Phosphoramidon Disodium

• CAT Number: R010298
• CAS Number: 164204-38-0
• Molecular Formula: C23H32N3Na2O10P
• Molecular Weight: 587.47
• Purity: ≥95%
• Synonyms: disodium;(2S)-3-(1H-indol-3-yl)-2-[[(2S)-4-methyl-2-[[oxido-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]pentanoyl]amino]propanoate
• InChI: InChI=1S/C23H34N3O10P.2Na/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15;;/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34);;/q;2*+1/p-2/t12-,16-,17-,18-,19+,20+,23-;;/m0../s1
• InChIKey: OQKHVXFOYFBMDJ-ODIUWQMJSA-L
• SMILES: CC1C(C(C(C(O1)OP(=O)(NC(CC(C)C)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)[O-])[O-])O)O)O.[Na+].[Na+]

Phosphoramidon Disodium, a microbial metabolite, is a specific metalloprotease thermolysin inhibitor with an IC50 of 0.4 μg/mL. Phosphoramidon Disodium also inhibits endothelin-converting enzyme (ECE), neutral endopeptidase (NEP), and angiotensin-converting enzyme (ACE) with IC50 values of 3.5, 0.034, and 78 μM, respectively[1][2][3].
Phosphoramidon (1-500 μM; 30 min) inhibits ET-converting enzyme (ECE) activity in a dose-dependent manner in solubilized rabbit lung membranes[5].
Phosphoramidon (0.25 mg/kg per min; i.v.) suppresses the hypertensive effect of big endothelin-1 in rats[4].
Phosphoramidon (1-30 mg/kg; i.v.; once) blocks the pressor activity of porcine big endothelin-1-(1-39) in rats[5].

Reference

[1]. Umezawa S, , et al. A new microbial metabolite phosphoramidon (isolation and structure). Tetrahedron Letters, 1972, 13(1): 97-100.

[2]. Suda H, et al. A thermolysin inhibitor produced by actinomycetes: phosphoramidon. The Journal of antibiotics, 1973, 26(10): 621-623.

[3]. Kukkola PJ, et al. Differential structure-activity relationships of phosphoramidon analogues for inhibition of three metalloproteases: endothelin-converting enzyme, neutral endopeptidase, and angiotensin-converting enzyme.J CardiovascPharmacol. 1995;26Suppl 3:S65-8.
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[4]. Matsumura Y, et al. Phosphoramidon, a metalloproteinase inhibitor, suppresses the hypertensive effect of big endothelin-1. Eur J Pharmacol. 1990 Aug 21;185(1):103-6.
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[5]. McMahon EG, et al. Phosphoramidon blocks the pressor activity of porcine big endothelin-1-(1-39) in vivo and conversion of big endothelin-1-(1-39) to endothelin-1-(1-21) in vitro. Proc Natl Acad Sci U S A. 1991 Feb 1;88(3):703-7.
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