Drug Information

General Information
Drug ID
DR00027
Drug Name
Ganciclovir
Synonyms
2'-NDG; 2'-Nor-2'-deoxyguanosine; 2-(6-Amino-purin-9-ylmethoxy)-propane-1,3-diol; 2-Amino-1,9-((2-hydroxy-1-(hydroxymethyl)ethoxy)methyl)-6-H-purin-6-one; 2-Amino-9-(2-hydroxy-1-hydroxymethyl-ethoxymethyl)-1,9-dihydro-purin-6-one; 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-(1,3-dihydroxypropan-2-yloxymethyl)-3H-purin-6-one; 2-amino-9-(2-hydroxy-1-hydroxymethylethoxymethyl)-6,9-dihydro-1H-6-purinone; 2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-1,9-dihydro-6H-purin-6-one; 2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-3H-purin-6-one; 9-((1,3-Dihydroxy-2-propoxy)methyl)guanine; 9-((2-Hydroxy-1-(hydroxymethyl)ethoxy)methyl)guanine; 9-(1,3-DIHYDROXY-PROPOXYMETHANE)GUANINE; 9-[(1,3-Dihydroxy-2-propoxy)methyl]guanine; BIOLF-62; BW 759; BW 759U; BW-759U; BW-795; BW-B 759U; Biolf 62; Citovirax; Cymevan; Cymeven; Cymevene; Cymevene (TN); Cytovene; Cytovene (TN); Cytovene-IV; DRG-0018; G 2536; GA2; GANCICLOVIR SODIUM; GCV; GCV & 1110U81; GCV & MSL; Ganciclovir & C34-dgA immunotoxin; Ganciclovir & D5-dgA immunotoxin; Ganciclovir (JAN/USP/INN); Ganciclovir [USAN:INN:BAN:JAN]; Ganciclovirum; Ganciclovirum [Latin]; Gancyclovir; Guanine, 9-((2-hydroxy-1-(hydroxymethyl)ethoxy)methyl)-and MSL, neutralizing monoclonal antibody; HHEMG; Hydroxyacyclovir; IN1478; MB3795; RS-21592; ST-605; Virgan; Vitrasert; Vitrasert (TN); Zirgan
Drug Type
Small molecular drug
Indication Cytomegalovirus infections [ICD11:1D82] Approved [1]
Therapeutic Class
Antiviral Agents
Structure
3D MOL 2D MOL
Formula
C9H13N5O4
Canonical SMILES
C1=NC2=C(N1COC(CO)CO)N=C(NC2=O)N
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)
InChIKey
IRSCQMHQWWYFCW-UHFFFAOYSA-N
CAS Number
CAS 82410-32-0
Pharmaceutical Properties Molecular Weight 255.23 Topological Polar Surface Area 135
Heavy Atom Count 18 Rotatable Bond Count 5
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
XLogP
-2.5
PubChem CID
135398740
PubChem SID
10321977 ,11111224 ,11111225 ,11466867 ,11467987 ,11486454 ,12013652 ,14749970 ,14798783 ,16217245 ,17405102 ,23929519 ,24278453 ,25622077 ,26758755 ,29222588 ,3720872 ,46507294 ,47216865 ,47515408 ,47589082 ,48185084 ,48185085 ,48334596 ,48404464 ,48404465 ,49681203 ,49698657 ,49974979 ,5006228 ,50106328 ,50106329 ,50113251 ,53777645 ,53800918 ,56312143 ,56312588 ,56424026 ,57321811 ,617697 ,7298558 ,76491727 ,7840003 ,7847399 ,7887702 ,7979369 ,81041223 ,8139883 ,85231063 ,866342
ChEBI ID
ChEBI:465284
TTD Drug ID
D05ARP
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
ASCT2 Transporter Info Alanine/serine/cysteine/threonine transporter 2 Substrate [3]
BCRP Transporter Info Breast cancer resistance protein Substrate [4]
MATE1 Transporter Info Multidrug and toxin extrusion protein 1 Substrate [5]
MATE2 Transporter Info Multidrug and toxin extrusion protein 2 Substrate [5]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [6]
MRP5 Transporter Info Multidrug resistance-associated protein 5 Substrate [7]
OAT1 Transporter Info Organic anion transporter 1 Substrate [2]
OAT3 Transporter Info Organic anion transporter 3 Substrate [8]
Drug-Transporter Activity Data
Drug-Transporter Activity Data 1-Oct Transporter Info Km =516.2 microM Proximal tubule (S2) cells-OCT1 [2]
MATE1 Transporter Info Km =5120 microM Human embryonic kidney cells (HEK293)-MATE1 [5]
MATE2 Transporter Info Km =4280 microM Human embryonic kidney cells (HEK293)-MATE2K [5]
OAT1 Transporter Info Km =896 microM Proximal tubule (S2) cells-OAT1 [2]
References
1 Valganciclovir was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24.
3 Amino Acid Transporter ATB0,+ as a delivery system for drugs and prodrugs. Curr Drug Targets Immune Endocr Metabol Disord. 2005 Dec;5(4):357-64.
4 Side populations of glioblastoma cells are less sensitive to HSV-TK/GCV suicide gene therapy system than the non-side population. In Vitro Cell Dev Biol Anim. 2010 Jun;46(6):497-501.
5 Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71.
6 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
7 Cellular export of drugs and signaling molecules by the ATP-binding cassette transporters MRP4 (ABCC4) and MRP5 (ABCC5). Drug Metab Rev. 2005;37(1):253-78.
8 FDA Drug Development and Drug Interactions

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