Laquinimod - Moligand™, ≥98% , CAS No.248281-84-7

CAS: 248281-84-7 Cat. No.: L126699 Molecular Weight: 356.8 EC Number: 692-155-1

GRADE & PURITY Moligand™, ≥98%

Synonyms

908SY76S4G | HY-13010 | 5-CHLORO-N-ETHYL-4-HYDROXY-1-METHYL-2-OXO-N-PHENYL-1,2-DIHYDROQUINOLINE-3-CARBOXAMIDE | FMOC-CL ChloroforMic acid 9-fluorenylMethyl ester | MFCD08689859 | 5-Chloro-N-Et-4-hydroxy-1-methyl-2-oxo-N-Ph-1,2-dihydroquinoline-3-carboxami

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Laquinimod is a potent immunomodulator. Phase 3.

Specifications

Synonyms

908SY76S4G | HY-13010 | 5-CHLORO-N-ETHYL-4-HYDROXY-1-METHYL-2-OXO-N-PHENYL-1, 2-DIHYDROQUINOLINE-3-CARBOXAMIDE | FMOC-CL ChloroforMic acid 9-fluorenylMethyl ester | MFCD08689859 | 5-Chloro-N-Et-4-hydroxy-1-methyl-2-oxo-N-Ph-1, 2-dihydroquinoline-3-carboxami

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Laquinimod (ABR-215062) is a potent immunomodulator. Laquinimod is a novel oral drug that is currently being evaluated for the treatment of relapsing-remitting (RR) multiple sclerosis (MS). Laquinimod has demonstrated significant activity

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504771346
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504771346
• Canonical Smiles: CCN(C1=CC=CC=C1)C(=O)C2=C(C3=C(C=CC=C3Cl)N(C2=O)C)O
• IUPAC Name: 5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenylquinoline-3-carboxamide
• InChIKey: GKWPCEFFIHSJOE-UHFFFAOYSA-N
• INCHI: 1S/C19H17ClN2O3/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24/h4-11,23H,3H2,1-2H3
• Isomeric SMILES: CCN(C1=CC=CC=C1)C(=O)C2=C(C3=C(C=CC=C3Cl)N(C2=O)C)O
• Molecular Weight: 356.8
• Reaxy-Rn: 9650600
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9650600&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Anilides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Anilides
• Intermediate Tree Nodes: Not available
• Direct Parent: Aromatic anilides
• Alternative Parents: Quinoline-3-carboxamides Chloroquinolines Hydroquinolones Hydroxyquinolines Hydroquinolines Pyridinecarboxylic acids and derivatives Pyridinones Hydroxypyridines Aryl chlorides Tertiary carboxylic acid amides Vinylogous acids Heteroaromatic compounds Vinylogous amides Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Aromatic anilide - Quinoline-3-carboxamide - Haloquinoline - Dihydroquinolone - Hydroxyquinoline - Chloroquinoline - Dihydroquinoline - Quinoline - Pyridine carboxylic acid or derivatives - Hydroxypyridine - Pyridinone - Aryl chloride - Aryl halide - Pyridine - Heteroaromatic compound - Vinylogous amide - Tertiary carboxylic acid amide - Vinylogous acid - Lactam - Carboxamide group - Azacycle - Carboxylic acid derivative - Organoheterocyclic compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

Discover Target: ADRB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

Discover Target: DRD2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

Discover Target: HTR2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH1 Tclin Histamine H1 receptor (7573 Activities)

Discover Target: HRH1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

Discover Target: PDE3A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

Discover Target: ADRA2C

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

Discover Target: ADORA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

Discover Target: ADORA3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)

Discover Target: CHRNA4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MC3R Tchem Melanocortin receptor 3 (5659 Activities)

Discover Target: MC3R

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR1I2 Tchem Pregnane X receptor (6667 Activities)

Discover Target: NR1I2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

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Jurkat (10389 Activities)

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Associated Targets(non-human)

Pde4d Phosphodiesterase 4D (4 Activities)

Discover Target: Pde4d

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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Mus musculus (284745 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO 61 mg/mL (170.96 mM);Water <1 mg/mL (<1 mM);Ethanol 1 mg/mL (2.8 mM)
• Molecular Weight: 356.800 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 356.093 Da
• Monoisotopic Mass: 356.093 Da
• Topological Polar Surface Area: 60.900 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 571.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Ye Xiong, Yanqiong Fu, Zhuoli Li, Yu Zheng, Maiyin Cui, Chan Zhang, Xin Yi Huang, Yong Jian, Bai Hui Chen.  (2023)  Laquinimod Inhibits Microglial Activation, Astrogliosis, BBB Damage, and Infarction and Improves Neurological Damage after Ischemic Stroke.  ACS Chemical Neuroscience,      [PMID:37161270] [10.1021/acschemneuro.2c00740]