ID

DB00249|APRD00504|EXPT01835|

名称

Idoxuridine

描述

An analog of deoxyuridine that inhibits viral DNA synthesis. The drug is used as an antiviral agent.

cas号

54-42-2

唯一标识码

LGP81V5245

状态

solid

组

approved,investigational,

指示

For use in keratoconjunctivitis and keratitis caused by herpes simplex virus.

药效学

In chemical structure idoxuridine closely approximates the configuration of thymidine, one of the four building blocks of DNA (the genetic material of the Herpes virus). As a result, idoxuridine is able to replace thymidine in the enzymatic step of viral replication or "growth". The consequent production of faulty DNA results in a pseudostructure which cannot infect or destroy tissue. In short, by pre-empting a vital building block in the genetic material of the Herpes simplex virus, Herplex-D topical solution destroys the infective and destructive capacity of the viral material. The virus infected cell may only be attacked during the period of active synthesis of DNA. This occurs early in the development of the Herpes simplex lesion, but at different times in different cells. Therefore, ideally, the affected area should remain saturated with the antiviral agent.

作用机制

Idoxuridine acts as an antiviral agent by inhibiting viral replication by substituting itself for thymidine in viral DNA. This in turn inhibits thymidylate phosphorylase and viral DNA polymerases from properly functioning. The effect of Idoxuridine results in the inability of the virus to reproduce or to infect/destroy tissue.

毒性

Hypersensitivity or increased sensitivity of eyes to light. LD₅₀=3080 mg/kg (orally in mice).

代谢

Idoxuridine is rapidly inactivated by deaminases or nucleotidases.

吸收

Systemic absorption is unlikely following ocular administration even when nasolacrimal secretions are swallowed, since vidarabine is rapidly deaminated in the gastrointestinal tract.

半衰期

分类

description:This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
direct-parent:Pyrimidine 2'-deoxyribonucleosides
kingdom:Organic compounds
superclass:Nucleosides, nucleotides, and analogues
class:Pyrimidine nucleosides
subclass:Pyrimidine 2'-deoxyribonucleosides
alternative-parent:Aryl iodides
alternative-parent:Azacyclic compounds
alternative-parent:Halopyrimidines
alternative-parent:Heteroaromatic compounds
alternative-parent:Hydrocarbon derivatives
alternative-parent:Hydropyrimidines
alternative-parent:Hydroxypyrimidines
alternative-parent:Organic oxides
alternative-parent:Organoiodides
alternative-parent:Organonitrogen compounds
alternative-parent:Organopnictogen compounds
alternative-parent:Oxacyclic compounds
alternative-parent:Primary alcohols
alternative-parent:Pyrimidones
alternative-parent:Secondary alcohols
alternative-parent:Tetrahydrofurans
substituent:Alcohol
substituent:Aromatic heteromonocyclic compound
substituent:Aryl halide
substituent:Aryl iodide
substituent:Azacycle
substituent:Halopyrimidine
substituent:Heteroaromatic compound
substituent:Hydrocarbon derivative
substituent:Hydropyrimidine
substituent:Hydroxypyrimidine
substituent:Organic nitrogen compound
substituent:Organic oxide
substituent:Organic oxygen compound
substituent:Organohalogen compound
substituent:Organoheterocyclic compound
substituent:Organoiodide
substituent:Organonitrogen compound
substituent:Organooxygen compound
substituent:Organopnictogen compound
substituent:Oxacycle
substituent:Primary alcohol
substituent:Pyrimidine
substituent:Pyrimidine 2'-deoxyribonucleoside
substituent:Pyrimidone
substituent:Secondary alcohol
substituent:Tetrahydrofuran

消除途径

种类

Anti-Infective Agents
D000890
Antiinfectives for Systemic Use

Antiviral Agents
D000998
Antivirals for Systemic Use

Carbohydrates
D002241
Deoxyribonucleosides
D003853
Deoxyuridine
D003857
Dermatologicals
D003879
Direct Acting Antivirals

Enzyme Inhibitors
D004791
Glycosides
D006027
Nucleic Acid Synthesis Inhibitors
D019384
Nucleic Acids, Nucleotides, and Nucleosides
D009706
Nucleoside Analog Antiviral

Nucleosides
D009705
Nucleosides and Nucleotides Excl. Reverse Transcriptase Inhibitors

Ophthalmologicals

Pyrimidine Nucleosides
D011741
Pyrimidines
D011743
Ribonucleosides
D012263
Sensory Organs

盐类

蛋白质结合

清除

同义词

language:english; code:; name;(+)-5-Iodo-2'-deoxyuridine
language:english; code:; name;1-(2-Deoxy-beta-D-ribofuranosyl)-5-iodouracil
language:english; code:; name;1-beta-D-2'-Deoxyribofuranosyl-5-iodouracil
language:english; code:; name;1beta-D-2'-Deoxyribofuranosyl-5-iodouracil
language:english; code:iupac; name;2'-Deoxy-5-iodouridine
language:english; code:; name;5-iodo-2'-deoxyuridine
language:english; code:; name;5-Iododeoxyuridine
language:english; code:; name;5-Iodouracil deoxyriboside
language:english; code:; name;Idoxuridin
language:spanish; code:inn; name;Idoxuridina
language:english; code:inn/usan; name;Idoxuridine
language:latin; code:inn; name;Idoxuridinum
language:english; code:; name;IdU
language:english; code:; name;Iododeoxyridine
language:english; code:; name;Iodoxuridine
language:german; code:; name;Joddeoxiuridin

国际品牌

HerpidAstellasHerpiduCiba VisionIduleaEleaIdustatinSanofiKeresidGlaxoSmithKlineOftan IDUSantenVirexenViñas

配送量

产品

name:Dendrid
labeller:ALCON LABORATORIES, INC.
ndc-id:
ndc-product-code:0065-0029
dpd-id:
ema-product-code:
ema-ma-number:
started-marketing-on:1963-06-28
ended-marketing-on:1995-12-31
dosage-form:Solution / drops
strength:1 mg/1mL
route:Ophthalmic
fda-application-number:NDA014169
generic:false
over-the-counter:false
approved:true
country:US
source:FDA NDC
name:Herplex
labeller:Allergan
ndc-id:
ndc-product-code:
dpd-id:00001120
ema-product-code:
ema-ma-number:
started-marketing-on:1963-12-31
ended-marketing-on:2011-08-04
dosage-form:Solution / drops
strength:
route:Ophthalmic
fda-application-number:
generic:false
over-the-counter:false
approved:true
country:Canada
source:DPD
name:Herplex D
labeller:Allergan
ndc-id:
ndc-product-code:
dpd-id:00001317
ema-product-code:
ema-ma-number:
started-marketing-on:1967-12-31
ended-marketing-on:2011-08-04
dosage-form:Liquid
strength:
route:Topical
fda-application-number:
generic:false
over-the-counter:false
approved:true
country:Canada
source:DPD
name:Sandoz Idoxuridine
labeller:Sandoz Canada Incorporated
ndc-id:
ndc-product-code:
dpd-id:02237187
ema-product-code:
ema-ma-number:
started-marketing-on:1999-02-15
ended-marketing-on:2019-08-01
dosage-form:Liquid
strength:
route:Topical
fda-application-number:
generic:true
over-the-counter:false
approved:true
country:Canada
source:DPD

混合物

name:Dendrid
ingredients:Idoxuridine
name:Herplex D
ingredients:Idoxuridine
name:Herplex
ingredients:Idoxuridine
name:Sandoz Idoxuridine
ingredients:Idoxuridine

包装者

name:Medisca Inc.
url:http://www.medisca.com

生产者

generic:否; url:; name;Glaxosmithkline
generic:否; url:; name;Alcon laboratories inc
generic:否; url:; name;Allergan pharmaceutical

价格

Idoxuridine powder
273.88(单位：USD）
g

受影响的生物体

Herpes simplex virus

剂量

form:Solution / drops
route:Ophthalmic
strength:1 MG/ML
form:Solution / drops
route:Ophthalmic
strength:1 mg/1mL
form:Solution
route:Topical
strength:5 g
form:Solution / drops
route:Ophthalmic
strength:
form:Liquid
route:Topical
strength:
form:Ointment
route:Ophthalmic
strength:5 G
form:Ointment
route:Ophthalmic
strength:3 G
form:Cream
route:Topical
strength:3 %
form:Ointment
route:Ophthalmic
strength:1.5 %
form:Solution
route:Topical
strength:40 %

atc代码

Antivirals
CHEMOTHERAPEUTICS FOR TOPICAL USE
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
DERMATOLOGICALS
Nucleosides and nucleotides excl. reverse transcriptase inhibitors
DIRECT ACTING ANTIVIRALS
ANTIVIRALS FOR SYSTEMIC USE
ANTIINFECTIVES FOR SYSTEMIC USE
Antivirals
ANTIINFECTIVES
OPHTHALMOLOGICALS
SENSORY ORGANS

fda标签

化学品安全技术说明书

//s3-us-west-2.amazonaws.com/drugbank/msds/DB00249.pdf?1265922741

专利

食物相互作用

药物相互作用

序列

实验性质

Water Solubility
2000 mg/L (at 25 °C)
MERCK INDEX (1996)
Melting Point
193
British Patent 1,024,156.
logP
-0.96
NARURKAR,MM & MITRA,AK (1988)

外部标识符

resource：Drugs Product Database (DPD)
identifier：8313
resource：ChEBI
identifier：147675
resource：PubChem Compound
identifier：5905
resource：PubChem Substance
identifier：46507573
resource：KEGG Drug
identifier：D00342
resource：ChemSpider
identifier：5694
resource：BindingDB
identifier：50370388
resource：PharmGKB
identifier：PA164781019
resource：PDB
identifier：ID2
resource：Therapeutic Targets Database
identifier：DAP000997
resource：Wikipedia
identifier：Idoxuridine
resource：ChEMBL
identifier：CHEMBL788
resource：ZINC
identifier：ZINC000003834173
resource：RxCUI
identifier：5653

外部链接

Drugs.com
http://www.drugs.com/mtm/idoxuridine-ophthalmic.html

路径

目标

id:BE0004796
name:DNA
organism:Humans
action:other
Komissarova NV, Tiunova AA, Anokhin KV: Selective impairments to memory consolidation in chicks produced by 5'-iodo-2'-deoxyuridine. Neurosci Behav Physiol. 2010 Feb;40(2):215-23. doi: 10.1007/s11055-009-9237-0. Epub 2009 Dec 22.
Komissarova NV, Tiunova AA, Anokhin KV: [Selective disruption of memory consolidation in chicks produced by 5'-iodo-2'-deoxyuridine]. Zh Vyssh Nerv Deiat Im I P Pavlova. 2008 Nov-Dec;58(6):700-10.
known-action:yes
id:BE0000458
name:Thymidine kinase
organism:HHV-1
action:unknown
Wild K, Bohner T, Folkers G, Schulz GE: The structures of thymidine kinase from herpes simplex virus type 1 in complex with substrates and a substrate analogue. Protein Sci. 1997 Oct;6(10):2097-106.
known-action:unknown
name:Thymidine kinase
general-function:Thymidine kinase activity
specific-function:In latent infection, may allow the virus to be reactivated and to grow in cells lacking a high concentration of phosphorylated nucleic acid precursors, such as nerve cells that do not replicate their genome.
gene-name:TK
locus:-
cellular-location:
transmembrane-regions:
signal-regions:
theoretical-pi:7.7
molecular-weight:40896.475
chromosome-location:
organism:HHV-1
external-identifiers:GenBank Gene DatabaseAF243477GenBank Protein Database8100965UniProtKBQ9QNF7UniProt AccessionKITH_HHV1
synonyms:2.7.1.21UL23
amino-acid-sequence:>lcl|BSEQ0010320|Thymidine kinase MASYPCHQHASAFDQAARSRGHSNRRTALRPRRQQEATEVRLEQKMPTLLRVYIDGPHGM GKTTTTQLLVALGSRDDIVYVPEPMTYWQVLGASETIANIYTTQHRLDQGEISAGDAAVV MTSAQITMGMPYAVTDAVLAPHIGGEAGSSHAPPPALTLIFDRHPIAALLCYPAARYLMG SMTPQAVLAFVALIPPTLPGTNIVLGALPEDRHIDRLAKRQRPGERLDLAMLAAIRRVYG LLANTVRYLQGGGSWREDWGQLSGTAVPPQGAEPQSNAGPRPHIGDTLFTLFRAPELLAP NGDLYNVFAWALDVLAKRLRPMHVFILDYDQSPAGCRDALLQLTSGMVQTHVTTPGSIPT ICDLARTFAREMGEAN
gene-sequence:>lcl|BSEQ0000912|1131 bp ATGGCTTCGTACCCCTGCCATCAACACGCGTCTGCGTTCGACCAGGCTGCGCGTTCTCGC GGCCATAGCAACCGACGTACGGCGTTGCGCCCTCGCCGGCAGCAAGAAGCCACGGAAGTC CGCCTGGAGCAGAAAATGCCCACGCTACTGCGGGTTTATATAGACGGTCCTCACGGGATG GGGAAAACCACCACCACGCAACTGCTGGTGGCCCTGGGTTCGCGCGACGATATCGTCTAC GTACCCGAGCCGATGACTTACTGGCAGGTGCTGGGGGCTTCCGAGACAATCGCGAACATC TACACCACACAACACCGCCTCGACCAGGGTGAGATATCGGCCGGGGACGCGGCGGTGGTA ATGACAAGCGCCCAGATAACAATGGGCATGCCTTATGCCGTGACCGACGCCGTTCTGGCT CCTCATATCGGGGGGGAGGCTGGGAGCTCACATGCCCCGCCCCCGGCCCTCACCCTCATC TTCGACCGCCATCCCATCGCCGCCCTCCTGTGCTACCCGGCCGCGCGATACCTTATGGGC AGCATGACCCCCCAGGCCGTGCTGGCGTTCGTGGCCCTCATCCCGCCGACCTTGCCCGGC ACAAACATCGTGTTGGGGGCCCTTCCGGAGGACAGACACATCGACCGCCTGGCCAAACGC CAGCGCCCCGGCGAGCGGCTTGACCTGGCTATGCTGGCCGCGATTCGCCGCGTTTACGGG CTGCTTGCCAATACGGTGCGGTATCTGCAGGGCGGCGGGTCGTGGCGGGAGGATTGGGGA CAGCTTTCGGGGACGGCCGTGCCGCCCCAGGGTGCCGAGCCCCAGAGCAACGCGGGCCCA CGACCCCATATCGGGGACACGTTATTTACCCTGTTTCGGGCCCCCGAGTTGCTGGCCCCC AACGGCGACCTGTATAACGTGTTTGCCTGGGCCTTGGACGTCTTGGCCAAACGCCTCCGT CCCATGCACGTCTTTATCCTGGATTACGACCAATCGCCCGCCGGCTGCCGGGACGCCCTG CTGCAACTTACCTCCGGGATGGTCCAGACCCACGTCACCACCCCAGGCTCCATACCGACG ATCTGCGACCTGGCGCGCACGTTTGCCCGGGAGATGGGGGAGGCTAACTGA
pfams:PF00693Herpes_TK
go-classifiers:functionATP bindingfunctionthymidine kinase activityprocessDNA biosynthetic processprocessTMP biosynthetic process

酶

载体

运输工具

药物反应

效应

不良反应