NAV

Brincidofovir

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

Identification

Name
Brincidofovir
Accession Number
DB12151
Description

Brincidofovir is under investigation for the prevention of Outcomes, Survival Rates, and Cytomegalovirus Disease. Brincidofovir has been investigated for the prevention and treatment of CMV, Adenovirus, BK Virus (BKV), Adenoviruses (AdV), and Epstein-Barr (EBV), among others.

Brincidofovir is an oral antiviral drug candidate for the treatment of smallpox infections and complications resulting from smallpox vaccine. It is a lipid mimic of cidofovir formed by linking a lipid 3-hexadecyloxy-1-propanol, to the phosphonate group of cidofovir. Brincidofovir is designed to cross cellular membranes by passive diffusion (vida supra, Phospholipid Mimics Designed to Facilitate Uptake in the Small Intestine). Uptake by this mechanism should be more efficient and lead to a more rapid accumulation of cidofovir in the cytoplasm of the target cell. Once it has reached the cytoplasm, CDV is phosphorylated by host cell nucleoside kinases to form the active antiviral agent cidofovir diphosphate.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Similar Structures
Weight
Average: 561.701
Monoisotopic: 561.354288024
Chemical Formula
C27H52N3O7P
Synonyms
Not Available
External IDs
  • CMX 001
  • CMX-001
  • CMX001

Pharmacology

Indication
Not Available
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Affected organisms
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.
DrugInteraction
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AbacavirBrincidofovir may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseBrincidofovir may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Brincidofovir which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Brincidofovir which could result in a higher serum level.
AcetaminophenBrincidofovir may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Brincidofovir which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Brincidofovir which could result in a higher serum level.
AclidiniumBrincidofovir may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineBrincidofovir may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Brincidofovir which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
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Food Interactions
Not Available

Products

Product Ingredients
IngredientUNIICASInChI Key
Brincidofovir Sodium8UN8SA9Z5C496765-79-8CRDDLOITBKEPRN-UQIIZPHYSA-M

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
Aminopyrimidines and derivatives / Phosphonic acid esters / Imidolactams / Hydropyrimidines / Organic phosphonic acids / Heteroaromatic compounds / Dialkyl ethers / Azacyclic compounds / Primary amines / Primary alcohols
show 4 more
Substituents
Alcohol / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Dialkyl ether / Ether / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
6794O900AX
CAS number
444805-28-1
InChI Key
WXJFKKQWPMNTIM-VWLOTQADSA-N
InChI
InChI=1S/C27H52N3O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-35-20-16-21-37-38(33,34)24-36-25(23-31)22-30-18-17-26(28)29-27(30)32/h17-18,25,31H,2-16,19-24H2,1H3,(H,33,34)(H2,28,29,32)/t25-/m0/s1
IUPAC Name
({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)[3-(hexadecyloxy)propoxy]phosphinic acid
SMILES
CCCCCCCCCCCCCCCCOCCCOP(O)(=O)CO[C@H](CO)CN1C=CC(N)=NC1=O

References

General References
  1. Quenelle DC, Prichard MN, Keith KA, Hruby DE, Jordan R, Painter GR, Robertson A, Kern ER: Synergistic efficacy of the combination of ST-246 with CMX001 against orthopoxviruses. Antimicrob Agents Chemother. 2007 Nov;51(11):4118-24. Epub 2007 Aug 27. [PubMed:17724153]
  2. Parker S, Touchette E, Oberle C, Almond M, Robertson A, Trost LC, Lampert B, Painter G, Buller RM: Efficacy of therapeutic intervention with an oral ether-lipid analogue of cidofovir (CMX001) in a lethal mousepox model. Antiviral Res. 2008 Jan;77(1):39-49. Epub 2007 Sep 4. [PubMed:17904231]
PubChem Compound
483477
PubChem Substance
347828447
ChemSpider
424003
ChEMBL
CHEMBL203321
ZINC
ZINC000014141521
Wikipedia
Brincidofovir

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAdenovirus Infections1
3CompletedTreatmentCMV1
3TerminatedPreventionCompare Efficacy of BCV to vGCV for Prevention of CMV Disease in Kidney Transplant Recipients Who Are CMV Seropositive Pretransplant1
3TerminatedPreventionCytomegalovirus Disease1
2CompletedPreventionCytomegalovirus (CMV) Infection1
2CompletedTreatmentAdenovirus Disease1
2TerminatedTreatmentAdenovirus2
2WithdrawnTreatmentEbola Virus Disease1
2WithdrawnTreatmentEbola Viruses1
2, 3CompletedTreatmentDisease or Condition Caused by CMV, ADV, HSV, VAVC, VARV or / Male or Female Patients With a Serious or Immediately Life-threatening / Monkeypox Viruses(s) Who Have a Life Expectancy of ≥ 2 Weeks and for / Whom no Comparable or Satisfactory Alternative Therapy is Available1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00124 mg/mLALOGPS
logP4.4ALOGPS
logP3.85ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)1.07ChemAxon
pKa (Strongest Basic)1.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area143.91 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity149.9 m3·mol-1ChemAxon
Polarizability64.81 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created on October 20, 2016 15:29 / Updated on June 12, 2020 10:53