Platelet Activating Factor

Identification

Generic Name
Platelet Activating Factor
DrugBank Accession Number
DB02261
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 523.6832
Monoisotopic: 523.363789599
Chemical Formula
C26H54NO7P
Synonyms
  • 1-hexadecyl-2-acetyl-glycero-3-phosphocholine
  • Blood platelet-activating factor
  • PAF
  • PAF 16
  • PAF acether
  • Platelet-activating factor

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGanglioside GM2 activatorNot AvailableHumans
UPlatelet-activating factor receptorNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbciximabThe therapeutic efficacy of Platelet Activating Factor can be decreased when used in combination with Abciximab.
AcenocoumarolThe therapeutic efficacy of Platelet Activating Factor can be decreased when used in combination with Acenocoumarol.
Alpha-1-proteinase inhibitorAlpha-1-proteinase inhibitor may increase the thrombogenic activities of Platelet Activating Factor.
AlteplaseThe therapeutic efficacy of Platelet Activating Factor can be decreased when used in combination with Alteplase.
Aminocaproic acidThe risk or severity of adverse effects can be increased when Aminocaproic acid is combined with Platelet Activating Factor.
AncrodThe therapeutic efficacy of Platelet Activating Factor can be decreased when used in combination with Ancrod.
AnistreplaseThe therapeutic efficacy of Platelet Activating Factor can be decreased when used in combination with Anistreplase.
Antithrombin AlfaThe therapeutic efficacy of Platelet Activating Factor can be decreased when used in combination with Antithrombin Alfa.
Antithrombin III humanThe therapeutic efficacy of Platelet Activating Factor can be decreased when used in combination with Antithrombin III human.
ApixabanThe therapeutic efficacy of Platelet Activating Factor can be decreased when used in combination with Apixaban.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1-alkyl,2-acetylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acetyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Glycerophospholipids
Sub Class
Glycerophosphocholines
Direct Parent
1-alkyl,2-acetylglycero-3-phosphocholines
Alternative Parents
Phosphocholines / Glycerol ethers / Dialkyl phosphates / Tetraalkylammonium salts / Carboxylic acid esters / Monocarboxylic acids and derivatives / Dialkyl ethers / Organopnictogen compounds / Organic salts / Organic oxides
show 3 more
Substituents
1-alkyl,2-acetylglycero-3-phosphocholine / Aliphatic acyclic compound / Alkyl phosphate / Amine / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Dialkyl phosphate / Ether
show 15 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
2-acetyl-1-alkyl-sn-glycero-3-phosphocholine (CHEBI:44811) / 1-alkyl,2-acylglycerophosphocholines (LMGP01020046)
Affected organisms
Not Available

Chemical Identifiers

UNII
42EWD89I80
CAS number
74389-68-7
InChI Key
HVAUUPRFYPCOCA-AREMUKBSSA-N
InChI
InChI=1S/C26H54NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21-31-23-26(34-25(2)28)24-33-35(29,30)32-22-20-27(3,4)5/h26H,6-24H2,1-5H3/t26-/m1/s1
IUPAC Name
(2-{[(2R)-2-(acetyloxy)-3-(hexadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
SMILES
CCCCCCCCCCCCCCCCOC[C@H](CO[P@@]([O-])(=O)OCC[N+](C)(C)C)OC(C)=O

References

Synthesis Reference

Aiya Sato, Michihiro Sugano, Kouhei Furuya, Takeshi Oshima, Harumitsu Kuwano, Tadashi Hata, Hideyuki Haruyama, "Platelet activating factor antagonists, named "the phomactins", their preparation and use." U.S. Patent US5308867, issued October, 1980.

US5308867
General References
Not Available
Human Metabolome Database
HMDB0062195
PubChem Compound
108156
PubChem Substance
46508665
ChemSpider
97241
BindingDB
85035
ChEBI
44811
ChEMBL
CHEMBL1235246
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
PFS
PDB Entries
1tjj

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000225 mg/mLALOGPS
logP2.71ALOGPS
logP2.01ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity151.67 m3·mol-1ChemAxon
Polarizability63.09 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9853
Blood Brain Barrier+0.8739
Caco-2 permeable-0.5288
P-glycoprotein substrateSubstrate0.5468
P-glycoprotein inhibitor INon-inhibitor0.708
P-glycoprotein inhibitor IINon-inhibitor0.8673
Renal organic cation transporterNon-inhibitor0.837
CYP450 2C9 substrateNon-substrate0.8951
CYP450 2D6 substrateNon-substrate0.8167
CYP450 3A4 substrateSubstrate0.5503
CYP450 1A2 substrateNon-inhibitor0.8835
CYP450 2C9 inhibitorNon-inhibitor0.895
CYP450 2D6 inhibitorNon-inhibitor0.9047
CYP450 2C19 inhibitorNon-inhibitor0.8362
CYP450 3A4 inhibitorNon-inhibitor0.7665
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9636
Ames testNon AMES toxic0.6905
CarcinogenicityCarcinogens 0.6219
BiodegradationReady biodegradable0.9563
Rat acute toxicity2.8285 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6381
hERG inhibition (predictor II)Non-inhibitor0.6618
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-1912020000-cd0b0948116f9c94f643

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipase activator activity
Specific Function
The large binding pocket can accommodate several single chain phospholipids and fatty acids, GM2A also exhibits some calcium-independent phospholipase activity (By similarity). Binds gangliosides a...
Gene Name
GM2A
Uniprot ID
P17900
Uniprot Name
Ganglioside GM2 activator
Molecular Weight
20838.1 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Platelet activating factor receptor activity
Specific Function
Receptor for platelet activating factor, a chemotactic phospholipid mediator that possesses potent inflammatory, smooth-muscle contractile and hypotensive activity. Seems to mediate its action via ...
Gene Name
PTAFR
Uniprot ID
P25105
Uniprot Name
Platelet-activating factor receptor
Molecular Weight
39203.075 Da
References
  1. Qian C, Hwang SB, Libertine-Garahan L, Eckman JB, Cai X, Scannell RT, Yeh CG: Anti-inflammatory activities of LDP-392, a dual PAF receptor antagonist and 5-lipoxygenase inhibitor. Pharmacol Res. 2001 Sep;44(3):213-20. [Article]
  2. Pegorier S, Stengel D, Durand H, Croset M, Ninio E: Oxidized phospholipid: POVPC binds to platelet-activating-factor receptor on human macrophages. Implications in atherosclerosis. Atherosclerosis. 2006 Oct;188(2):433-43. Epub 2005 Dec 28. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 12, 2020 16:52