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Compound Detail

CHEMBL182

GANCICLOVIR
💊 Approved Drug
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💊 Approved Drug
Nc1nc2c(ncn2COC(CO)CO)c(=O)[nH]1

Basic Information

ChEMBL ID CHEMBL182
Name GANCICLOVIR
Phase Approved
Structure Type MOL
InChI Key IRSCQMHQWWYFCW-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1159869

Known Names

BW 759U BW-759U Cymevene Cytovene Ganciclovir Gancyclovir Ganzyk-rtu NSC-759656 RS-21592 Valganciclovir hydrochloride impurity a Virgan Vitrasert +2 more
30
Targets
556
Activities
3
Assay Types
29
PK Parameters
20
Publications
14
Known Names
20
Indications
1
Mechanisms

Molecular Properties

255.2
MW (Da)
-1.97
ALogP
8
HBA
4
HBD
139.3
PSA (Ų)
0.49
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1989
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -vir
USAN Year 1987

Extended Properties

Molecular Formula C9H13N5O4
MW 255.23
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness 0.38

Mechanism of Action

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

Indications

Cytomegalovirus Retinitis Eye Infections HIV Infections Virus Diseases Conjunctivitis Cytomegalovirus Infections Infections Carcinoma, Hepatocellular Diabetes Mellitus, Type 1 Fallopian Tube Neoplasms Glioblastoma Graft vs Host Disease Lymphoma Ovarian Neoplasms Peritoneal Neoplasms Central Nervous System Neoplasms Kidney Diseases Melanoma Mesothelioma Neuroblastoma

ATC Classification

J05AB06
ganciclovir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE
S01AD09
ganciclovir
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
teratogenicity
Country: United States

Activity Summary

EC50 379 meas. best 8.92
IC50 176 meas. best 8.72
Kd 1 meas. best 4.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
E6SM
CHEMBL614149
EC50 8.92 8.92 1.2 2
ADMET
CHEMBL612558
IC50 8.72 6.6115 1.9 13
Cytomegalovirus
CHEMBL613134
EC50 8.59 5.6505 2.6 20
Human alphaherpesvirus 2
CHEMBL370
EC50 8.0 7.1459 10.0 37
Human alphaherpesvirus 1
CHEMBL377
EC50 8.0 6.6697 10.0 66
Human betaherpesvirus 5
CHEMBL371
EC50 7.4 5.5259 40.0 176
Human gammaherpesvirus 4
CHEMBL613124
IC50 7.3 7.3 50.0 1
HEL
CHEMBL613888
EC50 7.22 5.8318 60.0 11
Human alphaherpesvirus 2
CHEMBL370
IC50 7.0 5.75 100.0 2
Human alphaherpesvirus 1
CHEMBL377
IC50 7.0 5.5493 100.0 28
Human betaherpesvirus 5
CHEMBL371
IC50 6.85 5.3633 140.0 73
HEL
CHEMBL613888
IC50 6.3 5.69 500.0 4
Homo sapiens
CHEMBL372
EC50 6.3 6.3 500.0 1
Cytomegalovirus
CHEMBL613134
IC50 6.23 5.64 590.0 5
Human alphaherpesvirus 3
CHEMBL613132
EC50 6.23 5.678 590.0 5
HFF
CHEMBL614071
IC50 6.22 5.5045 600.0 20
Unchecked
CHEMBL612545
EC50 6.05 5.8367 900.0 6
Felid alphaherpesvirus 1
CHEMBL612743
EC50 6.05 5.555 900.0 10
Unchecked
CHEMBL612545
IC50 5.89 5.89 1300.0 1
Transitional endoplasmic reticulum ATPase
CHEMBL1075145
IC50 5.89 5.89 1300.0 1
MRC5
CHEMBL614181
IC50 5.85 5.6229 1400.0 7
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.68 5.5333 2100.0 3
Human alphaherpesvirus 3
CHEMBL613132
IC50 5.55 5.55 2800.0 1
MEF
CHEMBL614342
IC50 5.47 5.47 3400.0 1
KB
CHEMBL398
IC50 5.46 5.46 3500.0 1
Hepatitis B virus
CHEMBL613497
EC50 5.4 5.4 4000.0 1
Human gammaherpesvirus 4
CHEMBL613124
EC50 5.3 5.096 5000.0 5
MEF
CHEMBL614342
EC50 5.3 5.3 5000.0 1
Human immunodeficiency virus 1
CHEMBL378
EC50 5.3 5.3 5000.0 1
Murid betaherpesvirus 1
CHEMBL613495
EC50 5.26 5.26 5500.0 1
MRC5
CHEMBL614181
EC50 5.03 5.03 9400.0 1
Human herpesvirus 5 strain AD169
CHEMBL613123
EC50 4.92 4.92 12000.0 1
Macacine alphaherpesvirus 1
CHEMBL3301403
EC50 4.84 4.7122 14500.0 27
Purine nucleoside phosphorylase
CHEMBL1169594
Kd 4.8 4.8 15848.9 1
CFU-GM
CHEMBL614779
IC50 4.72 4.72 19000.0 1
Caviid betaherpesvirus 2
CHEMBL614682
EC50 4.59 4.59 25900.0 1
Osteoclast-like
CHEMBL614359
IC50 4.52 4.52 30000.0 1
Human adenovirus 2
CHEMBL613715
IC50 4.46 4.46 35000.0 1
Human gammaherpesvirus 8
CHEMBL612780
IC50 4.16 4.125 70000.0 2
Vaccinia virus
CHEMBL613493
EC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 209.7 - Rattus norvegicus
AUC 182.0 ng.hr.mL-1 Rattus norvegicus
AUC 170.0 ng.hr.mL-1 Rattus norvegicus
AUC 82.5 ng.hr.mL-1 Rattus norvegicus
AUC 78.4 ng.hr.mL-1 Rattus norvegicus
AUC 1720.0 ng.hr.mL-1 Rattus norvegicus
AUC 1700.0 ng.hr.mL-1 Rattus norvegicus
CL 4.6 mL.min-1.kg-1 Homo sapiens
CL 4.6 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 4.6 mL.min-1.kg-1 Homo sapiens
CL 7.49 L/hr Homo sapiens
CL 10.2 L/hr Homo sapiens
CL 9.65 L/hr Homo sapiens
CL 6.34 L/hr Homo sapiens
F 3.6 % Rattus norvegicus
F 7.3 % Homo sapiens
F 0.825 % Homo sapiens
F 0.76 % Homo sapiens
Fu 0.99 - Homo sapiens
Fu 0.99 - Homo sapiens
Ka 0.895 /hr Homo sapiens
Ka 0.971 /hr Homo sapiens
MRT 3.7 hr Homo sapiens
T1/2 3.7 hr Homo sapiens
Vd 31.9 l Homo sapiens
Vd 32.0 l Homo sapiens
Vd 31.1 l Homo sapiens
Vd 32.0 l Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
E6SM EC50 = 1.2 nM 8.92 Effective concentration required to inhibit Herpes simplex virus-2 (HSV-2) induc... 11495586
E6SM EC50 = 1.2 nM 8.92 Effective concentration required to inhibit Herpes simplex virus-1 (HSV-1) induc... 11495586
ADMET IC50 = 1.9 nM 8.72 Cytotoxicity against human OST TK- cells expressing HSV1 TK 17181158
Cytomegalovirus EC50 = 2.6 nM 8.59 Antiviral activity against HCMV 33508479
Human alphaherpesvirus 1 EC50 = 10.0 nM 8.0 Antiviral activity against HSV-1 KOS infected in HEL cells assessed as inhibitio... 23795238
Human alphaherpesvirus 1 EC50 = 10.0 nM 8.0 Antiviral activity against HSV1 KOS infected in HEL cells assessed as inhibition... 21232828
Human alphaherpesvirus 2 EC50 = 10.0 nM 8.0 Antiviral activity against Human herpesvirus 2 strain G infected in human HEL ce... 30286952
Human alphaherpesvirus 2 EC50 = 10.0 nM 8.0 Antiviral activity against HSV-2 G infected in HEL cells assessed as inhibition ... 23795238
Human alphaherpesvirus 1 EC50 = 10.0 nM 8.0 Antiviral activity against Herpes simplex virus 1 KOS infected in human HEL cell... 30286952
Human alphaherpesvirus 2 EC50 = 13.0 nM 7.89 Antiviral activity against HSV2 G infected in HEL cells assessed as inhibition o... 23099097
Human alphaherpesvirus 1 EC50 = 15.0 nM 7.82 Antiviral activity against HSV1 KOS infected in HEL cells assessed as inhibition... 23099097
Human alphaherpesvirus 1 EC50 = 17.0 nM 7.77 Antiviral activity against Herpes simplex virus 1 strain KOS assessed as reducti... 21745746
ADMET IC50 = 18.0 nM 7.75 Cytotoxicity against human OST TK- cells expressing HSV1 TK in presence of 2.5 u... 17181158
Human alphaherpesvirus 1 EC50 = 19.0 nM 7.72 Antiviral activity against HSV1 KOS in HEL cells 17181162
Human alphaherpesvirus 2 EC50 = 19.0 nM 7.72 Antiviral activity against Herpes simplex virus 2 G infected in HEL cells assess... 29550734
Human alphaherpesvirus 1 EC50 = 20.0 nM 7.7 Antiviral activity against Herpes simplex virus 1 KOS infected in HEL cells asse... 26001344
Human alphaherpesvirus 1 EC50 = 20.0 nM 7.7 Antiviral activity against HSV1 KOS in human HEL cells assessed as protection ag... 19281225
Human alphaherpesvirus 1 EC50 = 20.0 nM 7.7 Antiviral activity against HSV1 KOS infected in HEL cells assessed as inhibition... 22459876
Human alphaherpesvirus 2 EC50 = 20.0 nM 7.7 Antiviral activity against HSV-2 G strain infected in HEL cells assessed as redu... 35933787
Human alphaherpesvirus 2 EC50 = 20.0 nM 7.7 Antiviral activity against Herpes simplex virus 2 G infected in HEL cells assess... 29880251

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 152
20385869 10.1128/aac.00186-10 Human betaherpesvirus 5 63
2163454 10.1021/jm00169a028 Mus musculus 36
19858259 10.1128/aac.01435-08 Macacine alphaherpesvirus 1 25
20047911 10.1128/aac.01596-09 Human betaherpesvirus 5 25
3009811 10.1021/jm00155a015 Mus musculus 24
16472241 10.2174/1570163043334794 Hepatotoxicity 18
17709468 10.1128/aac.00736-07 Human betaherpesvirus 5 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
1849998 10.1021/jm00108a026 Mus musculus 13
17043128 10.1128/aac.00633-06 Human betaherpesvirus 5 13
2329561 10.1021/jm00167a019 Mus musculus 12
22417649 10.1016/j.bmc.2012.02.031 Murid betaherpesvirus 1 12
19738014 10.1128/aac.00085-09 Homo sapiens 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
1652016 10.1021/jm00112a010 ESM 11
2329551 10.1021/jm00167a002 Human betaherpesvirus 5 11
2822928 10.1021/jm00394a017 Homo sapiens 10
19226140 10.1021/jm8014662 Human betaherpesvirus 5 10
2993615 10.1021/jm00147a020 Mus musculus 9

Data from ChEMBL 36 via Core Engine