You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameErythrityl Tetranitrate
Accession NumberDB01613
TypeSmall Molecule
GroupsApproved
Description

A vasodilator with general properties similar to nitroglycerin. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1020)

Structure
Thumb
Synonyms
SynonymLanguageCode
(2R*,3S)-rel-1,2,3,4-butanetetroltetranitrateNot AvailableNot Available
1,2,3,4-Butanetetralyl tetranitrateNot AvailableNot Available
Eritrityl tetranitrateNot AvailableINN
Eritrityli tetranitrasLatinINN
Erythritol tetranitrateNot AvailableNot Available
Erythrol tetranitrateNot AvailableNot Available
ETNNot AvailableNot Available
Meso-erythritol tetranitrateNot AvailableNot Available
Tetranitrate d'eritrityleFrenchINN
Tetranitrato de eritritiloSpanishINN
TetranitrinNot AvailableNot Available
TetranitrolNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
CardilateNot Available
Brand mixturesNot Available
Categories
CAS number7297-25-8
WeightAverage: 302.11
Monoisotopic: 301.998221676
Chemical FormulaC4H6N4O12
InChI KeySNFOERUNNSHUGP-ZXZARUISSA-N
InChI
InChI=1S/C4H6N4O12/c9-5(10)17-1-3(19-7(13)14)4(20-8(15)16)2-18-6(11)12/h3-4H,1-2H2/t3-,4+
IUPAC Name
(2S,3R)-2,3,4-tris(nitrooxy)butyl nitrate
SMILES
[O-][N+](=O)OC[C@@H](O[N+]([O-])=O)[C@H](CO[N+]([O-])=O)O[N+]([O-])=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassOrganic Oxoanionic Compounds
SubclassOrganic Nitrates
Direct parentOrganic Nitrates
Alternative parentsNitrate Esters; Nitro Compounds; Polyamines
Substituentsorganic nitric acid or derivative; nitro compound; polyamine
Classification descriptionThis compound belongs to the organic nitrates. These are organic compounds containing the nitrate oxoanion, with the formula NO3-.
Pharmacology
IndicationFor the prevention of angina.
PharmacodynamicsErythrityl Tetranitrate is a vasodilator with general properties similar to nitroglycerin.
Mechanism of actionSimilar to other nitrites and organic nitrates, erythrityl tetranitrate is converted to an active intermediate compound which activates the enzyme guanylate cyclase. This stimulates the synthesis of cyclic guanosine 3',5'-monophosphate (cGMP) which then activates a series of protein kinase-dependent phosphorylations in the smooth muscle cells, eventually resulting in the dephosphorylation of the myosin light chain of the smooth muscle fiber. The subsequent release of calcium ions results in the relaxation of the smooth muscle cells and vasodilation.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include increased intracranial pressure, with any or all of persistent throbbing headache, confusion, and moderate fever; Vertigo; Palpitations; Visual disturbances; Nausea and vomiting (possibly with colic and even bloody diarrhea); Syncope (especially in the upright posture); Air hunger and dyspnea, later followed by reduced ventilatory effort; Diaphoresis, with the skin either flushed or cold and clammy; Heart block and bradycardia; Paralysis; Coma; Seizures; Death.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.7733
Blood Brain Barrier + 0.9089
Caco-2 permeable - 0.5825
P-glycoprotein substrate Non-substrate 0.7905
P-glycoprotein inhibitor I Non-inhibitor 0.6464
P-glycoprotein inhibitor II Non-inhibitor 0.8955
Renal organic cation transporter Non-inhibitor 0.835
CYP450 2C9 substrate Non-substrate 0.9002
CYP450 2D6 substrate Non-substrate 0.8936
CYP450 3A4 substrate Non-substrate 0.5357
CYP450 1A2 substrate Non-inhibitor 0.7871
CYP450 2C9 substrate Non-inhibitor 0.7619
CYP450 2D6 substrate Non-inhibitor 0.9081
CYP450 2C19 substrate Non-inhibitor 0.6943
CYP450 3A4 substrate Non-inhibitor 0.8885
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8212
Ames test AMES toxic 0.8896
Carcinogenicity Carcinogens 0.6703
Biodegradation Ready biodegradable 0.9161
Rat acute toxicity 2.7983 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Strong inhibitor 0.5607
hERG inhibition (predictor II) Non-inhibitor 0.9098
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point61 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.195ALOGPS
logP1.68ALOGPS
logP1.23ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area220.2 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity53.25 m3·mol-1ChemAxon
Polarizability20.27 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
ChEBI60072
ChEMBLCHEMBL2107583
Therapeutic Targets DatabaseDAP001060
PharmGKBPA164746528
ATC CodesC01DA13
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
DihydroergotaminePossible antagonism of action
ErgotaminePossible antagonism of action
MethysergidePossible antagonism of action
Food Interactions
  • Avoid alcohol.
  • Take on empty stomach: 1 hour before or 2 hours after meals.

Targets

1. Atrial natriuretic peptide receptor 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Atrial natriuretic peptide receptor 1 P16066 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Schroder H, Noack E: Structure-activity relationship of organic nitrates for activation of guanylate cyclase. Arch Int Pharmacodyn Ther. 1987 Dec;290(2):235-46. Pubmed

2. Atrial natriuretic peptide receptor 2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Atrial natriuretic peptide receptor 2 P20594 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Lange K, Koenig A, Roegler C, Seeling A, Lehmann J: NO donors. Part 18: Bioactive metabolites of GTN and PETN—synthesis and vasorelaxant properties. Bioorg Med Chem Lett. 2009 Jun 1;19(11):3141-4. Epub 2008 Apr 26. Pubmed

Comments
comments powered by Disqus
Drug created on August 29, 2007 14:04 / Updated on September 16, 2013 17:15