Brincidofovir
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MedKoo CAT#: 319653

CAS#: 444805-28-1

Description: Brincidofovir, also known as CMX001, HDP-CDV and HDPCDV, is DNA polymerase inhibitor potentially for the treatment of cytomegalovirus, adenovirus, smallpox, and ebolavirus infections. Brincidofovir is a prodrug of cidofovir. Conjugated to a lipid, the compound is designed to release cidofovir intracellularly, allowing for higher intracellular and lower plasma concentrations of cidofovir, effectively increasing its activity against dsDNA viruses, as well as oral bioavailability.

Chemical Structure

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Brincidofovir
CAS# 444805-28-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319653
Name: Brincidofovir
CAS#: 444805-28-1
Chemical Formula: C27H52N3O7P
Exact Mass: 561.35
Molecular Weight: 561.701
Elemental Analysis: C, 57.73; H, 9.33; N, 7.48; O, 19.94; P, 5.51

Price and Availability

Size Price Availability Quantity
5mg USD 350 Ready to ship
10mg USD 550 Ready to ship
25mg USD 950 Ready to ship
50mg USD 1650 Ready to ship
100mg USD 2950 Ready to ship
200mg USD 5250 Ready to ship
Bulk inquiry

Synonym: CMX001; CMX 001; CMX-001; HDP-CDV; HDPCDV; Brincidofovir; hexadecyloxypropyl-CDV; 1-O-hexadecyloxypropyl Cidofovir; HDP (S)-HPMPC;

IUPAC/Chemical Name: 3-(hexadecyloxy)propyl hydrogen ((((S)-1-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate

InChi Key: WXJFKKQWPMNTIM-VWLOTQADSA-N

InChi Code: 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

SMILES Code: OC[C@H](CN1C=CC(N)=NC1=O)OCP(O)(OCCCOCCCCCCCCCCCCCCCC)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: 1. Hutson CL, Kondas AV, Mauldin MR, Doty JB, Grossi IM, Morgan CN, Ostergaard SD, Hughes CM, Nakazawa Y, Kling C, Martin BE, Ellison JA, Carroll DS, Gallardo-Romero NF, Olson VA. Pharmacokinetics and Efficacy of a Potential Smallpox Therapeutic, Brincidofovir, in a Lethal Monkeypox Virus Animal Model. mSphere. 2021 Feb 3;6(1):e00927-20. doi: 10.1128/mSphere.00927-20. Erratum in: mSphere. 2021 Feb 17;6(1): PMID: 33536322; PMCID: PMC7860987. 2. Zaitseva M, McCullough KT, Cruz S, Thomas A, Diaz CG, Keilholz L, Grossi IM, Trost LC, Golding H. Postchallenge administration of brincidofovir protects healthy and immune-deficient mice reconstituted with limited numbers of T cells from lethal challenge with IHD-J-Luc vaccinia virus. J Virol. 2015 Mar;89(6):3295-307. doi: 10.1128/JVI.03340-14. Epub 2015 Jan 14. PMID: 25589648; PMCID: PMC4337519.
In vitro activity: This study investigated the effects of BCV (brincidofovir) in BKPyV-infected and uninfected primary human urothelial cells (HUCs), the target cells of BKPyV in PyVHC. The BCV concentrations causing 50 and 90% reductions (EC50 and EC90) in the number of intracellular BKPyV genome equivalents per cell (icBKPyV) were 0.27 μM and 0.59 μM, respectively. At 0.63 μM, BCV reduced viral late gene expression by 90% and halted progeny release. Reference: Antimicrob Agents Chemother. 2015;59(6):3306-16. https://pubmed.ncbi.nlm.nih.gov/25801568/
In vivo activity: A three-dose regimen of 20 mg/kg BCV (brincidofovir) administered every 48 h starting either on day 1 or day 2 postchallenge protected 100% of mice. Initiating BCV treatment earlier was more efficient in reducing viral loads and in providing protection from pox lesion development. All BCV-treated mice that survived challenge were also protected from rechallenge with IHD-J-Luc or WRvFire VACV without additional treatment. In immune-deficient mice, BCV protected animals from lethality and reduced viral loads while animals were on the drug. Reference: J Virol. 2015 Mar;89(6):3295-307. https://pubmed.ncbi.nlm.nih.gov/25589648/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 1.0 1.78

Preparing Stock Solutions

The following data is based on the product molecular weight 561.70 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Trost LC, Rose ML, Khouri J, Keilholz L, Long J, Godin SJ, Foster SA. The efficacy and pharmacokinetics of brincidofovir for the treatment of lethal rabbitpox virus infection: a model of smallpox disease. Antiviral Res. 2015 May;117:115-21. doi: 10.1016/j.antiviral.2015.02.007. Epub 2015 Mar 4. PMID: 25746331. 2. Tylden GD, Hirsch HH, Rinaldo CH. Brincidofovir (CMX001) inhibits BK polyomavirus replication in primary human urothelial cells. Antimicrob Agents Chemother. 2015;59(6):3306-16. doi: 10.1128/AAC.00238-15. Epub 2015 Mar 23. PMID: 25801568; PMCID: PMC4432119. 3. Hutson CL, Kondas AV, Mauldin MR, Doty JB, Grossi IM, Morgan CN, Ostergaard SD, Hughes CM, Nakazawa Y, Kling C, Martin BE, Ellison JA, Carroll DS, Gallardo-Romero NF, Olson VA. Pharmacokinetics and Efficacy of a Potential Smallpox Therapeutic, Brincidofovir, in a Lethal Monkeypox Virus Animal Model. mSphere. 2021 Feb 3;6(1):e00927-20. doi: 10.1128/mSphere.00927-20. Erratum in: mSphere. 2021 Feb 17;6(1): PMID: 33536322; PMCID: PMC7860987. 4. Zaitseva M, McCullough KT, Cruz S, Thomas A, Diaz CG, Keilholz L, Grossi IM, Trost LC, Golding H. Postchallenge administration of brincidofovir protects healthy and immune-deficient mice reconstituted with limited numbers of T cells from lethal challenge with IHD-J-Luc vaccinia virus. J Virol. 2015 Mar;89(6):3295-307. doi: 10.1128/JVI.03340-14. Epub 2015 Jan 14. PMID: 25589648; PMCID: PMC4337519.
In vitro protocol: 1. Trost LC, Rose ML, Khouri J, Keilholz L, Long J, Godin SJ, Foster SA. The efficacy and pharmacokinetics of brincidofovir for the treatment of lethal rabbitpox virus infection: a model of smallpox disease. Antiviral Res. 2015 May;117:115-21. doi: 10.1016/j.antiviral.2015.02.007. Epub 2015 Mar 4. PMID: 25746331. 2. Tylden GD, Hirsch HH, Rinaldo CH. Brincidofovir (CMX001) inhibits BK polyomavirus replication in primary human urothelial cells. Antimicrob Agents Chemother. 2015;59(6):3306-16. doi: 10.1128/AAC.00238-15. Epub 2015 Mar 23. PMID: 25801568; PMCID: PMC4432119.
In vivo protocol: 1. Hutson CL, Kondas AV, Mauldin MR, Doty JB, Grossi IM, Morgan CN, Ostergaard SD, Hughes CM, Nakazawa Y, Kling C, Martin BE, Ellison JA, Carroll DS, Gallardo-Romero NF, Olson VA. Pharmacokinetics and Efficacy of a Potential Smallpox Therapeutic, Brincidofovir, in a Lethal Monkeypox Virus Animal Model. mSphere. 2021 Feb 3;6(1):e00927-20. doi: 10.1128/mSphere.00927-20. Erratum in: mSphere. 2021 Feb 17;6(1): PMID: 33536322; PMCID: PMC7860987. 2. Zaitseva M, McCullough KT, Cruz S, Thomas A, Diaz CG, Keilholz L, Grossi IM, Trost LC, Golding H. Postchallenge administration of brincidofovir protects healthy and immune-deficient mice reconstituted with limited numbers of T cells from lethal challenge with IHD-J-Luc vaccinia virus. J Virol. 2015 Mar;89(6):3295-307. doi: 10.1128/JVI.03340-14. Epub 2015 Jan 14. PMID: 25589648; PMCID: PMC4337519.

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6: Hutson CL, Kondas AV, Mauldin MR, Doty JB, Grossi IM, Morgan CN, Ostergaard SD, Hughes CM, Nakazawa Y, Kling C, Martin BE, Ellison JA, Carroll DS, Gallardo- Romero NF, Olson VA. Pharmacokinetics and Efficacy of a Potential Smallpox Therapeutic, Brincidofovir, in a Lethal Monkeypox Virus Animal Model. mSphere. 2021 Feb 3;6(1):e00927-20. doi: 10.1128/mSphere.00927-20. Erratum in: mSphere. 2021 Feb 17;6(1): PMID: 33536322; PMCID: PMC7860987.


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10: Hill JA, Nichols WG, Marty FM, Papanicolaou GA, Brundage TM, Lanier R, Zerr DM, Boeckh MJ. Oral brincidofovir decreases the incidence of HHV-6B viremia after allogeneic HCT. Blood. 2020 Apr 23;135(17):1447-1451. doi: 10.1182/blood.2019004315. PMID: 32076716; PMCID: PMC7180083.


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12: Siegrist EA, Sassine J. Antivirals With Activity Against Mpox: A Clinically Oriented Review. Clin Infect Dis. 2023 Jan 6;76(1):155-164. doi: 10.1093/cid/ciac622. PMID: 35904001; PMCID: PMC9825831.


13: Al-Heeti OM, Cathro HP, Ison MG. Adenovirus Infection and Transplantation. Transplantation. 2022 May 1;106(5):920-927. doi: 10.1097/TP.0000000000003988. Epub 2021 Nov 24. PMID: 34856601; PMCID: PMC9050944.


14: Imran M, Alshammari MK, Arora MK, Dubey AK, Das SS, Kamal M, Alqahtani ASA, Sahloly MAY, Alshammari AH, Alhomam HM, Mahzari AM, Abida, Rabaan AA, Dzinamarira T. Oral Brincidofovir Therapy for Monkeypox Outbreak: A Focused Review on the Therapeutic Potential, Clinical Studies, Patent Literature, and Prospects. Biomedicines. 2023 Jan 19;11(2):278. doi: 10.3390/biomedicines11020278. PMID: 36830816; PMCID: PMC9953536.


15: Soheili M, Nasseri S, Afraie M, Khateri S, Moradi Y, Mahdavi Mortazavi SM, Gilzad-Kohan H. Monkeypox: Virology, Pathophysiology, Clinical Characteristics, Epidemiology, Vaccines, Diagnosis, and Treatments. J Pharm Pharm Sci. 2022;25:297-322. doi: 10.18433/jpps33138. PMID: 36130588.


16: Hiwarkar P, Amrolia P, Sivaprakasam P, Lum SH, Doss H, O'Rafferty C, Petterson T, Patrick K, Silva J, Slatter M, Lawson S, Rao K, Steward C, Gassas A, Veys P, Wynn R; United Kingdom Paediatric Bone Marrow Transplant Group. Brincidofovir is highly efficacious in controlling adenoviremia in pediatric recipients of hematopoietic cell transplant. Blood. 2017 Apr 6;129(14):2033-2037. doi: 10.1182/blood-2016-11-749721. Epub 2017 Feb 2. PMID: 28153824.


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19: Guo S, Zhang Y, Liu Z, Wang D, Liu H, Li L, Chen Q, Yang D, Liu Q, Guo H, Mou S, Chen H, Wang X. Brincidofovir is a robust replication inhibitor against African swine fever virus in vivo and in vitro. Emerg Microbes Infect. 2023 Dec;12(2):2220572. doi: 10.1080/22221751.2023.2220572. PMID: 37272334.


20: Sulejmani N, Nagai S, Safwan M, Rizzari MD, Raoufi M, Abouljoud MS, Ramesh M. Brincidofovir as Salvage Therapy for Adenovirus Disease in Intestinal Transplant Recipients. Pharmacotherapy. 2018 Apr;38(4):470-475. doi: 10.1002/phar.2094. Epub 2018 Mar 28. PMID: 29457839.