[14]apixaban

ID: ALA3526474

PubChem CID: 54590406

Max Phase: Preclinical

Molecular Formula: C25H25N5O4

Molecular Weight: 459.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-n2nc(C(N)=O)c3c2C(=O)N(c2ccc(N4CCCC[14C]4=O)cc2)CC3)cc1

Standard InChI:  InChI=1S/C25H25N5O4/c1-34-19-11-9-18(10-12-19)30-23-20(22(27-30)24(26)32)13-15-29(25(23)33)17-7-5-16(6-8-17)28-14-3-2-4-21(28)31/h5-12H,2-4,13-15H2,1H3,(H2,26,32)/i21+2

Standard InChI Key:  QNZCBYKSOIHPEH-HWILPRLSSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   11.2989   -6.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9056   -5.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0804   -5.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6484   -6.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0416   -7.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8669   -7.2507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1817   -5.0489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5256   -4.5474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8476   -5.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0701   -4.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4445   -5.2733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9218   -3.9262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2600   -7.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8281   -8.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2233   -9.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0485   -9.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4806   -8.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.4418  -10.1521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0098  -10.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4030  -11.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2282  -11.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6602  -10.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2670  -10.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1882  -10.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1205   -6.5702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9696   -4.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5713   -5.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3593   -5.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5531   -4.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9533   -3.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1634   -4.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3431   -4.1120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4936   -3.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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  5  6  1  0
  1  6  1  0
  7  8  1  0
  8  9  2  0
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  9 10  1  0
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 20 21  1  0
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 22 23  1  0
 23 24  1  0
 19 24  1  0
 20 25  2  0
 16 19  1  0
  6 13  1  0
  1 26  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 27 32  2  0
 33 34  1  0
 30 33  1  0
  7 27  1  0
M  ISO  1  20  14
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 459.51

Molecular Weight (Monoisotopic): 459.1907

AlogP: 2.70

#Rotatable Bonds: 5

Polar Surface Area: 110.76

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.07

CX Basic pKa: ┄

CX LogP: 1.83

CX LogD: 1.83

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.63

Np Likeness Score: -1.04

References

1. Zhang D, He K, Herbst JJ, Kolb J, Shou W, Wang L, Balimane PV, Han YH, Gan J, Frost CE, Humphreys WG..  (2013)  Characterization of efflux transporters involved in distribution and disposition of apixaban.,  41  (4): [PMID:23382458] [10.1124/dmd.112.050260]

2. Wang L, He K, Maxwell B, Grossman SJ, Tremaine LM, Humphreys WG, Zhang D..  (2011)  Tissue distribution and elimination of [14C]apixaban in rats.,  39  (2): [PMID:21071521] [10.1124/dmd.110.036442]

3. Zhang D, Wei C, Hop CECA, Wright MR, Hu M, Lai Y, Khojasteh SC, Humphreys WG..  (2021)  Intestinal Excretion, Intestinal Recirculation, and Renal Tubule Reabsorption Are Underappreciated Mechanisms That Drive the Distribution and Pharmacokinetic Behavior of Small Molecule Drugs.,  64  (11.0): [PMID:34010555] [10.1021/acs.jmedchem.0c01720]

Source

Source(1):

• Scientific Literature