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
FDBF00027 N-methylacetamide Responsive image N(C(=O)C)C 0.0175
FDBF00034 N-propylformamide Responsive image C(NC=O)CC 0.0031
FDBF00038 N-methylbutanamide Responsive image N(C(=O)CCC)C 0.0024
FDBF00113 4-methylthiazole Responsive image s1cc(nc1)C 0.0017
FDBF00228 N-ethylacetamide Responsive image C(=O)(NCC)C 0.0089
FDBF00234 N-ethylpropanamide Responsive image C(=O)(NCC)CC 0.0038
FDBF00692 methyl carbamate Responsive image O(C(=O)N)C 0.0117
FDBF03096 N-[(1S)-1-methyl-2-phenyl-ethyl]acetamide Responsive image CC(=O)NC(C)Cc1ccccc1 0.0010
FDBF04048 methyl N-propylcarbamate Responsive image CCCNC(=O)OC 0.0007
FDBF04050 N-[(1R)-1-methylbutyl]formamide Responsive image C(C(NC=O)C)CC 0.0007
66 , 7