Details of the Drug

General Information of Drug (ID: DMCIGRB)

Drug Name

Fialuridine

Synonyms

FIAU

Indication

Disease Entry	ICD 11	Status	REF
Hepatitis B virus infection	1E51.0	Phase 2	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

372.09

Logarithm of the Partition Coefficient (xlogp)

-0.9

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

6

Chemical Identifiers

Formula: C9H10FIN2O5
IUPAC Name: 1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione
Canonical SMILES: C1=C(C(=O)NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)F)I
InChI: InChI=1S/C9H10FIN2O5/c10-5-6(15)4(2-14)18-8(5)13-1-3(11)7(16)12-9(13)17/h1,4-6,8,14-15H,2H2,(H,12,16,17)/t4-,5+,6-,8-/m1/s1
InChIKey: IPVFGAYTKQKGBM-BYPJNBLXSA-N

Cross-matching ID

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Herpes simplex virus DNA polymerase UL30 (HSV UL30)	TTIU7X1	DPOL_HHV11	Modulator	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
ATP synthase subunit a (ATP6)	OTPHOGLX	ATP6_HUMAN	Gene/Protein Processing	[3]
Cytochrome b (CYTB)	OTAHB98A	CYB_HUMAN	Gene/Protein Processing	[3]
Cytochrome c oxidase subunit 2 (COX2)	OTTMVBJJ	COX2_HUMAN	Gene/Protein Processing	[3]
Equilibrative nucleoside transporter 1 (SLC29A1)	OTLOOZZS	S29A1_HUMAN	Drug Response	[3]
Equilibrative nucleoside transporter 3 (SLC29A3)	OTGLX8XU	S29A3_HUMAN	Regulation of Drug Effects	[4]
NADH-ubiquinone oxidoreductase chain 3 (ND3)	OT1OC3K3	NU3M_HUMAN	Gene/Protein Processing	[3]
Ribonucleoside-diphosphate reductase large subunit (RRM1)	OTXGQOR9	RIR1_HUMAN	Drug Response	[3]
Thymidine kinase 2, mitochondrial (TK2)	OTS1V4XB	KITM_HUMAN	Drug Response	[3]

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Molecular Interaction Atlas (MIA)

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	ClinicalTrials.gov (NCT00000654) The Tolerance of HIV-Infected Patients With Herpes Group Virus Infections to Oral Doses of FIAU. U.S. National Institutes of Health.
2	Fialuridine and its metabolites inhibit DNA polymerase gamma at sites of multiple adjacent analog incorporation, decrease mtDNA abundance, and cause mitochondrial structural defects in cultured hepatoblasts. Proc Natl Acad Sci U S A. 1996 Apr 16;93(8):3592-7.
3	Mechanisms of Chronic Fialuridine Hepatotoxicity as Revealed in Primary Human Hepatocyte Spheroids. Toxicol Sci. 2019 Oct 1;171(2):385-395. doi: 10.1093/toxsci/kfz195.
4	Facilitated mitochondrial import of antiviral and anticancer nucleoside drugs by human equilibrative nucleoside transporter-3. Am J Physiol Gastrointest Liver Physiol. 2009 Apr;296(4):G910-22. doi: 10.1152/ajpgi.90672.2008. Epub 2009 Jan 22.