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MedKoo Cat#: 561755 | Name: Phosphoramidon disodium
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Description:

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

Phosphoramidon disodium is a neutral endopeptidase (neprilysin) inhibitor. It blocks degradation of amyloid β peptides and endothelin converting enzyme (ECE).

Chemical Structure

Phosphoramidon disodium
Phosphoramidon disodium
CAS#164204-38-0

Theoretical Analysis

MedKoo Cat#: 561755

Name: Phosphoramidon disodium

CAS#: 164204-38-0

Chemical Formula: C23H32N3Na2O10P

Exact Mass: 587.1621

Molecular Weight: 587.47

Elemental Analysis: C, 47.02; H, 5.49; N, 7.15; Na, 7.83; O, 27.23; P, 5.27

Price and Availability

Size Price Availability Quantity
5mg USD 290.00
10mg USD 490.00
25mg USD 970.00
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Related CAS #
No Data
Synonym
Phosphoramidon disodium;
IUPAC/Chemical Name
sodium (oxido(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)phosphoryl)-L-leucyl-L-tryptophanate
InChi Key
OQKHVXFOYFBMDJ-ODIUWQMJSA-L
InChi Code
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
SMILES Code
O[C@H]1[C@H](C)O[C@@H](OP(N[C@@H](CC(C)C)C(N[C@H](C(O[Na])=O)CC2=CNC3=CC=CC=C23)=O)(O[Na])=O)[C@H](O)[C@@H]1O
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:
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.
In vitro activity:
The structure-activity relationships of phosphoramidon analogues for inhibition of endothelin-converting enzyme (ECE), neutral endopeptidase 24.11 (NEP), and angiotensin-converting enzyme (ACE) were compared. Phosphoramidon inhibited ECE, NEP, and ACE activities with IC50 values of 3.5, 0.034, and 78 microM, respectively. Removal of the rhamnose moiety of phosphoramidon (dipeptide 3) reduced the potency for ECE (IC50 = 70 microM), whereas the potencies for NEP (0.003 microM) and ACE (0.20 microM) were increased. Reference: J Cardiovasc Pharmacol. 1995;26 Suppl 3:S65-8. https://pubmed.ncbi.nlm.nih.gov/8587470/
In vivo activity:
Intravenous (i.v.) injection of big endothelin-1 (1-39, 0.05-1.0 nmol/kg) to anaesthetized rats produced a dose-dependent and long-lasting hypertensive effect, the magnitude of which was similar to that evoked by ET-1 (1-21). In animals given phosphoramidon (0.25 mg/kg per min i.v.), a metalloproteinase inhibitor, the hypertensive effect of big endothelin-1 was markedly attenuated. The same dose of phosphoramidon did not influence the endothelin-1-induced hypertensive effect. Reference: Eur J Pharmacol. 1990 Aug 21;185(1):103-6. https://pubmed.ncbi.nlm.nih.gov/2226629/
Solvent mg/mL mM comments
Solubility
DMF 10.0 17.02
DMSO 71.3 121.42
PBS (pH 7.2) 10.0 17.02
Water 86.3 146.82
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 587.47 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. Kukkola PJ, Savage P, Sakane Y, Berry JC, Bilci NA, Ghai RD, Jeng AY. Differential structure-activity relationships of phosphoramidon analogues for inhibition of three metalloproteases: endothelin-converting enzyme, neutral endopeptidase, and angiotensin-converting enzyme. J Cardiovasc Pharmacol. 1995;26 Suppl 3:S65-8. PMID: 8587470. 2. McMahon EG, Palomo MA, Moore WM, McDonald JF, Stern MK. 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. doi: 10.1073/pnas.88.3.703. PMID: 1992461; PMCID: PMC50881. 3. Pross M, Lippert H, Mantke R, Krüger S, Günther T, Marusch F, Halangk W, Schulz HU. A proteinase inhibitor decreases tumor growth in a laparoscopic rat model. Surg Endosc. 2001 Aug;15(8):882-5. doi: 10.1007/s004640090029. Epub 2001 May 2. PMID: 11443463. 4. Matsumura Y, Hisaki K, Takaoka M, Morimoto S. Phosphoramidon, a metalloproteinase inhibitor, suppresses the hypertensive effect of big endothelin-1. Eur J Pharmacol. 1990 Aug 21;185(1):103-6. doi: 10.1016/0014-2999(90)90216-s. PMID: 2226629.
In vitro protocol:
1. Kukkola PJ, Savage P, Sakane Y, Berry JC, Bilci NA, Ghai RD, Jeng AY. Differential structure-activity relationships of phosphoramidon analogues for inhibition of three metalloproteases: endothelin-converting enzyme, neutral endopeptidase, and angiotensin-converting enzyme. J Cardiovasc Pharmacol. 1995;26 Suppl 3:S65-8. PMID: 8587470. 2. McMahon EG, Palomo MA, Moore WM, McDonald JF, Stern MK. 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. doi: 10.1073/pnas.88.3.703. PMID: 1992461; PMCID: PMC50881.
In vivo protocol:
1. Pross M, Lippert H, Mantke R, Krüger S, Günther T, Marusch F, Halangk W, Schulz HU. A proteinase inhibitor decreases tumor growth in a laparoscopic rat model. Surg Endosc. 2001 Aug;15(8):882-5. doi: 10.1007/s004640090029. Epub 2001 May 2. PMID: 11443463. 2. Matsumura Y, Hisaki K, Takaoka M, Morimoto S. Phosphoramidon, a metalloproteinase inhibitor, suppresses the hypertensive effect of big endothelin-1. Eur J Pharmacol. 1990 Aug 21;185(1):103-6. doi: 10.1016/0014-2999(90)90216-s. PMID: 2226629.
1: Koushik K, Sunkara G, Gwilt P, Kompella UB. Pathways and kinetics of deslorelin degradation in an airway epithelial cell line (Calu-1). Pharm Res. 2003 May;20(5):779-87. PubMed PMID: 12751634. 2: Descombes JJ, Mennecier P, Versluys D, Barou V, de Nanteuil G, Laubie M, Verbeuren TJ. S 17162 is a novel selective inhibitor of big ET-1 responses in the rat. J Cardiovasc Pharmacol. 1995;26 Suppl 3:S61-4. PubMed PMID: 8587469.