Identification

Name
Phosphoramidon
Accession Number
DB02557  (EXPT02764)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Phosphoramidon disodium3F7O684NXF164204-38-0OQKHVXFOYFBMDJ-ODIUWQMJSA-L
Categories
UNII
T3G94E2LB1
CAS number
36357-77-4
Weight
Average: 543.5039
Monoisotopic: 543.198180835
Chemical Formula
C23H34N3O10P
InChI Key
ZPHBZEQOLSRPAK-XLCYBJAPSA-N
InChI
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
IUPAC Name
(2S)-2-{[(2S)-1-hydroxy-2-{[hydroxy({[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]amino}-4-methylpentylidene]amino}-3-(1H-indol-3-yl)propanoic acid
SMILES
[H][[email protected]@](CC(C)C)(NP(O)(=O)O[[email protected]]1([H])O[[email protected]@]([H])(C)[[email protected]]([H])(O)[[email protected]@]([H])(O)[[email protected]@]1([H])O)C(O)=N[[email protected]@]([H])(CC1=CNC2=CC=CC=C12)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNeprilysin
inhibitor
Human
UKell blood group glycoproteinNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Phosphoramidon.Approved, Investigational
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Phosphoramidon.Approved, Investigational
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Phosphoramidon.Approved, Illicit, Investigational
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be decreased when it is combined with Phosphoramidon.Experimental, Investigational
AmineptineThe serum concentration of Amineptine can be increased when it is combined with Phosphoramidon.Illicit, Withdrawn
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Phosphoramidon.Approved
AmoxapineThe serum concentration of Amoxapine can be increased when it is combined with Phosphoramidon.Approved
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Phosphoramidon.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Phosphoramidon.Investigational
BoceprevirThe serum concentration of Phosphoramidon can be decreased when it is combined with Boceprevir.Approved, Withdrawn
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Phosphoramidon.Approved, Investigational
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with Phosphoramidon.Approved
CarbamazepineThe metabolism of Phosphoramidon can be increased when combined with Carbamazepine.Approved, Investigational
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Phosphoramidon.Investigational, Withdrawn
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Phosphoramidon.Approved
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Phosphoramidon.Approved, Vet Approved
Conjugated estrogensThe serum concentration of Conjugated estrogens can be decreased when it is combined with Phosphoramidon.Approved
CyclobenzaprineThe serum concentration of Cyclobenzaprine can be increased when it is combined with Phosphoramidon.Approved
CyclophosphamideThe risk or severity of adverse effects can be increased when Phosphoramidon is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Phosphoramidon.Approved, Investigational, Vet Approved
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Phosphoramidon.Approved
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Phosphoramidon.Approved
DibenzepinThe serum concentration of Dibenzepin can be increased when it is combined with Phosphoramidon.Experimental
DienestrolThe serum concentration of Dienestrol can be decreased when it is combined with Phosphoramidon.Approved, Investigational
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Phosphoramidon.Approved, Investigational
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Phosphoramidon.Approved
DiltiazemThe metabolism of Diltiazem can be decreased when combined with Phosphoramidon.Approved
DosulepinThe serum concentration of Dosulepin can be increased when it is combined with Phosphoramidon.Approved
DoxepinThe serum concentration of Doxepin can be increased when it is combined with Phosphoramidon.Approved
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Phosphoramidon.Approved, Investigational
EsmirtazapineThe serum concentration of Esmirtazapine can be increased when it is combined with Phosphoramidon.Investigational
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Phosphoramidon.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Estramustine can be decreased when it is combined with Phosphoramidon.Approved
Estrogens, esterifiedThe serum concentration of Estrogens, esterified can be decreased when it is combined with Phosphoramidon.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be decreased when it is combined with Phosphoramidon.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Phosphoramidon.Approved
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Phosphoramidon.Approved
GarlicThe serum concentration of Phosphoramidon can be decreased when it is combined with Garlic.Approved
HexestrolThe serum concentration of Hexestrol can be decreased when it is combined with Phosphoramidon.Withdrawn
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Phosphoramidon.Approved
IprindoleThe serum concentration of Iprindole can be increased when it is combined with Phosphoramidon.Experimental
LofepramineThe serum concentration of Lofepramine can be increased when it is combined with Phosphoramidon.Experimental
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Phosphoramidon.Approved, Investigational
MestranolThe serum concentration of Mestranol can be decreased when it is combined with Phosphoramidon.Approved
MethallenestrilThe serum concentration of Methallenestril can be decreased when it is combined with Phosphoramidon.Experimental
MethylergometrineThe serum concentration of Methylergometrine can be increased when it is combined with Phosphoramidon.Approved
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Phosphoramidon.Approved, Illicit
MirtazapineThe serum concentration of Mirtazapine can be increased when it is combined with Phosphoramidon.Approved
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Phosphoramidon.Approved, Withdrawn
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with Phosphoramidon.Approved
OpipramolThe serum concentration of Opipramol can be increased when it is combined with Phosphoramidon.Investigational
PethidineThe risk or severity of adverse effects can be increased when Phosphoramidon is combined with Pethidine.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Phosphoramidon.Approved
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with Phosphoramidon.Approved
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Phosphoramidon.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Phosphoramidon.Approved
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Phosphoramidon.Approved, Investigational
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Phosphoramidon.Approved
St. John's WortThe metabolism of Phosphoramidon can be increased when combined with St. John's Wort.Investigational, Nutraceutical
Synthetic Conjugated Estrogens, AThe serum concentration of Synthetic Conjugated Estrogens, A can be decreased when it is combined with Phosphoramidon.Approved
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Phosphoramidon.Approved, Investigational
TemsirolimusThe risk or severity of adverse effects can be increased when Phosphoramidon is combined with Temsirolimus.Approved
TianeptineThe serum concentration of Tianeptine can be increased when it is combined with Phosphoramidon.Approved, Investigational
TipranavirThe serum concentration of Phosphoramidon can be decreased when it is combined with Tipranavir.Approved, Investigational
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Phosphoramidon.Approved
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with Phosphoramidon.Approved
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Phosphoramidon.Approved, Investigational
VerapamilThe metabolism of Verapamil can be decreased when combined with Phosphoramidon.Approved
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Phosphoramidon.Approved
Food Interactions
Not Available

References

Synthesis Reference

Guillaume de Nanteuil, Georges Remond, Tony Verbeuren, "Preparation of phosphoramidon." U.S. Patent US5608045, issued December, 1989.

US5608045
General References
Not Available
External Links
KEGG Compound
C00563
PubChem Compound
445114
PubChem Substance
46506179
ChemSpider
392848
BindingDB
50251742
ChEBI
45353
ChEMBL
CHEMBL479579
Therapeutic Targets Database
DNC001121
HET
RDF
Wikipedia
Phosphoramidon
PDB Entries
1dmt / 1tlp / 3dbk / 3dwb / 3zuk / 4b52 / 4cth / 4zr5

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.752 mg/mLALOGPS
logP0.1ALOGPS
logP0.98ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area214.16 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity129.46 m3·mol-1ChemAxon
Polarizability51.5 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6948
Blood Brain Barrier-0.9264
Caco-2 permeable-0.704
P-glycoprotein substrateSubstrate0.6813
P-glycoprotein inhibitor INon-inhibitor0.578
P-glycoprotein inhibitor IINon-inhibitor0.8717
Renal organic cation transporterNon-inhibitor0.9636
CYP450 2C9 substrateNon-substrate0.7455
CYP450 2D6 substrateNon-substrate0.7995
CYP450 3A4 substrateSubstrate0.6024
CYP450 1A2 substrateNon-inhibitor0.8286
CYP450 2C9 inhibitorNon-inhibitor0.8278
CYP450 2D6 inhibitorNon-inhibitor0.891
CYP450 2C19 inhibitorNon-inhibitor0.7963
CYP450 3A4 inhibitorNon-inhibitor0.746
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.759
Ames testNon AMES toxic0.6604
CarcinogenicityNon-carcinogens0.8752
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7483 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9847
hERG inhibition (predictor II)Non-inhibitor0.8229
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0000090000-bfa44de21c3535a87530
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0002090000-33b035434d6b84041094
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0009010000-69688f69a2a7bcbc5163
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-8119000000-e07758fccb5a6b44deb1
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9101000000-7cff0ab9b41737048aa3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014m-0009030000-a5b6407e17e402eec55c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014j-0319000000-38a8b18f710de46326b4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0910000000-d18f2b765c3f2e8c04ce
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0950000000-aab9a1e87c46971532dc
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000b-0009840000-ef33a5933fe11f046ebd

Taxonomy

Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Leucine and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Hexoses / Indolyl carboxylic acids and derivatives / 3-alkylindoles / Phosphoric monoester monoamides / Substituted pyrroles / Benzenoids / Phosphate esters
show 15 more
Substituents
Alpha-dipeptide / Leucine or derivatives / N-acyl-l-alpha-amino acid / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Hexose monosaccharide / Indolyl carboxylic acid derivative / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives
show 35 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dipeptide, deoxyaldohexose phosphate (CHEBI:45353)

Targets

Details
1. Neprilysin
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Thermolysin-like specificity, but is almost confined on acting on polypeptides of up to 30 amino acids (PubMed:15283675, PubMed:8168535). Biologically important in the destruction of opioid peptide...
Gene Name
MME
Uniprot ID
P08473
Uniprot Name
Neprilysin
Molecular Weight
85513.225 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc endopeptidase with endothelin-3-converting enzyme activity. Cleaves EDN1, EDN2 and EDN3, with a marked preference for EDN3.
Specific Function
Metal ion binding
Gene Name
KEL
Uniprot ID
P23276
Uniprot Name
Kell blood group glycoprotein
Molecular Weight
82823.095 Da
References
  1. Claperon A, Rose C, Gane P, Collec E, Bertrand O, Ouimet T: The Kell protein of the common K2 phenotype is a catalytically active metalloprotease, whereas the rare Kell K1 antigen is inactive. Identification of novel substrates for the Kell protein. J Biol Chem. 2005 Jun 3;280(22):21272-83. Epub 2005 Mar 15. [PubMed:15769748]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 17:28