Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB03804
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
- Mechanism of Action
- Thymidine kinase, cytosolicInhibitor
- Thymidine kinase, cytosolic
Identification
- Generic Name
- 5-Bromothienyldeoxyuridine
- DrugBank Accession Number
- DB03804
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 5-Bromothienyldeoxyuridine (DB03804)
- Weight
- Average: 389.222
Monoisotopic: 387.972854873 - Chemical Formula
- C13H13BrN2O5S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AThymidine kinase, cytosolic inhibitorHumans UThymidine kinase ligandHHV-1 - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Pyrimidine nucleosides
- Sub Class
- Pyrimidine 2'-deoxyribonucleosides
- Direct Parent
- Pyrimidine 2'-deoxyribonucleosides
- Alternative Parents
- Pyrimidones / 2,5-disubstituted thiophenes / Aryl bromides / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Secondary alcohols / Lactams show 8 more
- Substituents
- 2,5-disubstituted thiophene / Alcohol / Aromatic heteromonocyclic compound / Aryl bromide / Aryl halide / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam show 19 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- IGUZFFOBAZCVRK-VAOFZXAKSA-N
- InChI
- InChI=1S/C13H13BrN2O5S/c14-10-2-1-9(22-10)6-4-16(13(20)15-12(6)19)11-3-7(18)8(5-17)21-11/h1-2,4,7-8,11,17-18H,3,5H2,(H,15,19,20)/t7-,8+,11+/m0/s1
- IUPAC Name
- 5-(5-bromothiophen-2-yl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
- SMILES
- [H][C@]1(O)C[C@@]([H])(O[C@]1([H])CO)N1C=C(C2=CC=C(Br)S2)C(=O)NC1=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 446725
- PubChem Substance
- 46507054
- ChemSpider
- 394009
- ChEMBL
- CHEMBL1231486
- ZINC
- ZINC000003802687
- PDBe Ligand
- BTD
- PDB Entries
- 1ki4
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.14 mg/mL ALOGPS logP 0.68 ALOGPS logP 1 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 9.69 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 99.1 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 79.18 m3·mol-1 Chemaxon Polarizability 33.17 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9373 Blood Brain Barrier + 0.5774 Caco-2 permeable - 0.796 P-glycoprotein substrate Non-substrate 0.6935 P-glycoprotein inhibitor I Non-inhibitor 0.8686 P-glycoprotein inhibitor II Non-inhibitor 0.9066 Renal organic cation transporter Non-inhibitor 0.8917 CYP450 2C9 substrate Non-substrate 0.736 CYP450 2D6 substrate Non-substrate 0.8496 CYP450 3A4 substrate Non-substrate 0.5665 CYP450 1A2 substrate Non-inhibitor 0.8183 CYP450 2C9 inhibitor Non-inhibitor 0.7663 CYP450 2D6 inhibitor Non-inhibitor 0.8865 CYP450 2C19 inhibitor Non-inhibitor 0.7999 CYP450 3A4 inhibitor Non-inhibitor 0.7929 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6264 Ames test Non AMES toxic 0.8369 Carcinogenicity Non-carcinogens 0.7499 Biodegradation Not ready biodegradable 0.8797 Rat acute toxicity 1.9001 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9801 hERG inhibition (predictor II) Non-inhibitor 0.7707
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0049000000-8f3da9ff05b15690f218 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004j-9044000000-b1f2f6626368fe821676 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00ds-1169000000-cb476c96b9a4bb4ccc64 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0190000000-916216b48c246f218ea4 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0191000000-f37af1c40ec0003cca59 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00fv-3593000000-c67d09a71c1e80cb5a43 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 171.45341 predictedDeepCCS 1.0 (2019) [M+H]+ 173.84898 predictedDeepCCS 1.0 (2019) [M+Na]+ 179.7615 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Cell-cycle-regulated enzyme of importance in nucleotide metabolism (PubMed:9575153). Catalyzes the first enzymatic step in the salvage pathway converting thymidine into thymidine monophosphate (PubMed:22385435). Transcriptional regulation limits expression to the S phase of the cell cycle and transient expression coincides with the oscillation in the intracellular dTTP concentration (Probable). Also important for the activation of anticancer and antiviral nucleoside analog prodrugs such as 1-b-d-arabinofuranosylcytosine (AraC) and 3c-azido-3c-deoxythymidine (AZT) (PubMed:22385435)
- Specific Function
- ATP binding
- Gene Name
- TK1
- Uniprot ID
- P04183
- Uniprot Name
- Thymidine kinase, cytosolic
- Molecular Weight
- 25468.455 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- HHV-1
- Pharmacological action
- Unknown
- Actions
- Ligand
- General Function
- Catalyzes the transfer of the gamma-phospho group of ATP to thymidine to generate dTMP in the salvage pathway of pyrimidine synthesis. The dTMP serves as a substrate for DNA polymerase during viral DNA replication. Allows the virus to be reactivated and to grow in non-proliferative cells lacking a high concentration of phosphorylated nucleic acid precursors.
- Specific Function
- ATP binding
- Gene Name
- TK
- Uniprot ID
- Q9QNF7
- Uniprot Name
- Thymidine kinase
- Molecular Weight
- 40896.475 Da
References
- Champness JN, Bennett MS, Wien F, Visse R, Summers WC, Herdewijn P, de Clerq E, Ostrowski T, Jarvest RL, Sanderson MR: Exploring the active site of herpes simplex virus type-1 thymidine kinase by X-ray crystallography of complexes with aciclovir and other ligands. Proteins. 1998 Aug 15;32(3):350-61. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22