Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H13N3O4 |
Molecular Weight | 227.2172 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=O)N(C=C1)[C@@H]2C[C@@H](O)[C@H](CO)O2
InChI
InChIKey=CKTSBUTUHBMZGZ-CHKWXVPMSA-N
InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m1/s1
Torcitabine is the beta-L-enantiomer of the natural nucleoside D-cytidine. The drug was under development as an antiviral agent for the treatment of chronic hepatitis B virus infection. Torcitabine has poor oral bioavailability, but its 3’,5’-derivative ester (val-L-dC) and the 3’-monovaline ester, valtorcitabine dihydrochloride, have excellent oral bioavailability and consequently the torcitabine prodrug, valtorcitabine, has replaced torcitabine in clinical development. Torcitabine is active against hepadnaviruses, specifically human hepatitis B virus (HBV), duck hepatitis virus (DHBV) and woodchuck hepatitis virus (WHV). Torcitabine triphosphate is a selective inhibitor of the polymerase enzyme of HBV.
Originator
Approval Year
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1557
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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NCI_THESAURUS |
C29575
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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NCI_THESAURUS |
C281
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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Code System | Code | Type | Description | ||
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MM-29
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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6BZN07BMW3
Created by
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DTXSID30960542
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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300000017952
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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PRIMARY | |||
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C73200
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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PRIMARY | |||
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CHEMBL554563
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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PRIMARY | |||
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159354
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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40093-94-5
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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8272
Created by
admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
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PRIMARY |
ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)