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Identification
NamePhosphoramidon
Accession NumberDB02557  (EXPT02764)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Phosphoramidon disodium
164204-38-0
Thumb
  • InChI Key: OQKHVXFOYFBMDJ-ODIUWQMJSA-L
  • Monoisotopic Mass: 587.1620698
  • Average Mass: 587.473
DBSALT001879
Categories
UNIIT3G94E2LB1
CAS number36357-77-4
WeightAverage: 543.5039
Monoisotopic: 543.198180835
Chemical FormulaC23H34N3O10P
InChI KeyZPHBZEQOLSRPAK-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][C@@](CC(C)C)(NP(O)(=O)O[C@]1([H])O[C@@]([H])(C)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O)C(O)=N[C@@]([H])(CC1=CNC2=CC=CC=C12)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
NeprilysinProteinunknown
inhibitor
HumanP08473 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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
AmineptineThe serum concentration of Amineptine can be increased when it is combined with Phosphoramidon.Illicit, Withdrawn
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Phosphoramidon.Approved
AmitriptylineThe serum concentration of Amitriptyline 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
BcgThe therapeutic efficacy of Bcg 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
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.Withdrawn
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Phosphoramidon.Approved, 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 Equine EstrogensThe serum concentration of Conjugated Equine 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
DienestrolThe serum concentration of Dienestrol can be decreased when it is combined with Phosphoramidon.Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Phosphoramidon.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Phosphoramidon.Approved
DihydroergotamineThe serum concentration of Dihydroergotamine 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
DyphyllineThe serum concentration of Dyphylline can be decreased when it is combined with Phosphoramidon.Approved
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Phosphoramidon.Approved, Investigational
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Phosphoramidon.Approved
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Phosphoramidon.Approved
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Phosphoramidon.Approved
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
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
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
PimozideThe serum concentration of Pimozide can be increased when it is combined 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
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Phosphoramidon.Approved
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.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
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Phosphoramidon.Approved
TianeptineThe serum concentration of Tianeptine can be increased when it is combined with Phosphoramidon.Approved
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 InteractionsNot Available
References
Synthesis Reference

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

US5608045
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid amide
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Indole or derivatives
  • Indole
  • Phosphoric monoester monoamide
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Substituted pyrrole
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Saccharide
  • Heteroaromatic compound
  • Pyrrole
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

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 peptides such as Met- and Leu-enkephalins by cleavage of a Gly-Phe bond (PubMed:17101991). Able to cleave angiotensin-1, angiotensin-2 and angiotensin 1-9 (PubMed:15283675). Involved in the degradation of at...
Gene Name:
MME
Uniprot ID:
P08473
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23