Compound Detail

CHEMBL5314375

CIDOFOVIR

💊 Approved Drug

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💊 Approved Drug

Nc1ccn(C[C@@H](CO)OCP(=O)(O)O)c(=O)n1.O.O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL5314375
Name	CIDOFOVIR
Phase	Approved
Structure Type	MOL
InChI Key	FPKARFMSZDBYQF-ILKKLZGPSA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL152
Active Moiety	CHEMBL4594372

Known Names

Cidofovir Cidofovir dihydrate GS-0504 Hpmpc dihydrate NSC-742135 Vistide

Targets

380

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

279.2

MW (Da)

-1.66

ALogP

HBA

HBD

147.9

PSA (Å²)

0.45

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1996
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Prodrug

USAN Stem	-vir
USAN Year	1994

Extended Properties

Molecular Formula	C8H18N3O8P
MW	315.22
Aromatic Rings	1
Heavy Atoms	18
NP-Likeness	0.33

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Human herpesvirus 1 DNA polymerase inhibitor	INHIBITOR	DNA polymerase catalytic subunit	✓	✓

Indications

Cytomegalovirus Retinitis Primary Immunodeficiency Diseases Virus Diseases Anus Neoplasms Anus Neoplasms Cytomegalovirus Infections Infections Papilloma Sarcoma Uterine Cervical Dysplasia Condylomata Acuminata Herpes Simplex HIV Infections Kidney Diseases Uterine Cervical Neoplasms

ATC Classification

J05AB12

cidofovir

Level 1: ANTIINFECTIVES FOR SYSTEMIC USE

Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning

hematological toxicity

Country: United States

Black Box Warning

teratogenicity

Country: United States

Black Box Warning

carcinogenicity

Country: United States

Black Box Warning

nephrotoxicity

Country: United States

Activity Summary

EC50 324 meas. best 7.4

IC50 55 meas. best 7.22

Kd 1 meas.

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Murid betaherpesvirus 1 CHEMBL613495	EC50	7.4	7.4	40.0	1
Human alphaherpesvirus 3 CHEMBL613132	EC50	7.36	6.4875	44.0	8
Human betaherpesvirus 5 CHEMBL371	EC50	7.35	6.2233	45.0	82
Human betaherpesvirus 5 CHEMBL371	IC50	7.22	6.1057	60.0	21
Human gammaherpesvirus 8 CHEMBL612780	EC50	7.19	7.19	64.0	1
HEL CHEMBL613888	EC50	6.8	6.2543	160.0	7
Unchecked CHEMBL612545	EC50	6.47	6.33	340.0	2
Human alphaherpesvirus 1 CHEMBL377	EC50	6.4	5.7159	400.0	63
Cytomegalovirus CHEMBL613134	EC50	6.37	5.9933	430.0	12
Human gammaherpesvirus 4 CHEMBL613124	EC50	6.32	6.32	480.0	1
NHDF CHEMBL614200	IC50	6.3	6.3	500.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	6.29	5.0857	510.0	14
Human alphaherpesvirus 2 CHEMBL370	EC50	6.16	5.7529	700.0	34
BK polyomavirus CHEMBL4888480	EC50	5.96	5.96	1100.0	1
Felid alphaherpesvirus 1 CHEMBL612743	EC50	5.89	5.89	1300.0	1
Human alphaherpesvirus 1 CHEMBL377	IC50	5.75	5.032	1800.0	5
HFF CHEMBL614071	IC50	5.72	5.1467	1900.0	3
Human adenovirus 2 CHEMBL613715	IC50	5.51	5.51	3100.0	1
Vaccinia virus CHEMBL613493	EC50	5.5	4.8084	3200.0	51
Cowpox virus CHEMBL612672	EC50	5.48	4.7921	3300.0	19
Simplexvirus CHEMBL613316	IC50	5.48	5.48	3300.0	1
Camelpox virus CHEMBL613332	EC50	5.28	5.1525	5300.0	4
Human adenovirus 2 CHEMBL613715	EC50	5.0	4.745	10000.0	4
MRC5 CHEMBL614181	IC50	5.0	5.0	10000.0	1
Osteoclast-like CHEMBL614359	IC50	5.0	5.0	10000.0	1
Vaccinia virus CHEMBL613493	IC50	4.94	4.559	11500.0	10
ADMET CHEMBL612558	EC50	4.84	4.565	14400.0	4
Simian virus 40 CHEMBL613051	EC50	4.75	4.7267	17800.0	3
Human adenovirus 5 CHEMBL612237	EC50	4.7	4.7	19900.0	2
Macacine alphaherpesvirus 1 CHEMBL3301403	EC50	4.67	4.605	21600.0	2
Human adenovirus 5 CHEMBL612237	IC50	4.62	4.62	24060.0	1
HFF CHEMBL614071	EC50	4.57	4.495	27000.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.52	4.52	30000.0	2
Ectromelia virus CHEMBL5291666	IC50	4.47	4.47	33980.0	1
Cowpox virus CHEMBL612672	IC50	4.33	4.325	46380.0	2
Solute carrier family 22 member 6 CHEMBL1641347	IC50	4.22	4.22	60000.0	1
ME-180 CHEMBL1075499	EC50	4.19	4.19	64700.0	1
Jurkat CHEMBL397	IC50	4.0	4.0	100000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	20101.68	ng.hr.mL-1	-
AUC	335028.0	ng.hr.mL-1	-
AUC	14400.0	ng.hr.mL-1	Macaca fascicularis
AUC	143503.66	ng.hr.mL-1	Macaca fascicularis
AUC	172204.39	ng.hr.mL-1	Macaca fascicularis
AUC	28700.73	ng.hr.mL-1	Macaca fascicularis
AUC	20939.25	ng.hr.mL-1	Homo sapiens
CL	2.5	mL.min-1.kg-1	Homo sapiens
CL	2.5	mL.min-1.kg-1	Homo sapiens
CL	0.3	mL.min-1.kg-1	Homo sapiens
CL	2.5	mL.min-1.kg-1	Homo sapiens
F	2.0	%	Homo sapiens
Fu	1.0	-	Homo sapiens
Fu	1.0	-	Homo sapiens
MRT	3.3	hr	Homo sapiens
T1/2	2.6	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Murid betaherpesvirus 1	EC50	=	40.0	nM	7.4	Antiviral activity against MCMV Smith replication	16539388
Human alphaherpesvirus 3	EC50	=	44.0	nM	7.36	Antiviral activity against VZV OKA expressing thymidine kinase infected in human...	21128666
Human betaherpesvirus 5	EC50	=	45.0	nM	7.35	Antiviral activity against foscarnet-resistant HCMV AD169 clone C infected in HE...	19226140
Human betaherpesvirus 5	IC50	=	60.0	nM	7.22	Antiviral activity against Human cytomegalovirus	19112024
Human gammaherpesvirus 8	EC50	=	64.0	nM	7.19	Antiviral activity against Human herpesvirus 8 infected in human BCBL1 cells ass...	19770274
Human alphaherpesvirus 3	EC50	=	70.0	nM	7.16	Antiviral activity against thymidine kinase-deficient VZV 07/1 infected in human...	21128666
Human betaherpesvirus 5	EC50	=	69.0	nM	7.16	Antiviral activity against wild type HCMV Davis infected in HEL cells assessed a...	19226140
Human betaherpesvirus 5	EC50	=	76.0	nM	7.12	Antiviral activity against wild type HCMV AD169 infected in HEL cells assessed a...	19226140
Human betaherpesvirus 5	EC50	=	92.0	nM	7.04	Antiviral activity against PMEDAP-resistant HCMV AD169 clone 4 infected in HEL c...	19226140
Human betaherpesvirus 5	EC50	=	95.0	nM	7.02	Antiviral activity against acyclovir-resistant HCMV AD169 clone 1 infected in HE...	19226140
Human alphaherpesvirus 3	EC50	=	100.0	nM	7.0	Antiviral activity against thymidine kinase-deficient Varicella-zoster virus 07/...	21745746
Human alphaherpesvirus 3	EC50	=	100.0	nM	7.0	Antiviral activity against VZV 07/1 infected in HEL cells assessed as protection...	21565516
Human betaherpesvirus 5	EC50	=	102.0	nM	6.99	Antiviral activity against Human cytomegalovirus Davis infected in HEL cells ass...	22459876
Human betaherpesvirus 5	IC50	=	110.0	nM	6.96	Antiviral activity against Human cytomegalovirus Towne infected in HFF cells ass...	21641218
Human betaherpesvirus 5	EC50	=	110.0	nM	6.96	Antiviral activity against acyclovir-resistant VZV 07/1 infected in HEL assessed...	20809641
Human betaherpesvirus 5	EC50	=	130.0	nM	6.89	Antiviral activity against acyclovir-resistant VZV OKA infected in HEL assessed ...	20809641
HEL	EC50	=	160.0	nM	6.8	Effective concentration against human cytomegalovirus AD-169 strain in HEL cell ...	15081019
Human betaherpesvirus 5	IC50	=	200.0	nM	6.7	Antiviral activity against Human CMV T2211 in HFF cells by SEAP assay	17043128
Human betaherpesvirus 5	EC50	=	220.0	nM	6.66	Antiviral activity against Cytomegalovirus CMV T2211 infected in HFF cells by SE...	17709468
Human betaherpesvirus 5	EC50	=	250.0	nM	6.6	Antiviral activity against HCMV Davis infected in HELF cells assessed as reducti...	36332548

Literature References

PubMed	DOI	Target Context	# Activities
16472241	10.2174/1570163043334794	Hepatotoxicity	18
27933957	10.1021/acs.jmedchem.6b00659	Unchecked	16
17116683	10.1128/aac.00879-06	Mus musculus	15
2544723	10.1021/jm00127a010	Cavia porcellus	15
19029322	10.1128/aac.01257-08	Vaccinia virus	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
18852271	10.1128/aac.00708-08	Vaccinia virus	13
19029322	10.1128/aac.01257-08	Cowpox virus	13
17043128	10.1128/aac.00633-06	Human betaherpesvirus 5	13
17893157	10.1128/aac.00838-07	Camelpox virus	12
28408228	10.1016/j.bmcl.2017.03.100	Human alphaherpesvirus 1	12
2544723	10.1021/jm00127a010	Mus musculus	12
19226140	10.1021/jm8014662	Human betaherpesvirus 5	10
21745746	10.1016/j.bmc.2011.06.045	Unchecked	10
17709468	10.1128/aac.00736-07	Human betaherpesvirus 5	9
17846137	10.1128/aac.00184-07	Vaccinia virus	9
17724153	10.1128/aac.00762-07	Cowpox virus	9
20070106	10.1021/jm901371v	Homo sapiens	8
-	10.1016/0960-894X(95)00278-2	HEL	8
18707089	10.1021/jm800050t	Human betaherpesvirus 5	8

Data from ChEMBL 36 via Core Engine