Responsive image

Common name


Cobicistat

IUPAC name


(1,3-thiazol-5-yl)methyl N-[(2R,5R)-5-[(2S)-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}-4-(morpholin-4-yl)butanamido]-1,6-diphenylhexan-2-yl]carbamate

SMILES


CC(C)C1=NC(CN(C)C(=O)N[C@@H](CCN2CCOCC2)C(=O)N[C@H](CC[C@H](CC2=CC=CC=C2)NC(=O)OCC2=CN=CS2)CC2=CC=CC=C2)=CS1

Compound class


Anti-HIV Agents; Antiinfectives for Systemic Use; Direct Acting Antivirals; Antivirals for Systemic Use; Cytochrome P-450 CYP3A Inhibitors; CYP2D6 Inducers; CYP2D6 Inducers (strong);

Therapeutic area


Cobicistat is a CYP3A inhibitor indicated to increase systemic exposure of atazanavir or darunavir (once daily dosing regimen) in combination with other antiretroviral agents in the treatment of HIV-1 infection. It is not interchangeable with ritonavir to increase systemic exposure of darunavir 600 mg twice daily, fosamprenavir, saquinavir, or tipranavir due to lack of exposure data. The use of cobicistat is not recommended with darunavir 600 mg twice daily, fosamprenavir, saquinavir or tipranavir. Complex or unknown mechanisms of drug interactions preclude extrapolation of ritonavir drug interactions to certain cobicistat interactions. Cobicistat and ritonavir when administered with either atazanavir or darunavir may result in different drug interactions when used with concomitant medications.

Common name


Cobicistat

IUPAC name


(1,3-thiazol-5-yl)methyl N-[(2R,5R)-5-[(2S)-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}-4-(morpholin-4-yl)butanamido]-1,6-diphenylhexan-2-yl]carbamate

SMILES


CC(C)C1=NC(CN(C)C(=O)N[C@@H](CCN2CCOCC2)C(=O)N[C@H](CC[C@H](CC2=CC=CC=C2)NC(=O)OCC2=CN=CS2)CC2=CC=CC=C2)=CS1

INCHI


InChI=1S/C40H53N7O5S2/c1-29(2)38-43-34(27-53-38)25-46(3)39(49)45-36(16-17-47-18-20-51-21-19-47)37(48)42-32(22-30-10-6-4-7-11-30)14-15-33(23-31-12-8-5-9-13-31)44-40(50)52-26-35-24-41-28-54-35/h4-13,24,27-29,32-33,36H,14-23,25-26H2,1-3H3,(H,42,48)(H,44,50)(H,45,49)/t32-,33-,36+/m1/s1

FORMULA


C40H53N7O5S2

Responsive image

Common name


Cobicistat

IUPAC name


(1,3-thiazol-5-yl)methyl N-[(2R,5R)-5-[(2S)-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}-4-(morpholin-4-yl)butanamido]-1,6-diphenylhexan-2-yl]carbamate

Molecular weight


776.023

clogP


7.629

clogS


-9.071

HBond Acceptor


8

HBond Donor


3

Total Polar
Surface Area


194.5

Number of Rings


5

Rotatable Bond


21

Drug ID Common name Structure CAS SMILE Frequency
FDBF00023 toluene Responsive image c1(ccccc1)C 0.1268
FDBF00026 propanamide Responsive image CCC(=O)N 0.0148
FDBF00141 ethylbenzene Responsive image c1(ccccc1)CC 0.0371
FDBF00710 4-methylmorpholine Responsive image O1CCN(CC1)C 0.0052
FDBF00865 isopropylcarbamic acid Responsive image O=C(O)NC(C)C 0.0010
FDBF01127 methylcarbamic acid Responsive image O=C(O)NC 0.0199
FDBF01143 N-isopropylacetamide Responsive image CC(C)NC(=O)C 0.0024
FDBF04052 N-propylpropanamide Responsive image C(CNC(=O)CC)C 0.0003
FDBF04055 methyl N-[(1S)-1-methylpropyl]carbamate Responsive image CCC(C)NC(=O)OC 0.0003
FDBF04058 N-isopropylbutanamide Responsive image CC(NC(=O)CCC)C 0.0003
66 , 7