Drug Information

General Information
Drug ID
DR00066
Drug Name
Cidofovir
Synonyms
(2S)-3-Hydroxy-2-phosphonylmethoxypropyl-cytosine; (S)-1-(3-Hydroxy-2-phosphonomethoxypropyl)cytosine; (S)-1-[3-hydroxy-2-(phosphonylmethoxy)-propyl]cytosine; (S)-2-(4-Amino-2-oxo-1(2H)-pyrimidinyl-1-(hydroxymethyl)ethoxy)methyl phosphonic acid; (S)-HPMPC; (s)-[[2-(4-amino-2-oxo-1(2h)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid; ({[(2S)-1-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid; 1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine; 1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]-cytosine dihydrate; CDV; Cidofovir (Vistide); Cidofovir (anhydrous); Cidofovir anhydrous; Cidofovirum; Forvade; GS 0504; GS 504; GS-0504; GS-504; GS504; HPMPC; Vistide; Vistide (TN); Vistide, Cidofovir; [(2S)-1-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxypropan-2-yl]oxymethylphosphonic acid
Drug Type
Small molecular drug
Indication Cytomegalovirus infections [ICD11:1D82] Approved [1]
Therapeutic Class
Anti-HIV Agents
Structure
3D MOL 2D MOL
Formula
C8H14N3O6P
Canonical SMILES
C1=CN(C(=O)N=C1N)CC(CO)OCP(=O)(O)O
InChI
InChI=1S/C8H14N3O6P/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16)/t6-/m0/s1
InChIKey
VWFCHDSQECPREK-LURJTMIESA-N
CAS Number
CAS 113852-37-2
Pharmaceutical Properties Molecular Weight 279.19 Topological Polar Surface Area 146
Heavy Atom Count 18 Rotatable Bond Count 6
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
XLogP
-3.6
PubChem CID
60613
PubChem SID
103208535 ,104253188 ,104321212 ,109692921 ,117588193 ,12014233 ,124757308 ,124896571 ,125164112 ,126628422 ,126655266 ,126664430 ,126669928 ,129535965 ,134222323 ,134338340 ,135018697 ,136920390 ,136946528 ,136949097 ,137005936 ,142388054 ,144115830 ,144206546 ,14848679 ,14972788 ,151994247 ,160963716 ,162011514 ,164778525 ,164807829 ,174007460 ,175268249 ,179149625 ,196106556 ,196403991 ,210275592 ,210281251 ,43117987 ,46506054 ,50007425 ,57314045 ,596838 ,76063703 ,7978941 ,8186963 ,85240541 ,91146456 ,92718864 ,93578310
ChEBI ID
CHEBI:3696
TTD Drug ID
D04AAW
DT(s) Transporting This Drug MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [2]
OAT1 Transporter Info Organic anion transporter 1 Substrate [3]
OAT3 Transporter Info Organic anion transporter 3 Substrate [3]
Drug-Transporter Activity Data
Drug-Transporter Activity Data OAT1 Transporter Info Km =30 microM Chinese hamster ovary (CHO) cells-OAT1 [4]
OAT1 Transporter Info Km =58 microM Chinese hamster ovary (CHO) cells-OAT1 [5]
OAT1 Transporter Info Km =46 microM Oocytes-OAT1 [6]
References
1 Cidofovir was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
3 Renal transport of adefovir, cidofovir, and tenofovir by SLC22A family members (hOAT1, hOAT3, and hOCT2). Pharm Res. 2007 Apr;24(4):811-5.
4 Transport of the dipeptidyl peptidase-4 inhibitor sitagliptin by human organic anion transporter 3, organic anion transporting polypeptide 4C1, and multidrug resistance P-glycoprotein. J Pharmacol Exp Ther. 2007 May;321(2):673-83.
5 Cytotoxicity of antiviral nucleotides adefovir and cidofovir is induced by the expression of human renal organic anion transporter 1. J Am Soc Nephrol. 2000 Mar;11(3):383-93.
6 The antiviral nucleotide analogs cidofovir and adefovir are novel substrates for human and rat renal organic anion transporter 1. Mol Pharmacol. 1999 Sep;56(3):570-80.

If you find any error in data or bug in web service, please kindly report it to Dr. Li and Dr. Fu.