139755-82-1

Basic information

• Product Name: DESMETHYL SILDENAFIL
• Synonyms: DESMETHYL SILDENAFIL;5-[2-Ethoxy-5-(1-piperazinylsulfonyl)phenyl]-1,6-dihydro-1-methyl-3-propyl- 7H-pyrazolo[4,3-d]pyrimidin-7-one;UK 103320;Sildenafil N-DesMethyl IMpurity;Sildenafil N-DesMethyl Metabolite;Sildenafil N-desmethy impurity;5-(2-Ethoxy-5-(piperazin-1-ylsulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one;Sildenafil N-desmethyl
• CAS NO: 139755-82-1
• Molecular Formula: C21H28N6O4S
• Molecular Weight: 460.55
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Pfizer compounds
• Mol File: 139755-82-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 158-160°C
• Boiling Point: 685.7°C at 760 mmHg
• Flash Point: 368.5°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 1.17E-18mmHg at 25°C
• Refractive Index: 1.683
• Storage Temp.: -20°C Freezer
• PKA: 10.05±0.20(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: DESMETHYL SILDENAFIL(CAS DataBase Reference)
• NIST Chemistry Reference: DESMETHYL SILDENAFIL(139755-82-1)
• EPA Substance Registry System: DESMETHYL SILDENAFIL(139755-82-1)

Safety Data

• Hazardous Substances Data: 139755-82-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 139755-82-1 differently. You can refer to the following data:
1. A metabolite of Sildenafil, an orally active selective type 5 cGMP phosphodiesterase inhibitor
2. A metabolite of Sildenafil (S435001), an orally active selective type 5 cGMP phosphodiesterase inhibitor.

InChI:InChI=1/C21H28N6O4S/c1-4-6-16-18-19(26(3)25-16)21(28)24-20(23-18)15-13-14(7-8-17(15)31-5-2)32(29,30)27-11-9-22-10-12-27/h7-8,13,22H,4-6,9-12H2,1-3H3,(H,23,24,28)

Upstream product

• 139755-83-2 sildenafil 

Relevant articles and documents

Structure elucidation of phototransformation products of unapproved analogs of the erectile dysfunction drug sildenafil in artificial freshwater with UPLC-Q Exactive-MS

In this study, four unapproved analogues of Sildenafil (SDF) were photodegraded under synthetic sunlight in artificial freshwater. Homosildenafil (H-SDF), hydroxyhomo-sildenafil (HH-SDF), norneosildenafil (NR-SDF) and thiosildenafil (T-SDF) were selected because they are frequently detected as adulterants in natural herbal products. Using UPLC-Orbitrap (QExactive)-MS, six photoproducts common to H-SDF, HH-SDF and T-SDF and nine unique transformation products of different molecular weights were identified based on their high-resolution (+)ESI product ion spectra. Mass spectral analysis of deuterated H-SDF, labeled on the N-ethyl group, allowed to gain mechanistic insight into the fragmentation pathway of the substituted piperazine ring and to support the postulated photoproduct structures. The mass spectral fragmentation confirmed the stepwise destruction of the piperazine ring eventually producing a sulfonic acid derivative (C17H20N4O5S: 392.1151Da). In contrast, the photodegradation of NR-SDF, which lacks a piperazine ring in its structure, formed only two prominent photoproducts originating from N,Ndealkylation of the sulfonamide followed by hydrolysis. The current work constitutes the first study on the photodegradation of analogs of erectile dysfunction drugs and the first detection of two transformation products (m/z 449 and 489) in environmental samples.