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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2014-06-23 13:37:13 UTC

Update Date

2019-07-23 07:17:04 UTC

HMDB ID

HMDB0061725

Secondary Accession Numbers

HMDB61725

Metabolite Identification

Common Name

Rilpivirine

Description

Rilpivirine, also known as TMC 278 or 278, TMC, belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent. Rilpivirine is a very strong basic compound (based on its pKa). Ripivirine treatment produces a significant and effective reduction in the viral load based on the study of HIV-1 RNA copies per ml or immunologic changes by the determination of counts of CD4+ and CD8+ cells. In humans, rilpivirine is involved in rilpivirine action pathway. Mainly hepatically metabolized by CYP3A. Rilpivirine was developed by Tilbotec, Inc. and FDA approved on May 20, 2011. It does not present activity against human DNA polymerases α, β and γ. It did not show any effect on mating or fertility in animal studies. The combinantion therapy (ripivirine and dolutegravir) presented the same viral supression found in previous three-drug therapies without integrase strand transfer inhibitor mutations or rilpivirine resistance. Its binding results in the blockage of RNA and DNA- dependent DNA polymerase activities, like HIV-1 replication. The internal conformational flexibility of rilpivirine and the plasticity of it interacting binding site gives it a very high potency and an unlikely generation of resistance compared to other NNRTI's.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231218062D          

 28 30  0  0  0  0            999 V2000
    3.0791    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.8876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.9501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    4.9501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 15  1  0  0  0  0
  2 15  2  0  0  0  0
  2 18  1  0  0  0  0
  3 18  1  0  0  0  0
  3 19  1  0  0  0  0
  4 18  2  0  0  0  0
  4 20  1  0  0  0  0
  5 27  3  0  0  0  0
  6 28  3  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  9 12  2  0  0  0  0
  9 14  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 10 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 23  2  0  0  0  0
 17 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  2  0  0  0  0
 23 27  1  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
 26 28  1  0  0  0  0
M  END

HMDB0061725
     RDKit          3D
Rilpivirine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -2.4427   -2.1208    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0838   -1.0960    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3904   -0.6565    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0114    0.2882    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3613    0.7491    0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1265    0.3323    1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4762    0.8597    1.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5418    1.2661    1.6646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    0.7944   -0.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9905    0.3596   -1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    0.9048   -2.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674   -0.5900   -0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0413   -1.0073   -0.7459 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054   -0.3807   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0056    0.6944    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082    1.3107    1.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    0.8042    0.7897 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4691   -0.2257   -0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7091   -0.7656   -0.4337 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -0.3393   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0735   -1.0978   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3434   -0.6964   -0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5662    0.4191    0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9356    0.7569    0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0290    1.0285    1.1658 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004    1.1402    1.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1883    0.7700    0.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3334   -0.8142   -0.5319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406   -2.9991    0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5386   -1.7457    1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1554   -2.4750    2.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9185   -1.0857    1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7784    1.4947   -0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7570   -0.4111    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7587    1.5400   -1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4489    0.1738   -2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    1.0460   -3.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078    1.8533   -2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262   -1.8265   -1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755    1.0524    0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0465    2.1490    1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227   -1.6028   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8820   -1.9664   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1698   -1.2920   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6560    2.0142    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3984    1.3929    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  3  0
  4  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  3  0
 23 26  1  0
 26 27  2  0
 18 28  2  0
 12  2  1  0
 28 14  1  0
 27 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  5 33  1  0
  6 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
 26 45  1  0
 27 46  1  0
M  END


  Mrv0541 02231218062D          

 28 30  0  0  0  0            999 V2000
    3.0791    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.8876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.9501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    4.9501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 15  1  0  0  0  0
  2 15  2  0  0  0  0
  2 18  1  0  0  0  0
  3 18  1  0  0  0  0
  3 19  1  0  0  0  0
  4 18  2  0  0  0  0
  4 20  1  0  0  0  0
  5 27  3  0  0  0  0
  6 28  3  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  9 12  2  0  0  0  0
  9 14  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 10 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 23  2  0  0  0  0
 17 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  2  0  0  0  0
 23 27  1  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061725

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(\C=C\C#N)=CC(C)=C1NC1=NC(NC2=CC=C(C=C2)C#N)=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19/h3-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+

> <INCHI_KEY>
YIBOMRUWOWDFLG-ONEGZZNKSA-N

> <FORMULA>
C22H18N6

> <MOLECULAR_WEIGHT>
366.4185

> <EXACT_MASS>
366.159294606

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
40.65300706894284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[4-({4-[(1E)-2-cyanoeth-1-en-1-yl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
5.473225503

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.334184948426305

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.926050194201839

> <JCHEM_PKA_STRONGEST_BASIC>
5.157807076065362

> <JCHEM_POLAR_SURFACE_AREA>
97.41999999999999

> <JCHEM_REFRACTIVITY>
111.73939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rilpivirine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061725
     RDKit          3D
Rilpivirine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -2.4427   -2.1208    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0838   -1.0960    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3904   -0.6565    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0114    0.2882    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3613    0.7491    0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1265    0.3323    1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4762    0.8597    1.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5418    1.2661    1.6646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    0.7944   -0.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9905    0.3596   -1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    0.9048   -2.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674   -0.5900   -0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0413   -1.0073   -0.7459 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054   -0.3807   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0056    0.6944    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082    1.3107    1.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    0.8042    0.7897 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4691   -0.2257   -0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7091   -0.7656   -0.4337 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -0.3393   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0735   -1.0978   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3434   -0.6964   -0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5662    0.4191    0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9356    0.7569    0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0290    1.0285    1.1658 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004    1.1402    1.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1883    0.7700    0.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3334   -0.8142   -0.5319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406   -2.9991    0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5386   -1.7457    1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1554   -2.4750    2.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9185   -1.0857    1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7784    1.4947   -0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7570   -0.4111    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7587    1.5400   -1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4489    0.1738   -2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    1.0460   -3.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078    1.8533   -2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262   -1.8265   -1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755    1.0524    0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0465    2.1490    1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227   -1.6028   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8820   -1.9664   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1698   -1.2920   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6560    2.0142    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3984    1.3929    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  3  0
  4  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  3  0
 23 26  1  0
 26 27  2  0
 18 28  2  0
 12  2  1  0
 28 14  1  0
 27 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  5 33  1  0
  6 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
 26 45  1  0
 27 46  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       5.748   0.770   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       7.081   3.080   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       8.415   5.390   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.748   3.080   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.414  -9.240   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      15.083   9.240   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.748  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082   5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.748   7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.416   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.082   8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.416   7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.414  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.750   8.470   0.000  0.00  0.00           C+0
CONECT    1    7   15                                                       
CONECT    2   15   18                                                       
CONECT    3   18   19                                                       
CONECT    4   18   20                                                       
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7   11   13                                                  
CONECT    9    7   12   14                                                  
CONECT   10   11   12   16                                                  
CONECT   11    8   10                                                       
CONECT   12    9   10                                                       
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15    1    2   17                                                  
CONECT   16   10   23                                                       
CONECT   17   15   20                                                       
CONECT   18    2    3    4                                                  
CONECT   19    3   21   22                                                  
CONECT   20    4   17                                                       
CONECT   21   19   24                                                       
CONECT   22   19   25                                                       
CONECT   23   16   27                                                       
CONECT   24   21   26                                                       
CONECT   25   22   26                                                       
CONECT   26   24   25   28                                                  
CONECT   27    5   23                                                       
CONECT   28    6   26                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0061725
HETATM    1  C1  UNL     1      -2.443  -2.121   1.482  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.084  -1.096   0.617  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.390  -0.656   0.879  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.011   0.288   0.100  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.361   0.749   0.363  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.127   0.332   1.344  1.00  0.00           C  
HETATM    7  C7  UNL     1      -8.476   0.860   1.525  1.00  0.00           C  
HETATM    8  N1  UNL     1      -9.542   1.266   1.665  1.00  0.00           N  
HETATM    9  C8  UNL     1      -4.274   0.794  -0.974  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.990   0.360  -1.228  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.207   0.905  -2.378  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.367  -0.590  -0.444  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.041  -1.007  -0.746  1.00  0.00           N  
HETATM   14  C12 UNL     1       0.105  -0.381  -0.215  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.006   0.694   0.644  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.108   1.311   1.166  1.00  0.00           C  
HETATM   17  N3  UNL     1       2.294   0.804   0.790  1.00  0.00           N  
HETATM   18  C15 UNL     1       2.469  -0.226  -0.032  1.00  0.00           C  
HETATM   19  N4  UNL     1       3.709  -0.766  -0.434  1.00  0.00           N  
HETATM   20  C16 UNL     1       5.000  -0.339  -0.063  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.073  -1.098  -0.530  1.00  0.00           C  
HETATM   22  C18 UNL     1       7.343  -0.696  -0.184  1.00  0.00           C  
HETATM   23  C19 UNL     1       7.566   0.419   0.599  1.00  0.00           C  
HETATM   24  C20 UNL     1       8.936   0.757   0.907  1.00  0.00           C  
HETATM   25  N5  UNL     1      10.029   1.029   1.166  1.00  0.00           N  
HETATM   26  C21 UNL     1       6.500   1.140   1.041  1.00  0.00           C  
HETATM   27  C22 UNL     1       5.188   0.770   0.714  1.00  0.00           C  
HETATM   28  N6  UNL     1       1.333  -0.814  -0.532  1.00  0.00           N  
HETATM   29  H1  UNL     1      -2.241  -2.999   0.825  1.00  0.00           H  
HETATM   30  H2  UNL     1      -1.539  -1.746   1.985  1.00  0.00           H  
HETATM   31  H3  UNL     1      -3.155  -2.475   2.261  1.00  0.00           H  
HETATM   32  H4  UNL     1      -4.918  -1.086   1.730  1.00  0.00           H  
HETATM   33  H5  UNL     1      -6.778   1.495  -0.297  1.00  0.00           H  
HETATM   34  H6  UNL     1      -6.757  -0.411   2.030  1.00  0.00           H  
HETATM   35  H7  UNL     1      -4.759   1.540  -1.592  1.00  0.00           H  
HETATM   36  H8  UNL     1      -1.449   0.174  -2.707  1.00  0.00           H  
HETATM   37  H9  UNL     1      -2.905   1.046  -3.236  1.00  0.00           H  
HETATM   38  H10 UNL     1      -1.708   1.853  -2.122  1.00  0.00           H  
HETATM   39  H11 UNL     1      -0.926  -1.827  -1.400  1.00  0.00           H  
HETATM   40  H12 UNL     1      -0.975   1.052   0.907  1.00  0.00           H  
HETATM   41  H13 UNL     1       1.047   2.149   1.837  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.623  -1.603  -1.107  1.00  0.00           H  
HETATM   43  H15 UNL     1       5.882  -1.966  -1.140  1.00  0.00           H  
HETATM   44  H16 UNL     1       8.170  -1.292  -0.551  1.00  0.00           H  
HETATM   45  H17 UNL     1       6.656   2.014   1.653  1.00  0.00           H  
HETATM   46  H18 UNL     1       4.398   1.393   1.099  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    3   12
CONECT    3    4   32
CONECT    4    5    9    9
CONECT    5    6    6   33
CONECT    6    7   34
CONECT    7    8    8    8
CONECT    9   10   35
CONECT   10   11   12   12
CONECT   11   36   37   38
CONECT   12   13
CONECT   13   14   39
CONECT   14   15   15   28
CONECT   15   16   40
CONECT   16   17   17   41
CONECT   17   18
CONECT   18   19   28   28
CONECT   19   20   42
CONECT   20   21   21   27
CONECT   21   22   43
CONECT   22   23   23   44
CONECT   23   24   26
CONECT   24   25   25   25
CONECT   26   27   27   45
CONECT   27   46
END

HMDB0061725
     RDKit          3D
Rilpivirine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -2.4427   -2.1208    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0838   -1.0960    0.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3904   -0.6565    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0114    0.2882    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3613    0.7491    0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1265    0.3323    1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4762    0.8597    1.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5418    1.2661    1.6646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    0.7944   -0.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9905    0.3596   -1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2074    0.9048   -2.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674   -0.5900   -0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0413   -1.0073   -0.7459 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054   -0.3807   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0056    0.6944    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082    1.3107    1.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    0.8042    0.7897 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4691   -0.2257   -0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7091   -0.7656   -0.4337 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997   -0.3393   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0735   -1.0978   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3434   -0.6964   -0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5662    0.4191    0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9356    0.7569    0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0290    1.0285    1.1658 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004    1.1402    1.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1883    0.7700    0.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3334   -0.8142   -0.5319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406   -2.9991    0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5386   -1.7457    1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1554   -2.4750    2.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9185   -1.0857    1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7784    1.4947   -0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7570   -0.4111    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7587    1.5400   -1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4489    0.1738   -2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    1.0460   -3.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078    1.8533   -2.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9262   -1.8265   -1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755    1.0524    0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0465    2.1490    1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227   -1.6028   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8820   -1.9664   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1698   -1.2920   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6560    2.0142    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3984    1.3929    1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  3  0
  4  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  3  0
 23 26  1  0
 26 27  2  0
 18 28  2  0
 12  2  1  0
 28 14  1  0
 27 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  5 33  1  0
  6 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
 26 45  1  0
 27 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-{[4-({4-[(e)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile	ChEBI
TMC 278	ChEBI
TMC278	ChEBI
278, TMC	HMDB
HCL, Rilpivirine	HMDB
Rilpivirine HCL	HMDB
Rilpivirine hydrochloride	HMDB
Hydrochloride, rilpivirine	HMDB
TMC-278	HMDB

Chemical Formula

C₂₂H₁₈N₆

Average Molecular Weight

366.4185

Monoisotopic Molecular Weight

366.159294606

IUPAC Name

4-{[4-({4-[(1E)-2-cyanoeth-1-en-1-yl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile

Traditional Name

rilpivirine

CAS Registry Number

Not Available

SMILES

CC1=CC(\C=C\C#N)=CC(C)=C1NC1=NC(NC2=CC=C(C=C2)C#N)=NC=C1

InChI Identifier

InChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19/h3-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+

InChI Key

YIBOMRUWOWDFLG-ONEGZZNKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzonitriles

Direct Parent

Benzonitriles

Alternative Parents

Substituents

Benzonitrile
M-xylene
Xylene
Styrene
Aniline or substituted anilines
Aminopyrimidine
Hydropyrimidine
Pyrimidine
Imidolactam
Heteroaromatic compound
Azacycle
Secondary amine
Nitrile
Carbonitrile
Organoheterocyclic compound
Amine
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aminopyrimidine (CHEBI:68606 )
nitrile (CHEBI:68606 )

Ontology

Physiological effect

Not Available

Disposition

Not Available

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Rilpivirine Action Pathway (PathBank: SMP0000744)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	3.8	ALOGPS
logP	5.47	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	5.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.74 m³·mol⁻¹	ChemAxon
Polarizability	40.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	187.397	30932474
DeepCCS	[M-H]-	185.039	30932474
DeepCCS	[M-2H]-	218.92	30932474
DeepCCS	[M+Na]+	194.054	30932474
AllCCS	[M+H]+	191.7	32859911
AllCCS	[M+H-H2O]+	188.8	32859911
AllCCS	[M+NH4]+	194.3	32859911
AllCCS	[M+Na]+	195.0	32859911
AllCCS	[M-H]-	190.6	32859911
AllCCS	[M+Na-2H]-	190.0	32859911
AllCCS	[M+HCOO]-	189.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rilpivirine	CC1=CC(\C=C\C#N)=CC(C)=C1NC1=NC(NC2=CC=C(C=C2)C#N)=NC=C1	5218.8	Standard polar	33892256
Rilpivirine	CC1=CC(\C=C\C#N)=CC(C)=C1NC1=NC(NC2=CC=C(C=C2)C#N)=NC=C1	3547.6	Standard non polar	33892256
Rilpivirine	CC1=CC(\C=C\C#N)=CC(C)=C1NC1=NC(NC2=CC=C(C=C2)C#N)=NC=C1	4030.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rilpivirine,1TMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(NC2=CC=C(C#N)C=C2)=N1)[Si](C)(C)C	3527.0	Semi standard non polar	33892256
Rilpivirine,1TMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(NC2=CC=C(C#N)C=C2)=N1)[Si](C)(C)C	3539.0	Standard non polar	33892256
Rilpivirine,1TMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(NC2=CC=C(C#N)C=C2)=N1)[Si](C)(C)C	5785.1	Standard polar	33892256
Rilpivirine,1TMS,isomer #2	CC1=CC(/C=C/C#N)=CC(C)=C1NC1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C)=N1	3536.0	Semi standard non polar	33892256
Rilpivirine,1TMS,isomer #2	CC1=CC(/C=C/C#N)=CC(C)=C1NC1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C)=N1	3461.2	Standard non polar	33892256
Rilpivirine,1TMS,isomer #2	CC1=CC(/C=C/C#N)=CC(C)=C1NC1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C)=N1	5646.3	Standard polar	33892256
Rilpivirine,2TMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C)=N1)[Si](C)(C)C	3377.6	Semi standard non polar	33892256
Rilpivirine,2TMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C)=N1)[Si](C)(C)C	3378.3	Standard non polar	33892256
Rilpivirine,2TMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C)=N1)[Si](C)(C)C	5190.8	Standard polar	33892256
Rilpivirine,1TBDMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(NC2=CC=C(C#N)C=C2)=N1)[Si](C)(C)C(C)(C)C	3730.1	Semi standard non polar	33892256
Rilpivirine,1TBDMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(NC2=CC=C(C#N)C=C2)=N1)[Si](C)(C)C(C)(C)C	3748.7	Standard non polar	33892256
Rilpivirine,1TBDMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(NC2=CC=C(C#N)C=C2)=N1)[Si](C)(C)C(C)(C)C	5711.8	Standard polar	33892256
Rilpivirine,1TBDMS,isomer #2	CC1=CC(/C=C/C#N)=CC(C)=C1NC1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C(C)(C)C)=N1	3718.1	Semi standard non polar	33892256
Rilpivirine,1TBDMS,isomer #2	CC1=CC(/C=C/C#N)=CC(C)=C1NC1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C(C)(C)C)=N1	3632.2	Standard non polar	33892256
Rilpivirine,1TBDMS,isomer #2	CC1=CC(/C=C/C#N)=CC(C)=C1NC1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C(C)(C)C)=N1	5580.4	Standard polar	33892256
Rilpivirine,2TBDMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C(C)(C)C)=N1)[Si](C)(C)C(C)(C)C	3710.7	Semi standard non polar	33892256
Rilpivirine,2TBDMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C(C)(C)C)=N1)[Si](C)(C)C(C)(C)C	3775.6	Standard non polar	33892256
Rilpivirine,2TBDMS,isomer #1	CC1=CC(/C=C/C#N)=CC(C)=C1N(C1=CC=NC(N(C2=CC=C(C#N)C=C2)[Si](C)(C)C(C)(C)C)=N1)[Si](C)(C)C(C)(C)C	5120.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Rilpivirine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0649000000-96980e5526a79d124034	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rilpivirine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 10V, Positive-QTOF	splash10-014i-0109000000-f0ca783d371380bc70e5	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 20V, Positive-QTOF	splash10-0udi-1219000000-e52f83b92e47c660600d	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 40V, Positive-QTOF	splash10-0zmj-4920000000-97a3c101caf2d43175bb	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 10V, Negative-QTOF	splash10-014i-0109000000-b3b95eac39ccf546b147	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 20V, Negative-QTOF	splash10-014i-0629000000-e93c0f34e547e8a4da81	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 40V, Negative-QTOF	splash10-00kf-2910000000-04ece45ca32dd4273a60	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 10V, Positive-QTOF	splash10-014i-0009000000-efe986bd6a1d1d4ca2a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 20V, Positive-QTOF	splash10-0fr6-0009000000-b5cb0a38cec89212efdc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 40V, Positive-QTOF	splash10-032c-0419000000-bf2ec0c5ebbff53474bf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 10V, Negative-QTOF	splash10-014i-0009000000-c838d008fa2a99068202	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 20V, Negative-QTOF	splash10-014i-0209000000-a8521253d42dfbf29767	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rilpivirine 40V, Negative-QTOF	splash10-014i-1910000000-8cb4bc72ef66b926a7d6	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Rilpivirine Action Pathway		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08864

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rilpivirine

METLIN ID

Not Available

PubChem Compound

6451164

PDB ID

Not Available

ChEBI ID

68606

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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Guillemont J, Pasquier E, Palandjian P, Vernier D, Gaurrand S, Lewi PJ, Heeres J, de Jonge MR, Koymans LM, Daeyaert FF, Vinkers MH, Arnold E, Das K, Pauwels R, Andries K, de Bethune MP, Bettens E, Hertogs K, Wigerinck P, Timmerman P, Janssen PA: Synthesis of novel diarylpyrimidine analogues and their antiviral activity against human immunodeficiency virus type 1. J Med Chem. 2005 Mar 24;48(6):2072-9. [PubMed:15771449 ]
Dalton P: Researcher presents vexing information on rilpivirine. Proj Inf Perspect. 2008 Sep;(46):10-2. [PubMed:19048650 ]
Fulco PP, McNicholl IR: Etravirine and rilpivirine: nonnucleoside reverse transcriptase inhibitors with activity against human immunodeficiency virus type 1 strains resistant to previous nonnucleoside agents. Pharmacotherapy. 2009 Mar;29(3):281-94. doi: 10.1592/phco.29.3.281. [PubMed:19249947 ]
Hughes CA, Robinson L, Tseng A, MacArthur RD: New antiretroviral drugs: a review of the efficacy, safety, pharmacokinetics, and resistance profile of tipranavir, darunavir, etravirine, rilpivirine, maraviroc, and raltegravir. Expert Opin Pharmacother. 2009 Oct;10(15):2445-66. doi: 10.1517/14656560903176446. [PubMed:19678794 ]
van 't Klooster G, Hoeben E, Borghys H, Looszova A, Bouche MP, van Velsen F, Baert L: Pharmacokinetics and disposition of rilpivirine (TMC278) nanosuspension as a long-acting injectable antiretroviral formulation. Antimicrob Agents Chemother. 2010 May;54(5):2042-50. doi: 10.1128/AAC.01529-09. Epub 2010 Feb 16. [PubMed:20160045 ]
Macarthur RD: Clinical Trial Report: TMC278 (Rilpivirine) Versus Efavirenz as Initial Therapy in Treatment-Naive, HIV-1-Infected Patients. Curr Infect Dis Rep. 2011 Feb;13(1):1-3. doi: 10.1007/s11908-010-0148-6. [PubMed:21308448 ]
Miller CD, Crain J, Tran B, Patel N: Rilpivirine: a new addition to the anti-HIV-1 armamentarium. Drugs Today (Barc). 2011 Jan;47(1):5-15. doi: 10.1358/dot.2011.47.1.1583188. [PubMed:21373646 ]
Schrijvers R, Desimmie BA, Debyser Z: Rilpivirine: a step forward in tailored HIV treatment. Lancet. 2011 Jul 16;378(9787):201-3. doi: 10.1016/S0140-6736(11)60992-6. [PubMed:21763920 ]
Cohen CJ, Andrade-Villanueva J, Clotet B, Fourie J, Johnson MA, Ruxrungtham K, Wu H, Zorrilla C, Crauwels H, Rimsky LT, Vanveggel S, Boven K: Rilpivirine versus efavirenz with two background nucleoside or nucleotide reverse transcriptase inhibitors in treatment-naive adults infected with HIV-1 (THRIVE): a phase 3, randomised, non-inferiority trial. Lancet. 2011 Jul 16;378(9787):229-37. doi: 10.1016/S0140-6736(11)60983-5. [PubMed:21763935 ]
Molina JM, Cahn P, Grinsztejn B, Lazzarin A, Mills A, Saag M, Supparatpinyo K, Walmsley S, Crauwels H, Rimsky LT, Vanveggel S, Boven K: Rilpivirine versus efavirenz with tenofovir and emtricitabine in treatment-naive adults infected with HIV-1 (ECHO): a phase 3 randomised double-blind active-controlled trial. Lancet. 2011 Jul 16;378(9787):238-46. doi: 10.1016/S0140-6736(11)60936-7. [PubMed:21763936 ]
Authors unspecified: Rilpivirine (Edurant)--a new drug for HIV infection. Med Lett Drugs Ther. 2011 Aug 22;53(1371):67-8. [PubMed:21860365 ]
Wilkin A, Pozniak AL, Morales-Ramirez J, Lupo SH, Santoscoy M, Grinsztejn B, Ruxrungtham K, Rimsky LT, Vanveggel S, Boven K: Long-term efficacy, safety, and tolerability of rilpivirine (RPV, TMC278) in HIV type 1-infected antiretroviral-naive patients: week 192 results from a phase IIb randomized trial. AIDS Res Hum Retroviruses. 2012 May;28(5):437-46. doi: 10.1089/AID.2011.0050. Epub 2011 Oct 17. [PubMed:21902621 ]
Bunupuradah T, Ananworanich J, Chetchotisakd P, Kantipong P, Jirajariyavej S, Sirivichayakul S, Munsakul W, Prasithsirikul W, Sungkanuparph S, Bowonwattanuwong C, Klinbuayaem V, Petoumenos K, Hirschel B, Bhakeecheep S, Ruxrungtham K: Etravirine and rilpivirine resistance in HIV-1 subtype CRF01_AE-infected adults failing non-nucleoside reverse transcriptase inhibitor-based regimens. Antivir Ther. 2011;16(7):1113-21. doi: 10.3851/IMP1906. [PubMed:22024527 ]
Rimsky L, Vingerhoets J, Van Eygen V, Eron J, Clotet B, Hoogstoel A, Boven K, Picchio G: Genotypic and phenotypic characterization of HIV-1 isolates obtained from patients on rilpivirine therapy experiencing virologic failure in the phase 3 ECHO and THRIVE studies: 48-week analysis. J Acquir Immune Defic Syndr. 2012 Jan 1;59(1):39-46. doi: 10.1097/QAI.0b013e31823df4da. [PubMed:22067667 ]
Ford N, Lee J, Andrieux-Meyer I, Calmy A: Safety, efficacy, and pharmacokinetics of rilpivirine: systematic review with an emphasis on resource-limited settings. HIV AIDS (Auckl). 2011;3:35-44. doi: 10.2147/HIV.S14559. Epub 2011 Apr 28. [PubMed:22096405 ]
Reinheimer C, Doerr HW, Sturmer M: Prevalence of TMC278 (rilpivirine) associated mutations in the Frankfurt Resistance Database. J Clin Virol. 2012 Mar;53(3):248-50. doi: 10.1016/j.jcv.2011.12.012. Epub 2011 Dec 30. [PubMed:22209291 ]
Hussar DA, Snell CW: Boceprevir, telaprevir, and rilpivirine hydrochloride. J Am Pharm Assoc (2003). 2012 Jan-Feb;52(1):120-6. doi: 10.1331/JAPhA.2012.12506. [PubMed:22257626 ]
Cohen CJ, Molina JM, Cahn P, Clotet B, Fourie J, Grinsztejn B, Wu H, Johnson MA, Saag M, Supparatpinyo K, Crauwels H, Lefebvre E, Rimsky LT, Vanveggel S, Williams P, Boven K: Efficacy and safety of rilpivirine (TMC278) versus efavirenz at 48 weeks in treatment-naive HIV-1-infected patients: pooled results from the phase 3 double-blind randomized ECHO and THRIVE Trials. J Acquir Immune Defic Syndr. 2012 May 1;60(1):33-42. doi: 10.1097/QAI.0b013e31824d006e. [PubMed:22343174 ]
Sanford M: Rilpivirine. Drugs. 2012 Mar 5;72(4):525-41. doi: 10.2165/11208590-000000000-00000. [PubMed:22356290 ]
Diaz-Delfin J, Domingo P, Mateo MG, Gutierrez Mdel M, Domingo JC, Giralt M, Villarroya F: Effects of rilpivirine on human adipocyte differentiation, gene expression, and release of adipokines and cytokines. Antimicrob Agents Chemother. 2012 Jun;56(6):3369-75. doi: 10.1128/AAC.00104-12. Epub 2012 Mar 19. [PubMed:22430974 ]
Fernandez-Montero JV, Vispo E, Anta L, de Mendoza C, Soriano V: Rilpivirine: a next-generation non-nucleoside analogue for the treatment of HIV infection. Expert Opin Pharmacother. 2012 May;13(7):1007-14. doi: 10.1517/14656566.2012.667802. [PubMed:22519768 ]
James C, Preininger L, Sweet M: Rilpivirine: a second-generation nonnucleoside reverse transcriptase inhibitor. Am J Health Syst Pharm. 2012 May 15;69(10):857-61. doi: 10.2146/ajhp110395. [PubMed:22555080 ]
O'Neal R: Rilpivirine and complera: new first-line treatment options. BETA. 2011 Fall-Winter;23(4):14-8. [PubMed:22567823 ]
Patel N, Miller CD: New option for management of HIV-1 infection in treatment-naive patients: once-daily, fixed-dose combination of rilpivirine-emtricitabine-tenofovir. HIV AIDS (Auckl). 2012;4:61-71. doi: 10.2147/HIV.S25149. Epub 2012 Apr 27. [PubMed:22570576 ]
Burugula L, Pilli NR, Makula A, Lodagala DS, Kandhagatla R: Liquid chromatography-tandem mass spectrometric assay for the non-nucleoside reverse transcriptase inhibitor rilpivirine in human plasma. Biomed Chromatogr. 2013 Feb;27(2):172-8. doi: 10.1002/bmc.2765. Epub 2012 Jun 22. [PubMed:22729755 ]
Anta L, Llibre JM, Poveda E, Blanco JL, Alvarez M, Perez-Elias MJ, Aguilera A, Caballero E, Soriano V, de Mendoza C: Rilpivirine resistance mutations in HIV patients failing non-nucleoside reverse transcriptase inhibitor-based therapies. AIDS. 2013 Jan 2;27(1):81-5. doi: 10.1097/QAD.0b013e3283584500. [PubMed:22842995 ]
Schafer JJ, Short WR: Rilpivirine, a novel non-nucleoside reverse transcriptase inhibitor for the management of HIV-1 infection: a systematic review. Antivir Ther. 2012;17(8):1495-502. doi: 10.3851/IMP2254. Epub 2012 Aug 10. [PubMed:22878339 ]
Lyseng-Williamson KA, Scott LJ: Emtricitabine/rilpivirine/tenofovir disoproxil fumarate single-tablet regimen: a guide to its use in HIV-1 infection. Clin Drug Investig. 2012 Oct 1;32(10):715-22. doi: 10.2165/11209870-000000000-00000. [PubMed:22921088 ]
Vingerhoets J, Rimsky L, Van Eygen V, Nijs S, Vanveggel S, Boven K, Picchio G: Pre-existing mutations in the rilpivirine Phase III trials ECHO and THRIVE: prevalence and impact on virological response. Antivir Ther. 2013;18(2):253-6. doi: 10.3851/IMP2358. Epub 2012 Sep 6. [PubMed:22951490 ]

Showing metabocard for Rilpivirine (HMDB0061725)

MOL for HMDB0061725 (Rilpivirine)

3D MOL for HMDB0061725 (Rilpivirine)

3D SDF for HMDB0061725 (Rilpivirine)

3D-SDF for HMDB0061725 (Rilpivirine)

PDB for HMDB0061725 (Rilpivirine)

3D PDB for HMDB0061725 (Rilpivirine)

SMILES for HMDB0061725 (Rilpivirine)

INCHI for HMDB0061725 (Rilpivirine)

Structure for HMDB0061725 (Rilpivirine)

3D Structure for HMDB0061725 (Rilpivirine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra