ABC01265AE

saxagliptin RRRR isomer

Saxagliptin RRRR isomer is a stereoisomer of the antidiabetic agent saxagliptin, characterized by the (R) configuration at all four stereocenters within its pyrrolidine core. The molecule features a substituted benzyl group, a sulfonamide moiety, and a chiral pyrrolidine ring with specific spatial orientation. This isomer arises from asymmetric synthesis pathways, differing from the parent drug's (RRSR) configuration. It serves as a critical reference standard for chiral HPLC analysis of saxagliptin's enantiomeric purity in pharmaceutical development.

On Request
Molecular Formula C18H25N3O2
Molecular Weight 315.4000
CAS Number 1564265-95-7 ✓ Verified
PubChem CID 76328589 ↗
Purity N/A
Product Type API Impurity
Parent Drug Saxagliptin
Lead Time On Request
IUPAC Name (1R,3R,5R)-2-[(2R)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

📝 Synonyms

1564265-95-7 (2'R,2R,cis)-Saxagliptin (1R,3R,5R)-2-[(2R)-2-Amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile (1R,3R,5R)-2-((2R)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetyl)-2-azabicyclo[3.1.0]hexane-3-carbonitrile (1R,3R,5R)-2-[(2R)-2-Amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile starbld0020360 CHEMBL3114068 SCHEMBL17642049 CS-0165385 (1R,3R,5R,2 inverted exclamation mark(R)R)-Saxagliptin (Saxagliptin Impurity pound(c)

🔬 Chemical Identifiers

C1[C@H]2C[C@H]2N([C@H]1C#N)C(=O)[C@@H](C34CC5CC(C3)CC(C5)(C4)O)N
InChI=1S/C18H25N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h10-15,23H,1-7,9,20H2/t10?,11?,12-,13+,14+,15-,17?,18?/m0/s1
QGJUIPDUBHWZPV-KJYYUUBBSA-N

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