Tìm theo
Ganciclovir
Các tên gọi khác (12 ) :
  • 2-(6-Amino-purin-9-ylmethoxy)-propane-1,3-diol
  • 2-amino-9-((1,3-Dihydroxypropan-2-yloxy)methyl)-1H-purin-6(9H)-one
  • 2-amino-9-((1,3-Dihydroxypropan-2-yloxy)methyl)-3H-purin-6(9H)-one
  • 2-amino-9-((1,3-Dihydroxypropan-2-yloxy)methyl)-9H-purin-6-ol
  • 2-Amino-9-(2-hydroxy-1-hydroxymethyl-ethoxymethyl)-1,9-dihydro-purin-6-one
  • 2-amino-9-(2-Hydroxy-1-hydroxymethylethoxymethyl)-6,9-dihydro-1H-6-purinone
  • 9-((2-Hydroxy-1-(hydroxymethyl)ethoxy)methyl)guanine
  • 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine
  • GA2
  • Ganciclovir
  • Ganciclovirum
  • Gancyclovir
antiviral agents
Thuốc Gốc
Small Molecule
CAS: 82410-32-0
ATC: J05AB06, J05AB14, S01AD09
ĐG : Alliance Medical Products , http://www.amp-us.com
CTHH: C9H13N5O4
PTK: 255.2306
An acyclovir analog that is a potent inhibitor of the Herpesvirus family including cytomegalovirus. Ganciclovir is used to treat complications from AIDS-associated cytomegalovirus infections. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C9H13N5O4
Phân tử khối
255.2306
Monoisotopic mass
255.096753929
InChI
InChI=1S/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-5(1-15)2-16/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)
InChI Key
InChIKey=IRSCQMHQWWYFCW-UHFFFAOYSA-N
IUPAC Name
2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-1H-purin-6-one
Traditional IUPAC Name
gancyclovir
SMILES
NC1=NC2=C(N=CN2COC(CO)CO)C(=O)N1
Độ tan chảy
250 dec °C
Độ hòa tan
4300 mg/L (at 25 °C)
logP
-1.66
logS
-1.4
pKa (strongest acidic)
10.16
pKa (Strongest Basic)
1.76
PSA
134.99 Å2
Refractivity
61.03 m3·mol-1
Polarizability
24.15 Å3
Rotatable Bond Count
5
H Bond Acceptor Count
7
H Bond Donor Count
4
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
caco2 Permeability
-6.27
Dược Lực Học : Ganciclovir is a synthetic nucleoside analogue of 2'-deoxyguanosine that inhibits replication of herpes viruses both in vitro and in vivo. Sensitive human viruses include cytomegalovirus (CMV), herpes simplex virus -1 and -2 (HSV-1, HSV-2), Epstein-Barr virus (EBV) and varicella zoster virus (VZV), however clinical studies have been limited to assessment of efficacy in patients with CMV infection. Ganciclovir is a prodrug that is structurally similar to acyclovir. It inhibits virus replication by its encorporation into viral DNA. This encorporation inhibits dATP and leads to defective DNA, ceasing or retarding the viral machinery required to spread the virus to other cells.
Cơ Chế Tác Dụng : An acyclovir analog that is a potent inhibitor of the Herpesvirus family including cytomegalovirus. Ganciclovir is used to treat complications from AIDS-associated cytomegalovirus infections. [PubChem] Ganciclovir's antiviral activity inhibits virus replication. This inhibitory action is highly selective as the drug must be converted to the active form by a virus-encoded cellular enzyme, thymidine kinase (TK). TK catalyzes phosphorylation of ganciclovir to the monophosphate, which is then subsequently converted into the diphosphate by cellular guanylate kinase and into the triphosphate by a number of cellular enzymes. In vitro, ganciclovir triphosphate stops replication of herpes viral DNA. When used as a substrate for viral DNA polymerase, ganciclovir triphosphate competitively inhibits dATP leading to the formation of 'faulty' DNA. This is where ganciclovir 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. Ganciclovir inhibits viral DNA polymerases more effectively than it does cellular polymerase, and chain elongation resumes when ganciclovir is removed.
Dược Động Học :
▧ Absorption :
Poorly absorbed systemically following oral administration. Bioavailability under fasting conditions is approximately 5%, and when administered with food, 6 to 9% (about 30% with a fatty meal).
▧ Volume of Distribution :
* 0.74 ± 0.15 L/kg
▧ Protein binding :
1 to 2%
▧ Metabolism :
Little to no metabolism, about 90% of plasma ganciclovir is eliminated unchanged in the urine.
▧ Route of Elimination :
Renal excretion of unchanged drug by glomerular filtration and active tubular secretion is the major route of elimination of ganciclovir.
▧ Half Life :
2.5 to 3.6 hours (mean 2.9 hours) when administered intravenously in adults. 3.1 to 5.5 hours when administered orally in adults. Renal function impairment causes a marked increase in half life (9 to 30 hours intravenously, 15.7 to 18.2 hours orally).
▧ Clearance :
* 128 +/- 63 mL/min [Patients with Renal Impairment (Clcr=50-79 mL/min)] * 57+/- 8 mL/min [Patients with Renal Impairment (Clcr=25-49 mL/min)] * 30 +/- 13 mL/min [Patients with Renal Impairment (Clcr<25 mL/min)] * 4.7+/- 2.2 mL/min/kg [pediatric patients, aged 9 months to 12 years]
Độc Tính : Oral, mouse LD50: > 2g/kg. Intravenous, dog LD50: > 150mg/kg. Symptoms of overdose include irreversible pancytopenia, worsening GI symptoms, and acute renal failure. Suspected cancer agent.
Chỉ Định : For induction and maintenance in the treatment of cytomegalovirus (CMV) retinitis in immunocompromised patients, including patients with acquired immunodeficiency syndrome (AIDS). Also used in the treatment of severe cytomegalovirus (CMV) disease, including CMV pneumonia, CMV gastrointestinal disease, and disseminated CMV infections, in immunocompromised patients.
Tương Tác Thuốc :
  • Abacavir The adverse/toxic effects of reverse transcriptase inhibitors (nucleoside), such as Abacavir, may be enhanced by Ganciclovir. There is a risk of hematologic toxicity. Diligent monitoring during concomitant therapy is required.
  • Didanosine The antiviral agent, ganciclovir, may increase the effect and toxicity of didanosine.
  • Probenecid Probenecid increases the effect and toxicity of ganciclovir/valganciclovir
  • Zidovudine Increased risk of hematologic toxicity. Concomitant therapy should be avoided.
Liều Lượng & Cách Dùng : Capsule - Oral
Implant - Intravitreal
Powder, for solution - Intravenous
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Cytovene
  • Công ty :
    Sản phẩm biệt dược : Cytovene IV
  • Công ty :
    Sản phẩm biệt dược : Vitrasert
  • Công ty :
    Sản phẩm biệt dược : Zirgan
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01004
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00333
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0004-6940-03
PharmGKB
http://www.pharmgkb.org/drug/PA449733
Wikipedia
http://en.wikipedia.org/wiki/Ganciclovir
RxList
http://www.rxlist.com/cgi/generic/vitrasert.htm
Drugs.com
http://www.drugs.com/cdi/ganciclovir-implant.html
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