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Compound Detail

CHEMBL991

STAVUDINE
💊 Approved Drug
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💊 Approved Drug
Cc1cn([C@H]2C=C[C@@H](CO)O2)c(=O)[nH]c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL991
Name STAVUDINE
Phase Approved
Structure Type MOL
InChI Key XNKLLVCARDGLGL-JGVFFNPUSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL485652

Known Names

BMY-27857 D-4T D4T Estavudina NSC-163661 NSC-759897 Sanilvudine Stavudine Stavudine (d4t) Stavudine (dt4) Stavudinum Zerit +1 more
20
Targets
215
Activities
4
Assay Types
23
PK Parameters
20
Publications
13
Known Names
7
Indications
1
Mechanisms

Molecular Properties

224.2
MW (Da)
-0.71
ALogP
5
HBA
2
HBD
84.3
PSA (Ų)
0.65
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1994
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

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

Extended Properties

Molecular Formula C10H12N2O4
MW 224.22
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness 0.95

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

HIV Infections HIV Infections Virus Diseases Acquired Immunodeficiency Syndrome AIDS Dementia Complex AIDS-Associated Nephropathy Acidosis, Lactic

ATC Classification

J05AF04
stavudine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
metabolic toxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States

Activity Summary

EC50 174 meas. best 8.05
IC50 36 meas. best 7.7
Ki 4 meas.
Kd 1 meas. best 4.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ADMET
CHEMBL612558
 EC50 8.05 7.5833 9.0 3
MT4
CHEMBL388
 EC50 7.75 6.735 18.0 6
ADMET
CHEMBL612558
 IC50 7.7 6.42 20.0 3
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 EC50 7.3 6.65 50.0 3
Human immunodeficiency virus 1
CHEMBL378
 EC50 7.23 6.0011 59.0 94
CEM-SS
CHEMBL614548
 EC50 7.23 7.23 59.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 7.22 6.12 60.0 2
CEM-c113
CHEMBL614545
 EC50 7.1 7.1 80.0 1
C8166
CHEMBL614533
 EC50 7.1 7.1 80.0 1
CCRF-CEM
CHEMBL382
 EC50 7.05 6.0265 90.0 26
Human immunodeficiency virus 1
CHEMBL378
 IC50 7.0 6.0167 100.0 9
Human immunodeficiency virus 2
CHEMBL380
 EC50 7.0 5.5817 100.0 24
Human immunodeficiency virus 2
CHEMBL380
 IC50 6.4 5.73 400.0 2
CCRF-CEM
CHEMBL382
 IC50 6.22 5.92 600.0 2
Human immunodeficiency virus
CHEMBL613758
 EC50 6.11 5.295 770.0 2
MT4
CHEMBL388
 IC50 5.92 5.92 1200.0 1
MT2
CHEMBL614184
 EC50 5.75 5.725 1800.0 2
Moloney murine sarcoma virus
CHEMBL613501
 EC50 5.6 5.6 2500.0 1
Porcine endogenous retrovirus
CHEMBL613016
 EC50 5.11 5.11 7800.0 1
L1210
CHEMBL386
 IC50 5.05 5.05 8900.0 1
CEM-TK(-)
CHEMBL614044
 EC50 5.0 5.0 10000.0 1
CEM-c113
CHEMBL614545
 IC50 5.0 5.0 10000.0 1
C3H/3T3
CHEMBL614372
 EC50 4.82 4.82 15000.0 1
No relevant target
CHEMBL2362975
 IC50 4.57 4.3933 26784.0 3
CEM-TK(+)
CHEMBL614029
 EC50 4.48 4.48 33300.0 1
Albumin
CHEMBL3253
 Kd 4.36 4.36 44000.0 1
Unchecked
CHEMBL612545
 IC50 4.28 4.2133 52939.0 3
MT2
CHEMBL614184
 IC50 4.15 4.15 71000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 8.2 mL.min-1.kg-1 Homo sapiens
CL 8.2 mL.min-1.kg-1 Homo sapiens
F 82.0 % Homo sapiens
F 25.0 % Macaca mulatta
F 83.0 % Macaca fascicularis
F 100.0 % Mus musculus
F 100.0 % Homo sapiens
Fu 1.0 - Homo sapiens
MRT 1.4 hr Homo sapiens
T1/2 - hr Homo sapiens
T1/2 144.0 hr -
T1/2 120.0 hr -
T1/2 72.0 hr -
T1/2 - hr -
T1/2 - hr -
T1/2 - hr -
T1/2 - hr -
T1/2 - hr -
T1/2 833.33 hr -
T1/2 0.8 hr Macaca mulatta
T1/2 1.4 hr Homo sapiens
T1/2 833.0 hr -
T1/2 26.0 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
ADMET EC50 = 9.0 nM 8.05 Antiviral activity against HIV I strain (LAV) in human peripheral blood mononucl... 2918508
MT4 EC50 = 18.0 nM 7.75 Antiviral activity was measured on HIV-1 in MT-4 cells 9554875
ADMET IC50 = 20.0 nM 7.7 Compound was tested for anti-HIV activity in normal peripheral blood mononuclear... 9873688
MT4 EC50 = 22.0 nM 7.66 Antiviral activity was measured on HIV-2 in MT-4 cells 9554875
ADMET IC50 = 40.0 nM 7.4 Compound was tested for anti-HIV activity in normal peripheral blood mononuclear... 9873688
ADMET EC50 = 40.0 nM 7.4 Effective concentration required to inhibit P24 antigen production in PHA-PBM ce... 12852759
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 50.0 nM 7.3 Effective concentration that reduces HIV-induced cytopathic effect by 50% was de... 8385224
ADMET EC50 = 50.0 nM 7.3 Tested in vitro for the antiviral activity in PBM cells infected with HIV-1 -
CEM-SS EC50 = 59.0 nM 7.23 Tested in vitro for the antiviral activity in CEM-SS cells infected with HIV-1 -
Human immunodeficiency virus 1 EC50 = 59.0 nM 7.23 Anti-HIV activity against HIV-1 infected in human CEM-SS cells assessed as inhib... 34695774
Human immunodeficiency virus 1 EC50 = 60.0 nM 7.22 Antiviral activity against HIV1 3B in human H9 cells assessed as inhibition of v... 11430019
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 60.0 nM 7.22 Inhibition of HIV1 reverse transcriptase 17562366
Human immunodeficiency virus 1 EC50 = 60.0 nM 7.22 Antiviral activity against HIV1 RF in human H9 cells assessed as inhibition of v... 11430019
Human immunodeficiency virus 1 EC50 = 62.0 nM 7.21 Antiviral activity against HIV1 in MAGI-CCR5 cells 17181162
CEM-c113 EC50 = 80.0 nM 7.1 Effective concentration that reduces HIV-induced cytopathic effect by 50% was de... 8385224
C8166 EC50 = 80.0 nM 7.1 Ability to inhibit the replication of HIV-1 IIIB infected C8166 cells -
CCRF-CEM EC50 = 90.0 nM 7.05 Effective concentration of compound achieving 50% protection in CEM cell lines a... 14980640
Human immunodeficiency virus 1 IC50 = 100.0 nM 7.0 Antiviral activity against HIV1 infected in human PBMC assessed as inhibition of... 19596885
Human immunodeficiency virus 2 EC50 = 100.0 nM 7.0 Effective concentration of compound to inhibit human immunodeficiency virus HIV-... 15715487
CCRF-CEM EC50 = 160.0 nM 6.8 Compound was evaluated for the inhibition of HIV replication using HIV-1 infecte... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 467
20439609 10.1128/aac.00068-10 Human immunodeficiency virus 1 62
16472241 10.2174/1570163043334794 Hepatotoxicity 18
19805555 10.1128/aac.00914-09 ADMET 17
17724147 10.1128/aac.00692-07 CCRF-CEM 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
18541728 10.1128/aac.00434-08 ADMET 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
19704131 10.1128/aac.00686-09 Human immunodeficiency virus 1 9
9554875 10.1021/jm970664s CCRF-CEM 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
3033243 10.1021/jm00388a020 Unchecked 7
3033243 10.1021/jm00388a020 ATH-8 cell line 7
9554875 10.1021/jm970664s ADMET 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
15715487 10.1021/jm040845b Human immunodeficiency virus 1 6
3497272 10.1021/jm00391a003 MT4 6
17876005 10.1128/aac.00687-07 Human immunodeficiency virus 1 5
2918510 10.1021/jm00123a020 Mus musculus 5
17724147 10.1128/aac.00692-07 Human immunodeficiency virus 1 5

Data from ChEMBL 36 via Core Engine