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363-24-6 molecular structure
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(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid

ChemBase ID: 793
Molecular Formular: C20H32O5
Molecular Mass: 352.46508
Monoisotopic Mass: 352.22497412
SMILES and InChIs

SMILES:
O[C@H]1[C@@H]([C@H](C(=O)C1)C/C=C\CCCC(=O)O)/C=C/[C@@H](O)CCCCC
Canonical SMILES:
CCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O
InChI:
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
InChIKey:
XEYBRNLFEZDVAW-ARSRFYASSA-N

Cite this record

CBID:793 http://www.chembase.cn/molecule-793.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
IUPAC Traditional name
dinoprostone
Brand Name
Cervidil
Prepidil
Prostarmon E
Prostin E
Prostin E2
Propess
Synonyms
(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid
Dinoprostone
Prostaglandin E2
Dinoprostone Prostaglandin E2
PGE2
Prostaglandin E2
Dinoprostone
(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic Acid
7-[3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic Acid
(-)-Prostaglandin E2
(15S)-Prostaglandin E2
Cervidil
Cerviprime
Cerviprost
Minprostin E2
Prepidil
Primiprost
Prostin E2
l-PGE2
Prostaglandin E2
CAS Number
363-24-6
EC Number
206-656-6
MDL Number
MFCD00077861
Beilstein Number
4709356
PubChem SID
24898683
160964256
24898100
24898775
46505549
PubChem CID
5280360

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.3033595  H Acceptors
H Donor LogD (pH = 5.5) 2.0038702 
LogD (pH = 7.4) 0.2647247  Log P 3.22527 
Molar Refractivity 99.4351 cm3 Polarizability 38.188305 Å3
Polar Surface Area 94.83 Å2 Rotatable Bonds 12 
Lipinski's Rule of Five true 
Log P 3.31  LOG S -3.9 
Solubility (Water) 4.40e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
58.1 mg/L expand Show data source
Chloroform expand Show data source
Ethanol expand Show data source
ethanol: soluble1 mg/mL expand Show data source
Methanol expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
65-66°C expand Show data source
Hydrophobicity(logP)
2.8 expand Show data source
Storage Condition
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
UK8000000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
60-61-22 expand Show data source
Safety Statements
53-22-26-36/37/39-45 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H302-H360 expand Show data source
GHS Precautionary statements
P201-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... PTGER1(5731), PTGER2(5732), PTGER3(5733), PTGER4(5734), PTGIR(5739)mouse ... Ptger1(19216), Ptger2(19217), Ptger3(19218), Ptger4(19219) expand Show data source
Purity
≥93% (HPLC) expand Show data source
≥98% (TLC) expand Show data source
Potency
0.25-100 ng/mL expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
suitable for cell culture expand Show data source
Biological Source
synthetic expand Show data source
Sterility
γ-irradiated expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00917 external link
Item Information
Drug Groups approved
Description Dinoprostone 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.
Indication For 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.
Pharmacology Dinoprostone is equivalent to prostaglandin E2 (PGE2). It stimulates labor and delivery by stimulating the uterine, and thus terminates pregnancy. Dinoprostone is also capable of stimulating the smooth muscle of the gastrointestinal tract of man. This activity may be responsible for the vomiting and/or diarrhea that is not uncommon when dinoprostone is used to terminate pregnancy.
Toxicity Oral, mouse: LD50 = 750 mg/kg; Oral, rat: LD50 = 500 mg/kg.
Affected Organisms
Humans and other mammals
Biotransformation Rapid metabolism of dinoprostone occurs primarily in the local tissues; any systemic absorption of the medication is cleared mainly in the maternal lungs and, secondarily, at sites such as the liver and kidneys.
Absorption Absorbed at a rate of 0.3 mg per hour over 12 hours while the vaginal system is in place.
Half Life Less than 5 minutes.
Protein Binding 73%, to albumin
Elimination The major route of elimination of the products of PGE2 metabolism is the kidneys.
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - P0409 external link
Physical form
powder -20 °C; stock-frozen in working aliquots, avoid repeated freeze/thaw
Biochem/physiol Actions
Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.The effect of PGE2 on the immune system is mixed. It inhibits T cell activation in vitro, suggesting it is an immunosuppressant. However, in vivo, it appears to effect expansion of the Th17 subset and differentiation of the Th1 subset of T helper cells, marking it as an immunoactivator.1
Prostaglandin E2 is a signaling molecule produced by activated platelets. The release of PGE2 by activated platelets is part of a mechanism by which activated platelets utilize adjacent erythrocytes to help in clot formation. This product was shown to lower the filterability of human erythrocytes by approximately 30% at a concentration of 10-10sup M and also caused a reduction in mean cell volume by about 10%. The cause of cell shrinkage was the induction of a PGE2- stimulated K+ efflux pathway leading to rapid loss of cellular K+ ions. This loss was shown to be Ca2+dependent. PGE2 has been shown to stimulate the production of interleukin-6 (IL-6) by neonatal mouse parietal bones. After 6 hours in culture, cells stimulated with 10-8sup M PGE2 produced significantly more IL-6 than controls. The pyrogenic activity of PGE2 was not inhibited by dexamethasone, unlike prostaglandin F2α.Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.
Sigma Aldrich - P4172 external link
Biochem/physiol Actions
Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.The effect of PGE2 on the immune system is mixed. It inhibits T cell activation in vitro, suggesting it is an immunosuppressant. However, in vivo, it appears to effect expansion of the Th17 subset and differentiation of the Th1 subset of T helper cells, marking it as an immunoactivator.1
Sigma Aldrich - P5640 external link
Biochem/physiol Actions
Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.The effect of PGE2 on the immune system is mixed. It inhibits T cell activation in vitro, suggesting it is an immunosuppressant. However, in vivo, it appears to effect expansion of the Th17 subset and differentiation of the Th1 subset of T helper cells, marking it as an immunoactivator.1
Sigma Aldrich - P6532 external link
Application
For use in cell culture applications for the study of prostaglandin regulated cell signaling and gene regulation.
Physical form
powder -20 °C; stock-frozen in working aliquots, avoid repeated freeze/thaw
Biochem/physiol Actions
Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.The effect of PGE2 on the immune system is mixed. It inhibits T cell activation in vitro, suggesting it is an immunosuppressant. However, in vivo, it appears to effect expansion of the Th17 subset and differentiation of the Th1 subset of T helper cells, marking it as an immunoactivator.1
Toronto Research Chemicals - P838610 external link
The most common and most biologically potent of mammalian prostaglandins. Isolated from sheep prostate. Oxytocic; abortifacient.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Van Dorp, D.A., et al.: Biochem. Biopphys. Acta, 90, 204 (1964)
  • • Hamberg, M., et al.: J. Biol. Chem., 246, 6713 (1964)
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PATENTS

PATENTS

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INTERNET

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