(5Z,13E,15R)-11α,15-ジヒドロキシ-16,16-ジメチル-9-オキソ-5,13-プロスタジエン-1-酸

16,16-Dimethyl-pge2

HCID 5283066

基本情報

CAS: 39746-25-3
標準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
分子式: C22H36O5
平均分子量: 380.5 g/mol
単同位体質量: 380.25627425

概要

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E2 is a prostanoid that is prostaglandin E2 in which both of the hydrogens at position 16 have been replaced by methyl groups.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.

名称と識別子

優先名称: 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
現地名: (5Z,13E,15R)-11α,15-ジヒドロキシ-16,16-ジメチル-9-オキソ-5,13-プロスタジエン-1-酸
英語名: 16,16-Dimethyl prostaglandin E2
分子式: C22H36O5
分子量: 380.52

名称と別名

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

名称をさらに表示

(5Z,13E,15R)-11α,15-ジヒドロキシ-16,16-ジメチル-9-オキソプロスタ-5,13-ジエン-1-酸(5Z,13E,15R)-11α,15-ジヒドロキシ-16,16-ジメチル-9-オキソ-5,13-プロスタジエン-1-酸16,16-ジメチルジノプロストン(5Z,11α,13E,15S)-11,15-ジヒドロキシ-16,16-ジメチル-9-オキソプロスタ-5,13-ジエン-1-酸16,16-ジメチルプロスタグランジンE216,16-ジメチルPGE2(5Z,11R,13E,15S)-11,15-ジヒドロキシ-16,16-ジメチル-9-オキソプロスタ-5,13-ジエン-1-酸(5Z)-7-[(1R,2R,3R)-3-ヒドロキシ-2-[(1E,3S)-3-ヒドロキシ-4,4-ジメチルオクタ-1-エン-1-イル]-5-オキソシクロペンチル]ヘプタ-5-エン酸(5Z)-7-[(1R,2R,3R)-3-ヒドロキシ-2-[(1E,3R)-3-ヒドロキシ-4,4-ジメチルオクタ-1-エン-1-イル]-5-オキソシクロペンチル]ヘプタ-5-エン酸16,16-ジメチル-PGE215r)-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

データベース識別子

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

物性

構造計算による物性

XLogP: 3.7
極性表面積: 94.8 Å²
水素結合供与体数: 3
水素結合受容体数: 5
回転可能結合数: 12
重原子数: 27
形式電荷: 0
複雑度: 535

実験および物理化学的性質

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

物理化学的性質

沸点: 541.271 · 541.271±50.00 °C(Press: 760.00 Torr)(predicted)
比重(密度): 1.119 · 1.119±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
闪点: -13 ℃ · -13℃
貯蔵温度: -20 °C · -20°C
溶解性: Soluble in methyl acetate
外見: 酢酸メチル溶液
酸解離定数(Pka): 4.754 · 4.754±0.10(predicted)
色: Colorless to light yellow
由来生物: 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

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全データ

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
Hazard Classifications: Eye Irrit. 2Flam. Liq. 2STOT SE 3
ストレージクラス: 3 - Flammable liquids

化学と産業

薬理情報

MeSH Pharmacological Classification · 1 件

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.

応用分野 · 1 件

説明16,16-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.

上流・下流製品情報

上流原料

Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-16,16-dimethyl-9-oxo-, methyl ester, (5Z,11α,13E,15R)- (9CI)

サプライヤー22 社

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]

陕西缔都化学有限公司029-029-81123119 17391733320 · [email protected]

Aladdin Scientific[email protected]

武汉易泰科技有限公司上海分公司18930552037 · [email protected]

化合物ノート

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