NAV

Zidovudine monophosphate

Identification

Generic Name
Zidovudine monophosphate
DrugBank Accession Number
DB03666
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 347.2212
Monoisotopic: 347.063084339
Chemical Formula
C10H14N5O7P
Synonyms
  • 3'-Azido-2',3'-deoxythymidine 5'-monophosphate
  • 3'-Azido-3'-deoxythymidine 5'-phosphate
  • AZTMP
  • Zdv 5'-monophosphate
  • ZDVMP
  • Zidovudine 5'-monophosphate
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThymidylate kinaseNot AvailableHumans
UThymidylate kinaseNot AvailableMycobacterium tuberculosis
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Pyrimidones
Alternative Parents
Monoalkyl phosphates / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Lactams / Azo imides / Azo compounds / Oxacyclic compounds
show 5 more
Substituents
Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Azo compound / Azo imide / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Monoalkyl phosphate
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
97YMU05VPJ
CAS number
29706-85-2
InChI Key
OIFWQOKDSPDILA-XLPZGREQSA-N
InChI
InChI=1S/C10H14N5O7P/c1-5-3-15(10(17)12-9(5)16)8-2-6(13-14-11)7(22-8)4-21-23(18,19)20/h3,6-8H,2,4H2,1H3,(H,12,16,17)(H2,18,19,20)/t6-,7+,8+/m0/s1
IUPAC Name
{[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid
SMILES
CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O

References

General References
Not Available
PubChem Compound
65374
PubChem Substance
46506173
ChemSpider
58846
ChEMBL
CHEMBL257695
ZINC
ZINC000012503817
PDBe Ligand
ATM
PDB Entries
1e98 / 1e99 / 1e9b / 1e9d / 1n5y / 1n6q / 1w2h / 2jau / 2tmk / 2wwi …
show 9 more

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
logP-0.42Chemaxon
pKa (Strongest Acidic)1.26Chemaxon
pKa (Strongest Basic)-4.2Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area154.83 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity72.58 m3·mol-1Chemaxon
Polarizability29.32 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7915
Blood Brain Barrier+0.5952
Caco-2 permeable-0.7704
P-glycoprotein substrateNon-substrate0.6451
P-glycoprotein inhibitor INon-inhibitor0.8248
P-glycoprotein inhibitor IINon-inhibitor0.9404
Renal organic cation transporterNon-inhibitor0.8913
CYP450 2C9 substrateNon-substrate0.6349
CYP450 2D6 substrateNon-substrate0.8583
CYP450 3A4 substrateSubstrate0.5607
CYP450 1A2 substrateNon-inhibitor0.8664
CYP450 2C9 inhibitorNon-inhibitor0.8531
CYP450 2D6 inhibitorNon-inhibitor0.9123
CYP450 2C19 inhibitorNon-inhibitor0.8415
CYP450 3A4 inhibitorNon-inhibitor0.8089
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9245
Ames testAMES toxic0.6044
CarcinogenicityNon-carcinogens0.8076
BiodegradationReady biodegradable0.7501
Rat acute toxicity2.4191 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8615
hERG inhibition (predictor II)Non-inhibitor0.8032
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-9411000000-7d066758e2445713d5e7
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]-190.0359586
predicted
DarkChem Lite v0.1.0
[M-H]-152.99413
predicted
DeepCCS 1.0 (2019)
[M+H]+190.6345586
predicted
DarkChem Lite v0.1.0
[M+H]+155.39369
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.5781586
predicted
DarkChem Lite v0.1.0
[M+Na]+161.30223
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thymidylate kinase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Uridylate kinase activity
Specific Function
Catalyzes the conversion of dTMP to dTDP.
Gene Name
DTYMK
Uniprot ID
P23919
Uniprot Name
Thymidylate kinase
Molecular Weight
23819.105 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. Thymidylate kinase
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the reversible phosphorylation of deoxythymidine monophosphate (dTMP) to deoxythymidine diphosphate (dTDP), using ATP as its preferred phosphoryl donor. Situated at the junction of both de novo and salvage pathways of deoxythymidine triphosphate (dTTP) synthesis, is essential for DNA synthesis and cellular growth. Has a broad specificity for nucleoside triphosphates, being highly active with ATP or dATP as phosphate donors, and less active with ITP, GTP, CTP and UTP.
Specific Function
Atp binding
Gene Name
tmk
Uniprot ID
P9WKE1
Uniprot Name
Thymidylate kinase
Molecular Weight
22634.285 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

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