Tìm theo
Vidarabine
Các tên gọi khác (8 ) :
  • 2-(6-AMINO-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
  • 9-beta-D-Arabinofuranosyl-9H-purin-6-amine
  • 9-beta-D-arabinofuranosyl-adenine
  • 9-beta-D-Arabinofuranosyladenine
  • 9-β-D-arabinofuranosyl-9H-purin-6-amine
  • 9-β-D-arabinofuranosyladenine
  • Spongoadenosine
  • Vidarabine
antiviral agents, antimetabolites
Thuốc Gốc
Small Molecule
CAS: 24356-66-9
ATC: J05AB03, S01AD06
ĐG : Medisca Inc. , http://www.medisca.com
CTHH: C10H13N5O4
PTK: 267.2413
A nucleoside antibiotic isolated from Streptomyces antibioticus. It has some antineoplastic properties and has broad spectrum activity against DNA viruses in cell cultures and significant antiviral activity against infections caused by a variety of viruses such as the herpes viruses, the vaccinia VIRUS and varicella zoster virus. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C10H13N5O4
Phân tử khối
267.2413
Monoisotopic mass
267.096753929
InChI
InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1
InChI Key
InChIKey=OIRDTQYFTABQOQ-UHTZMRCNSA-N
IUPAC Name
(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional IUPAC Name
adenine arabinoside
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O
Độ hòa tan
1.40e+01 g/l
logP
-2.115
logS
-1.3
pKa (strongest acidic)
12.45
pKa (Strongest Basic)
4.99
PSA
139.54 Å2
Refractivity
63.2 m3·mol-1
Polarizability
24.49 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
8
H Bond Donor Count
4
Physiological Charge
0
Number of Rings
3
Bioavailability
1
Rule of Five
true
Dược Lực Học : Vidarabine is a synthetic purine nucleoside analogue with in vitro and in vivo inhibitory activity against herpes simplex virus types 1 (HSV-1), 2 (HSV-2), and varicella-zoster virus (VZV). The inhibitory activity of Vidarabine is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts Vidarabine into Vidarabine monophosphate, a nucleotide analogue. The monophosphate is further converted into diphosphate by cellular guanylate kinase and into triphosphate by a number of cellular enzymes. in vitro, Vidarabine triphosphate stops replication of herpes viral DNA. When used as a substrate for viral DNA polymerase, Vidarabine triphosphate competitively inhibits dATP leading to the formation of 'faulty' DNA. This is where Vidarabine triphosphate is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand.
Cơ Chế Tác Dụng : A nucleoside antibiotic isolated from Streptomyces antibioticus. It has some antineoplastic properties and has broad spectrum activity against DNA viruses in cell cultures and significant antiviral activity against infections caused by a variety of viruses such as the herpes viruses, the vaccinia VIRUS and varicella zoster virus. [PubChem] Vidarabine stops replication of herpes viral DNA in 2 ways: 1) competitive inhibition of viral DNA polymerase, and consequently 2) incorporation into and termination of the growing viral DNA chain. This drug is a nucleoside analog and therefore has to be phosphorylated to be active. Vidarabine is sequentially phosphorylated by kinases to the triphosphate ara-ATP. This is the active form of vidarabine and is both an inhibitor and a substrate of viral DNA polymerase. When used as a substrate for viral DNA polymerase, ara-ATP competitively inhibits dATP leading to the formation of ‘faulty’ DNA. This is where ara-ATP is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand
Dược Động Học :
▧ Absorption :
Systemetic absorption of vidarabine should not be expected to occur following ocular administration and swallowing lacrimal secretions.
▧ Protein binding :
24-38%
▧ Metabolism :
In laboratory animals, vidarabine is rapidly deaminated in the gastrointestinal tract to Ara-Hx.
Độc Tính : Acute massive overdosage by oral ingestion of the ophthalmic ointment has not occurred. However, the rapid deamination to arabinosylhypoxanthine should preclude any difficulty. The oral LD50 for vidarabine is greater than 5020 mg/kg in mice and rats. No untoward effects should result from ingestion of the entire contents of the tube. Overdosage by ocular instillation is unlikely because any excess should be quickly expelled from the conjunctival sac.
Chỉ Định : For treatment of chickenpox - varicella, herpes zoster and herpes simplex
Liều Lượng & Cách Dùng : Ointment - Ophthalmic
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Arasena-A
  • Công ty :
    Sản phẩm biệt dược : Vira-A
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00194
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=32326
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506630
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07195
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00406
ChemSpider
http://www.chemspider.com/Chemical-Structure.29966.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/61570-367-71
PharmGKB
http://www.pharmgkb.org/drug/PA451876
Wikipedia
http://en.wikipedia.org/wiki/Vidarabine
RxList
http://www.rxlist.com/cgi/generic3/vidarabine.htm
Drugs.com
http://www.drugs.com/mtm/vidarabine-ophthalmic.html
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