Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Prostaglandin G2
- DrugBank Accession Number
- DB03866
- Background
A 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]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Prostaglandin G2 (DB03866)
- Weight
- Average: 368.4645
Monoisotopic: 368.219888756 - Chemical Formula
- C20H32O6
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism AProstaglandin G/H synthase 2 inhibitorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAceclofenac The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Acemetacin. Acetylsalicylic acid The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Acetylsalicylic acid. Alclofenac The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Alclofenac. Aminophenazone The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Aminophenazone. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Eicosanoids
- Direct Parent
- Prostaglandins and related compounds
- Alternative Parents
- Long-chain fatty acids / Hydroperoxy fatty acids / Heterocyclic fatty acids / Unsaturated fatty acids / 1,2-dioxanes / Allylic hydroperoxides / 1,2-dioxolanes / Dialkyl peroxides / Peroxols / Oxacyclic compounds show 5 more
- Substituents
- Aliphatic heteropolycyclic compound / Alkyl hydroperoxide / Allylic hydroperoxide / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkyl peroxide / Fatty acid / Heterocyclic fatty acid / Hydrocarbon derivative show 14 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- prostaglandins G (CHEBI:27647) / Prostaglandins (C05956) / Prostaglandins (LMFA03010009)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- AZ87DUD2Y8
- CAS number
- Not Available
- InChI Key
- SGUKUZOVHSFKPH-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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0003235
- KEGG Compound
- C05956
- PubChem Compound
- 5280883
- PubChem Substance
- 46509030
- ChemSpider
- 4444406
- ChEBI
- 27647
- ZINC
- ZINC000008220097
- PDBe Ligand
- PGX
- Wikipedia
- Prostaglandin_G2
- PDB Entries
- 1ddx
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 0.0264 mg/mL ALOGPS logP 4.31 ALOGPS logP 4.41 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 4.36 Chemaxon pKa (Strongest Basic) -4.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 85.22 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 99.39 m3·mol-1 Chemaxon Polarizability 40.85 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.859 Blood Brain Barrier + 0.8659 Caco-2 permeable - 0.5826 P-glycoprotein substrate Substrate 0.607 P-glycoprotein inhibitor I Non-inhibitor 0.7556 P-glycoprotein inhibitor II Non-inhibitor 0.9371 Renal organic cation transporter Non-inhibitor 0.8993 CYP450 2C9 substrate Non-substrate 0.818 CYP450 2D6 substrate Non-substrate 0.8386 CYP450 3A4 substrate Non-substrate 0.5401 CYP450 1A2 substrate Non-inhibitor 0.7686 CYP450 2C9 inhibitor Non-inhibitor 0.8485 CYP450 2D6 inhibitor Non-inhibitor 0.9119 CYP450 2C19 inhibitor Non-inhibitor 0.7986 CYP450 3A4 inhibitor Non-inhibitor 0.8137 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8634 Ames test Non AMES toxic 0.6094 Carcinogenicity Non-carcinogens 0.9048 Biodegradation Not ready biodegradable 0.6704 Rat acute toxicity 2.9740 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7324 hERG inhibition (predictor II) Non-inhibitor 0.8095
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-006x-5293000000-4f6f219630c974fad684 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0gb9-0009000000-fa8aaf9b3d16b82204b4 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0009000000-3bf4906569364c75a5a8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0019-0019000000-cd8b0cdbce3257cf755a Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014r-2379000000-d3aa6159664b84197d60 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-040s-2196000000-b229797b3d5183b95b81 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000f-9830000000-d349a2c46ad04a620fce Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 223.2530617 predictedDarkChem Lite v0.1.0 [M-H]- 198.73991 predictedDeepCCS 1.0 (2019) [M+H]+ 222.9631617 predictedDarkChem Lite v0.1.0 [M+H]+ 200.61024 predictedDeepCCS 1.0 (2019) [M+Na]+ 224.0817617 predictedDarkChem Lite v0.1.0 [M+Na]+ 206.21674 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dual cyclooxygenase and peroxidase in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response (PubMed:11939906, PubMed:16373578, PubMed:19540099, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). Similarly catalyzes successive cyclooxygenation and peroxidation of dihomo-gamma-linoleate (DGLA, C20:3(n-6)) and eicosapentaenoate (EPA, C20:5(n-3)) to corresponding PGH1 and PGH3, the precursors of 1- and 3-series prostaglandins (PubMed:11939906, PubMed:19540099). In an alternative pathway of prostanoid biosynthesis, converts 2-arachidonoyl lysophopholipids to prostanoid lysophopholipids, which are then hydrolyzed by intracellular phospholipases to release free prostanoids (PubMed:27642067). Metabolizes 2-arachidonoyl glycerol yielding the glyceryl ester of PGH2, a process that can contribute to pain response (PubMed:22942274). Generates lipid mediators from n-3 and n-6 polyunsaturated fatty acids (PUFAs) via a lipoxygenase-type mechanism. Oxygenates PUFAs to hydroperoxy compounds and then reduces them to corresponding alcohols (PubMed:11034610, PubMed:11192938, PubMed:9048568, PubMed:9261177). Plays a role in the generation of resolution phase interaction products (resolvins) during both sterile and infectious inflammation (PubMed:12391014). Metabolizes docosahexaenoate (DHA, C22:6(n-3)) to 17R-HDHA, a precursor of the D-series resolvins (RvDs) (PubMed:12391014). As a component of the biosynthetic pathway of E-series resolvins (RvEs), converts eicosapentaenoate (EPA, C20:5(n-3)) primarily to 18S-HEPE that is further metabolized by ALOX5 and LTA4H to generate 18S-RvE1 and 18S-RvE2 (PubMed:21206090). In vascular endothelial cells, converts docosapentaenoate (DPA, C22:5(n-3)) to 13R-HDPA, a precursor for 13-series resolvins (RvTs) shown to activate macrophage phagocytosis during bacterial infection (PubMed:26236990). In activated leukocytes, contributes to oxygenation of hydroxyeicosatetraenoates (HETE) to diHETES (5,15-diHETE and 5,11-diHETE) (PubMed:22068350, PubMed:26282205). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity). During neuroinflammation, plays a role in neuronal secretion of specialized preresolving mediators (SPMs) 15R-lipoxin A4 that regulates phagocytic microglia (By similarity)
- Specific Function
- enzyme binding
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22