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70-00-8 分子结构
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1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

ChemBase编号:315
分子式:C10H11F3N2O5
平均质量:296.1999496
单一同位素质量:296.06200612
SMILES和InChIs

SMILES:
FC(F)(F)c1cn([C@@H]2O[C@@H]([C@@H](O)C2)CO)c(=O)[nH]c1=O
Canonical SMILES:
OC[C@H]1O[C@H](C[C@@H]1O)n1cc(c(=O)[nH]c1=O)C(F)(F)F
InChI:
InChI=1S/C10H11F3N2O5/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7/h2,5-7,16-17H,1,3H2,(H,14,18,19)/t5-,6+,7+/m0/s1
InChIKey:
VSQQQLOSPVPRAZ-RRKCRQDMSA-N

引用这个纪录

CBID:315 http://www.chembase.cn/molecule-315.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
IUPAC传统名
trifluridine
商标名
F3DThd
F3T
F3TDR
Fluridine
TFDU
TFT
Trifluoromethyldeoxyuridine
Trifluorothymidine
Trifluridina [INN-Spanish]
Trifluridine [USAN:INN]
Trifluridinum [INN-Latin]
Virophta
Viroptic
trifluorothymine deoxyriboside
别名
α,α,α-Trifluorothymidine
2′-Deoxy-5-trifluoromethyluridine
Trifluorothymine deoxyriboside
Trifluridine
Trifluorothymidine
Trifluridine
Viroptic
Trifluorothymidine
5-Trifluorothymidine
2'-Deoxy-5-(trifluoromethyl)uridine
5-(Trifluoromethyl)-2'-deoxyuridine
Trifluorothymidine
CAS号
70-00-8
EC号
200-722-8
MDL号
MFCD00006534
PubChem SID
160963778
24900027
46506192
PubChem CID
6256

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 7.598577  质子受体
质子供体 LogD (pH = 5.5) -0.75803435 
LogD (pH = 7.4) -0.9644963  Log P -0.7546265 
摩尔折射率 56.3445 cm3 极化性 21.74243 Å3
极化表面积 99.1 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -0.45  LOG S -1.65 
溶解度 6.69e+00 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
1560 mg/L expand 查看数据来源
DMSO expand 查看数据来源
Methanol expand 查看数据来源
外观
White to Off-White Solid expand 查看数据来源
熔点
175-178°C expand 查看数据来源
190-193 °C(lit.) expand 查看数据来源
疏水性(logP)
-0.7 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Refrigerator expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
RTECS编号
XP2087500 expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
20/21/22-40 expand 查看数据来源
安全公开号
22-36 expand 查看数据来源
TSCA收录
false expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H302-H312-H332-H351 expand 查看数据来源
GHS警示性声明
P280 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
保存温度
-20°C expand 查看数据来源
纯度
≥99% (HPLC) expand 查看数据来源
95+% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
DrugBank -  DB00432 external link
Item Information
Drug Groups approved
Description An antiviral derivative of thymidine used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis due to herpes simplex virus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p557)
Indication Ophthalmic solution for the treatment of primay keratoconjunctivitis and recurrent epithelial keratitis due to herpes simplex virus, types 1 and 2.
Pharmacology Trifluridine is a fluorinated pyrimidine nucleoside with in vitro and in vivo activity against herpes simplex virus, types 1 and 2 and vacciniavirus. Some strains of adenovirus are also inhibited in vitro. Trifluridine is also effective in the treatment of epithelial keratitis that has not responded clinically to the topical administration of idoxuridine or when ocular toxicity or hypersensitivity to idoxuridine has occurred. In a smaller number of patients found to be resistant to topical vidarabine, trifluridine was also effective. Trifluridine interferes with DNA synthesis in cultured mammalian cells. However, its antiviral mechanism of action is not completely known.
Toxicity Overdosage by ocular instillation is unlikely because any excess solution should be quickly expelled from the conjunctival sac. Acute overdosage by accidental oral ingestion has not occurred. However, should such ingestion occur, the 75 mg dosage of trifluridine in a 7.5 mL bottle of trifluridine is not likely to produce adverse effects. Single intravenous doses of 1.5 to 30 mg/kg/day in children and adults with neoplastic disease produce reversible bone marrow depression as the only potentially serious toxic effect and only after three to five courses of therapy. The acute oral LD50 in the mouse and rat was 4379 mg/kg or higher.
Affected Organisms
Human Herpes Virus
Biotransformation One major metabolite, 5-carboxy-2'-deoxyuridine found on the endothelial side of the cornea, indicating localized metabolism.
Absorption Systemic absorption of trifluridine following therapeutic dosing with trifluridine ophthalmic appears to be negligible.
Half Life Approximately 12 to 18 minutes following ophthalmic administration.
References
Costin D, Dogaru M, Popa AS, Cijevschi I: [Trifluridine therapy in herpetic in keratitis] Rev Med Chir Soc Med Nat Iasi. 2004 Apr-Jun;108(2):409-12. [Pubmed]
Kuster P, Taravella M, Gelinas M, Stepp P: Delivery of trifluridine to human cornea and aqueous using collagen shields. CLAO J. 1998 Apr;24(2):122-4. [Pubmed]
O'Brien WJ, Taylor JL: Therapeutic response of herpes simplex virus-induced corneal edema to trifluridine in combination with immunosuppressive agents. Invest Ophthalmol Vis Sci. 1991 Aug;32(9):2455-61. [Pubmed]
Overman MJ, Kopetz S, Varadhachary G, Fukushima M, Kuwata K, Mita A, Wolff RA, Hoff P, Xiong H, Abbruzzese JL: Phase I clinical study of three times a day oral administration of TAS-102 in patients with solid tumors. Cancer Invest. 2008 Oct;26(8):794-9. [Pubmed]
Hong DS, Abbruzzese JL, Bogaard K, Lassere Y, Fukushima M, Mita A, Kuwata K, Hoff PM: Phase I study to determine the safety and pharmacokinetics of oral administration of TAS-102 in patients with solid tumors. Cancer. 2006 Sep 15;107(6):1383-90. [Pubmed]
Temmink OH, Prins HJ, van Gelderop E, Peters GJ: The Hollow Fibre Assay as a model for in vivo pharmacodynamics of fluoropyrimidines in colon cancer cells. Br J Cancer. 2007 Jan 15;96(1):61-6. Epub 2006 Dec 19. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1778 external link
Research Area: Infection
Biological Activity:
Trifluridine(Viroptic) is an anti-herpesvirus antiviral drug, used primarily on the eye. It is a nucleoside analogue, a modified form of deoxyuridine, similar enough to be incorporated into viral DNA replication, but the -CF3 group added to the uracil component blocks base pairing. [1]
Sigma Aldrich -  T2255 external link
Application
Trifluorothymidine (Trifluridine, TFT) is a substrate used to study the specificity and kinetics of thymidine kinase(s). TFT after phosphorylation may be incorporated into DNA where is induces DNA-damage, consequently TFT is useful for studies of DNA repair mechanisms. TFT may also be used to study mechanisms of inhibition of thymidylate synthase(s).

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Temmink OH, Prins HJ, van Gelderop E, Peters GJ: The Hollow Fibre Assay as a model for in vivo pharmacodynamics of fluoropyrimidines in colon cancer cells. Br J Cancer. 2007 Jan 15;96(1):61-6. Epub 2006 Dec 19. Pubmed
  • Costin D, Dogaru M, Popa AS, Cijevschi I: [Trifluridine therapy in herpetic in keratitis] Rev Med Chir Soc Med Nat Iasi. 2004 Apr-Jun;108(2):409-12. Pubmed
  • Kuster P, Taravella M, Gelinas M, Stepp P: Delivery of trifluridine to human cornea and aqueous using collagen shields. CLAO J. 1998 Apr;24(2):122-4. Pubmed
  • O'Brien WJ, Taylor JL: Therapeutic response of herpes simplex virus-induced corneal edema to trifluridine in combination with immunosuppressive agents. Invest Ophthalmol Vis Sci. 1991 Aug;32(9):2455-61. Pubmed
  • Overman MJ, Kopetz S, Varadhachary G, Fukushima M, Kuwata K, Mita A, Wolff RA, Hoff P, Xiong H, Abbruzzese JL: Phase I clinical study of three times a day oral administration of TAS-102 in patients with solid tumors. Cancer Invest. 2008 Oct;26(8):794-9. Pubmed
  • Hong DS, Abbruzzese JL, Bogaard K, Lassere Y, Fukushima M, Mita A, Kuwata K, Hoff PM: Phase I study to determine the safety and pharmacokinetics of oral administration of TAS-102 in patients with solid tumors. Cancer. 2006 Sep 15;107(6):1383-90. Pubmed
  • www.bentham.org/prc/samples/prc1-1/Higashi.pdf
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专利

专利

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