Gisadenafil besylate
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MedKoo CAT#: 575870

CAS#: 334827-98-4

Description: Gisadenafil besylate is a phosphodiesterase 5 (PDE5) inhibitor.

Chemical Structure

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Gisadenafil besylate
CAS# 334827-98-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 575870
Name: Gisadenafil besylate
CAS#: 334827-98-4
Chemical Formula: C29H39N7O8S2
Exact Mass: 0.00
Molecular Weight: 677.792
Elemental Analysis: C, 51.39; H, 5.80; N, 14.47; O, 18.88; S, 9.46

Price and Availability

Size Price Availability Quantity
5mg USD 240 2 Weeks
10mg USD 455 2 Weeks
25mg USD 825 2 Weeks
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Synonym: Gisadenafil besylate; UK 369003 besylate; UK369003 besylate; UK-369003 besylate

IUPAC/Chemical Name: 5-[2-ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]-3-pyridinyl]-3-ethyl-2,6-dihydro-2-(2-methoxyethyl)-7H-pyrazolo[4,3-d]pyrimidin-7-one, monobenzenesulfonate

InChi Key: STFRDYSZKVPPQF-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H33N7O5S.C6H6O3S/c1-5-18-19-20(27-30(18)12-13-34-4)22(31)26-21(25-19)17-14-16(15-24-23(17)35-7-3)36(32,33)29-10-8-28(6-2)9-11-29;7-10(8,9)6-4-2-1-3-5-6/h14-15H,5-13H2,1-4H3,(H,25,26,31);1-5H,(H,7,8,9)

SMILES Code: CCC1=C(C2=NN1CCOC)NC(C3=C(OCC)N=CC(S(=O)(N4CCN(CC4)CC)=O)=C3)=NC2=O.OS(C5=CC=CC=C5)(=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Gisadenafil besylate (UK 369003-26) is a specific, orally active phosphodiesterase 5 (PDE5) inhibitor with an IC50 of 3.6 nM and prevents degradation of cyclic guanosine monophosphate (cGMP).
In vitro activity: This was directly tested with recombinant PDE5A and PDE1A overexpressed in COS-7 cells (Figure 4A). Using this approach, the study found the IC50 of gisadenafil for PDE5A to be 3.6 nM, similar to its reported IC50 of 1.23 nM. In contrast, this study found the IC50 of gisadenafil for PDE1A to be 9.1 μM, an approximately 2500-fold difference in specificity. Reference: J Neuroinflammation. 2012 Nov 20;9:253. https://pubmed.ncbi.nlm.nih.gov/23167821/
In vivo activity: Longer (5 minute) exposures to CO2 were also performed in animals treated with gisadenafil to determine if these changes to CVR were reproducible under extended hypercapnia. Tat-tg animals treated with gisadenafil showed marked improvement (P = 0.003, nonparametric permutation test) in CVR (42.9% peak increase in CBF) compared to non-treated Tat-tg animals (21.5% peak increase in CBF) (Figure 4C). Reference: J Neuroinflammation. 2012 Nov 20;9:253. https://pubmed.ncbi.nlm.nih.gov/23167821/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 72.6 107.10
Water 5.9 8.69

Preparing Stock Solutions

The following data is based on the product molecular weight 677.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Silva J, Polesskaya O, Knight W, Zheng JT, Granger M, Lopez T, Ontiveros F, Feng C, Yan C, Kasischke KA, Dewhurst S. Transient hypercapnia reveals an underlying cerebrovascular pathology in a murine model for HIV-1 associated neuroinflammation: role of NO-cGMP signaling and normalization by inhibition of cyclic nucleotide phosphodiesterase-5. J Neuroinflammation. 2012 Nov 20;9:253. doi: 10.1186/1742-2094-9-253. PMID: 23167821; PMCID: PMC3526511.
In vitro protocol: 1. Silva J, Polesskaya O, Knight W, Zheng JT, Granger M, Lopez T, Ontiveros F, Feng C, Yan C, Kasischke KA, Dewhurst S. Transient hypercapnia reveals an underlying cerebrovascular pathology in a murine model for HIV-1 associated neuroinflammation: role of NO-cGMP signaling and normalization by inhibition of cyclic nucleotide phosphodiesterase-5. J Neuroinflammation. 2012 Nov 20;9:253. doi: 10.1186/1742-2094-9-253. PMID: 23167821; PMCID: PMC3526511.
In vivo protocol: 1. Silva J, Polesskaya O, Knight W, Zheng JT, Granger M, Lopez T, Ontiveros F, Feng C, Yan C, Kasischke KA, Dewhurst S. Transient hypercapnia reveals an underlying cerebrovascular pathology in a murine model for HIV-1 associated neuroinflammation: role of NO-cGMP signaling and normalization by inhibition of cyclic nucleotide phosphodiesterase-5. J Neuroinflammation. 2012 Nov 20;9:253. doi: 10.1186/1742-2094-9-253. PMID: 23167821; PMCID: PMC3526511.

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1. Rawson, D.J., Ballard, S., Barber, C., et al. The discovery of UK-369003, a novel PDE5 inhibitor with the potential for oral bioavailability and dose-proportional pharmacokinetics. Bioorg. Med. Chem. 20(1), 498-509 (2012).

2. Silva, J., Polesskaya, O., Knight, W., et al. Transient hypercapnia reveals an underlying cerebrovascular pathology in a murine model for HIV-1 associated neuroinflammation: role of NO-cGMP signaling and normalization by inhibition of cyclic nucleotide phosphodiesterase-5. J. Neuroinflammation 9, 253 (2012).