16,16-Dimethyl-pge2

HCID 5283066CAS 39746-25-3

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Grundinformationen

Standard-SMILES: CCCCC(C)(C)[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O
InChIKey: QAOBBBBDJSWHMU-WMBBNPMCSA-N
Summenformel: C22H36O5
Durchschnittliche Molmasse: 380,5 g/mol
Monoisotopische Masse: 380,25627425

Überblick

16,16-dimethylprostaglandin E2 is a prostanoid that is prostaglandin E2 in which both of the hydrogens at position 16 have been replaced by methyl groups. A synthetic analogue of prostaglandin E2, it is a potent inhibitor of pancreatic function and growth of experimental tumors. It also protects the gastric mucosa, prevents ulceration, and promotes the healing of peptic ulcers. It has a role as an anti-ulcer drug, a gastrointestinal drug and a radiation protective agent. It is a secondary allylic alcohol, a monocarboxylic acid, a prostanoid and a member of cyclopentanones.

Namen und Bezeichner

Bevorzugter Name: 16,16-Dimethyl-pge2
IUPAC: (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4,4-dimethyloct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
Englischer Name: 16,16-Dimethyl prostaglandin E2
Summenformel: C22H36O5
Molmasse: 380.52

Namen und Synonyme

16,16-Dimethyl-pge216,16-dimethylprostaglandin E239746-25-316,16-Dimethyl-prostaglandin E2dmpge2FT1050M790V82VAC(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4,4-dimethyloct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acidFT-1050CHEBI:1410469-oxo-11R,15R-dihydroxy-16,16-dimethyl-5Z,13E-prostadienoic acid(5Z,11alpha,13E,15R)-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-5,13-dien-1-oic acid

Weitere Namen anzeigen

15r)-13eopentyl)-16-dimethyl PGE2QAOBBBBDJSWHMU-WMBBNPMCSA-N16,16-Dimethyl dinoprostoneSuppliedasayellow,viscousoil16-Dimethyl prostaglandin E216,16-DimethylprostaglandineE2

16,16 Dimethyl PGE216,16 Dimethylprostaglandin E2E2, 16,16-Dimethylprostaglandin(Z)-7-((1R,2R,3R)-3-hydroxy-2-((E,3R)-3-hydroxy-4,4-dimethyloct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acidRefChem:78926Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-16,16-dimethyl-9-oxo-, (5Z,11alpha,13E,15R)-630-974-816,16-dimethyl prostaglandin E2

Datenbank-Bezeichner

CAS: 39746-25-3
PubChem CID: 5283066
DTXSID: DTXSID201025748
ChEMBL: CHEMBL1221529
ChEBI: CHEBI:141046
UNII: M790V82VAC
EC Number: 630-974-8
Nikkaji: J71.095D

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,7
Polarare Oberfläche (TPSA): 94,8 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 12
Schwere Atome: 27
Formalladung: 0
Komplexität: 535

Experimentelle und physikochemische Eigenschaften

LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]

Physikochemische Eigenschaften

Siedepunkt: 541.271 · 541.271±50.00 °C(Press: 760.00 Torr)(predicted)
Dichte: 1.119 · 1.119±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
Flammpunkt: -13 ℃ · -13℃
storage temp.: -20 °C · -20°C
Löslichkeit: Soluble in methyl acetate
Aggregatzustand: methyl acetate solution
pka: 4.754 · 4.754±0.10(predicted)
Farbe: Colorless to light yellow
Biologische Quelle: synthetic (organic)
InChIKey: QAOBBBBDJSWHMU-WMBBNPMCSA-N
SMILES: CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

wgk: 3
ridadr: UN 1231 3/PG 2
risk_code: 11-20/21/22-36/37/38-67-66-36
hazard_code: F,Xn,Xi
safety_code: 16-26-36
Speicherklasse: 3 - Flammable liquids
Hazard Classifications: Eye Irrit. 2Flam. Liq. 2STOT SE 3

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 1 Eintrag

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.

Anwendungen · 1 Eintrag

Beschreibung16,16-dimethyl PGE2 is a competitive inhibitor of 15-hydroxy PGDH, but it is not a substrate for the enzyme. Because of its resistance to metabolism by 15-hydroxy PGDH, it has a prolonged half-life in vivo. 16,16-dimethyl PGE2 acts as an agonist on most EP receptor subtypes, and has been used experimentally to induce cervical ripening, uterine contraction, and prevent ulceration of the gastric mucosa in rats and dogs. The Kd for activation of isolated EP2 receptors is about 1 nM. 16,16-dimethyl PGE2 can be used to preserve the self-renewal properties while preventing the differentiation of hematopoietic stem cells during expansion in culture.