L8P

({[(2S)-1-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid

Created:	2011-02-01
Last modified:	2020-06-05

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1 entries where L8P is found as a standalone ligand2 entries where L8P is found in a polymer sequence

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Chemical Details
Formal Charge	0
Atom Count	32
Chiral Atom Count	1
Bond Count	32
Aromatic Bond Count	0

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Chemical Component Summary
Name	({[(2S)-1-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid
Synonyms	Cidofovir
Systematic Name (OpenEye OEToolkits)	[(2S)-1-(4-azanyl-2-oxo-pyrimidin-1-yl)-3-hydroxy-propan-2-yl]oxymethylphosphonic acid
Formula	C₈ H₁₄ N₃ O₆ P
Molecular Weight	279.187
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=P(O)(O)COC(CN1C=CC(=NC1=O)N)CO
SMILES	CACTVS	3.370	NC1=NC(=O)N(C[CH](CO)OC[P](O)(O)=O)C=C1
SMILES	OpenEye OEToolkits	1.7.0	C1=CN(C(=O)N=C1N)CC(CO)OCP(=O)(O)O
Canonical SMILES	CACTVS	3.370	NC1=NC(=O)N(C[C@@H](CO)OC[P](O)(O)=O)C=C1
Canonical SMILES	OpenEye OEToolkits	1.7.0	C1=CN(C(=O)N=C1N)C[C@@H](CO)OCP(=O)(O)O
InChI	InChI	1.03	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	InChI	1.03	VWFCHDSQECPREK-LURJTMIESA-N

Drug Info: DrugBank

DrugBank ID	DB00369
Name	Cidofovir
Groups	approved
Description	Cidofovir is an injectable antiviral medication employed in the treatment of cytomegalovirus (CMV) retinitis in patients diagnosed with AIDS. It suppresses CMV replication through selective inhibition of viral DNA synthesis.[FDA label] It was manufactured by _Gilead_ and initially approved by the FDA in 1996, but has since been discontinued.[L6223]
Synonyms	Cidofovir anhydrous Cidofovir Cidofovirum (S)-(3-(4-amino-2-Oxopyrimidin-1(2H)-yl)-1-hydroxypropan-2-yloxy)methylphosphonic acid ({[(S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid Cidofovir dihydrate CDV (S)-1-[3-Hydroxy-2-(phosphonylmethoxy)propyl]cytosine (S)-1-(3-Hydroxy-2-phosphonomethoxypropyl)cytosine 1-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine [[(S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid (S)-HPMPC 1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine [(S)-2-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-1-hydroxymethyl-ethoxymethyl]-phosphonic acid (S)-1-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine
Brand Names	Vistide Mar-cidofovir Cidofovir Cidofovir Dihydrate
Indication	For the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Categories	Anti-Infective Agents Antiinfectives for Systemic Use Antiviral Agents Antivirals for Systemic Use Cytomegalovirus Nucleoside Analog DNA Polymerase Inhibitor Cytosine Direct Acting Antivirals Drugs that are Mainly Renally Excreted Enzyme Inhibitors Nephrotoxic agents Nucleic Acid Synthesis Inhibitors Nucleosides and Nucleotides Nucleosides and Nucleotides Excl. Reverse Transcriptase Inhibitors OAT1/SLC22A6 inhibitors OAT1/SLC22A6 Substrates Organophosphonates Organophosphorus Compounds Pyrimidines Pyrimidinones
ATC-Code	J05AB12
CAS number	113852-37-2

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
DNA polymerase catalytic subunit	MFFNPYLSGGVTGGAVAGGRRQRSQPGSAQGSGKRPPQKQFLQIVPRGVM...	unknown	inhibitor
Thymidine phosphorylase	MAALMTPGTGAPPAPGDFSGEGSQGLPDPSPEPKQLPELIRMKRDGGRLS...	unknown	inhibitor
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	substrate,inhibitor

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682