An inhibitor of neutrophil elastase
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GW 311616A

Item No. 27957

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,3aS,6aR)-hexahydro-3-(1-methylethyl)-1-(methylsulfonyl)-4-[(2E)-1-oxo-4-(1-piperidinyl)-2-buten-1-yl]-pyrrolo[3,2-b]pyrrol-2(1H)-one, monohydrochloride
CAS Number
197890-44-1
Molecular Formula
C19H31N3O4S • HCl
Formula Weight
434.0
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:4): 0.25 mg/mlEthanol: 10 mg/ml
SMILES
O=C(N1CC[C@](N2S(C)(=O)=O)([H])[C@]1([H])[C@H](C(C)C)C2=O)/C=C/CN3CCCCC3.Cl
InChi Code
InChI=1S/C19H31N3O4S.ClH/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;1H/b8-7+;/t15-,17+,18-;/m1./s1
InChi Key
UFCZUKYPBPXODT-OFTZGUNKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $90

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    5 mg

    $262

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    10 mg

    $436

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    NET Formation Screening & Analysis Services
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    Product Description

    GW 311616A is an inhibitor of neutrophil elastase (IC50 = 100 nM).1 It is selective for neutrophil elastase (IC50 = 22 nM for the human enzyme) over trypsin, cathepsin G, and plasmin (IC50s = >100 µM for all), as well as chymotrypsin and tissue plasminogen activator (IC50s = >3 µM for both), in cell-free assays. GW 311616A (20 µM) inhibits the formation of neutrophil extracellular traps (NETs) induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in isolated human neutrophils.2 It inhibits intraneutrophil elastase activity in isolated dog blood six hours after administration of a 0.22 mg/kg dose.3 GW 311616A also inhibits neutrophil elastase in the liver in a mouse model of liver ischemia-reperfusion injury when administered at a dose of 2 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Benedek, B., Kopp, B., and Melzig, M.F. Achillea millefolium L. s.l. – is the anti-inflammatory activity mediated by protease inhibition? J. Ethnopharmacol. 113(2), 312-317 (2007).

    2. Nakabo, S., Ohmura, K., Akizuki, S., et al. Activated neutrophil carbamylates albumin via the release of myeloperoxidase and reactive oxygen species regardless of NETosis. Mod. Rheumatol. 30(2), 345-349 (2019).

    3. Macdonald, S.J.F., Dowle, M.D., Harrison, L.A., et al. The discovery of a potent, intracellular, orally bioavailable, long duration inhibitor of human neutrophil elastase–GW311616A a development candidate. Bioorg. Med. Chem. Lett. 11(7), 895-898 (2001).

    4. Uchida, Y., Freitas, M.C., Zhao, D., et al. The inhibition of neutrophil elastase ameliorates mouse liver damage due to ischemia and reperfusion. Liver Transpl. 15(8), 939-947 (2009).