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Compound Detail

CHEMBL853

ZALCITABINE
💊 Approved Drug
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💊 Approved Drug
Nc1ccn([C@H]2CC[C@@H](CO)O2)c(=O)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL853
Name ZALCITABINE
Phase Approved
Structure Type MOL
InChI Key WREGKURFCTUGRC-POYBYMJQSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1201384

Known Names

Ddc (ddc) Dideoxycytidine Hivid NSC-606170 RO 24-2027/000 Ro-24-2027-000 RO-24-2027/000 RO-24-2027000 RO-242027000 Zalcitabina Zalcitabine Zalcitabine (dideoxycytidine,ddc)
20
Targets
107
Activities
4
Assay Types
9
PK Parameters
20
Publications
12
Known Names
2
Indications
1
Mechanisms

Molecular Properties

211.2
MW (Da)
-0.50
ALogP
6
HBA
2
HBD
90.4
PSA (Ų)
0.69
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1992
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -citabine
USAN Year 1991

Extended Properties

Molecular Formula C9H13N3O3
MW 211.22
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness 1.28

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Human immunodeficiency virus type 1 reverse transcriptase inhibitor INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase ✓ ✓

Indications

Virus Diseases HIV Infections

ATC Classification

J05AF03
zalcitabine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

EC50 73 meas. best 9.0
IC50 30 meas. best 7.96
Ki 3 meas. best 7.29
Kd 1 meas. best 4.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 9.0 6.7126 1.0 27
Human immunodeficiency virus 1
CHEMBL378
 IC50 7.96 6.68 11.0 5
ADMET
CHEMBL612558
 EC50 7.8 7.48 16.0 2
CEM-SS
CHEMBL614548
 EC50 7.7 7.255 20.0 4
CCRF-CEM
CHEMBL382
 IC50 7.66 5.4767 22.0 6
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 EC50 7.51 7.51 31.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 Ki 7.29 7.29 51.0 1
C-X-C chemokine receptor type 4
CHEMBL2107
 EC50 7.06 7.06 88.0 1
C8166
CHEMBL614533
 IC50 6.9 6.9 125.0 1
CCRF-CEM
CHEMBL382
 EC50 6.72 6.62 189.0 2
MT4
CHEMBL388
 EC50 6.63 5.975 236.0 6
Human immunodeficiency virus
CHEMBL613758
 EC50 6.52 6.52 300.0 1
MT2
CHEMBL614184
 EC50 6.48 6.085 331.0 4
Human immunodeficiency virus 2
CHEMBL380
 EC50 6.4 5.9282 400.0 11
Human immunodeficiency virus 2
CHEMBL380
 IC50 6.3 5.9133 500.0 3
Unchecked
CHEMBL612545
 EC50 6.1 5.89 800.0 3
MT4
CHEMBL388
 IC50 6.0 5.9 1000.0 2
HepG2
CHEMBL395
 IC50 5.85 5.85 1400.0 1
HepG2
CHEMBL395
 EC50 5.85 5.7233 1400.0 3
Hepatitis B virus
CHEMBL613497
 EC50 5.64 5.64 2300.0 1
Human adenovirus 2
CHEMBL613715
 IC50 5.48 5.48 3300.0 1
Human adenovirus 2
CHEMBL613715
 EC50 5.14 4.86 7200.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.14 5.14 7200.0 1
Mus musculus
CHEMBL375
 EC50 4.86 4.75 13800.0 2
HeLa
CHEMBL399
 IC50 4.42 4.42 38000.0 1
Albumin
CHEMBL3253
 Kd 4.36 4.36 44000.0 1
CEM-SS
CHEMBL614548
 IC50 4.21 4.21 61000.0 1
MT2
CHEMBL614184
 IC50 4.08 4.08 83800.0 1
HL-60
CHEMBL383
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.1 mL.min-1.kg-1 Homo sapiens
CL 5.6 mL.min-1.kg-1 Homo sapiens
CL 5.6 mL.min-1.kg-1 Homo sapiens
F 80.0 % Homo sapiens
F 20.0 % Homo sapiens
F 80.0 % Homo sapiens
MRT 1.6 hr Homo sapiens
T1/2 22.7 - -
T1/2 1.2 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Antiviral activity against HIV1 RF in human H9 cells assessed as inhibition of v... 11430019
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of v... 11430019
Human immunodeficiency virus 1 EC50 = 9.0 nM 8.05 Antiviral activity against HIV-1 infected in human CEM-TK(-) cells assessed as r... 33711763
Human immunodeficiency virus 1 EC50 = 10.0 nM 8.0 Antiviral activity against HIV-1 infected in human CEM-SS cells assessed as redu... 33711763
Human immunodeficiency virus 1 IC50 = 11.0 nM 7.96 Antiviral activity against HIV-1 infected in PBMC (unknown origin) assessed as i... 37393791
Human immunodeficiency virus 1 EC50 = 15.0 nM 7.82 Antiviral activity against HIV-1 infected in human CEM-TK(-) cells assessed as r... 33711763
ADMET EC50 = 16.0 nM 7.8 Effective conc. required to achieve 50% inhibition of HIV-1 IIIB multiplication ... 10821705
Human immunodeficiency virus 1 EC50 = 16.0 nM 7.8 Antiviral activity against HIV-1 infected in human CEM-SS cells assessed as redu... 33711763
CEM-SS EC50 = 20.0 nM 7.7 Compound was evaluated for the antiviral activity against HIV-1 strain IIIB in C... 9873509
CCRF-CEM IC50 = 22.0 nM 7.66 Concentration of compound required to inhibit the synthesis of mitochondrial DNA... 8145230
Human immunodeficiency virus 1 EC50 = 30.0 nM 7.52 Inhibition of HIV-1 replication in H9 lymphocytic cells. -
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 31.0 nM 7.51 Effective concentration required to achieve 50% inhibition of HIV-1 LAI replicat... 10821705
CEM-SS EC50 = 50.0 nM 7.3 Compound was evaluated for the antiviral activity against HIV-1 strain RF in CEM... 9873509
CEM-SS EC50 = 50.0 nM 7.3 Compound was evaluated for the antiviral activity against HIV-1 strain SK1 in CE... 9873509
Human immunodeficiency virus type 1 reverse transcriptase Ki = 51.0 nM 7.29 Inhibitory constant against HIV-1 reverse transcriptase 15801860
Human immunodeficiency virus 1 EC50 = 67.0 nM 7.17 Antiviral activity against HIV-1 infected in human CEM-SS cells assessed as redu... 33711763
ADMET EC50 = 70.0 nM 7.16 Effective conc. required to achieve 50% inhibition of HIV-2 D194 multiplication ... 10821705
CCRF-CEM IC50 = 70.0 nM 7.16 Inhibitory concentration against mitochondrial DNA synthesis CEM cells 9438017
Human immunodeficiency virus 1 EC50 = 79.0 nM 7.1 Antiviral activity against HIV1 infected in human H9 cells assessed as protectio... 25587934
Human immunodeficiency virus 1 EC50 = 83.0 nM 7.08 Antiviral activity against HIV-1 infected in human MT4 cells assessed as reducti... 33711763

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 192
16472241 10.2174/1570163043334794 Hepatotoxicity 18
19805555 10.1128/aac.00914-09 ADMET 17
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
9873509 10.1016/s0960-894x(98)00380-1 CEM-SS 10
- 10.1016/S0960-894X(97)00422-8 HepG2 10
20805401 10.1128/aac.00794-10 HepG2 9
20070106 10.1021/jm901371v Homo sapiens 8
8632437 10.1021/jm950797i MT2 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
33711763 10.1016/j.ejmech.2021.113315 Human immunodeficiency virus 1 8
33711763 10.1016/j.ejmech.2021.113315 ADMET 8
1351945 10.1021/jm00090a008 ATH-8 cell line 8
17470651 10.1128/aac.00039-07 ADMET 7
3497272 10.1021/jm00391a003 MT4 6
15715486 10.1021/jm0495172 CHO 6
7932583 10.1021/jm00047a013 Unchecked 6
8388473 10.1021/jm00057a002 Rattus norvegicus 6
28595015 10.1021/acs.jmedchem.7b00067 HepG2 6

Data from ChEMBL 36 via Core Engine