Sildenafil Citrate - Moligand™, ≥98%(HPLC) , Phosphodiesterase 5A inhibitor, CAS No.171599-83-0, Phosphodiesterase 5A inhibitor

CAS: 171599-83-0 Cat. No.: S129663 Molecular Weight: 666.70 EC Number: 638-824-3

GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

SILDENAFIL CITRATE [MART.] | Wan Ai Ke | 5-(2-ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 2-hydroxypropane-1,2,3-tricarboxylate | AKOS015856298 | SILDENAFIL CITRATE (USP MONOGRAPH) | 5-{2-etho

Storage

Argon charged,Room temperature

Shipped In

Normal

Specifications

Synonyms

SILDENAFIL CITRATE [MART.] | Wan Ai Ke | 5-(2-ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4, 3-d]pyrimidin-7(6H)-one 2-hydroxypropane-1, 2, 3-tricarboxylate | AKOS015856298 | SILDENAFIL CITRATE (USP MONOGRAPH) | 5-{2-etho

Specifications & Purity

Moligand™, ≥98%(HPLC)

Biochemical and Physiological Mechanisms

Sildenafil, Citrate is a citrate form of Sildenafil. Sildenafil is a selective inhibitor of PDE5 (type 5 cGMP phosphodiesterase) which catalyzes the hydrolysis of 3', 5'-cyclic guanosine monophosphate (cGMP). As a PDE5 inhibitor, Sildenafil has been report

Storage

Argon charged, Room temperature

Shipped In

Normal

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Phosphodiesterase 5A inhibitor

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 488202863
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488202863
• Canonical Smiles: CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• IUPAC Name: 5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one;2-hydroxypropane-1,2,3-tricarboxylic acid
• InChIKey: DEIYFTQMQPDXOT-UHFFFAOYSA-N
• INCHI: 1S/C22H30N6O4S.C6H8O7/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28;7-3(8)1-6(13,5(11)12)2-4(9)10/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
• Isomeric SMILES: CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• WGK Germany: 3
• RTECS: TL4284390
• Molecular Weight: 666.70
• Reaxy-Rn: 9035645

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: Tricarboxylic acids and derivatives Pyrazolopyrimidines Benzenesulfonyl compounds Phenoxy compounds Phenol ethers Pyrimidones Alkyl aryl ethers N-methylpiperazines Organosulfonamides Alpha hydroxy acids and derivatives Tertiary alcohols Sulfonyls Pyrazoles Heteroaromatic compounds Trialkylamines Lactams Azacyclic compounds Carboxylic acids Hydrocarbon derivatives Organopnictogen compounds Carbonyl compounds Organic oxides
• Molecular Framework: Not available
• Substituents: Benzenesulfonamide - Pyrazolopyrimidine - Benzenesulfonyl group - Tricarboxylic acid or derivatives - Phenoxy compound - Phenol ether - Alkyl aryl ether - Pyrimidone - N-methylpiperazine - N-alkylpiperazine - Alpha-hydroxy acid - 1,4-diazinane - Hydroxy acid - Piperazine - Pyrimidine - Organosulfonic acid amide - Sulfonyl - Azole - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Heteroaromatic compound - Tertiary alcohol - Pyrazole - Tertiary aliphatic amine - Tertiary amine - Lactam - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Carboxylic acid - Ether - Amine - Organic nitrogen compound - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organosulfur 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: citrate salt

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 (3 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

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

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

CA3 Tclin Carbonic anhydrase III (753 Activities)

Discover Target: CA3

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

CA6 Tclin Carbonic anhydrase VI (993 Activities)

Discover Target: CA6

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

CA1 Tclin Carbonic anhydrase I (13240 Activities)

Discover Target: CA1

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

CA5B Tclin Carbonic anhydrase VB (957 Activities)

Discover Target: CA5B

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

CA5A Tclin Carbonic anhydrase VA (1168 Activities)

Discover Target: CA5A

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

CA14 Tclin Carbonic anhydrase XIV (1305 Activities)

Discover Target: CA14

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

CA12 Tclin Carbonic anhydrase XII (6231 Activities)

Discover Target: CA12

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

CA9 Tclin Carbonic anhydrase IX (8255 Activities)

Discover Target: CA9

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

Homo sapiens (32628 Activities)

Explore this target

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

ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

Discover Target: ABCC2

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

ABCB11 Tchem Bile salt export pump (2311 Activities)

Discover Target: ABCB11

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

ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)

Discover Target: ABCC3

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

ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

Discover Target: ABCC4

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

Associated Targets(non-human)

Ca7 Carbonic anhydrase VII (3 Activities)

Discover Target: Ca7

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

PDE6C Phosphodiesterase 6C (1 Activities)

Discover Target: PDE6C

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

Ca13 Carbonic anhydrase XIII (322 Activities)

Discover Target: Ca13

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

CA4 Carbonic anhydrase IV (1713 Activities)

Discover Target: CA4

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

Sus scrofa (849 Activities)

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

Rattus norvegicus (775804 Activities)

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Serum (58 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Insoluble in ether
• Sensitivity: Moisture sensitive
• Melt Point(°C): 187-192℃
• Molecular Weight: 666.700 g/mol
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 12
• Exact Mass: 666.232 Da
• Monoisotopic Mass: 666.232 Da
• Topological Polar Surface Area: 250.000 Ų
• Heavy Atom Count: 46
• Formal Charge: 0
• Complexity: 1070.000
• 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: 2

XLogP3

References

1. Ma Yufeng, Zhang Fengsen, Zhong Yijing, Huang Yongchun, Yixizhuoma , Jia Qiangqiang, Zhang Shoude.  (2023)  A label-free LC/MS-based enzymatic activity assay for the detection of PDE5A inhibitors.  Frontiers in Chemistry,      [PMID:36860644] [10.3389/fchem.2023.1097027]

2. Shihua Yu, Zhigang Liu, Weixian Wang, Li Jin, Weiqing Xu, Yuqing Wu.  (2017)  Disperse magnetic solid phase microextraction and surface enhanced Raman scattering (Dis-MSPME-SERS) for the rapid detection of trace illegally chemicals.  TALANTA,      [PMID:29136854] [10.1016/j.talanta.2017.09.054]