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Loperamide hydrochloride

Loperamide hydrochloride structure

CAS No:
34552-83-5
Formula:
C29H33ClN2O2.ClH
Chemical Name:
Loperamide hydrochloride
Synonyms:
1-Piperidinebutanamide,4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-,hydrochloride (1:1);1-Piperidinebutanamide,4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-,monohydrochloride;4-(p-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinobutyramide hydrochloride;Loperamide hydrochloride;R 18553;Lopemin;Imodium;Loperazine;Lopodium;PJ 185;Arret;Imosec;Fortasec;Maalox Antidiarrheal;Imossel;Blox;Tebloc;Dissenten;Suprasec;Loperyl;Brek;Lopemid;Imodium A-D;NSC 696356
Categories:
Active Pharmaceutical Ingredients > Digestive System Drugs

Description

Loperamide hydrochloride is an opiate receptor agonist for the treatment of diarrhea.

Loperamide hydrochloride is a hydrochloride obtained by combining loperamide with one equivalent of hydrochloric acid. Used for treatment of diarrhoea resulting from gastroenteritis or inflammatory bowel disease. It has a role as a mu-opioid receptor agonist, an antidiarrhoeal drug and an anticoronaviral agent. It contains a loperamide(1+).|Loperamide Hydrochloride is the hydrochloride salt form of loperamide, a synthetic, piperidine derivative and opioid agonist with antidiarrheal activity. Loperamide acts on the mu-receptors in the intestinal mucosa. This leads to a decrease in gastrointestinal motility by decreasing the circular and longitudinal smooth muscle activity of the intestinal wall. This slows intestinal transit and allows for more water and electrolyte absorption from the intestines. Loperamide is not significantly absorbed from the gut and does not cross the blood-brain barrier. Therefore it has no central nervous system effects.|One of the long-acting synthetic ANTIDIARRHEALS; it is not significantly absorbed from the gut, and has no effect on the adrenergic system or central nervous system, but may antagonize histamine and interfere with acetylcholine release locally.

Loperamide hydrochloride Basic Attributes

Molecular Weight：

513.5

Exact Mass：

512.199707

EC Number：

252-082-4

UNII：

77TI35393C

NSC Number：

759568|696356

NCI Thesaurus Code：

C1584

HScode：

29333990

Characteristics

PSA：

43.8

XLogP3：

5.82790

Appearance：

Crystals, practically insoluble in water

Density：

1.1905 (rough estimate)

Melting Point：

222-223 °C

Boiling Point：

647.2ºC at 760 mmHg

Flash Point：

345.2ºC

Water Solubility：

>77 [ug/mL]

Storage Conditions：

Store at RT

Toxicity：

LD50 in mice (mg/kg): 75 s.c.; 28 i.p.; 105 orally; in rats (mg/kg): 185 orally (Niemegeers)

Collision Cross Section：

219.4 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Packing level：

Ⅲ

Hazard category：

6.1(b)

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

safety instructions：

RTECS Number：

TM4960000

Marks：

Precautionary statement(s)：

P301 + P310

Hazard Statements：

H301

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 106 companies from 5 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Miscellaneous agents found useful in the symptomatic treatment of diarrhea. They have no effect on the agent(s) that cause diarrhea, but merely alleviate the condition. (See all compounds classified as Antidiarrheals.)

MeSH Entry Terms：

Hydrochloride, Loperamide

Loperamide hydrochloride Use and Manufacturing

Methods of Manufacturing

Preparation of 4-[4-(4-diphenyl)-4-hvdroxypiperidino1-N, N- dimethyl-2, 2-diphenylbutyramide hydrochloride (loperamide)0.111 g (5.2-10-4 mol, 1 eq) of 4, 4-chlorophenyl-4-hydroxypiperidine, 0.062 g (5.8-10-4 mol, 1.11 eq) of sodium carbonate, 0.0009 g (0.24percent by weight) of potassium iodide were weighed and dissolved in 0.5 ml_ of glycerol formal. The resulting mixture was stirred for 15 minutes. Afterwards 0.2089 g (6.03-10-4 mol, 1.15 eq) of N, N-dimethyl-(3, 3-diphenyltetrahydro-2- furyliden)ammonium bromide were added and heated at 6O

Uses

A Ca2+ channel protein inhibitor and MOR activator.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:513.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:7
Exact Mass:512.1997337
Monoisotopic Mass:512.1997337
Topological Polar Surface Area:43.8
Heavy Atom Count:35
Complexity:623
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

The chemical structure of this product is similar to that of haloperidol and pethidine, but the therapeutic dose has no effect on the central nervous system. The effect on intestinal smooth muscle is similar to that of opioids. It can inhibit the contraction of intestinal smooth muscle and reduce intestinal peristalsis. It can also reduce the release of acetylcholine from the nerve endings of the intestinal wall, and directly inhibit the peristaltic reflex through the local interaction of cholinergic and non-cholinergic neurons. This product can prolong the residence time of food in the small intestine, promote the absorption of water, electrolytes and glucose, and inhibit intestinal excessive secretion caused by prostaglandins, cholera toxin and other enterotoxins. In addition, this product can also increase the tension of the anal sphincter and inhibit fecal incontinence or urgency.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Loperamide Hydrochloride
Manufacturer	Shanghai SPH New ASIA Pharmaceutical Co., Ltd.

Loperamide Hydrochloride Capsules
Ingredients	The main ingredient of this product is loperamide hydrochloride. The structural formula is: Molecular formula: C29H33ClN2O2HCl Molecular weight: 513.51
Indication	No interaction has been found when this product is taken simultaneously with other drugs.
Specifications	2mg
Manufacturer	Shanghai Sine Tianping Pharmaceutical Co., Ltd.

Loperamide Hydrochloride Granules
Ingredients	Active ingredient: Loperamide hydrochloride. Chemical name: 4-p-chlorophenyl-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenyl-1-piperidinylbutyramide hydrochloride Molecular weight: C29H33ClN2O2.HCl
Indication	Preclinical data show that loperamide is a precursor of P-glycoprotein. When loperamide (single dose 16 mg) is used in combination with P-glycoprotein inhibitors such as quinidine and ritonavir, it can lead to pharmacokinetic interactions between loperamide and P-glycoprotein inhibitors. The clinical relevance of this pharmacokinetic interaction between loperamide and P-glycoprotein inhibitors is unclear. There are no reports of interactions between this product and other drugs.
Specifications	(1mg:1g)*36 bags

See More Related Drugs

Registered Holders

VAMSI LABS LTD

United States
Active
Vasudha Pharma Chem Ltd

United States
Active
PMC ISOCHEM

France
Active

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