IMAZAPYR, (S)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H15N3O3
Molecular Weight	261.2765
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)[C@]1(C)NC(=NC1=O)C2=NC=CC=C2C(O)=O

InChI

InChIKey=CLQMBPJKHLGMQK-ZDUSSCGKSA-N

InChI=1S/C13H15N3O3/c1-7(2)13(3)12(19)15-10(16-13)9-8(11(17)18)5-4-6-14-9/h4-7H,1-3H3,(H,17,18)(H,15,16,19)/t13-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C13H15N3O3
Molecular Weight	261.2765
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.invasive.org/gist/products/handbook/17.imazapyr.pdf | https://www.ncbi.nlm.nih.gov/pubmed/25035913 | https://www.ncbi.nlm.nih.gov/pubmed/20416927

S(-)-imazapyr is an enantiomer of herbicide imazapyr. It is the less potent inhibitor of plant acetolactate synthase than R(+) enantiomer. The R(+) enantiomer has greater herbicidal activity and degrades faster than S(-) enantiomer.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetolactate synthase 5 Target ID: CHEMBL4263 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25035913 \| https://www.ncbi.nlm.nih.gov/pubmed/20416927	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Enantioselective effects of herbicide imazapyr on Arabidopsis thaliana.	2014	25035913
Faster degradation of herbicidally-active enantiomer of imidazolinones in soils.	2010-05	20416927

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Arabidopsis thaliana acetolactate synthase (ALS) activity was inhibited more by (+)-imazapyr than (±)-imazapyr or (-)-imazapyr. At 100 mg/L of imazapyr, ALS activity was 78%, 43%, and 19% with (-)-, (±)-, and (+)-imazapyr, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:14:05 GMT 2025` Edited by `admin` on `Mon Mar 31 22:14:05 GMT 2025`
Record UNII	5FJ9JCJ9QP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

IMAZAPYR, (S)-

Common Name

English

(S)-IMAZAPYR

Preferred Name

English

3-PYRIDINECARBOXYLIC ACID, 2-((4S)-4,5-DIHYDRO-4-METHYL-4-(1-METHYLETHYL)-5-OXO-1H-IMIDAZOL-2-YL)-

Systematic Name

English

2-((4S)-4,5-DIHYDRO-4-METHYL-4-(1-METHYLETHYL)-5-OXO-1H-IMIDAZOL-2-YL)-3-PYRIDINECARBOXYLIC ACID

Systematic Name

English

2-((4S)-4-ISOPROPYL-4-METHYL-5-OXO-2-IMIDAZOLIN-2-YL) NICOTINIC ACID

Systematic Name

English

Code System Code Type Description

FDA UNII

5FJ9JCJ9QP

Created by admin on Mon Mar 31 22:14:05 GMT 2025 , Edited by admin on Mon Mar 31 22:14:05 GMT 2025

PRIMARY

EPA CompTox

DTXSID901116314

Created by admin on Mon Mar 31 22:14:05 GMT 2025 , Edited by admin on Mon Mar 31 22:14:05 GMT 2025

PRIMARY

PUBCHEM

766746

Created by admin on Mon Mar 31 22:14:05 GMT 2025 , Edited by admin on Mon Mar 31 22:14:05 GMT 2025

PRIMARY

CAS

355841-28-0

Created by admin on Mon Mar 31 22:14:05 GMT 2025 , Edited by admin on Mon Mar 31 22:14:05 GMT 2025

PRIMARY

Details

SMILES

InChI

DescriptionSources: https://www.invasive.org/gist/products/handbook/17.imazapyr.pdf | https://www.ncbi.nlm.nih.gov/pubmed/25035913 | https://www.ncbi.nlm.nih.gov/pubmed/20416927

Approval Year

Targets

Conditions

PubMed

Sample Use Guides

Description
Sources: https://www.invasive.org/gist/products/handbook/17.imazapyr.pdf | https://www.ncbi.nlm.nih.gov/pubmed/25035913 | https://www.ncbi.nlm.nih.gov/pubmed/20416927