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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL991
CHEMBL991
Compound Name STAVUDINE
ChEMBL Synonyms ZERIT XR | ZERIT | STAVUDINE | BMY-27857 | D4T
Max Phase 4 (Approved)
Trade Names STAVUDINE | ZERIT | ZERIT XR
Molecular Formula C10H12N2O4

Additional synonyms for CHEMBL991 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC1=CN([C@@H]2O[C@H](CO)C=C2)C(=O)NC1=O
Standard InChI InChI=1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)1 ...
Download InChI
Standard InChI Key XNKLLVCARDGLGL-JGVFFNPUSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL991

Molecule Features

CHEMBL991 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Human immunodeficiency virus type 1 reverse transcriptase inhibitor Human immunodeficiency virus type 1 reverse transcriptase FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Acquired Immunodeficiency SyndromeD000163EFO:0000765AIDS3ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection3ClinicalTrials

Clinical Data

ClinicalTrials.gov STAVUDINE
The Cochrane Collaboration STAVUDINE

Metabolites for CHEMBL991

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL991. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1820 Thymidine kinase Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1) 1.000
CHEMBL3415 Thymidine kinase Human herpesvirus 2 1.000
CHEMBL247 Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 1.000
CHEMBL4714 Pyrimidinergic receptor P2Y6 Homo sapiens 1.000
CHEMBL2366516 Reverse transcriptase Human immunodeficiency virus 1 1.000
CHEMBL4398 Purinergic receptor P2Y2 Homo sapiens 1.000
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.999
CHEMBL2361 Thymidylate kinase Mycobacterium tuberculosis 0.999
CHEMBL5328 Thymidylate synthase Lactobacillus casei 0.997
CHEMBL1914 Butyrylcholinesterase Homo sapiens 0.778
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 0.530
CHEMBL2123 Pyrimidinergic receptor P2Y4 Homo sapiens 0.308



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2361 Thymidylate kinase Mycobacterium tuberculosis 1.000
CHEMBL4580 Thymidine kinase, mitochondrial Homo sapiens 1.000
CHEMBL2883 Thymidine kinase, cytosolic Homo sapiens 1.000
CHEMBL1820 Thymidine kinase Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1) 1.000
CHEMBL1795127 Thymidine kinase Human herpesvirus 1 1.000
CHEMBL3106 Thymidine phosphorylase Homo sapiens 1.000
CHEMBL5328 Thymidylate synthase Lactobacillus casei 1.000
CHEMBL3415 Thymidine kinase Human herpesvirus 2 1.000
CHEMBL2366516 Reverse transcriptase Human immunodeficiency virus 1 1.000
CHEMBL4398 Purinergic receptor P2Y2 Homo sapiens 1.000
CHEMBL247 Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 1.000
CHEMBL4714 Pyrimidinergic receptor P2Y6 Homo sapiens 1.000
CHEMBL1914 Butyrylcholinesterase Homo sapiens 1.000
CHEMBL2123 Pyrimidinergic receptor P2Y4 Homo sapiens 0.999
CHEMBL4518 Purinergic receptor P2Y14 Homo sapiens 0.996
CHEMBL4696 Glycogen phosphorylase, muscle form Oryctolagus cuniculus 0.982
CHEMBL1828 DNA polymerase alpha subunit Homo sapiens 0.940
CHEMBL2331070 Acid ceramidase Rattus norvegicus 0.905
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.452
CHEMBL3526 Muscle glycogen phosphorylase Homo sapiens 0.311

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
224.2 224.0797 -0.71 2 84.32 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 2 0 6 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.47 - -.65 -.65 1 16 0.65

Structural Alerts

There are 1 structural alerts for CHEMBL991. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J05 - ANTIVIRALS FOR SYSTEMIC USE
J05A - DIRECT ACTING ANTIVIRALS
J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors
J05AF04 - stavudine

ChemSpider ChemSpider:XNKLLVCARDGLGL-JGVFFNPUSA-N
DailyMed stavudine
PubChem SID: 144208591 SID: 144210900 SID: 170464820 SID: 17389053 SID: 17389074 SID: 26719688 SID: 26751536 SID: 29215013 SID: 49718181 SID: 50104116 SID: 50104117 SID: 56422159 SID: 7971664 SID: 855856 SID: 90341632
Wikipedia Stavudine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL991



ACToR 3056-17-5 132425-31-1
BindingDB 50013111
Brenda 146954 8488 156695 128098 28913 11762
ChEBI 63581
ChemicalBook CB4450928
DrugBank DB00649
DrugCentral 2478
eMolecules 739264 536927
EPA CompTox Dashboard DTXSID1023819
FDA SRS BO9LE4QFZF
Human Metabolome Database HMDB0014787
IBM Patent System 957CF1CEB0CB484E6586C1150D2E1416
KEGG Ligand C07312
LINCS LSM-5983
Mcule MCULE-5741755105 MCULE-9252477726
MolPort MolPort-002-507-283
NIH Clinical Collection SAM001246729 SAM002589948
Nikkaji J83.276F
PharmGKB PA451494
PubChem 18283
PubChem: Drugs of the Future 12014136
PubChem: Thomson Pharma 14822772 14749176
SureChEMBL SCHEMBL38661
ZINC ZINC000000137884

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/XNKLLVCARDGLGL-JGVFFNPUSA-N spacer
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