Distearoylphosphatidylcholine

Distearoylphosphatidylcholine is a phosphatidylcholine, a kind of phospholipid. It is a natural constituent of cell membranes, eg. soybean phosphatidylcholines are mostly different 18-carbon phosphatidylcholines (including minority of saturated DSPC), and their hydrogenation results in 85% DSPC.[1] It can be used to prepare lipid nanoparticles which are used in mRNA vaccines,[2][3] In particular, it forms part of the drug delivery system for the Moderna and Pfizer COVID-19 vaccines.[4][5]

Distearoylphosphatidylcholine
Names
Systematic IUPAC name
(2R)-2,3-Bis(octadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
Other names
1,2-distearoyl-sn-glycero-3-phosphocholine, DSPC, 18:0 PC
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.011.309
EC Number
  • 212-440-2
UNII
  • InChI=1S/C44H88NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h42H,6-41H2,1-5H3/t42-/m1/s1
    Key: NRJAVPSFFCBXDT-HUESYALOSA-N
  • O=C(OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C)CCCCCCCCCCCCCCCCC
Properties
C44H88NO8P
Molar mass 790.161 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references


See also
Moderna COVID-19 vaccine nanoparticle ingredients
Others

References
  1. van Hoogevest P, Wendel A (2014). "The use of natural and synthetic phospholipids as pharmaceutical excipients". The European Journal of Lipid Science and Technology. 116 (9): 1088–1107. doi:10.1002/ejlt.201400219. PMC 4207189. PMID 25400504.
  2. Puri A, Loomis K, Smith B, Lee JH, Yavlovich A, Heldman E, Blumenthal R (2009). "Lipid-based nanoparticles as pharmaceutical drug carriers: from concepts to clinic". Critical Reviews in Therapeutic Drug Carrier Systems. 26 (6): 523–80. doi:10.1615/critrevtherdrugcarriersyst.v26.i6.10. PMC 2885142. PMID 20402623.
  3. Salvatori G, Luberto L, and Marra E (2020). "SARS-CoV-2 SPIKE PROTEIN: an optimal immunological target for vaccines". Journal of Translational Medicine. 18 (1): 222. doi:10.1186/s12967-020-02392-y. PMC 7268185. PMID 32493510.
  4. "Moderna COVID-19 Vaccine Standing Orders for Administering Vaccine to Persons 18 Years of Age and Older" (PDF). Centers for Disease Control and Prevention (CDC).
  5. "Pfizer-BioNTech COVID-19 Vaccine EUA Fact Sheet for Recipients and Caregivers". Food and Drug Administration (FDA). 29 June 2022.
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