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Merck
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Principaux documents

B6309

Sigma-Aldrich

(R)-Butaprost

≥98% (HPLC)

Synonyme(s) :

(1R,2R,3R)-3-Hydroxy-2-[(1E,4R)-4-hydroxy-4-(1-propylcyclobutyl)-1-butenyl]-5-oxo-cyclopentaneheptanoic acid methyl ester

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About This Item

Formule empirique (notation de Hill):
C24H40O5
Numéro CAS:
Poids moléculaire :
408.57
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Niveau de qualité

Essai

≥98% (HPLC)

Forme

oil

Couleur

light yellow

Solubilité

DMSO: freely soluble
ethanol: freely soluble

Auteur

Bayer

Température de stockage

−20°C

Chaîne SMILES 

CCCC1(CCC1)[C@H](O)C\C=C\[C@H]2[C@H](O)CC(=O)[C@@H]2CCCCCCC(=O)OC

InChI

1S/C24H40O5/c1-3-14-24(15-9-16-24)22(27)12-8-11-19-18(20(25)17-21(19)26)10-6-4-5-7-13-23(28)29-2/h8,11,18-19,21-22,26-27H,3-7,9-10,12-17H2,1-2H3/b11-8+/t18-,19-,21-,22-/m1/s1

Clé InChI

XRISENIKJUKIHD-LHQZMKCDSA-N

Application

(R)-Butaprost has been used as a prostanoid receptor (EP)-specific agonist to study its effects on protein kinase A (PKA) regulatory subunits in MCF7 cells. It may be used as EP2 agonist in Madin-Darby canine kidney and mouse cortical collecting duct (mpkCCD14) cells. It may also be used as EP2 agonist in human fetal lung fibroblasts (HFL-1) cells to test its effect on vascular endothelial growth factor (VEGF) production.

Actions biochimiques/physiologiques

Butaprost comprises hydroxy-cyclopentanone ring and ω-chain. It aids protection in events of glutamate based N-methyl-D-aspartate receptor toxicity. Butaprost inhibits conjunctival fibrosis and lowers the intraocular pressure in post glaucoma filtration surgery. It also promotes wound healing by reducing the subconjunctival scarring Tenon′s fibroblasts. Butaprost plays a protective role in pulmonary fibrosis and aids protection against the aggregated amyloid β (Aβ) peptides in Alzheimer′s disease.
(R)-Butaprost is a selective EP2 prostanoid receptor agonist.

Caractéristiques et avantages

This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


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Consulter la Bibliothèque de documents

Anti-scarring effects of butaprost on human subconjunctival Tenon's fibroblasts
Shin JH, et al.
International journal of ophthalmology, 10(7), 1028-1028 (2017)
cAMP-dependent activation of the Rac guanine exchange factor P-REX1 by type I protein kinase A (PKA) regulatory subunits
Adame-Garcia SR, et al.
Test, 294(7), 2232-2246 (2019)
Prostanoid receptor EP2 as a therapeutic target: Miniperspective
Ganesh T
Journal of Medicinal Chemistry, 57(11), 4454-4465 (2014)
Mudit Vaid et al.
American journal of cancer research, 5(11), 3325-3338 (2016-01-26)
Melanoma is a highly aggressive form of skin cancer and a leading cause of death from skin diseases mainly due to its propensity to metastasis. Due to metastatic tendency, melanoma is often associated with activation of Wnt/β-catenin signaling mechanism. Blocking
Yunyun Su et al.
Cancer immunology, immunotherapy : CII, 60(1), 111-122 (2010-10-21)
Previous studies document that PGE(2) and adenosine suppress production of inflammatory cytokines. The present study demonstrates for the first time that (1) PGE(2) and 2-chloroadenosine (CADO; a stable analog of adenosine) directly inhibit the cytolytic function of human tumor-infiltrating lymphocytes

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