distearoylphosphatidylcholine

{{chembox

| Name = Distearoylphosphatidylcholine

| ImageFile = File:Distearoylphosphatidylcholine-line.png

| SystematicName = (2R)-2,3-Bis(octadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate

| OtherNames = 1,2-distearoyl-sn-glycero-3-phosphocholine, DSPC, 18:0 PC

| Section1 = {{Chembox Identifiers

| CASNo = 4539-70-2

| CASNo_Comment = (racemic)

| CASNo1 = 816-94-4

| CASNo1_Comment = (R enantiomer)

| ChEBI = 83718

| ChemSpiderID = 85004

| EC_number = 212-440-2

| PubChem = 94190

| UNII = 043IPI2M0K

| StdInChI=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

| StdInChIKey = NRJAVPSFFCBXDT-HUESYALOSA-N

| SMILES = O=C(OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C)CCCCCCCCCCCCCCCCC

}}

| Section2 = {{Chembox Properties

| C=44 | H=88 | N=1 | O=8 | P=1

}}

}}

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.{{cite journal |vauthors= van Hoogevest P, Wendel A |title= The use of natural and synthetic phospholipids as pharmaceutical excipients |journal= The European Journal of Lipid Science and Technology |volume= 116 |issue= 9 |pages= 1088–1107 |date= 2014 |pmid= 25400504 |pmc= 4207189 |doi= 10.1002/ejlt.201400219 }}

It can be used to prepare lipid nanoparticles which are used in mRNA vaccines,{{cite journal | vauthors = Puri A, Loomis K, Smith B, Lee JH, Yavlovich A, Heldman E, Blumenthal R | title = Lipid-based nanoparticles as pharmaceutical drug carriers: from concepts to clinic | journal = Critical Reviews in Therapeutic Drug Carrier Systems | volume = 26 | issue = 6 | pages = 523–80 | date = 2009 | pmid = 20402623 | pmc = 2885142 | doi = 10.1615/critrevtherdrugcarriersyst.v26.i6.10 }}{{cite journal | vauthors = Salvatori G, Luberto L, and Marra E| title = SARS-CoV-2 SPIKE PROTEIN: an optimal immunological target for vaccines.| volume = 18 | year = 2020 | doi = 10.1186/s12967-020-02392-y | journal = Journal of Translational Medicine| issue = 1| page = 222| pmid = 32493510| pmc = 7268185| doi-access = free}} In particular, it forms part of the drug delivery system for the Moderna and Pfizer COVID-19 vaccines.{{cite web | url=https://www.cdc.gov/vaccines/covid-19/info-by-product/moderna/downloads/standing-orders.pdf | title=Moderna COVID-19 Vaccine Standing Orders for Administering Vaccine to Persons 18 Years of Age and Older | publisher=Centers for Disease Control and Prevention (CDC)}}{{cite web | url=https://www.fda.gov/media/144414/download | archive-url=https://web.archive.org/web/20201212030300/https://www.fda.gov/media/144414/download | url-status=dead | archive-date=December 12, 2020 | title=Pfizer-BioNTech COVID-19 Vaccine EUA Fact Sheet for Recipients and Caregivers | date=29 June 2022 | publisher=Food and Drug Administration (FDA)}}