety Statements  45
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)

Loperamide hydrochloride price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 34014 Loperamide hydrochloride VETRANAL , analytical standard 34552-83-5 100mg-r $44.5 2020-08-18 Buy
Sigma-Aldrich 34014 Loperamide hydrochloride VETRANAL?, analytical standard 100 mg $45.9 2021-03-22 Buy
Sigma-Aldrich L0750000 Loperamide hydrochloride European Pharmacopoeia (EP) Reference Standard $190 2021-03-22 Buy
Sigma-Aldrich 1370000 Loperamide hydrochloride United States Pharmacopeia (USP) Reference Standard 34552-83-5 200mg $366 2020-08-18 Buy
TCI Chemical L0154 Loperamide Hydrochloride >98.0%(T)(HPLC) 34552-83-5 5g $83 2021-03-22 Buy

Loperamide hydrochloride Chemical Properties,Uses,Production

Chemical Properties

White Solid

Originator

Imodium,Janssen,UK,1975

Uses

Labeled Loperamide, which is used as an antidiarrheal

Uses

Ca channel blocker

Uses

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

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.

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.

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

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.

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.

Loperamide hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products


Loperamide hydrochloride Suppliers

Global( 312)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan DaKen Chemical CO.,LTD.
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Henan Tianfu Chemical Co.,Ltd.
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BOC Sciences
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1-631-614-7828 inquiry@bocsci.com United States 19906 58
CONIER CHEM AND PHARMA LIMITED
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career henan chemical co
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0086-371-86658258 factory@coreychem.com CHINA 29867 58

View Lastest Price from Loperamide hydrochloride manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2020-10-29 Loperamide hydrochloride
34552-83-5
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-06-05 Loperamide hydrochloride
34552-83-5
US $560.00 / KG 1KG 98% 1-500kg Baoji Guokang Bio-Technology Co., Ltd.
2021-06-04 Loperamide hydrochloride
34552-83-5
US $714.00 / KG 1Kg/Bag 99% 1000kg Baoji Guokang Bio-Technology Co., Ltd.

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