NAV

Brivudine monophosphate

Identification

Generic Name
Brivudine monophosphate
DrugBank Accession Number
DB04438
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 413.115
Monoisotopic: 411.967114593
Chemical Formula
C11H14BrN2O8P
Synonyms
  • Bvdu 5'-monophosphate
  • BVDU-MP
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThymidine kinaseNot AvailableHHV-3
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
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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'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine deoxyribonucleotides
Direct Parent
Pyrimidine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Monoalkyl phosphates / Pyrimidones / Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Tetrahydrofurans / Ureas / Lactams / Secondary alcohols / Vinyl bromides
show 8 more
Substituents
Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Bromoalkene / Haloalkene / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
O7N0Y11U8K
CAS number
80860-82-8
InChI Key
LKWCVKAHHUJPQO-PIXDULNESA-N
InChI
InChI=1S/C11H14BrN2O8P/c12-2-1-6-4-14(11(17)13-10(6)16)9-3-7(15)8(22-9)5-21-23(18,19)20/h1-2,4,7-9,15H,3,5H2,(H,13,16,17)(H2,18,19,20)/b2-1+/t7-,8+,9+/m0/s1
IUPAC Name
{[(2R,3S,5R)-5-{5-[(1E)-2-bromoethenyl]-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl}-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
SMILES
O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(\C=C\Br)C(=O)NC1=O

References

General References
Not Available
PubChem Compound
6505368
PubChem Substance
46507968
ChemSpider
5005362
ChEMBL
CHEMBL1231519
PDBe Ligand
BVP
PDB Entries
1osn / 2jaw / 2w0s / 4xsc

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility3.97 mg/mLALOGPS
logP-0.76ALOGPS
logP-0.62Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)1.23Chemaxon
pKa (Strongest Basic)-3.2Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area145.63 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity78.55 m3·mol-1Chemaxon
Polarizability31.79 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.65
Blood Brain Barrier+0.8401
Caco-2 permeable-0.7691
P-glycoprotein substrateNon-substrate0.694
P-glycoprotein inhibitor INon-inhibitor0.7415
P-glycoprotein inhibitor IINon-inhibitor0.8932
Renal organic cation transporterNon-inhibitor0.9048
CYP450 2C9 substrateNon-substrate0.6779
CYP450 2D6 substrateNon-substrate0.8391
CYP450 3A4 substrateSubstrate0.5184
CYP450 1A2 substrateNon-inhibitor0.8232
CYP450 2C9 inhibitorNon-inhibitor0.8376
CYP450 2D6 inhibitorNon-inhibitor0.897
CYP450 2C19 inhibitorNon-inhibitor0.8091
CYP450 3A4 inhibitorNon-inhibitor0.7213
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8507
Ames testNon AMES toxic0.617
CarcinogenicityNon-carcinogens0.8035
BiodegradationNot ready biodegradable0.8944
Rat acute toxicity2.3548 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9547
hERG inhibition (predictor II)Non-inhibitor0.8103
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1028900000-ed2ffbc3d3c8a0787993
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-8002900000-03299f15a287bfa8ccc9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-b282885faf6ef2f59b99
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1194000000-3cd831ca6178b89af40a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-581795072ebdd3213c1d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xr-1390000000-7aeeb962be273c512fe3
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.3916
predicted
DeepCCS 1.0 (2019)
[M+H]+181.287
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.69392
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thymidine kinase
Kind
Protein
Organism
HHV-3
Pharmacological action
Unknown
General Function
Thymidine kinase activity
Specific Function
In latent infection, may allow the virus to be reactivated and to grow in cells lacking a high concentration of phosphorylated nucleic acid precursors, such as nerve cells that do not replicate the...
Gene Name
Not Available
Uniprot ID
P0C0E6
Uniprot Name
Thymidine kinase
Molecular Weight
37842.57 Da
References
  1. Bird LE, Ren J, Wright A, Leslie KD, Degreve B, Balzarini J, Stammers DK: Crystal structure of varicella zoster virus thymidine kinase. J Biol Chem. 2003 Jul 4;278(27):24680-7. Epub 2003 Apr 9. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52