Brincidofovir

Brincidofovir
Clinical data
Trade names	Tembexa
Other names	CMX001; Cidofovir-HDP; hexadecyloxypropyl-cidofovir
License data	US DailyMed: Brincidofovir;
Routes of; administration	By mouth
ATC code	J05AB17 (WHO) ;
Legal status
Legal status	CA: ℞-only; US: ℞-only;
Identifiers
	IUPAC name ({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)[3-(hexadecyloxy)propoxy]phosphinic acid;
CAS Number	444805-28-1 ; Sodium salt: 496765-79-8 ;
PubChem CID	483477;
DrugBank	DB12151; Sodium salt: DBSALT002145;
ChemSpider	424003; Sodium salt: 21259112;
UNII	6794O900AX; Sodium salt: 8UN8SA9Z5C ;
KEGG	D10547;
ChEMBL	ChEMBL203321;
CompTox Dashboard (EPA)	DTXSID60196190 ;
Chemical and physical data
Formula	C27H52N3O7P
Molar mass	561.701 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCCCCCCCCCCCOCCCOP(=O)(O)CO[C@H](CO)Cn1ccc(N)nc1=O;
	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; Key:WXJFKKQWPMNTIM-VWLOTQADSA-N;

Brincidofovir, sold under the brand name Tembexa, is an antiviral drug used to treat smallpox. Brincidofovir is a prodrug of cidofovir.^[3] 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.^[4]

The most common side effects include diarrhea, nausea, vomiting, and abdominal pain.^[2] It carries an FDA-mandated black box warning of an increased risk of death with extended use.^[5]^[6] Brincidofovir was approved for medical use in the United States in June 2021.

^ "Regulatory Decision Summary for Tembexa". Drug and Health Products Portal. 11 December 2023. Retrieved 2 April 2024.
^ ^a ^b "FDA approves drug to treat smallpox". U.S. Food and Drug Administration (FDA). 4 June 2021. Archived from the original on 8 June 2021. Retrieved 7 June 2021. This article incorporates text from this source, which is in the public domain.
^ Cite error: The named reference Chimerix was invoked but never defined (see the help page).
^ Florescu DF, Keck MA (October 2014). "Development of CMX001 (Brincidofovir) for the treatment of serious diseases or conditions caused by dsDNA viruses". Expert Review of Anti-Infective Therapy. 12 (10): 1171–1178. doi:10.1586/14787210.2014.948847. PMID 25120093. S2CID 25854860.
^ "FDA Tembexa Product Insert" (PDF).
^ "DailyMed - TEMBEXA- brincidofovir tablet, film coated". dailymed.nlm.nih.gov.

[1] "Regulatory Decision Summary for Tembexa". Drug and Health Products Portal. 11 December 2023. Retrieved 2 April 2024.

[FDA_Tembexa-2] "FDA approves drug to treat smallpox". U.S. Food and Drug Administration (FDA). 4 June 2021. Archived from the original on 8 June 2021. Retrieved 7 June 2021. This article incorporates text from this source, which is in the public domain.

[Chimerix-3] Cite error: The named reference Chimerix was invoked but never defined (see the help page).

[4] Florescu DF, Keck MA (October 2014). "Development of CMX001 (Brincidofovir) for the treatment of serious diseases or conditions caused by dsDNA viruses". Expert Review of Anti-Infective Therapy. 12 (10): 1171–1178. doi:10.1586/14787210.2014.948847. PMID 25120093. S2CID 25854860.

[FDA_Tembexa_PI-5] "FDA Tembexa Product Insert" (PDF).

[6] "DailyMed - TEMBEXA- brincidofovir tablet, film coated". dailymed.nlm.nih.gov.

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