Prodrug Information
Prodrug General Information | Top | |||||
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Prodrug ID |
D2JA5L
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Prodrug Name |
Fosamprenavir
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Synonyms |
Telzir; GW433908; Fosamprenavir [INN]; FOS-APV; VX 175; GW 433908; UNII-WOU1621EEG; Fosamprenavir (INN); HSDB 7340; VX-175; WOU1621EEG; CHEBI:82941; GW-433908; [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-1-phenyl-3-phosphonooxybutan-2-yl]carbamate; Amprenavir phosphate; Telzir(TM); Lexiva (TM); GW433908A (*Sodium Salt*); GW433908G (*Calcium Salt*); 226700-81-8; CHEMBL1664; SCHEMBL34080; DTXSID2048296; CS-M2417; ZINC3941829; GW433908A; AKOS032960329; DB01319; AS-56492; FPV; HY-78726; LS-187013; LS-187787; A12583; D02497; Q1385311
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Indication | Mother-to-fetus HIV transmission [ICD-11: JB63.7; ICD-10: B20-B24] | Approved | [1] | |||
Activation |
Prodrug |
Parent Drug |
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2D MOL 3D MOL | 2D MOL 3D MOL | |||||
(1) Bioconversion Enzyme:
Alkaline phosphatase
(EC 3.1)
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[1] | |||||
Prodrug Strategy |
Classical prodrug strategy
[Carrier linked prodrug]
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Improved property |
Increase solubility
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[3] | ||||
Description |
The prodrug is 10-fold more water soluble, and reduces the required dosage regimen from 8 times to only twice daily compared to its parent active compound.
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[2] | ||||
Formula |
C25H36N3O9PS
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Canonical SMILES |
CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)OP(=O)(O)O)S(=O)(=O)C3=CC=C(C=C3)N
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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
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InChIKey |
MLBVMOWEQCZNCC-OEMFJLHTSA-N
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CAS Number |
CAS 226700-79-4
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PubChem Compound ID | ||||||
ChEBI ID |
CHEBI:82941
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Parent Drug General Information | Top | |||||
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Parent Drug ID |
DU70HO
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Parent Drug Name |
Amprenavir
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Synonyms |
Agenerase; Prozei; VX-478; Vertex VX478; 141W94; Amprenavir (agenerase); KVX-478; VX 478; DRG-0258; UNII-5S0W860XNR; C25H35N3O6S; CHEBI:40050; HSDB 7157
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Formula |
C25H35N3O6S
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Canonical SMILES |
CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
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InChI |
1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1
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InChIKey |
YMARZQAQMVYCKC-OEMFJLHTSA-N
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CAS Number |
CAS 161814-49-9
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PubChem Compound ID | ||||||
ChEBI ID |
CHEBI:40050
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Target and Pathway | Top | |||||
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Target(s) | Human immunodeficiency virus Protease (HIV PR) | Target Info | Inhibitor | [1] |
References | Top | |||||
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REF 1 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2016 | |||||
REF 2 | Fosamprenavir : clinical pharmacokinetics and drug interactions of the amprenavir prodrug. Clin Pharmacokinet. 2006;45(2):137-68. | |||||
REF 3 | Prodrugs: design and clinical applications. Nat Rev Drug Discov. 2008 Mar;7(3):255-70. |
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