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Loperamide hydrochloride

CAS No.
34552-83-5
Chemical Name:
Loperamide hydrochloride
Synonyms
LOPERAMIDE HCL;suprasec;imodium;blox;pj185;imosec;Imosse;r18553;Clalet;Imossel
CBNumber:
CB8758181
Molecular Formula:
C29H34Cl2N2O2
Molecular Weight:
513.5
MDL Number:
MFCD00058581
MOL File:
34552-83-5.mol
MSDS File:
SDS
Modify Date:2022-08-15 17:38:20

Loperamide hydrochloride Properties

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℃)
Merck 14,5571
CAS DataBase Reference 34552-83-5(CAS DataBase Reference)
FDA UNII 77TI35393C
NCI Dictionary of Cancer Terms Imodium; loperamide hydrochloride
NCI Drug Dictionary Imodium A-D

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P301+P330+P331+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(34)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich BP635 Loperamide hydrochloride British Pharmacopoeia (BP) Reference Standard 34552-83-5 100MG $240 2022-05-15 Buy
Sigma-Aldrich 5.08162 Loperamide Hydrochloride - CAS 34552-83-5 - Calbiochem 34552-83-5 1g $101 2022-05-15 Buy
Sigma-Aldrich 34014 Loperamide hydrochloride VETRANAL?, analytical standard 34552-83-5 100mg $52.1 2022-05-15 Buy
Sigma-Aldrich 1370000 Loperamide hydrochloride United States Pharmacopeia (USP) Reference Standard 34552-83-5 200mg $400 2022-05-15 Buy
TCI Chemical L0154 Loperamide Hydrochloride >98.0%(T)(HPLC) 34552-83-5 5g $87 2022-04-27 Buy
Product number Packaging Price Buy
BP635 100MG $240 Buy
5.08162 1g $101 Buy
34014 100mg $52.1 Buy
1370000 200mg $400 Buy
L0154 5g $87 Buy

Loperamide hydrochloride Chemical Properties,Uses,Production

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.

Loperamide hydrochloride Preparation Products And Raw materials

Global( 509)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Zhanyao Biotechnology Co. Ltd
15369953316 +8615369953316 admin@zhanyaobio.com China 2152 58
Shanghai Biolang Biotechnology Co., Ltd.
+86-15970428662 +86-13397199602 Niky@biolang.cn China 519 58
APOLLO HEALTHCARE RESOURCES
+6596580999 sales@apollo-healthcare.com.sg Singapore 312 58
Henan DaKen Chemical CO.,LTD.
+86-371-66670886 info@dakenchem.com China 16708 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 22021 55
ATK CHEMICAL COMPANY LIMITED
21-51619050 ivan@atkchemical.com China 30656 60
Shanxi Naipu Import and Export Co.,Ltd
+86-13734021967 +8613734021967 kaia@neputrading.com China 1011 58
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3623 58
HEBEI YINGONG NEW MATERIAL TECHNOLOGY CO.,LTD
+86-86-18903210395 +86-19930599843 cindy@hbyingong.com China 755 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254 linda@hubeijusheng.com CHINA 28229 58

View Lastest Price from Loperamide hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2022-08-18 Loperamide Hydrochloride
34552-83-5
US $20.00 / kg 1kg 99% 5000 Ton Hebei Duling International Trade Co. LTD
2022-07-16 Loperamide Hydrochloride
34552-83-5
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
2022-07-08 Loperamide hydrochloride
34552-83-5
US $1.00 / mg 100mg 98.0% 5ton/month ANHUI SHENGZHIKAI BIOTECHNOLOGY CO.,LTD
blox butyramidehcl dissenten fortasec imosec LABOTEST-BB LT00134703 LOSERAMIN LOPERAMIDE HYDROCHLORIDE 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 4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-a,a-diphenyl-1-piperidinebutanamide Hydrochloride Arret. B Imosse px. Brel. Dossemten 4-(4-Chlorophenyl)-4-hydroxy-N,N-(dimethyl-d6)-a,a-diphenyl-1-piperidinebutanamide Hydrochloride Fortasec-d6 Imodium-d6 Imosec-d6 Imossel-d PJ-185-d6 px. Brel. Dossemten-d6 R-18553-d6 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-.alpha.,.alpha.-diphenyl-, monohydrochloride 4-(p-chlorophenyl)-4-hydroxy-n,n-dimethyl-α,α-diphenyl-1-piperidinebutyramide hydrochloride LOPERAMIDEHYDROCHLORIDE,USP Loperamide hydrochloride, Vetranal LOPERAMIDE HYDROCHLROIDE 4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,a-diphenyl-1-piperidinebutanamide Hydrochloride Imossel lopemid lopemin loperyl pj185 r18553 4-(4-Chlorophenyl)-4-hydroxy-N,N-(dimethyl-d6)-α,a-diphenyl-1-piperidinebutanamide Hydrochloride Imossel-d6 4-(4-Chlorophenyl)-N,N-dimethyl-alpha,alpha-diphenyl-4-hydroxy-1-piperidinebutanamide hydrochloride Cagudalin Clalet Taipemin 4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutanamidehydrochloride Loperamide Hydrochloride (200 mg) Loperamide hydrochlo LUPERAMIDE HCL 4-(4-Chlorophenyl)-4-hydroxy-N,N-(diMethyl-d6)-α,α-diphenyl-1-piperidinebutanaMide Hydrochloride Arret-d6 Blox-d6 Brek-d6 Dissenten-d6 IModiuM A-D-d6 LopeMid-d6 LopeMin-d6 Loperazine-d6 Loperyl-d6 LopodiuM-d6 Maalox Antidiarrheal-d6