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MedKoo Cat#: 575870 | Name: Gisadenafil besylate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Gisadenafil besylate is a phosphodiesterase 5 (PDE5) inhibitor.

Chemical Structure

Gisadenafil besylate
Gisadenafil besylate
CAS#334827-98-4 (besylate)

Theoretical Analysis

MedKoo Cat#: 575870

Name: Gisadenafil besylate

CAS#: 334827-98-4 (besylate)

Chemical Formula: C29H39N7O8S2

Exact Mass: 0.0000

Molecular Weight: 677.79

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 350.00 2 Weeks
10mg USD 600.00 2 Weeks
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Related CAS #
334826-98-1 (free base) 334827-98-4 (besylate)
Synonym
Gisadenafil besylate; UK 369003 besylate; UK369003 besylate; UK-369003 besylate; UK 369003-26; UK369003-26; UK-369003-26
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
View handling instruction
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/
Solvent mg/mL mM
Solubility
DMSO 72.6 107.10
Water 5.9 8.69
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.
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).