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

MedKoo CAT#: 598715

CAS#: 224785-90-4

Description: Vardenafil, also known as BAY 38-9456, is a PDE5 inhibitor used for treating erectile dysfunction. Vardenafil's indications and contra-indications are the same as with other PDE5 inhibitors; it is closely related in function to sildenafil citrate (Viagra) and tadalafil (Cialis). The difference between the vardenafil molecule and sildenafil citrate is a nitrogen atom's position and the change of sildenafil's piperazine ring methyl group to an ethyl group. Tadalafil is structurally different from both sildenafil and vardenafil. Vardenafil's relatively short effective time is comparable to but somewhat longer than sildenafil's.


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Vardenafilis not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 598715
Name: Vardenafil
CAS#: 224785-90-4
Chemical Formula: C23H35N6O4S
Exact Mass: 491.244
Molecular Weight: 491.63
Elemental Analysis: C, 56.19; H, 7.18; N, 17.09; O, 13.02; S, 6.52


Related CAS #: 224789-15-5 (2HCl)   224785-90-4 (free)   330808-88-3 (HCl trihydrate)  

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

IUPAC/Chemical Name: 2-(2-ethoxy-5-((4-ethylpiperazin-1-yl)sulfonyl)phenyl)-5-methyl-7-propyl-3,5,6,7-tetrahydro-4H-5l4-imidazo[1,5-a][1,3,5]triazin-4-one

InChi Key: UWRWYSQUBZFWPU-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H35N6O4S/c1-5-10-27-16-21-24-22(25-23(30)29(21,4)17-27)19-15-18(8-9-20(19)33-7-3)34(31,32)28-13-11-26(6-2)12-14-28/h8-9,15-16H,5-7,10-14,17H2,1-4H3,(H,24,25,30)

SMILES Code: O=C(NC(C1=CC(S(=O)(N2CCN(CC)CC2)=O)=CC=C1OCC)=N3)[N]4(C)C3=CN(CCC)C4


Technical Data

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:
>3 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).

Harmonized System Code:
2934.99.03.00


References

1: Sandqvist A, Henrohn D, Egeröd H, Hedeland M, Wernroth L, Bondesson U, Schneede J, Wikström G. Acute vasodilator response to vardenafil and clinical outcome in patients with pulmonary hypertension. Eur J Clin Pharmacol. 2015 Oct;71(10):1165-73. doi: 10.1007/s00228-015-1914-z. Epub 2015 Aug 5. PubMed PMID: 26242227.

2: El-Awady MS, Said E. Vardenafil ameliorates immunologic- and non-immunologic-induced allergic reactions. Can J Physiol Pharmacol. 2014 Mar;92(3):175-80. doi: 10.1139/cjpp-2013-0316. Epub 2013 Nov 26. PubMed PMID: 24593781.

3: Ashour AE, Rahman AF, Kassem MG. Vardenafil dihydrochloride. Profiles Drug Subst Excip Relat Methodol. 2014;39:515-44. doi: 10.1016/B978-0-12-800173-8.00009-X. Review. PubMed PMID: 24794912.

4: Minareci E, Sadan G. An evaluation of vardenafil as a calcium channel blocker in pulmonary artery in rats. Indian J Pharmacol. 2014 Mar-Apr;46(2):185-90. doi: 10.4103/0253-7613.129315. PubMed PMID: 24741191; PubMed Central PMCID: PMC3987188.

5: Aziret M, Irkorucu O, Reyhan E, Erdem H, Das K, Ozkara S, Surmelioglu A, Sozen S, Bali I, Cetinkunar S, Deger KC. The effects of vardenafil and pentoxifylline administration in an animal model of ischemic colitis. Clinics (Sao Paulo). 2014 Nov;69(11):763-9. doi: 10.6061/clinics/2014(11)10. PubMed PMID: 25518035; PubMed Central PMCID: PMC4255201.

6: Gamidov SI, Iremashvili VV, Popova AIu. [Modernity in the treatment of erectile dysfunction: Levitra (vardenafil) in the form of oral dispersible tablet]. Urologiia. 2013 May-Jun;(3):102-4, 106. Review. Russian. PubMed PMID: 23987060.

7: Shin YS, Lee SW, Park K, Chung WS, Kim SW, Hyun JS, Moon DG, Yang SK, Ryu JK, Yang DY, Moon KH, Min KS, Park JK. Effect of levitra on sustenance of erection (EROS): an open-label, prospective, multicenter, single-arm study to investigate erection duration measured by stopwatch with flexible dose vardenafil administered for 8 weeks in subjects with erectile dysfunction. Int J Impot Res. 2015 May-Jun;27(3):95-102. doi: 10.1038/ijir.2014.39. Epub 2014 Dec 4. PubMed PMID: 25471318.

8: Herbert LP, Becker-Krail DB, Cory WC. Persistent phototransformation products of vardenafil (Levitra®) and sildenafil (Viagra®). Chemosphere. 2015 Sep;134:557-62. doi: 10.1016/j.chemosphere.2014.12.011. Epub 2015 Jan 10. PubMed PMID: 25585868.

9: Fahmy UA. Nanoethosomal transdermal delivery of vardenafil for treatment of erectile dysfunction: optimization, characterization, and in vivo evaluation. Drug Des Devel Ther. 2015 Nov 18;9:6129-37. doi: 10.2147/DDDT.S94615. eCollection 2015. PubMed PMID: 26604700; PubMed Central PMCID: PMC4655965.

10: Korneev IA. [Levitra (oral dispersible tablet)--an innovative drug for the treatment of patients with erectile dysfunction]. Urologiia. 2013 Mar-Apr;(2):106-8, 110-1. Review. Russian. PubMed PMID: 23789375.

11: Yurtcu E, Togrul C, Ozyer S, Uzunlar O, Karatas YH, Seckin KD, Caydere M, Hucumenoglu S, Cicek N. Dose dependent protective effects of vardenafil on ischemia-reperfusion injury with biochemical and histopathologic evaluation in rat ovary. J Pediatr Surg. 2015 Jul;50(7):1205-9. doi: 10.1016/j.jpedsurg.2014.12.013. Epub 2015 Jan 14. PubMed PMID: 25783344.

12: Hartmann U, Hanisch JU, Mattern A. The real-life perception of efficacy, attitude, satisfaction and safety of vardenafil therapy (REPEAT): a prospective, non-interventional, observational study. Aging Male. 2014 Jun;17(2):117-24. doi: 10.3109/13685538.2013.873783. Epub 2014 Jan 7. PubMed PMID: 24397688.

13: Sousa RC, Moreira Neto AA, Capelozzi VL, Ab'Saber AM, Rodrigues OR. Effects of vardenafil on the kidney of Wistar rats submitted to acute ischemia and reperfusion. Acta Cir Bras. 2015 May;30(5):339-44. doi: 10.1590/S0102-865020150050000005. PubMed PMID: 26016933.

14: Fan YF, Zhang R, Jiang X, Wen L, Wu DC, Liu D, Yuan P, Wang YL, Jing ZC. The phosphodiesterase-5 inhibitor vardenafil reduces oxidative stress while reversing pulmonary arterial hypertension. Cardiovasc Res. 2013 Aug 1;99(3):395-403. doi: 10.1093/cvr/cvt109. Epub 2013 May 6. PubMed PMID: 23650288.

15: Sanford M. Vardenafil orodispersible tablet. Drugs. 2012 Jan 1;72(1):87-98. doi: 10.2165/11208270-000000000-00000. Review. PubMed PMID: 22191797.

16: Kyriazis I, Kallidonis P, Georgiopoulos I, Al-Aown A, Sakellaropoulos G, Stolzenburg JU, Liatsikos E. In vitro evaluation of ureteral contractility: a comparative assessment of human, porcine and sheep ureteral response to vardenafil. Urol Int. 2015;94(2):234-9. doi: 10.1159/000358601. Epub 2014 Sep 5. PubMed PMID: 25196240.

17: Reneerkens OA, Sambeth A, Ramaekers JG, Steinbusch HW, Blokland A, Prickaerts J. The effects of the phosphodiesterase type 5 inhibitor vardenafil on cognitive performance in healthy adults: a behavioral-electroencephalography study. J Psychopharmacol. 2013 Jul;27(7):600-8. doi: 10.1177/0269881113477747. Epub 2013 Feb 20. PubMed PMID: 23427190.

18: Kaya B, Çerkez C, Işılgan SE, Göktürk H, Yığman Z, Serel S, Can B, Ergün H. Comparison of the effects of systemic sildenafil, tadalafil, and vardenafil treatments on skin flap survival in rats. J Plast Surg Hand Surg. 2015;49(6):358-62. doi: 10.3109/2000656X.2015.1041024. Epub 2015 Jun 24. PubMed PMID: 26107909.

19: Sandqvist AM, Henrohn D, Schneede J, Hedeland M, Egeröd HC, Bondesson UG, Wikström BG. High inter-individual variability of vardenafil pharmacokinetics in patients with pulmonary hypertension. Eur J Clin Pharmacol. 2013 Feb;69(2):197-207. doi: 10.1007/s00228-012-1323-5. Epub 2012 Jun 26. PubMed PMID: 22732766.

20: Kim E, Seftel A, Goldfischer E, Baygani S, Burns P. Comparative efficacy of tadalafil once daily in men with erectile dysfunction who demonstrated previous partial responses to as-needed sildenafil, tadalafil, or vardenafil. Curr Med Res Opin. 2015 Feb;31(2):379-89. doi: 10.1185/03007995.2014.989317. Epub 2014 Dec 2. PubMed PMID: 25455432.