Phosphoramidon | CAS#36357-77-4 | thermolysin inhibitor

MedKoo Cat#: 598004 | Name: Phosphoramidon

Description:

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

Phosphoramidon is a membrane metallo-endopeptidase & endothelin-converting enzyme inhibitor; thermolysin inhibitor from culture filtrate of Streptomyces tanashiensis.

Chemical Structure

Phosphoramidon

CAS#36357-77-4

Theoretical Analysis

MedKoo Cat#: 598004

Name: Phosphoramidon

CAS#: 36357-77-4

Chemical Formula: C23H34N3O10P

Exact Mass: 543.1982

Molecular Weight: 543.50

Elemental Analysis: C, 50.83; H, 6.31; N, 7.73; O, 29.44; P, 5.70

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Phosphoramidon;

IUPAC/Chemical Name

(hydroxy(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)phosphoryl)-L-leucyl-L-tryptophan

InChi Key

ZPHBZEQOLSRPAK-XLCYBJAPSA-N

InChi Code

InChI=1S/C23H34N3O10P/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)/t12-,16-,17-,18-,19+,20+,23-/m0/s1

SMILES Code

O=C(O)[C@H](CC1=CNC2=C1C=CC=C2)NC([C@H](CC(C)C)NP(O)(O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)=O)=O

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).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 543.50 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.

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

1: Barage SH, Sonawane KD. Exploring mode of phosphoramidon and Aβ peptide binding to hECE-1 by molecular dynamics and docking studies. Protein Pept Lett. 2014;21(2):140-52. PubMed PMID: 24000822. 2: Sun Q, Yang Q, Gong S, Fu Q, Xiao Q. Synthesis and enzymatic evaluation of phosphoramidon and its β anomer: Anomerization of α-l-rhamnose triacetate upon phosphitylation. Bioorg Med Chem. 2013 Nov 1;21(21):6778-87. doi: 10.1016/j.bmc.2013.07.052. Epub 2013 Aug 8. PubMed PMID: 23988485. 3: dos Santos MH, da Costa AF, Ferreira BJ, Souza SL, da Silva Lannes P, Santos GS, Mattos-Guaraldi AL, Nagao PE. A phosphoramidon-sensitive metalloprotease induces apoptosis of human endothelial cells by Group B Streptococcus. Antonie Van Leeuwenhoek. 2013 Dec;104(6):1125-33. doi: 10.1007/s10482-013-0034-y. Epub 2013 Sep 20. PubMed PMID: 24052367. 4: Richter S, Wuest M, Bergman CN, Krieger S, Rogers BE, Wuest F. Metabolically Stabilized (68)Ga-NOTA-Bombesin for PET Imaging of Prostate Cancer and Influence of Protease Inhibitor Phosphoramidon. Mol Pharm. 2016 Apr 4;13(4):1347-57. doi: 10.1021/acs.molpharmaceut.5b00970. Epub 2016 Mar 23. PubMed PMID: 26973098. 5: Kaloudi A, Nock BA, Lymperis E, Krenning EP, de Jong M, Maina T. Improving the In Vivo Profile of Minigastrin Radiotracers: A Comparative Study Involving the Neutral Endopeptidase Inhibitor Phosphoramidon. Cancer Biother Radiopharm. 2016 Feb;31(1):20-8. doi: 10.1089/cbr.2015.1935. PubMed PMID: 26844849. 6: Hanson LR, Hafez D, Svitak AL, Burns RB, Li X, Frey WH 2nd, Marr RA. Intranasal phosphoramidon increases beta-amyloid levels in wild-type and NEP/NEP2-deficient mice. J Mol Neurosci. 2011 Mar;43(3):424-7. doi: 10.1007/s12031-010-9460-8. Epub 2010 Oct 13. PubMed PMID: 20941644. 7: Pollock DM, Divish BJ, Milicic I, Novosad EI, Burres NS, Opgenorth TJ. In vivo characterization of a phosphoramidon-sensitive endothelin-converting enzyme in the rat. Eur J Pharmacol. 1993 Feb 16;231(3):459-64. PubMed PMID: 8449237. 8: Pruhs RJ, Peña RT, Quock RM. Antagonism of phosphoramidon-induced antinociception in mice by mu- but not kappa-opioid receptor blockers. Life Sci. 2007 Apr 17;80(19):1816-20. Epub 2007 Feb 22. PubMed PMID: 17379253. 9: Isaka D, Emoto N, Raharjo SB, Yokoyama M, Matsuo M. The effects of phosphoramidon on the expression of human endothelin-converting enzyme-1 (ECE-1) isoforms. J Cardiovasc Pharmacol. 2003 Jul;42(1):136-41. PubMed PMID: 12827039. 10: Chen L, McNeill JR, Wilson TW, Gopalakrishnan V. Differential effects of phosphoramidon on contractile responses to angiotensin II in rat blood vessels. Br J Pharmacol. 1995 Apr;114(8):1599-604. PubMed PMID: 7599928; PubMed Central PMCID: PMC1510379. 11: Thompson JE, Sheppard D. Phosphoramidon potentiates the increase in lung resistance mediated by tachykinins in guinea pigs. Am Rev Respir Dis. 1988 Feb;137(2):337-40. PubMed PMID: 2449105. 12: Jelicks LA, Chandra M, Shirani J, Shtutin V, Tang B, Christ GJ, Factor SM, Wittner M, Huang H, Weiss LM, Mukherjee S, Bouzahzah B, Petkova SB, Teixeira MM, Douglas SA, Loredo ML, D'Orleans-Juste P, Tanowitz HB. Cardioprotective effects of phosphoramidon on myocardial structure and function in murine Chagas' disease. Int J Parasitol. 2002 Nov;32(12):1497-506. Erratum in: Int J Parasitol. 2003 Feb;33(2):217. PubMed PMID: 12392915. 13: Matsumura Y, Tsukahara Y, Kojima T, Murata S, Murakami A, Takada K, Takaoka M, Morimoto S. Effects of phosphoramidon on endothelin-1 and big endothelin-1 production in human aortic endothelial cells. Biol Pharm Bull. 1995 Mar;18(3):401-6. PubMed PMID: 7550091. 14: Jelicks LA, Chandra M, Shtutin V, Petkova SB, Tang B, Christ GJ, Factor SM, Wittner M, Huang H, Douglas SA, Weiss LM, Orleans-Juste PD, Shirani J, Tanowitz HB. Phosphoramidon treatment improves the consequences of chagasic heart disease in mice. Clin Sci (Lond). 2002 Aug;103 Suppl 48:267S-271S. PubMed PMID: 12193101. 15: Krassói I, Pataricza J, Torday LL, Kun A, Papp JG. Improvement by phosphoramidon of damaged endothelial function in porcine coronary artery. Ann Thorac Surg. 2000 Sep;70(3):878-82. PubMed PMID: 11016327. 16: Bhavsar TM, Cerreta JM, Liu M, Reznik SE, Cantor JO. Phosphoramidon, an endothelin-converting enzyme inhibitor, attenuates lipopolysaccharide-induced acute lung injury. Exp Lung Res. 2008 Mar;34(3):141-54. doi: 10.1080/01902140701884430. PubMed PMID: 18307123. 17: Polosa R, Santonocito G, Magrì S, Paolino G, Armato F, Pagano C, Crimi N. Neutral endopeptidase inhibition with inhaled phosphoramidon: no effect on bronchial responsiveness to adenosine 5'-monophosphate (AMP) in asthma. Eur Respir J. 1997 Nov;10(11):2460-4. PubMed PMID: 9426079. 18: Wu-Wong JR, Chiou WJ, Opgenorth TJ. Phosphoramidon modulates the number of endothelin receptors in cultured Swiss 3T3 fibroblasts. Mol Pharmacol. 1993 Aug;44(2):422-9. PubMed PMID: 8355669. 19: Vemulapalli S, Watkins RW, Brown A, Cook J, Bernardino V, Chiu PJ. Disparate effects of phosphoramidon on blood pressure in SHR and DOCA-salt hypertensive rats. Life Sci. 1993;53(10):783-93. PubMed PMID: 8355566. 20: Cosentino F, McMahon EG, Carter JS, Katusić ZS. Effect of endothelinA-receptor antagonist BQ-123 and phosphoramidon on cerebral vasospasm. J Cardiovasc Pharmacol. 1993;22 Suppl 8:S332-5. PubMed PMID: 7509979.