P2E

(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxo-cyclopentyl]hept-5-enoic acid

Created: 2009-06-04
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count57
Chiral Atom Count4
Bond Count57
Aromatic Bond Count0
2D diagram of P2E
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Chemical Component Summary

Name(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxo-cyclopentyl]hept-5-enoic acid
SynonymsProstaglandin E2
Systematic Name (OpenEye OEToolkits)(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxo-cyclopentyl]hept-5-enoic acid
FormulaC20 H32 O5
Molecular Weight352.465
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C1CC(O)C(/C=C/C(O)CCCCC)C1C\C=C/CCCC(=O)O
SMILESCACTVS3.341CCCCC[CH](O)C=C[CH]1[CH](O)CC(=O)[CH]1CC=CCCCC(O)=O
SMILESOpenEye OEToolkits1.5.0CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
Canonical SMILESCACTVS3.341 CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 CCCCC[C@@H](\C=C\[C@H]1[C@@H](CC(=O)[C@@H]1C\C=C/CCCC(=O)O)O)O
InChIInChI1.03 InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
InChIKeyInChI1.03 XEYBRNLFEZDVAW-ARSRFYASSA-N

Drug Info: DrugBank

DrugBank IDDB00917 
NameDinoprostone
Groups approved
DescriptionDinoprostone is a naturally occurring prostaglandin E2 (PGE2). It has important effects in labour. It also stimulates osteoblasts to release factors which stimualtes bone resorption by osteoclasts. As a prescription drug it is used as a vaginal suppository, to prepare the cervix for labour and to induce labour.
Synonyms
  • Dinoproston
  • Dinoprostone
  • (E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid
  • Dinoprostona
  • Dinoprostonum
Brand Names
  • Prepidil Gel
  • Prepidil
  • Dinoprostone
  • Prostin E2 Vaginal Gel
  • Prostin E2
IndicationFor the termination of pregnancy during the second trimester (from the 12th through the 20th gestational week as calculated from the first day of the last normal menstrual period), as well as for evacuation of the uterine contents in the management of missed abortion or intrauterine fetal death up to 28 weeks of gestational age as calculated from the first day of the last normal menstrual period. Also used in the management of nonmetastatic gestational trophoblastic disease (benign hydatidiform mole). Other indications include improving the cervical inducibility (cervical "ripening") in pregnant women at or near term with a medical or obstetrical need for labor induction, and the management of postpartum hemorrhage.
Categories
  • Autacoids
  • Biological Factors
  • Dinoprostone, antagonists & inhibitors
  • Eicosanoids
  • Fatty Acids
ATC-CodeG02AD02
CAS number363-24-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin E2 receptor EP2 subtypeMGNASNDSQSEDCETRQWLPPGESPAISSVMFSAGVLGNLIALALLARRW...unknownagonist
Prostaglandin E2 receptor EP1 subtypeMSPCGPLNLSLAGEATTCAAPWVPNTSAVPPSGASPALPIFSMTLGAVSN...unknownagonist
Prostaglandin E2 receptor EP3 subtypeMKETRGYGGDAPFCTRLNHSYTGMWAPERSAEARGNLTRPPGSGEDCGSV...unknownagonist
Prostaglandin E2 receptor EP4 subtypeMSTPGVNSSASLSPDRLNSPVTIPAVMFIFGVVGNLVAIVVLCKSRKEQK...unknownagonist
Prostaglandin D2 receptor 2MSANATLKPLCPILEQMSRLQSHSNTSIRYIDHAAVLLHGLASLLGLVEN...unknownagonist
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL548
PubChem 5280360
ChEMBL CHEMBL548
ChEBI CHEBI:15551