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
FDBF00003 formamide Responsive image C(=O)N 0.1240
FDBF01130 1,1,3-trimethylurea Responsive image O=C(NC)N(C)C 0.0007
FDBF01132 ethylcarbamic acid Responsive image O=C(O)NCC 0.0034
FDBF02005 N-ethylbutanamide Responsive image O=C(NCC)CCC 0.0010
FDBF02927 [(1S)-1-methylpropyl]carbamic acid Responsive image CC(CC)NC(=O)O 0.0007
FDBF02928 [(1R)-1-methyl-2-phenyl-ethyl]carbamic acid Responsive image c1(ccccc1)CC(C)NC(=O)O 0.0007
FDBF04044 3-ethyl-1,1-dimethyl-urea Responsive image CN(C(=O)NCC)C 0.0003
FDBF04049 1,1-dimethyl-3-propyl-urea Responsive image CCCNC(=O)N(C)C 0.0003
FDBF04053 [(1S)-1-methylbutyl]carbamic acid Responsive image C(C)CC(C)NC(=O)O 0.0003
FDBF04054 N-isopropylpropanamide Responsive image CC(NC(=O)CC)C 0.0003
66 , 7