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Identification
NameProstaglandin G2
Accession NumberDB03866  (EXPT02577)
TypeSmall Molecule
GroupsExperimental
DescriptionA cyclic endoperoxide intermediate produced by the action of CYCLOOXYGENASE on ARACHIDONIC ACID. It is further converted by a series of specific enzymes to the series 2 prostaglandins. [PubChem]
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIINot Available
CAS numberNot Available
WeightAverage: 368.4645
Monoisotopic: 368.219888756
Chemical FormulaC20H32O6
InChI KeySGUKUZOVHSFKPH-YNNPMVKQSA-N
InChI
InChI=1S/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
IUPAC Name
(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
SMILES
[H][C@@](CCCCC)(OO)\C=C\[C@@]1([H])[C@@]2([H])C[C@]([H])(OO2)[C@]1([H])C\C=C/CCCC(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Prostaglandin G/H synthase 2ProteinunknownNot AvailableHumanP35354 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Lornoxicam Action PathwayDrug actionSMP00700
Phenylbutazone Action PathwayDrug actionSMP00701
Salsalate Action PathwayDrug actionSMP00707
Acetaminophen Action PathwayDrug actionSMP00710
Arachidonic Acid MetabolismMetabolicSMP00075
Meloxicam Action PathwayDrug actionSMP00106
Mefenamic Acid Action PathwayDrug actionSMP00109
Magnesium salicylate Action PathwayDrug actionSMP00698
Nepafenac Action PathwayDrug actionSMP00702
Salicylate-sodium Action PathwayDrug actionSMP00708
Ketorolac Action PathwayDrug actionSMP00098
Suprofen Action PathwayDrug actionSMP00101
Valdecoxib Action PathwayDrug actionSMP00116
Diflunisal Action PathwayDrug actionSMP00289
Leukotriene C4 Synthesis DeficiencyDiseaseSMP00353
Trisalicylate-choline Action PathwayDrug actionSMP00703
Etodolac Action PathwayDrug actionSMP00084
Ibuprofen Action PathwayDrug actionSMP00086
Diclofenac Action PathwayDrug actionSMP00093
Bromfenac Action PathwayDrug actionSMP00102
Antipyrine Action PathwayDrug actionSMP00692
Antrafenine Action PathwayDrug actionSMP00693
Fenoprofen Action PathwayDrug actionSMP00696
Flurbiprofen Action PathwayDrug actionSMP00697
Lumiracoxib Action PathwayDrug actionSMP00699
Tenoxicam Action PathwayDrug actionSMP00706
Salicylic Acid Action PathwayDrug actionSMP00709
Piroxicam Action PathwayDrug actionSMP00077
Acetylsalicylic Acid Action PathwayDrug actionSMP00083
Ketoprofen Action PathwayDrug actionSMP00085
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AceclofenacThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Aceclofenac.Approved
AcetovanilloneThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Acetovanillone.Investigational
Acetylsalicylic acidThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Acetylsalicylic acid.Approved, Vet Approved
AdapaleneThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Adapalene.Approved
AnisodamineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Anisodamine.Investigational
AntipyrineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Antipyrine.Approved
ApremilastThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Apremilast.Approved, Investigational
AzapropazoneThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Azapropazone.Withdrawn
AzelastineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Azelastine.Approved
BalsalazideThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Balsalazide.Approved, Investigational
BenoxaprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Benoxaprofen.Withdrawn
Betulinic AcidThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Betulinic Acid.Investigational
BromfenacThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Bromfenac.Approved
BucillamineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Bucillamine.Investigational
CarprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Carprofen.Approved, Vet Approved, Withdrawn
CastanospermineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Castanospermine.Experimental
CelecoxibThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Celecoxib.Approved, Investigational
ChloroquineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Chloroquine.Approved, Vet Approved
ClonixinThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Clonixin.Approved
CurcuminThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Curcumin.Investigational
D-LimoneneThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with D-Limonene.Investigational
DiclofenacThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Diclofenac.Approved, Vet Approved
DiflunisalThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Diflunisal.Approved
DroxicamThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Droxicam.Approved
DuvelisibThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Duvelisib.Investigational
E6201The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with E6201.Investigational
EbselenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Ebselen.Investigational
EpirizoleThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Epirizole.Approved
EtanerceptThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Etanercept.Approved, Investigational
EtodolacThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Etodolac.Approved, Investigational, Vet Approved
EtofenamateThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Etofenamate.Approved
EtoricoxibThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Etoricoxib.Approved, Investigational
Evening primrose oilThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Evening primrose oil.Approved
exisulindThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with exisulind.Investigational
FenbufenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Fenbufen.Approved
FenoprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Fenoprofen.Approved
FloctafenineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Floctafenine.Approved, Withdrawn
FlunixinThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Flunixin.Vet Approved
FlurbiprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Flurbiprofen.Approved, Investigational
HigenamineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Higenamine.Investigational
HMPL-004The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with HMPL-004.Investigational
IbuprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Ibuprofen.Approved
IbuproxamThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Ibuproxam.Withdrawn
IcatibantThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Icatibant.Approved
IndomethacinThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Indomethacin.Approved, Investigational
IndoprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Indoprofen.Withdrawn
IsoxicamThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Isoxicam.Withdrawn
KebuzoneThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Kebuzone.Experimental
KetoprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Ketoprofen.Approved, Vet Approved
KetorolacThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Ketorolac.Approved
LeflunomideThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Leflunomide.Approved, Investigational
LisofyllineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Lisofylline.Investigational
LornoxicamThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Lornoxicam.Approved
LoxoprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Loxoprofen.Approved
LumiracoxibThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Lumiracoxib.Approved, Investigational
Magnesium salicylateThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Magnesium salicylate.Approved
MasoprocolThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Masoprocol.Approved
Meclofenamic acidThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Meclofenamic acid.Approved, Vet Approved
Mefenamic acidThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Mefenamic acid.Approved
MeloxicamThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Meloxicam.Approved, Vet Approved
MesalazineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Mesalazine.Approved
MetamizoleThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Metamizole.Withdrawn
MizoribineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Mizoribine.Investigational
Mycophenolate mofetilThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Mycophenolate mofetil.Approved, Investigational
Mycophenolic acidThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Mycophenolic acid.Approved
NabumetoneThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Nabumetone.Approved
NafamostatThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Nafamostat.Investigational
NaftifineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Naftifine.Approved
NaproxenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Naproxen.Approved, Vet Approved
NCX 4016The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with NCX 4016.Investigational
NepafenacThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Nepafenac.Approved
Niflumic AcidThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Niflumic Acid.Approved
NimesulideThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Nimesulide.Approved, Withdrawn
NitroaspirinThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Nitroaspirin.Investigational
OlopatadineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Olopatadine.Approved
OlsalazineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Olsalazine.Approved
OrgoteinThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Orgotein.Vet Approved
OxaprozinThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Oxaprozin.Approved
OxyphenbutazoneThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Oxyphenbutazone.Withdrawn
ParecoxibThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Parecoxib.Approved
PhenylbutazoneThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
PimecrolimusThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Pimecrolimus.Approved, Investigational
PirfenidoneThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Pirfenidone.Investigational
PiroxicamThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Piroxicam.Approved, Investigational
PropacetamolThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Propacetamol.Approved
PTC299The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with PTC299.Investigational
ResveratrolThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Resveratrol.Experimental, Investigational
RofecoxibThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Rofecoxib.Investigational, Withdrawn
SalicylamideThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Salicylamide.Approved
Salicylic acidThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Salicylic acid.Approved, Vet Approved
SalsalateThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Salsalate.Approved
SeratrodastThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Seratrodast.Approved, Investigational
SRT501The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with SRT501.Investigational
SulfasalazineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Sulfasalazine.Approved
SulindacThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Sulindac.Approved
SuprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Suprofen.Approved, Withdrawn
TenoxicamThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Tenoxicam.Approved
TepoxalinThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Tepoxalin.Vet Approved
TeriflunomideThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Teriflunomide.Approved
Tiaprofenic acidThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Tiaprofenic acid.Approved
TinoridineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Tinoridine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Tolfenamic Acid.Approved
TolmetinThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Tolmetin.Approved
TranilastThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Tranilast.Approved, Investigational
Trisalicylate-cholineThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Trisalicylate-choline.Approved
ValdecoxibThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Valdecoxib.Investigational, Withdrawn
ZaltoprofenThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Zaltoprofen.Approved
ZileutonThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Zileuton.Approved, Investigational, Withdrawn
ZomepiracThe therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Zomepirac.Withdrawn
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.859
Blood Brain Barrier+0.8659
Caco-2 permeable-0.5826
P-glycoprotein substrateSubstrate0.607
P-glycoprotein inhibitor INon-inhibitor0.7556
P-glycoprotein inhibitor IINon-inhibitor0.9371
Renal organic cation transporterNon-inhibitor0.8993
CYP450 2C9 substrateNon-substrate0.818
CYP450 2D6 substrateNon-substrate0.8386
CYP450 3A4 substrateNon-substrate0.5401
CYP450 1A2 substrateNon-inhibitor0.7686
CYP450 2C9 inhibitorNon-inhibitor0.8485
CYP450 2D6 inhibitorNon-inhibitor0.9119
CYP450 2C19 inhibitorNon-inhibitor0.7986
CYP450 3A4 inhibitorNon-inhibitor0.8137
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8634
Ames testNon AMES toxic0.6094
CarcinogenicityNon-carcinogens0.9048
BiodegradationNot ready biodegradable0.6704
Rat acute toxicity2.9740 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7324
hERG inhibition (predictor II)Non-inhibitor0.8095
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0264 mg/mLALOGPS
logP4.31ALOGPS
logP4.41ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity99.39 m3·mol-1ChemAxon
Polarizability40.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0119000000-06893304af83e030a39bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zmr-3369000000-b1d0f67eea930b11ae4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1003-9400000000-7fbd48d8b1a086fc44d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-4a1c6a9bb1b35fe201efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r2-2149000000-16bc14c91731cdc79586View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9162000000-ad0929ccdcab78d69a99View in MoNA
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroperoxy fatty acid
  • Heterocyclic fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Ortho-dioxane
  • Ortho-dioxolane
  • Dialkyl peroxide
  • Hydroperoxide
  • Oxacycle
  • Organoheterocyclic compound
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23