Responsive image

Common name


Fosamprenavir

IUPAC name


{[(2R,3S)-1-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid

SMILES


CC(C)CN(C[C@@H](OP(O)(O)=O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1

Compound class


Anti-HIV Agents; Protease Inhibitors; HIV Protease Inhibitors; Prodrugs; Antiinfectives for Systemic Use; Direct Acting Antivirals; Antivirals for Systemic Use; CYP3A4 Inhibitors;

Therapeutic area


Indicated in combination with other antiretroviral agents for the treatment of human immunodeficiency virus (HIV-1) infection, as well as postexposure prophylaxis of HIV infection in individuals who have had occupational or nonoccupational exposure to potentially infectious body fluids of a person known to be infected with HIV when that exposure represents a substantial risk for HIV transmission. The use of fosamprenavir is pending revision due to a potential association between the drug and myocardial infarction and dyslipidemia in HIV infected adults.

Common name


Fosamprenavir

IUPAC name


{[(2R,3S)-1-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid

SMILES


CC(C)CN(C[C@@H](OP(O)(O)=O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1

INCHI


InChI=1S/C25H36N3O9PS/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32)/t21-,23-,24+/m0/s1

FORMULA


C25H36N3O9PS

Responsive image

Common name


Fosamprenavir

IUPAC name


{[(2R,3S)-1-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid

Molecular weight


585.607

clogP


0.629

clogS


-3.274

HBond Acceptor


9

HBond Donor


5

Total Polar
Surface Area


177.72

Number of Rings


3

Rotatable Bond


14

Drug ID Common name Structure CAS SMILE Frequency
FDBF00012 isobutane Responsive image C(C)(C)C 0.0611
FDBF00040 ethanamine Responsive image CCN 0.0677
FDBF00576 N-(dihydroxy-λ3-sulfanyl)methanamine Responsive image CN[S](O)O 0.0038
FDBF01132 ethylcarbamic acid Responsive image O=C(O)NCC 0.0034
FDBF01296 2-methylpropan-1-amine Responsive image NCC(C)C 0.0017
FDBF01632 N-(dihydroxy-λ3-sulfanyl)-N,2-dimethyl-propan-1-amine Responsive image C(C(C)C)N(C)[S](O)O 0.0010
FDBF02924 N-(dihydroxy-λ3-sulfanyl)-N-methyl-ethanamine Responsive image [S](O)(O)N(CC)C 0.0003
FDBF02926 N-ethyl-2-methyl-propan-1-amine Responsive image C(C)(C)CNCC 0.0003
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
38 , 4