Alamifovir

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Alamifovir
DrugBank Accession Number
DB06368
Background

Alamifovir is an antiviral agent specific for HBV.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 575.42
Monoisotopic: 575.082695914
Chemical Formula
C19H20F6N5O5PS
Synonyms
  • Alamifovir
External IDs
  • LY 582563
  • LY-582563
  • LY582563
  • MCC 478
  • MCC-478

Pharmacology

Indication

Investigated for use/treatment in hepatitis (viral, B).

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Pharmacodynamics

Not Available

Mechanism of action

Alamifovir is a purine nucleotide analogue prodrug that shows potent activity against wild type and lamivudine resistant hepatitis B virus in preclinical studies.

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
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
0N739K2A8A
CAS number
193681-12-8
InChI Key
VDBGPMJFHCJMOL-UHFFFAOYSA-N
InChI
InChI=1S/C19H20F6N5O5PS/c1-32-12-2-4-13(5-3-12)37-16-14-15(28-17(26)29-16)30(10-27-14)6-7-33-11-36(31,34-8-18(20,21)22)35-9-19(23,24)25/h2-5,10H,6-9,11H2,1H3,(H2,26,28,29)
IUPAC Name
bis(2,2,2-trifluoroethyl) [(2-{2-amino-6-[(4-methoxyphenyl)sulfanyl]-9H-purin-9-yl}ethoxy)methyl]phosphonate
SMILES
COC1=CC=C(SC2=C3N=CN(CCOCP(=O)(OCC(F)(F)F)OCC(F)(F)F)C3=NC(N)=N2)C=C1

References

General References
  1. Chan C, Abu-Raddad E, Golor G, Watanabe H, Sasaki A, Yeo KP, Soon D, Sinha VP, Flanagan SD, He MM, Wise SD: Clinical pharmacokinetics of alamifovir and its metabolites. Antimicrob Agents Chemother. 2005 May;49(5):1813-22. [Article]
  2. Soon DK, Lowe SL, Teng CH, Yeo KP, McGill J, Wise SD: Safety and efficacy of alamifovir in patients with chronic hepatitis B virus infection. J Hepatol. 2004 Nov;41(5):852-8. [Article]
PubChem Compound
213052
ChemSpider
429846
BindingDB
50115494
ChEMBL
CHEMBL106502
ZINC
ZINC000003964493

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 Solubility0.164 mg/mLALOGPS
logP3.06ALOGPS
logP4.24Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)16.4Chemaxon
pKa (Strongest Basic)4.26Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area123.61 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity122.07 m3·mol-1Chemaxon
Polarizability46.56 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9266
Blood Brain Barrier+0.9326
Caco-2 permeable-0.5808
P-glycoprotein substrateSubstrate0.5474
P-glycoprotein inhibitor IInhibitor0.5618
P-glycoprotein inhibitor IINon-inhibitor0.573
Renal organic cation transporterNon-inhibitor0.5564
CYP450 2C9 substrateNon-substrate0.9176
CYP450 2D6 substrateNon-substrate0.7962
CYP450 3A4 substrateNon-substrate0.544
CYP450 1A2 substrateNon-inhibitor0.5117
CYP450 2C9 inhibitorNon-inhibitor0.5386
CYP450 2D6 inhibitorNon-inhibitor0.8086
CYP450 2C19 inhibitorNon-inhibitor0.5251
CYP450 3A4 inhibitorInhibitor0.7029
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7159
Ames testNon AMES toxic0.5503
CarcinogenicityNon-carcinogens0.8415
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6199 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.839
hERG inhibition (predictor II)Inhibitor0.639
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/MSsplash10-004i-0000190000-5f28830fdf4c78aa419c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0000090000-6a561633db11998b0d58
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0010390000-f7ce818bbc5f2f95fc9d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0109100000-4a1f8fe3ba20c47aa00a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00fr-0961020000-2d7289fe209a7f946ba9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f83-0409200000-85a655baa1a20ae2da7d
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at March 19, 2008 16:27 / Updated at February 21, 2021 18:52