Marvin  11291210402D          

 25 29  0  0  1  0            999 V2000
    8.3484   -4.5188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0773   -4.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6192   -4.1329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8063   -4.5188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0773   -3.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0636   -5.3336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9213   -5.3336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1786   -4.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4495   -4.0472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4495   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4495   -2.3319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4924   -6.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7789   -5.3336    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2489   -5.3336    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3484   -5.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6341   -5.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6341   -6.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0628   -6.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3484   -7.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9019   -7.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9019   -6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0628   -5.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1876   -7.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6562   -7.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7771   -7.0263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  6  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  3  0  0  0  0
  7 12  1  0  0  0  0
 12  6  1  0  0  0  0
  7 13  1  1  0  0  0
  6 14  1  1  0  0  0
 15 16  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 22  1  0  0  0  0
 24 18  1  0  0  0  0
 18 19  1  0  0  0  0
 23 20  1  0  0  0  0
 24 20  1  0  0  0  0
 23 17  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 18 25  1  0  0  0  0
M  END
> <ID>
CHEBI:71272

> <NAME>
saxagliptin

> <DEFINITION>
A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2S)-amino(3-hydroxyadamantan-1-yl)acetic acid with the amino group of (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile. Used in its monohydrate form for the treatment of Type II diabetes.

> <STAR>
3

> <SYNONYM>
BMS-477118; BMS 477118; (1S,3S,5S)-2-((2S)-Amino(3-hydroxytricyclo(3.3.1.13,7)dec-1-yl)acetyl)-2-azabicyclo(3.1.0)hexane-3-carbonitrile

> <IUPAC_NAME>
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

> <INN>
saxagliptin

> <FORMULA>
C18H25N3O2

> <MASS>
315.41000

> <MONOISOTOPIC_MASS>
315.19468

> <CHARGE>
0

> <SMILES>
[H][C@]12C[C@@H](C#N)N(C(=O)[C@@H](N)C34CC5CC(CC(O)(C5)C3)C4)[C@@]1([H])C2

> <INCHI>
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?/m1/s1

> <INCHIKEY>
QGJUIPDUBHWZPV-SGTAVMJGSA-N

> <CAS_REGISTRY_NUMBER>
361442-04-8

> <REAXYS_REGISTRY_NUMBER>
10201614

> <CHEMIDPLUS>
361442-04-8

> <DRUGBANK_ACCESSION>
DB06335

> <KEGG_DRUG_ACCESSION>
D08996

> <WIKIPEDIA_ACCESSION>
Saxagliptin

> <PUBMED_CITATION>
22001114; 22066527; 22081481; 22098472; 22132773; 22149373; 22192246; 22221000; 22232748; 22248301; 22292415; 22313154; 22313172; 22334441; 22349123; 22475049; 22496391; 22564773; 22668067; 22776778; 22823746; 22828124; 22932707; 22943617; 23137182

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