LIDAMIDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H16N4O
Molecular Weight	220.2709
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(=N)NC(=O)NC1=C(C)C=CC=C1C

InChI

InChIKey=RRHJHSBDJDZUGL-UHFFFAOYSA-N

InChI=1S/C11H16N4O/c1-7-5-4-6-8(2)9(7)14-11(16)15-10(12)13-3/h4-6H,1-3H3,(H4,12,13,14,15,16)

HIDE SMILES / InChI

Molecular Formula	C11H16N4O
Molecular Weight	220.2709
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://onlinelibrary.wiley.com/doi/10.1002/ddr.430070202/abstract | https://www.ncbi.nlm.nih.gov/pubmed/582538 | https://www.ncbi.nlm.nih.gov/pubmed/3404458

Lidamidine, also known as WHR-1142A and Lidaral, is an alpha2-adrenergic receptor agonist that inhibits intestinal secretion, reduces intestinal transit, and inhibits smooth muscle contraction. Lidamidine hydrochloride is used to treat diarrhoea and other gastrointestinal disorders. Lidamidine’s intestinal antisecretory effects are mediated through the activation of peripheral alpha-2 adrenoceptors. Lidamidine crosses the blood brain barrier poorly and is therefore devoid of the centrally mediated alpha-2 effects that have limited the use of other alpha-2 adrenoceptor agonists in the intestinal tract.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-2 114 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2891549 \| http://en.pharmacodia.com/web/drug/1_7306.html \| http://onlinelibrary.wiley.com/doi/10.1002/ddr.430070202/abstract \|	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Diarrhea 36 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2979258 https://www.ncbi.nlm.nih.gov/pubmed/3940258	Primary		Approved 8583	Lidarral Approved Use Lidamidine Hydrochloride. Lidamidine is an alpha2-adrenergic receptor stimulant used as the hydrochloride for the management of diarrhoea and other gastrointestinal disorders.

Doses

Dose	Population	Adverse events
14.8 mg 2 times / day multiple, oral Studied dose Dose: 14.8 mg, 2 times / day Route: oral Route: multiple Dose: 14.8 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3551969/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3551969/	Sources: https://pubmed.ncbi.nlm.nih.gov/3551969/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 550 Nav1.5 116 CYP19A1 429 Cav1.2 58 CYP2C19 2057 CYP1A2 2153	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47510#section=BioAssay-Results Page: 6.0	inconclusive [IC50 43.6486 uM]
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ0ODQxNiJ9fQ==	no [IC50 >1000 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47510#section=BioAssay-Results Page: 31.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47510#section=BioAssay-Results Page: 86.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47510#section=BioAssay-Results Page: 81.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47510#section=BioAssay-Results Page: 80.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47510#section=BioAssay-Results Page: 79.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/47510#section=BioAssay-Results Page: 58 \| 59	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Cav1.2 63	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTQwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ0ODQxNiJ9fQ==
Nav1.5 119	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTgwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ0ODQxNiJ9fQ==
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDQ4NDE2In19

PubMed

Title	Date	PubMed
In vivo antimotility and antidiarrheal activity of lidamidine hydrochloride (WHR-1142A), a novel antidiarrheal agent. Comparison with diphenoxylate and loperamide.	1978	582536

Patents

Sample Use Guides

In Vivo Use Guide

Lidamidine HCL (4 mg) or placebo was taken orally t.i.d. with food. Lidamidine decreased the augmented mechanical response to food, reduced rectal sensitivity, and relieved symptoms of patients with irritable bowel syndrome.

Route of Administration: Oral

In Vitro Use Guide

The effects of clonidine and lidamidine on ion transport in the intestine of the rabbit were determined. In the ileum both clonidine (10(-6) M) and lidamidine (10(-3) M) (a) decreased the short circuit current (-1.9 +/- 0.3 and -2.0 +/- 0.4 muEq/h . cm2, respectively) and potential difference; (b) increased net sodium absorption (2.0 +/- 0.6 and 1.8 +/- 0.4 muEq/h . cm2) and chloride absorption (3.4 +/- 0.5 and 3.4 +/- 0.6 muEq/h . cm2); and (c) increased tissue conductance (8.7 +/- 1.7 and 10.0 +/- 1.6 mmho/cm2).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:23:38 GMT 2025` Edited by `admin` on `Mon Mar 31 18:23:38 GMT 2025`
Record UNII	Q8X04W8418
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LIDAMIDINE

Official Name

English

LIDAMIDINE [MI]

Preferred Name

English

Lidamidine [WHO-DD]

Common Name

English

lidamidine [INN]

Common Name

English

1-(METHYLAMIDINO)-3-(2,6-XYLYL)UREA

Systematic Name

English

UREA, N-(2,6-DIMETHYLPHENYL)-N'-(IMINO(METHYLAMINO)METHYL)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C266