Basic information
- CAS
39746-25-3- 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- Molecular formula
- C22H36O5
- Average molar mass
- 380.5 g/mol
- Monoisotopic mass
- 380.25627425
Overview
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E2 is a prostanoid that is prostaglandin E2 in which both of the hydrogens at position 16 have been replaced by methyl groups.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.
Names & identifiers
- Preferred 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
- English name
- 16,16-Dimethyl prostaglandin E2
- Molecular formula
- C22H36O5
- Molecular weight
- 380.52
Names & synonyms
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
Show more names
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
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 12
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 535
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
Physicochemical properties
- Boiling point
- 541.271 · 541.271±50.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.119 · 1.119±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- Flash point
- -13 ℃ · -13℃
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in methyl acetate
- form
- methyl acetate solution
- pka
- 4.754 · 4.754±0.10(predicted)
- color
- Colorless to light yellow
- biological source
- 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
- FDA UNII
- 790 V82VAC · M790V82VAC
Safety & regulation
GHS classification
GHS Classification
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.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- ridadr
- UN 1231 3/PG 2
- risk_code
- 11-20/21/22-36/37/38-67-66-36
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xn,Xi
- safety_code
- 16-26-36
- Storage Class
- 3 - Flammable liquids
- target organs
- Central nervous system
- Hazard statements
- H225-H319-H336
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 2STOT SE 3
- Precautionary statements
- P210-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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.
Applications
Description16,16-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.
Upstream & downstream products
Upstream raw materials
Suppliers22 total
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
Related reactions
2 records
Compound notes
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