Tìm theo
Didanosine
Các tên gọi khác (11 ) :
  • 2,3-Dideoxyinosine
  • 9-((2R,5S)-5-(Hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
  • 9-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one
  • 9-((2S,5R)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol
  • 9-[(2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-one
  • DDI
  • DdIno
  • Didanosina
  • Didanosine
  • Didanosinum
  • Dideoxyinosine
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 69655-05-6
ATC: J05AF02
ĐG : Advanced Pharmaceutical Services Inc.
CTHH: C10H12N4O3
PTK: 236.2273
A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C10H12N4O3
Phân tử khối
236.2273
Monoisotopic mass
236.09094027
InChI
InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1
InChI Key
InChIKey=BXZVVICBKDXVGW-NKWVEPMBSA-N
IUPAC Name
9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
Traditional IUPAC Name
didanosine
SMILES
OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O
Độ tan chảy
160-163 °C
Độ hòa tan
15.8 mg/mL
logP
-1.24
logS
-1.6
pKa (strongest acidic)
6.94
pKa (Strongest Basic)
2.75
PSA
88.74 Å2
Refractivity
58.59 m3·mol-1
Polarizability
22.9 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
6
H Bond Donor Count
2
Physiological Charge
-1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Didanosine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Didanosine differs from other nucleoside analogues, as it does not have any of the regular bases, instead it has hypoxanthine attached to the sugar ring. Didanosine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. Didanosine is effective against HIV, and usually used in combination with other antiviral therapy. Switching from long term AZT treatment to didanosine has been shown to be beneficial. Didanosine has weak acid stability and therefore, it is often combined with an antacid.
Cơ Chế Tác Dụng : A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite. [PubChem] Didanosine (ddI) is metabolized intracellularly by a series of cellular enzymes to its active moiety, dideoxyadenosine triphosphate (ddATP), which inhibits the HIV reverse transcriptase enzyme competitively by competing with natural dATP. It also acts as a chain terminator by its incorporation into viral DNA as the lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.
Dược Động Học :
▧ Absorption :
Rapidly absorbed (bioavailability 30-40%) with peak plasma concentrations appearing within 0.5 and 1.5 hrs.
▧ Protein binding :
Low (<5%)
▧ Metabolism :
Rapidly metabolized intracellularly to its active moiety, 2,3-dideoxyadenosine-5-triphosphate (ddA-TP). It is then further metabolized hepatically to yield hypoxanthine, xanthine, and uric acid.
▧ Route of Elimination :
Based on data from in vitro and animal studies, it is presumed that the metabolism of didanosine in man occurs by the same pathways responsible for the elimination of endogenous purines. Purines are eliminated by the kidneys.
▧ Half Life :
30 minutes in plasma and more than 12 hours in intracellular environment.
Độc Tính : Side effects include pancreatitis, peripheral neuropathy, diarrhea, hyperuricemia and hepatic dysfunction
Chỉ Định : For use, in combination with other antiretroviral agents, in the treatment of HIV-1 infection in adults.
Tương Tác Thuốc :
  • Ganciclovir The antiviral agent, ganciclovir, may increase the effect and toxicity of didanosine.
  • Tenofovir Tenofovir may decrease the therapeutic effects and increase the adverse effects of Didanosine. Monitor for changes in virologic response and Didanosine toxicity during concomitant therapy.
  • Tipranavir Tipranavir may decrease the concentration of Didanosine.
  • Tobramycin Increased risk of nephrotoxicity
  • Trovafloxacin Didanosine may decrease the absorption of orally administered Trovafloxacin. The Didanosine formulation contains magnesium and aluminum ions that intefere with Trovafloxacin absorption. Administer Trovafloxacin 2 hours before or 6 hours after the Didanosine dose to minimize the interaction. This interaction is not observed with enteric coated Didanosine.
  • Valganciclovir The adverse/toxic effects of Didanosine, a reverse transcriptase inhibitor (nucleoside), may be enhanced by Valganciclovir. There is a significant risk of hematologic toxicity. Concomitant therapy should be avoided.
  • Voriconazole Didanosine may interfere with the absorption of orally administered voriconazole. Enteric coated didanosine does not exert this effect. Didanosine buffered formulations should be administered at least 2 hours from oral voriconazole administration.
  • Zalcitabine Additive toxicities (peripheral neuropathy)
Liều Lượng & Cách Dùng : Capsule, coated - Oral
Powder, for solution - Oral
Tablet - Oral
Dữ Kiện Thương Mại
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Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00900
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=50599
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506255
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06953
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00296
ChemSpider
http://www.chemspider.com/Chemical-Structure.45864.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0087-6632-41
PharmGKB
http://www.pharmgkb.org/drug/PA449301
Wikipedia
http://en.wikipedia.org/wiki/Didanosine
RxList
http://www.rxlist.com/cgi/generic3/didanosine.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/vid1482.shtml
Drugs.com
http://www.drugs.com/cdi/didanosine-chewable-dispersible-buffered-tablets.html
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