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Avacopan

CAT: 0931-T8223-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0931-T8223-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
1346623-17-3
Target
Complement System
Related Pathways
Immunology/Inflammation
Purity
0.999
Bioactivity
Avacopan (CCX168) is a C5aR antagonist (IC50=0.1 nM) with selective and oral activity. Avacopan blocks the action of C5a and prevents the development of GN induced by anti-myeloperoxidase antibodies in a mouse model of AAV. Avacopan can be used to treat anti-neutrophil cytoplasmic antibody (ANCA) -related vasculitis.
Smiles
C(=O)(N1[C@H]([C@@H](C(NC2=CC(C(F)(F)F)=C(C)C=C2)=O)CCC1)C3=CC=C(NC4CCCC4)C=C3)C5=C(C)C=CC=C5F
Molecular Formula
C33H35F4N3O2
Molecular Weight
581.64
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Avacopan

Anti-neutrophil cytoplasmic (auto)antibody (ANCA)-associated vasculitis (AAV) is a rare (estimated incidence of 3 cases per 100,000 per year) form of "pauci-immune" systemic small-vessel vasculitis typified by the presence of ANCAs in the serum. The full spectrum of AAV includes granulomatosis with polyangiitis (GPA), microscopic polyangiitis (MPA), eosinophilic granulomatosis with polyangiitis (EGPA), and drug-induced AAV. AAV may be associated with necrotizing and crescentic glomerulonephritis (NCGN). Despite complex pathophysiology, studies over the past ~2 decades have identified a key role for the alternative complement pathway and, in particular, the interaction between the anaphylatoxin fragment C5a and its cognate C5aR receptor in AAV. Avacopan (formerly CCX168) is an allosteric C5aR antagonist indicated for use in AAV. Avacopan was granted FDA approval on October 8, 2021, and is currently marketed under the name TAVNEOS by ChemoCentryx, Inc. On January 19, 2022, the European Commission approved avacopan for the treatment of adult patients with severe, active granulomatosis polyangiitis (GPA) or microscopic polyangiitis (MPA) - the two main forms of ANCA-associated vasculitis - in combination with [rituximab] or [cyclophosphamide]. Avacopan was approved by Health Canada on April 20, 2022.

CAS Number1346623-17-3
PubChem CID49841217
IUPAC Name(2R,3S)-2-[4-(cyclopentylamino)phenyl]-1-(2-fluoro-6-methylbenzoyl)-N-[4-methyl-3-(trifluoromethyl)phenyl]piperidine-3-carboxamide
Molecular FormulaC33H35F4N3O2
Molecular Weight581.6
XLogP7.2
Topological Polar Surface Area61.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Heavy Atom Count42
Formal Charge0
Complexity917
SMILES
CC1=C(C(=CC=C1)F)C(=O)N2CCC[C@@H]([C@@H]2C3=CC=C(C=C3)NC4CCCC4)C(=O)NC5=CC(=C(C=C5)C)C(F)(F)F
InChI
InChI=1S/C33H35F4N3O2/c1-20-12-15-25(19-27(20)33(35,36)37)39-31(41)26-10-6-18-40(32(42)29-21(2)7-5-11-28(29)34)30(26)22-13-16-24(17-14-22)38-23-8-3-4-9-23/h5,7,11-17,19,23,26,30,38H,3-4,6,8-10,18H2,1-2H3,(H,39,41)/t26-,30-/m0/s1
InChIKey
PUKBOVABABRILL-YZNIXAGQSA-N
Chemical Structure
2D Structure
2D structure of Avacopan
CAS: 1346623-17-3
CID: 49841217
Formula: C33H35F4N3O2
MW: 581.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight581.6
XLogP37.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Exact Mass581.26654002
Monoisotopic Mass581.26654002
Topological Polar Surface Area61.4 Ų
Heavy Atom Count42
Formal Charge0
Complexity917
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
BA5880-100Avacopan

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