1323942-09-1

Basic information

• Product Name: (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-benzoyl-4b,12-difluoro-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-azapentaleno[2,1-a]phenanthren-2-one
• Synonyms: (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-benzoyl-4b,12-difluoro-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-azapentaleno[2,1-a]phenanthren-2-one
• CAS NO: 1323942-09-1
• Molecular Weight: 525.593
• Mol File: 1323942-09-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-benzoyl-4b,12-difluoro-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-azapentaleno[2,1-a]phenanthren-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-benzoyl-4b,12-difluoro-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-azapentaleno[2,1-a]phenanthren-2-one(1323942-09-1)
• EPA Substance Registry System: (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-benzoyl-4b,12-difluoro-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-azapentaleno[2,1-a]phenanthren-2-one(1323942-09-1)

Safety Data

• Hazardous Substances Data: 1323942-09-1(Hazardous Substances Data)

Upstream product

• 1323942-08-0 acetic acid 2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-benzoyl-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthrene-6b-yl)-2-oxo-ethyl ester 
• 2326-26-3 acetic acid 2-((6S,8S,9R,10S,11S,13S,14S)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15-decahydro-3H-cyclopenta[a]phenanthrene-17-yl)-2-oxo-ethyl ester 
• 1323941-32-7 acetic acid 2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4-aH-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester hydrochloride 
• 1323941-31-6 (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-6b-(2-acetoxy-acetyl)-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,6b,7,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthrene-8-carboxylic acid vinyl ester 
• 1323941-15-6 acetic acid 2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-benzyl-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester 

Relevant articles and documents

Novel Pyrrolidine Derivatives of Budesonide as Long Acting Inhaled Corticosteroids for the Treatment of Pulmonary Inflammatory Diseases

Inhaled corticosteroids (ICSs) represent the first line therapy for the treatment of asthma and are also extensively utilized in chronic obstructive pulmonary disease. Our goal was to develop a new ICS with a basic group, which can allow solid state feature modulation, achieving at the same time high local anti-inflammatory effect and low systemic exposure. Through a rational drug design approach, a new series of pyrrolidine derivatives of budesonide was identified. Within the series, several compounds showed nanomolar binding affinity (Ki) with GR that mostly correlated with the effect in inducing GR nuclear translocation in CHO cells and anti-inflammatory effects in macrophagic cell lines. Binding and functional cell-based assays allowed identifying compound 17 as a potent ICS agonist with a PK profile showing an adequate lung retention and low systemic exposure in vivo. Finally, compound 17 proved to be more potent than budesonide in a rat model of acute pulmonary inflammation.