GW311616 - ≥99% , CAS No.198062-54-3

CAS: 198062-54-3 Cat. No.: G647148 Formula: C₁₉H₃₁N₃O₄S Molecular Weight: 397.53 PubChem CID: 9800961

GRADE & PURITY ≥99%

Synonyms

GW 311616 | L8012V52PN | MS-26715 | PYRROLO(3,2-B)PYRROL-2(1H)-ONE, HEXAHYDRO-3-(1-METHYLETHYL)-1-(METHYLSULFONYL)-4-(1-OXO-4-(1-PIPERIDINYL)-2-BUTENYL)-, (3S-(3.ALPHA.,3A.ALPHA.,4(E),6A.BETA.))- | (3aR,6S,6aS)-4-methylsulfonyl-1-[(E)-4-piperidin-1-ylbut-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

GW-311616 is a potent, orally bioavailable, long duration and selective human neutrophil elastase ( HNE ) inhibitor with IC 50 value of 22 nM and K i value of 0.31 nM

In Vitro

GW-311616 (150 μM; 48 hours) markedly suppresses NE activity in U937 and K562 cells lines. GW-311616 (20-320 μM; 48 hours; U937 cells) treatment inhibits proliferation and induces apoptosis in leukemia cells. GW-311616 (150 μM; U937 cells) treatment can increase the protein expression levels of Bax and decrease the expression of Bcl-2. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Viability AssayCell Line: U937 and K562 cells Concentration: 150 μM Incubation Time: 48 hours Result: Markedly suppressed NE activity. Apoptosis AnalysisCell Line: U937 cells Concentration: 20 μM, 40 μM, 80 μM, 160 μM, 320 μM Incubation Time: 48 hours Result: The rate of apoptosis was enhanced. Western Blot AnalysisCell Line: U937 cells Concentration: 150 μM Incubation Time: 48 hours Result: Increased the protein expression levels of Bax and decreased the expression of Bcl-2.

In Vivo

GW-311616 (2 mg/kg; oral administration) rapidly abolishes the circulation of neutrophil elastase (NE) in dogs, while >90% inhibition is maintained for 4 days. This prolonged effect is independent to be due to penetration of neutrophils in bone marrow by orally administrated GW-311616. GW-311616 has moderate terminal elimination half-life (t 1/2 ) of 1.1 hours and 1.5 hours for dog (2 mg/kg, oral), rat (2 mg/kg, oral), respectively. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Dogs (9-month-old)Dosage: 0.22 mg/kg, 0.66 mg/kg and 2 mg/kg (Pharmacokinetic study) Administration: Oral administration Result: At 0.22 mg/kg, greater than 50% inhibition of elastase was achieved 6 hours after dosing, with activity returning towards control values. Single oral dose of 2 mg/kg rapidly abolished circulating enzyme activity, and greater than 90% inhibition was maintained for 4 days.

Form:Solid

IC50& Target:IC50: 22 nM (HNE), Ki: 0.31 nM (HNE)

Specifications

Synonyms

GW 311616 | L8012V52PN | MS-26715 | PYRROLO(3,2-B)PYRROL-2(1H)-ONE, HEXAHYDRO-3-(1-METHYLETHYL)-1-(METHYLSULFONYL)-4-(1-OXO-4-(1-PIPERIDINYL)-2-BUTENYL)-, (3S-(3.ALPHA.,3A.ALPHA.,4(E),6A.BETA.))- | (3aR,6S,6aS)-4-methylsulfonyl-1-[(E)-4-piperidin-1-ylbut-

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

GW-311616 is a potent, orally bioavailable, long duration and selective human neutrophil elastase ( HNE ) inhibitor with IC 50 value of 22 nM and K i value of 0.31 nM.

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.

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

Canonical Smiles

CC(C)C1C2C(CCN2C(=O)C=CCN3CCCCC3)N(C1=O)S(=O)(=O)C

IUPAC Name

(3aR,6S,6aS)-4-methylsulfonyl-1-[(E)-4-piperidin-1-ylbut-2-enoyl]-6-propan-2-yl-3,3a,6,6a-tetrahydro-2H-pyrrolo[3,2-b]pyrrol-5-one

InChIKey

NDNKNUMSTIMSHQ-URZKGLGPSA-N

INCHI

1S/C19H31N3O4S/c1-14(2)17-18-15(22(19(17)24)27(3,25)26)9-13-21(18)16(23)8-7-12-20-10-5-4-6-11-20/h7-8,14-15,17-18H,4-6,9-13H2,1-3H3/b8-7+/t15-,17+,18-/m1/s1

Isomeric SMILES

CC(C)[C@H]1[C@H]2[C@@H](CCN2C(=O)/C=C/CN3CCCCC3)N(C1=O)S(=O)(=O)C

Alternate CAS

198062-54-3

PubChem CID

9800961

MeSH Entry Terms

GW 311616;GW311616;GW311616A

Molecular Weight

397.53

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pyrrolidines
      • Subclass N-acylpyrrolidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pyrrolidines
• Subclass: N-acylpyrrolidines
• Intermediate Tree Nodes: Not available
• Direct Parent: N-acylpyrrolidines
• Alternative Parents: Pyrrolidine-2-ones Piperidines Tertiary carboxylic acid amides Sulfonyls Organosulfonic acids and derivatives Trialkylamines Lactams Amino acids and derivatives Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: N-acylpyrrolidine - Piperidine - Pyrrolidone - 2-pyrrolidone - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Tertiary carboxylic acid amide - Amino acid or derivatives - Tertiary aliphatic amine - Tertiary amine - Carboxamide group - Lactam - Azacycle - Carboxylic acid derivative - Amine - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organosulfur compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
• 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(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 66.67 mg/mL (167.71 mM; Need ultrasonic)
• Molecular Weight: 397.500 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 397.204 Da
• Monoisotopic Mass: 397.204 Da
• Topological Polar Surface Area: 86.400 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 707.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 198062-54-3, the molecular formula is C19H31N3O4S, and the molecular weight is 397.53 g/mol. InChIKey NDNKNUMSTIMSHQ-URZKGLGPSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.