
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

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 |
---|---|---|---|---|
FDBF00005 | benzene |
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c1ccccc1 | 0.2824 |
FDBF00067 | butane |
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CCCC | 0.0680 |
FDBF00068 | N-methylethanamine |
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N(CC)C | 0.0429 |
FDBF00069 | N-methylpropan-1-amine |
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N(CCC)C | 0.0148 |
FDBF00072 | N-methylbutan-1-amine |
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N(CCCC)C | 0.0034 |
FDBF01138 | phenethylcarbamic acid |
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O=C(O)NCCc1ccccc1 | 0.0017 |
FDBF01627 | N-(dihydroxy-λ3-sulfanyl)-N-methyl-methanamine |
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[S](O)(O)N(C)C | 0.0041 |
FDBF01628 | N-(dihydroxy-λ3-sulfanyl)-2-methyl-propan-1-amine |
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[S](O)(O)NCC(C)C | 0.0010 |
FDBF02923 | propylcarbamic acid |
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CCCNC(=O)O | 0.0014 |
FDBF02925 | [(3S)-tetrahydrofuran-3-yl] N-isopropylcarbamate |
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CC(C)NC(=O)OC1COCC1 | 0.0003 |