Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H10FN3O3 |
Molecular Weight | 227.1924 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=O)N(C=C1F)[C@H]2O[C@@H](CO)C=C2
InChI
InChIKey=HSBKFSPNDWWPSL-VDTYLAMSSA-N
InChI=1S/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m1/s1
Elvucitabine (ACH-126443 or beta-L-Fd4C) is a reverse transcriptase inhibitor exerting antiviral properties. Elvucitabine, an L-cytosine nucleoside analog, is intracellularly phosphorylated to its active 5′-triphosphate metabolite, which has an intracellular half-life of at least 20 hours. Elvucitabine triphosphate inhibits the activity of HIV reverse transcriptase by competing with natural substrates and by causing DNA chain termination after incorporation into viral DNA. Elvucitabine has also demonstrated in vitro and in vivo activity against HBV. Achillion, under license from Vion is developing elvucitabine for the potential treatment of HIV and hepatitis B virus (HBV) infection.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Design and synthesis of 2',3'-dideoxy-2',3'-didehydro-beta-L-cytidine (beta-L-d4C) and 2',3'-dideoxy 2',3'-didehydro-beta-L-5-fluorocytidine (beta-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human immunodeficiency virus (HIV) in vitro. | 1996 Apr 26 |
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Anti-hepatitis B virus activity and metabolism of 2',3'-dideoxy-2',3'-didehydro-beta-L(-)-5-fluorocytidine. | 1998 Jul |
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Metabolism of 2',3'-dideoxy-2',3'-didehydro-beta-L(-)-5-fluorocytidine and its activity in combination with clinically approved anti-human immunodeficiency virus beta-D(+) nucleoside analogs in vitro. | 1998 Jul |
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Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C. | 1998 Nov 17 |
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Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues. | 1999 Jun 15 |
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Novel 4'-substituted stavudine analog with improved anti-human immunodeficiency virus activity and decreased cytotoxicity. | 2004 May |
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In vitro activity of structurally diverse nucleoside analogs against human immunodeficiency virus type 1 with the K65R mutation in reverse transcriptase. | 2005 Mar |
Patents
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1557
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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NCI_THESAURUS |
C97452
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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Code System | Code | Type | Description | ||
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C73201
Created by
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DTXSID20171185
Created by
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DB06236
Created by
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100000163593
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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ELVUCITABINE
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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C099405
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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469717
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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M09BUF90C0
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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SUB177918
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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181785-84-2
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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CHEMBL38700
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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OO-44
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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8364
Created by
admin on Sat Dec 16 16:18:08 GMT 2023 , Edited by admin on Sat Dec 16 16:18:08 GMT 2023
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PRIMARY |
ACTIVE MOIETY