E 4021 Sodium Salt

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

MedKoo CAT#: 528805

CAS#: 150452-18-9 (Sodium)

Description: E 4021 is a PDE5A inhibitor potentially for the treatment of pulmonary arterial hypertension.


Price and Availability

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E 4021 sodium is 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#: 528805
Name: E 4021 Sodium Salt
CAS#: 150452-18-9 (Sodium)
Chemical Formula: C22H20ClN4NaO4
Exact Mass: 440.1251
Molecular Weight: 462.86
Elemental Analysis: C, 57.09; H, 4.36; Cl, 7.66; N, 12.10; Na, 4.97; O, 13.83


Related CAS #: 150452-19-0 (free acid)   150452-18-9 (sodium)    

Synonym: E-4021; E4021; E 4021; E 4021 Sodium.

IUPAC/Chemical Name: sodium 1-(4-((benzo[d][1,3]dioxol-5-ylmethyl)amino)-6-chloroquinazolin-2-yl)piperidine-4-carboxylate

InChi Key: LDYABEHPDDRNAF-UHFFFAOYSA-M

InChi Code: InChI=1S/C22H21ClN4O4.Na/c23-15-2-3-17-16(10-15)20(24-11-13-1-4-18-19(9-13)31-12-30-18)26-22(25-17)27-7-5-14(6-8-27)21(28)29;/h1-4,9-10,14H,5-8,11-12H2,(H,28,29)(H,24,25,26);/q;+1/p-1

SMILES Code: O=C(C1CCN(C2=NC(NCC3=CC=C(OCO4)C4=C3)=C5C=C(Cl)C=CC5=N2)CC1)[O-].[Na+]


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:
>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).

Harmonized System Code:
293490


References

1: Yamaguchi K, Oka M, Nishino M, Hanasato N, Kira S, Fukuchi Y. [E 4021, a cGMP phosphodiesterase inhibitor, is a selective pulmonary vasodilator in chronically hypoxic pulmonary hypertensive rats]. Nihon Kokyuki Gakkai Zasshi. 1998 Jan;36(1):23-8. Japanese. PubMed PMID: 9611972.

2: Oka M. Phosphodiesterase 5 inhibition restores impaired ACh relaxation in hypertensive conduit pulmonary arteries. Am J Physiol Lung Cell Mol Physiol. 2001 Mar;280(3):L432-5. PubMed PMID: 11159025.

3: Hayakawa H, Hirata Y, Kakoki M, Suzuki Y, Nishimatsu H, Nagata D, Suzuki E, Kikuchi K, Nagano T, Kangawa K, Matsuo H, Sugimoto T, Omata M. Role of nitric oxide-cGMP pathway in adrenomedullin-induced vasodilation in the rat. Hypertension. 1999 Feb;33(2):689-93. PubMed PMID: 10024329.

4: Nishimatsu H, Hirata Y, Shindo T, Kurihara H, Suzuki E, Sata M, Satonaka H, Takeda R, Nagata D, Kakoki M, Hayakawa H, Kangawa K, Matsuo H, Kitamura T, Nagai R. Endothelial responses of the aorta from adrenomedullin transgenic mice and knockout mice. Hypertens Res. 2003 Feb;26 Suppl:S79-84. PubMed PMID: 12630815.

5: Nishimatsu H, Hirata Y, Hayakawa H, Nagata D, Satonaka H, Suzuki E, Horie S, Takeuchi T, Ohta N, Homma Y, Minowada S, Nagai R, Kawabe K, Kitamura T. Effects of intracavernous administration of adrenomedullin on erectile function in rats. Peptides. 2001 Nov;22(11):1913-8. PubMed PMID: 11754981.

6: Matsumori A, Ono K, Sato Y, Shioi T, Nose Y, Sasayama S. Differential modulation of cytokine production by drugs: implications for therapy in heart failure. J Mol Cell Cardiol. 1996 Dec;28(12):2491-9. PubMed PMID: 9004165.

7: Kühn R, Uckert S, Stief CG, Truss MC, Lietz B, Bischoff E, Schramm M, Jonas U. Relaxation of human ureteral smooth muscle in vitro by modulation of cyclic nucleotide-dependent pathways. Urol Res. 2000 Apr;28(2):110-5. PubMed PMID: 10850633.

8: Dukarm RC, Steinhorn RH, Russell JA, Lakshminrusimha S, Swartz D, Cummings JJ. Selective type 5 phosphodiesterase inhibition alters pulmonary hemodynamics and lung liquid production in near-term fetal lambs. J Appl Physiol (1985). 2005 Dec;99(6):2331-6. PubMed PMID: 16123210; PubMed Central PMCID: PMC2746949.

9: Kakinuma Y, Miyauchi T. [Endothelin receptor antagonist, phosphodiesterase inhibitor, thromboxane inhibitor]. Nihon Rinsho. 2001 Jun;59(6):1139-44. Review. Japanese. PubMed PMID: 11411126.

10: Thompson WJ, Piazza GA, Li H, Liu L, Fetter J, Zhu B, Sperl G, Ahnen D, Pamukcu R. Exisulind induction of apoptosis involves guanosine 3',5'-cyclic monophosphate phosphodiesterase inhibition, protein kinase G activation, and attenuated beta-catenin. Cancer Res. 2000 Jul 1;60(13):3338-42. PubMed PMID: 10910034.

11: Marx D, Tassabehji M, Heer S, Hüttenbrink KB, Szelenyi I. Modulation of TNF and GM-CSF release from dispersed human nasal polyp cells and human whole blood by inhibitors of different PDE isoenzymes and glucocorticoids. Pulm Pharmacol Ther. 2002;15(1):7-15. Review. PubMed PMID: 11969359.

12: Zhou L, Thompson WJ, Potter DE. Functional identification of phosphodiesterase activity in human trabecular meshwork cells. J Ocul Pharmacol Ther. 2000 Aug;16(4):317-22. PubMed PMID: 10977127.

13: Fujiwara M, Andersson K, Persson K. Nitric oxide-induced cGMP accumulation in the mouse bladder is not related to smooth muscle relaxation. Eur J Pharmacol. 2000 Aug 4;401(2):241-50. PubMed PMID: 10924933.

14: Watanabe N, Adachi H, Takase Y, Ozaki H, Matsukura M, Miyazaki K, Ishibashi K, Ishihara H, Kodama K, Nishino M, Kakiki M, Kabasawa Y. 4-(3-Chloro-4-methoxybenzyl)aminophthalazines: synthesis and inhibitory activity toward phosphodiesterase 5. J Med Chem. 2000 Jun 29;43(13):2523-9. PubMed PMID: 10891111.

15: Dukarm RC, Russell JA, Morin FC 3rd, Perry BJ, Steinhorn RH. The cGMP-specific phosphodiesterase inhibitor E4021 dilates the pulmonary circulation. Am J Respir Crit Care Med. 1999 Sep;160(3):858-65. PubMed PMID: 10471609.

16: Ohnishi M, Oka M, Muramatsu M, Sato K, Kira S, Fukuchi Y. E4021, a selective phosphodiesterase 5 inhibitor, potentiates the vasodilator effect of inhaled nitric oxide in isolated perfused rat lungs. J Cardiovasc Pharmacol. 1999 Apr;33(4):619-24. PubMed PMID: 10218733.

17: D'Amours MR, Granovsky AE, Artemyev NO, Cote RH. Potency and mechanism of action of E4021, a type 5 phosphodiesterase isozyme-selective inhibitor, on the photoreceptor phosphodiesterase depend on the state of activation of the enzyme. Mol Pharmacol. 1999 Mar;55(3):508-14. PubMed PMID: 10051534.

18: Kakoki M, Hirata Y, Hayakawa H, Nishimatsu H, Suzuki Y, Nagata D, Suzuki E, Kikuchi K, Nagano T, Omata M. Effects of vasodilatory beta-adrenoceptor antagonists on endothelium-derived nitric oxide release in rat kidney. Hypertension. 1999 Jan;33(1 Pt 2):467-71. PubMed PMID: 9931149.

19: Watanabe N, Kabasawa Y, Takase Y, Matsukura M, Miyazaki K, Ishihara H, Kodama K, Adachi H. 4-Benzylamino-1-chloro-6-substituted phthalazines: synthesis and inhibitory activity toward phosphodiesterase 5. J Med Chem. 1998 Aug 27;41(18):3367-72. PubMed PMID: 9719589.

20: Adachi H, Nishino M. Coronary artery diameter increase induced by a phosphodiesterase 5 inhibitor, E4021, in conscious pigs. Jpn J Pharmacol. 1998 May;77(1):99-102. PubMed PMID: 9639065.