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Details

Stereochemistry ABSOLUTE
Molecular Formula C36H72NO8P
Molecular Weight 677.9325
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE

SMILES

CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC

InChI

InChIKey=CITHEXJVPOWHKC-UUWRZZSWSA-N
InChI=1S/C36H72NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37(3,4)5)45-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h34H,6-33H2,1-5H3/t34-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10866960 | http://www.sciencedirect.com/science/article/pii/S1818087614000725

1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE (dimyristoyl phosphatidylcholine, DMPC) is a synthetic phospholipid used in liposomes and lipid bilayers for the study of biological membranes. DMPC is a frequently studied artificial lipid because it undergoes a phase transition at a convenient temperature. Upon cooling below 23.6°C it undergoes a transition from the liquid crystalline phase to the solid rippled phase, characterized by periodic corrugations of the bilayer.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
ABELCET

Approved Use

ABELCET is indicated for the treatment of invasive fungal infections in patients who are refractory to or intolerant of conventional amphotericin B therapy. This is based on open-label treatment of patients judged by their physicians to be intolerant to or failing conventional amphotericin B therapy

Launch Date

1.28735995E12
Diagnostic
IMAGENT

Approved Use

Reconstituted Imagent (Perflexane Lipid Microspheres) Injectable Suspension is indicated for use in subjects with suboptimal echocardiograms to opacify the left ventricular chamber and to improve the delineation of the left ventricular endocardial border

Launch Date

1.02271681E12
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
300 mg/dL
33 mg/kg single, intravenous
dose: 33 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PHOSPHOLIPIDS plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
703.2 mg × h/dL
33 mg/kg single, intravenous
dose: 33 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PHOSPHOLIPIDS plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.3 h
33 mg/kg single, intravenous
dose: 33 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PHOSPHOLIPIDS plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Interaction of human and bovine A-1 apolipoproteins with L-alpha-dimyristoyl phosphadicylcholine and L-alpha-myristoyl lysophosphatidylcholine.
1977 Apr 10
Physical properties of isolated complexes of human and bovine A-I apolipoproteins with L-alpha-dimyristoyl phosphatidylcholine.
1977 Apr 10
Antibodies to liposomal phosphatidylcholine and phosphatidylsulfocholine.
1990 Jan
Selective inhibitory effects of hybrid liposomes on the growth of HIV type 1-infected cells in vitro.
2008 Aug 15
Synthetic dimyristoylphosphatidylcholine liposomes assimilating into high-density lipoprotein promote regression of atherosclerotic lesions in cholesterol-fed rabbits.
2010 Oct
Patents

Sample Use Guides

Cholesterol-fed rabbits infused weekly with dimyristoylphosphatidylcholine (DMPC) liposomes (300 mg/kg body weight) for five weeks had significantly decreased aortic cholesterol contents compared with saline-infused cholesterol-fed controls. Atherosclerotic plaque volume, as measured by a type of new magnetic resonance imaging analysis, also decreased significantly after DMPC treatment.
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: A good correlation between fifty-percent inhibitory concentration (IC(50)) of hybrid liposomes (HL) composed of dimyristoylphosphatidylcholine and polyoxyethylene(n) dodecyl ether on the growth of MOLT-4/IIIB cells (MOLT-4 cells chronically infected with human immunodeficiency virus (HIV)) and the membrane fluidity of HL was obtained.
Unknown
Name Type Language
1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
II  
Common Name English
DMPC, R-
Common Name English
1,2-DITETRADECANOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
Common Name English
DIMYRISTOYLPHOSPHATIDYLCHOLINE, L-
Common Name English
DIMYRISTOYL LECITHIN [ORANGE BOOK]
Common Name English
DIMYRISTOYL PHOSPHATIDYLCHOLINE, R-ISOMER
Common Name English
1,2-DIMYRISTOYL-PHOSPHATIDYLCHOLINE, R-
Common Name English
3,5,9-TRIOXA-4-PHOSPHATRICOSAN-1-AMINIUM, 4-HYDROXY-N,N,N-TRIMETHYL-10-OXO-7-((1-OXOTETRADECYL)OXY)-, INNER SALT, 4-OXIDE, (7R)-
Common Name English
DIMYRISTOYL LECITHIN
ORANGE BOOK  
Common Name English
DMPC, L-
Common Name English
DIMYRISTOYLPHOSPHATIDYLCHOLINE, R-
Common Name English
1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE [II]
Common Name English
DIMYRISTOYL PHOSPHATIDYLCHOLINE, L-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C927
Created by admin on Fri Dec 15 15:52:09 UTC 2023 , Edited by admin on Fri Dec 15 15:52:09 UTC 2023
Code System Code Type Description
PUBCHEM
5459377
Created by admin on Fri Dec 15 15:52:09 UTC 2023 , Edited by admin on Fri Dec 15 15:52:09 UTC 2023
PRIMARY
ECHA (EC/EINECS)
242-085-9
Created by admin on Fri Dec 15 15:52:09 UTC 2023 , Edited by admin on Fri Dec 15 15:52:09 UTC 2023
PRIMARY
WIKIPEDIA
Dimyristoylphosphatidylcholine
Created by admin on Fri Dec 15 15:52:09 UTC 2023 , Edited by admin on Fri Dec 15 15:52:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID00860227
Created by admin on Fri Dec 15 15:52:09 UTC 2023 , Edited by admin on Fri Dec 15 15:52:09 UTC 2023
PRIMARY
FDA UNII
52QK2NZ2T0
Created by admin on Fri Dec 15 15:52:09 UTC 2023 , Edited by admin on Fri Dec 15 15:52:09 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201501
Created by admin on Fri Dec 15 15:52:09 UTC 2023 , Edited by admin on Fri Dec 15 15:52:09 UTC 2023
PRIMARY
CHEBI
45240
Created by admin on Fri Dec 15 15:52:09 UTC 2023 , Edited by admin on Fri Dec 15 15:52:09 UTC 2023
PRIMARY
CAS
18194-24-6
Created by admin on Fri Dec 15 15:52:09 UTC 2023 , Edited by admin on Fri Dec 15 15:52:09 UTC 2023
PRIMARY
NCI_THESAURUS
C61726
Created by admin on Fri Dec 15 15:52:09 UTC 2023 , Edited by admin on Fri Dec 15 15:52:09 UTC 2023
PRIMARY