Brincidofovir
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
- 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.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- 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.
Drug Interaction Unlock Additional DataAbacavir Brincidofovir may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Brincidofovir may decrease the excretion rate of Acarbose which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Brincidofovir which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Brincidofovir which could result in a higher serum level. Acetaminophen Brincidofovir may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Brincidofovir which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Brincidofovir which could result in a higher serum level. Aclidinium Brincidofovir may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Brincidofovir may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Brincidofovir which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Brincidofovir Sodium 8UN8SA9Z5C 496765-79-8 CRDDLOITBKEPRN-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
- 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]
- 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]
- External Links
- PubChem Compound
- 483477
- PubChem Substance
- 347828447
- ChemSpider
- 424003
- ChEMBL
- CHEMBL203321
- ZINC
- ZINC000014141521
- Wikipedia
- Brincidofovir
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Adenovirus Infections 1 3 Completed Treatment CMV 1 3 Terminated Prevention Compare Efficacy of BCV to vGCV for Prevention of CMV Disease in Kidney Transplant Recipients Who Are CMV Seropositive Pretransplant 1 3 Terminated Prevention Cytomegalovirus Disease 1 2 Completed Prevention Cytomegalovirus (CMV) Infection 1 2 Completed Treatment Adenovirus Disease 1 2 Terminated Treatment Adenovirus 2 2 Withdrawn Treatment Ebola Virus Disease 1 2 Withdrawn Treatment Ebola Viruses 1 2, 3 Completed Treatment Disease 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 Available 1
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
Property Value Source Water Solubility 0.00124 mg/mL ALOGPS logP 4.4 ALOGPS logP 3.85 ChemAxon logS -5.6 ALOGPS pKa (Strongest Acidic) 1.07 ChemAxon pKa (Strongest Basic) 1.75 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 143.91 Å2 ChemAxon Rotatable Bond Count 26 ChemAxon Refractivity 149.9 m3·mol-1 ChemAxon Polarizability 64.81 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created on October 20, 2016 15:29 / Updated on June 12, 2020 10:53