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Loperamide hydrochloride

Product Name
Loperamide hydrochloride
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
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Loperamide hydrochloride Property

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.
pka
8.66(at 25℃)
form 
neat
Merck 
14,5571
CAS DataBase Reference
34552-83-5(CAS DataBase Reference)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P321Specific treatment (see … on this label).

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

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N-Bromosuccinimide Price

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

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Loperamide hydrochloride Suppliers

Qufu Haida Tiancheng Biochemical Co., Ltd.
Tel
0537-4531868
Email
qfhdtc@126.com
Country
China
ProdList
38
Advantage
55
wuhan dingxingtong Chemical Technology Co., Ltd Co., Ltd
Tel
027-59207796-
Fax
027-59207796
Email
w13429867250@163.com
Country
China
ProdList
2042
Advantage
58
Shandong Yihong Chemical Co. LTD
Tel
152-69100373-
Fax
0539-7910696
Email
977495915@qq.com
Country
China
ProdList
455
Advantage
58
Wuhan Huajiu Pharmaceutical Technology Co.,Ltd.
Tel
027-59218639-
Fax
027-59218639
Email
730880265@qq.com
Country
China
ProdList
2901
Advantage
58
Wuhan Biocar Pharmacy Co.,Ltd
Tel
Fax
027-86589876
Email
1217387561@qq.com
Country
China
ProdList
55
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15878
Advantage
69
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24555
Advantage
81
Energy Chemical
Tel
021-58432009-
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44043
Advantage
61
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028-
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12282
Advantage
60
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View Lastest Price from Loperamide hydrochloride manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Loperamide hydrochloride 34552-83-5
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-10-29
Wuhan Mulei New Material Technology Co. Ltd
Product
Loperamide hydrochloride 34552-83-5
Price
US $10.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
5000tons per month
Release date
2021-04-02
Hebei Zhanyao Biotechnology Co. Ltd
Product
Loperamide hydrochloride 34552-83-5
Price
US $0.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
Above 99%
Supply Ability
5000kg/month
Release date
2021-03-08

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