LERIMAZOLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H18N2
Molecular Weight	202.2954
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(C)=C(CC2=NCCN2)C(C)=C1

InChI

InChIKey=DUHARNKZLBMPBS-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-9-6-10(2)12(11(3)7-9)8-13-14-4-5-15-13/h6-7H,4-5,8H2,1-3H3,(H,14,15)

HIDE SMILES / InChI

Molecular Formula	C13H18N2
Molecular Weight	202.2954
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28706452 | https://www.ncbi.nlm.nih.gov/pubmed/28628756 | https://medkoo.com/products/7827

Lerimazoline is a sympathomimetic drug that belongs to the imidazoline class of compounds, and is used as a nasal decongestant. Lerimazoline displayed high affinity for the 5-HT1A receptor and for the 5-HT1D receptor. Binding affinity estimates for α1-adrenoceptor, 5-HT2A, and D2 receptors were more than ten times lower. The mechanism of vasoconstrictor action of lerimazoline encompasses both, the activation of 5-HT2A, and to a lesser degree α1 -adrenergic receptors. These results also suggest that lerimazoline is an “atypical” decongestant. It inhibits secretion of nasal mucus. Lerimazoline causes hypertension.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 1d (5-HT1d) receptor 52 Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9632357 \| https://www.ncbi.nlm.nih.gov/pubmed/28628756	Agonist 2678	72.0 nM [Ki]
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28628756	Agonist 2678	162.5 nM [Ki]
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28628756	Agonist 2678	4.2 µM [Ki]
Adrenergic receptor alpha-1 169 Target ID: CHEMBL1907610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28628756	Agonist 2678	6.66 µM [Ki]

PubMed

Title	Date	PubMed
Atypical sympathomimetic drug lerimazoline mediates contractile effects in rat aorta predominantly by 5-HT2A receptors.	2017 Aug 20	28628756
Elucidation of the profound antagonism of contractile action of phenylephrine in rat aorta effected by an atypical sympathomimetic decongestant.	2017 Jul	28706452

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:04:16 UTC 2023` Edited by `admin` on `Sat Dec 16 09:04:16 UTC 2023`
Record UNII	1YZY0ACA91
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LERIMAZOLINE

Official Name

English

Lerimazoline [WHO-DD]

Common Name

English

ST-71

Code

English

lerimazoline [INN]

Common Name

English

1H-IMIDAZOLE, 4,5-DIHYDRO-2-((2,4,6-TRIMETHYLPHENYL)METHYL)-

Systematic Name

English

Code System Code Type Description

INN

9846