Vardenafil hydrochloride trihydrate
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MedKoo CAT#: 326826

CAS#: 330808-88-3

Description: Vardenafil, also known as BAY 38-9456, is a PDE5 inhibitor used for treating erectile dysfunction. Vardenafil (VAR) is synthetic, highly selective, and potent inhibitor of phosphodiesterase-5 which competitively inhibits cyclic guanosine monophosphate (cGMP) hydrolysis and thus increases cGMP levels. It is clinically approved for treatment of erectile dysfunction in men, including diabetic and postprostatectomy patients.


Chemical Structure

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Vardenafil hydrochloride trihydrate
CAS# 330808-88-3

Theoretical Analysis

MedKoo Cat#: 326826
Name: Vardenafil hydrochloride trihydrate
CAS#: 330808-88-3
Chemical Formula: C23H40Cl2N6O7S
Exact Mass: 0.00
Molecular Weight: 615.568
Elemental Analysis: C, 44.88; H, 6.55; Cl, 11.52; N, 13.65; O, 18.19; S, 5.21

Price and Availability

Size Price Availability Quantity
250mg USD 110 Ready to ship
500mg USD 200 Ready to ship
1g USD 350 Ready to ship
2g USD 650 Ready to ship
5g USD 950
10g USD 1450 2 Weeks
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Related CAS #: 330808-88-3 (HCl trihydrate)   224789-15-5 (2HCl)   224785-90-4 (free)  

Synonym: BAY 38-9456; BAY-38-9456; BAY38-9456; Vardenafil hydrochloride trihydrate; Vardenafil HCl; Levitra; Staxyn; Vivanza

IUPAC/Chemical Name: 2-(2-ethoxy-5-((4-ethylpiperazin-1-yl)sulfonyl)phenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one dihydrochloride trihydrate

InChi Key: NEAUGLIJDBPHAY-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H32N6O4S.2ClH.3H2O/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28;;;;;/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30);2*1H;3*1H2

SMILES Code: O=C1N=C(C2=CC(S(=O)(N3CCN(CC)CC3)=O)=CC=C2OCC)NN4C1=C(C)N=C4CCC.[H]Cl.[H]Cl.[H]O[H].[H]O[H].[H]O[H]

Appearance: White to light yellow solid powder

Purity: >96% (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: Related CAS# CAS#224789-15-5 (Vardenafil dihydrochloride); CAS#224785-90-4 (Vardenafil free base). CAS#330808-88-3 (Vardenafil hydrochloride trihydrate)

Product Data:
Safety Data Sheet (SDS):
Biological target: Vardenafil HCl Trihydrate (BAY38-9456) is a new type PDE inhibitor with IC50 of 0.7 and 180 nM for PDE5 and PDE1, respectively.
In vitro activity: This study determined the protective role of vardenafil on H2O2-induced endothelial cell injury in cultured human umbilical vein endothelial cells (HUVECs). Vardenafil decreased the number of TUNEL-positive cells, increased the Bcl2/Bax ratio, and ameliorated the numbers of BrdU-positive cells in H2O2-treated HUVECs. The bone morphogenetic protein receptor (BMPR)/p-Smad/MSX2 pathway was enhanced in response to H2O2, and vardenafil treatment could normalize this pathway. To determine whether the BMP pathway is involved, the BMP pathway was blocked using dorsomorphin, which abolished the protective effects of vardenafil. It was found that vardenafil improved the H2O2-induced downregulation of BMP-binding endothelial regulator protein (BMPER), which possibly intersects with the BMP pathway in the regulation of endothelial cell injury in response to oxidative stress. Vardenafil can attenuate H2O2-induced endothelial cell injury in HUVECs. Vardenafil decreases apoptosis through an improved Bcl-2/Bax ratio and increases cell proliferation. Vardenafil also protects against endothelial cell injury through ameliorating the intracellular oxidative stress level and BMPER expression. In conclusion, the protective role of vardenafil on H2O2-induced endothelial cell injury is mediated through BMPR/p-Smad/MSX2 in HUVECs. Reference: Cardiovasc Drugs Ther. 2020 Feb;34(1):41-52. https://pubmed.ncbi.nlm.nih.gov/32096002/
In vivo activity: This study tested the hypothesis that vardenafil, a common drug used for improving erectile dysfunction and able to partially normalize transepithelial chloride transport in cystic fibrosis (CF), modulates CF lung inflammation. Inflammatory markers in lungs of F508del-CF and wild-type mice were monitored in response to lipopolysaccharide from Pseudomonas aeruginosa (LPS). The effect of pretreatment with vardenafil (0.14 mg/kg) was evaluated. Under LPS-induced inflammation, vardenafil reduced responses in LDH activity by 55% in wild-type mice and by 35% in F508del-CF mice. The immunomodulatory effect of vardenafil was confirmed on responses of pro-inflammatory TNF-α, IL-6 and IL-1β (Fig. 2D-F). Indeed, both F508del-CF and wild-type mice treated with vardenafil showed a lessened (1.5 to 3 times lower) production of cytokines as compared to the corresponding non-vardenafil pretreated LPS challenged group. Under influence of vardenafil, significant reduction (by 66%) in CCL-2 response was observed in the LPS-challenged CF group, but not in the corresponding wild-type group. Additionally, IL-1β response was significantly attenuated by vardenafil in CF only. Altogether, these data indicate that vardenafil has an anti-inflammatory effect that seems to be more pronounced in F508del-CF mice, in particular on macrophage infiltration, CCL-2 and IL-1β responses. Reference: J Cyst Fibros. 2012 Jul;11(4):266-73. https://pubmed.ncbi.nlm.nih.gov/22503062/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 51.0 82.85
Ethanol 50.0 81.23
H2O 10.0 16.25

Preparing Stock Solutions

The following data is based on the product molecular weight 615.57 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. Mao F, Han B, Jiang D, Zhang X, Pang T, Fan Y. The Phosphodiesterase-5 Inhibitor Vardenafil Improves the Activation of BMP Signaling in Response to Hydrogen Peroxide. Cardiovasc Drugs Ther. 2020 Feb;34(1):41-52. doi: 10.1007/s10557-020-06939-5. PMID: 32096002. 2. Dhooghe B, Bouzin C, Mottais A, Hermans E, Delion M, Panin N, Noel S, Leal T. Vardenafil increases intracellular accumulation of the most prevalent mutant cystic fibrosis transmembrane conductance regulator (CTFR) in human bronchial epithelial cells. Biol Open. 2020 Aug 25;9(8):bio053116. doi: 10.1242/bio.053116. PMID: 32747447; PMCID: PMC7473651. 3. Lubamba B, Huaux F, Lebacq J, Marbaix E, Dhooghe B, Panin N, Wallemacq P, Leal T. Immunomodulatory activity of vardenafil on induced lung inflammation in cystic fibrosis mice. J Cyst Fibros. 2012 Jul;11(4):266-73. doi: 10.1016/j.jcf.2012.03.003. Epub 2012 Apr 12. PMID: 22503062. 4. Ahmed N, Bakhashwain NF, Alsehemi AF, El-Agamy DS. Hepatoprotective role of vardenafil against experimentally induced hepatitis in mice. J Biochem Mol Toxicol. 2017 Mar;31(3). doi: 10.1002/jbt.21867. Epub 2016 Oct 20. PMID: 27762466.
In vitro protocol: 1. Mao F, Han B, Jiang D, Zhang X, Pang T, Fan Y. The Phosphodiesterase-5 Inhibitor Vardenafil Improves the Activation of BMP Signaling in Response to Hydrogen Peroxide. Cardiovasc Drugs Ther. 2020 Feb;34(1):41-52. doi: 10.1007/s10557-020-06939-5. PMID: 32096002. 2. Dhooghe B, Bouzin C, Mottais A, Hermans E, Delion M, Panin N, Noel S, Leal T. Vardenafil increases intracellular accumulation of the most prevalent mutant cystic fibrosis transmembrane conductance regulator (CTFR) in human bronchial epithelial cells. Biol Open. 2020 Aug 25;9(8):bio053116. doi: 10.1242/bio.053116. PMID: 32747447; PMCID: PMC7473651.
In vivo protocol: 1. Lubamba B, Huaux F, Lebacq J, Marbaix E, Dhooghe B, Panin N, Wallemacq P, Leal T. Immunomodulatory activity of vardenafil on induced lung inflammation in cystic fibrosis mice. J Cyst Fibros. 2012 Jul;11(4):266-73. doi: 10.1016/j.jcf.2012.03.003. Epub 2012 Apr 12. PMID: 22503062. 2. Ahmed N, Bakhashwain NF, Alsehemi AF, El-Agamy DS. Hepatoprotective role of vardenafil against experimentally induced hepatitis in mice. J Biochem Mol Toxicol. 2017 Mar;31(3). doi: 10.1002/jbt.21867. Epub 2016 Oct 20. PMID: 27762466.

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8: Rice KR, Dean RC. Vardenafil: efficacy, tolerability and future directions. Expert Opin Drug Metab Toxicol. 2009 May;5(5):553-62. doi: 10.1517/17425250902884108 . Review. PubMed PMID: 19416089.

9: Mirone V, Fusco F, Rossi A, Sicuteri R, Montorsi F. Tadalafil and vardenafil vs sildenafil: a review of patient-preference studies. BJU Int. 2009 May;103(9):1212-7. doi: 10.1111/j.1464-410X.2008.08267.x. Epub 2008 Dec 8. Review. Erratum in: BJU Int. 2011 Apr;107(7):1166. PubMed PMID: 19154480.

10: Eardley I, Lee JC, Guay AT. Global experiences with vardenafil in men with erectile dysfunction and underlying conditions. Int J Clin Pract. 2008 Oct;62(10):1594-603. doi: 10.1111/j.1742-1241.2008.01852.x. Review. PubMed PMID: 18822030.

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15: Montorsi F, Salonia A, Briganti A, Barbieri L, Zanni G, Suardi N, Cestari A, Montorsi P, Rigatti P. Vardenafil for the treatment of erectile dysfunction: a critical review of the literature based on personal clinical experience. Eur Urol. 2005 May;47(5):612-21. Epub 2005 Jan 26. Review. PubMed PMID: 15826752.

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19: Markou S, Perimenis P, Gyftopoulos K, Athanasopoulos A, Barbalias G. Vardenafil (Levitra) for erectile dysfunction: a systematic review and meta-analysis of clinical trial reports. Int J Impot Res. 2004 Dec;16(6):470-8. Review. PubMed PMID: 15229625.

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