N-Desmethyl Sildenafil - ≥99% , CAS No.139755-82-1

CAS: 139755-82-1 Cat. No.: N352320 Molecular Weight: 460.55 EC Number: 641-939-1

GRADE & PURITY ≥99%

Synonyms

BCP34330 | D70714 | MFCD00908398 | UK-103320 | FT-0666208 | AKOS027322024 | SCHEMBL19518061 | 5-[2-Ethoxy-5-(piperazine-1-sulfonyl)-phenyl]-1-methyl-3-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one | J-007308 | Q27282788 | HY-117605 | BDBM50287543 | 5-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

N-Desmethyl Sildenafil is a metabolite of Sildenafil . Sildenafil is a selective inhibitor of the type 5 cGMP phosphodiesterase (PDE5 inhibitor) which catalyzes the hydrolysis of 3',5'-cyclic guanosine monophosphate (cGMP). As a PDE5 inhibitor, Sildenafil has been reported to enhance neuro-, synapto- and angiogenesis in rat models of stroke and also is reported to be a mild vasodilator. Sildenafil has also been shown to prevent indomethacin-induced small intestinal ulceration formation through an NO/cGMP- dependent mechanism.

Specifications

Synonyms

BCP34330 | D70714 | MFCD00908398 | UK-103320 | FT-0666208 | AKOS027322024 | SCHEMBL19518061 | 5-[2-Ethoxy-5-(piperazine-1-sulfonyl)-phenyl]-1-methyl-3-propyl-1, 6-dihydro-pyrazolo[4, 3-d]pyrimidin-7-one | J-007308 | Q27282788 | HY-117605 | BDBM50287543 | 5-

Specifications & Purity

≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥99%

Product Properties

• pKa: pKa: 10.05 (Predicted), pKa: 7.75 (Predicted)

Names and Identifiers

• Canonical Smiles: CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCNCC4)OCC)C
• IUPAC Name: 5-(2-ethoxy-5-piperazin-1-ylsulfonylphenyl)-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one
• InChIKey: UZTKBZXHEOVDRL-UHFFFAOYSA-N
• INCHI: 1S/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)
• Isomeric SMILES: CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCNCC4)OCC)C
• Molecular Weight: 460.55
• Reaxy-Rn: 7672894
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7672894&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzenesulfonamides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzenesulfonamides
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzenesulfonamides
• Alternative Parents: Benzenesulfonyl compounds Pyrazolopyrimidines Phenoxy compounds Phenol ethers Alkyl aryl ethers Pyrimidones Organosulfonamides Piperazines Vinylogous amides Sulfonyls Heteroaromatic compounds Pyrazoles Azacyclic compounds Dialkylamines Hydrocarbon derivatives Organic oxides Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Benzenesulfonamide - Pyrazolopyrimidine - Benzenesulfonyl group - Phenoxy compound - Phenol ether - Alkyl aryl ether - Pyrimidone - Pyrimidine - 1,4-diazinane - Organosulfonic acid amide - Piperazine - Sulfonyl - Azole - Organosulfonic acid or derivatives - Vinylogous amide - Pyrazole - Organic sulfonic acid or derivatives - Heteroaromatic compound - Secondary aliphatic amine - Ether - Azacycle - Organoheterocyclic compound - Secondary amine - Organooxygen compound - Organonitrogen compound - Amine - Organic oxide - Organic nitrogen compound - Organosulfur compound - Hydrocarbon derivative - Organic oxygen compound - Organopnictogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PDE5A Tclin cGMP-specific 3',5'-cyclic phosphodiesterase (2 Activities)

Discover Target: PDE5A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

Discover Target: PDE5A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3 (1749 Activities)

Discover Target: PDE3A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE1A Tclin Phosphodiesterase 1 (671 Activities)

Discover Target: PDE1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in methanol, chloroform, and dichloromethane.
• Refractive Index: n20D1.68
• Boil Point(°C): 685.7° C at 760 mmHg
• Melt Point(°C): 158-160° C
• Molecular Weight: 460.600 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 460.189 Da
• Monoisotopic Mass: 460.189 Da
• Topological Polar Surface Area: 126.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 810.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Tian Wei, Yongyi Zhang, Jianxin Huang, Jinyi Yang, Yuanxin Tian, Yudong Shen.  (2024)  Rapid detection of multiple sildenafil and tadalafil adulterants in dietary supplements by dual-labeled probe time-resolved fluorescence immunochromatography assay.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2024.103905]