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targets (2)
for drugs
Identification
Name Erythrityl Tetranitrate
Accession Number DB01613
Type small molecule
Groups approved
Description

A vasodilator with general properties similar to nitroglycerin. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1020)
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
1,2,3,4-Butanetetralyl tetranitrate
Eritritile tetranitrato [dcit]
Eritrityl tetranitrate
Eritrityli tetranitras [inn-latin]
Erythritol tetranitrate
Erythrol tetranitrate
ETN
Meso-erythritol tetranitrate
Nitroerythrit
Nitroerythrite
Nitroerythrol
Tetranitrate d'eritrityle [inn-french]
Tetranitrato de eritritilo [inn-spanish]
First Prev Next Last
Salts Not Available
Brand names
Name Company
Cardilate
Cardiloid
Cardivell
Cardiwell
Tetranitrin
Tetranitrol
Brand mixtures Not Available
Categories
  • Vasodilator Agents
  • Nitrates and Nitrites
CAS number 7297-25-8
Weight Average: 302.11
Monoisotopic: 301.998221676
Chemical Formula C4H6N4O12
InChI Key InChIKey=SNFOERUNNSHUGP-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+
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the prevention of angina.
Pharmacodynamics Erythrityl Tetranitrate is a vasodilator with general properties similar to nitroglycerin.
Mechanism of action Similar 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.
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 Symptoms 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
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 61 °C PhysProp
Predicted Properties
Property Value Source
water solubility 1.95e-01 g/l ALOGPS
logP 1.68 ALOGPS
logP 1.23 ChemAxon
logS -3.2 ALOGPS
pKa (strongest basic) -5.5 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 12 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 220.2 ChemAxon
rotatable bond count 11 ChemAxon
refractivity 53.25 ChemAxon
polarizability 20.27 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
ChEBI 60072 Link_out
ChEMBL 60072 Link_out
Therapeutic Targets Database DAP001060 Link_out
PharmGKB PA164746528 Link_out
ATC Codes
  • C01DA13
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Dihydroergotamine Possible antagonism of action
Ergotamine Possible antagonism of action
Methysergide Possible 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 A

Pharmacological action: yes
Actions: agonist

Receptor for atrial natriuretic peptide. Has guanylate cyclase activity on binding of ANF

Organism class: human
UniProt ID: P16066 Link_out
Gene: NPR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 B

Pharmacological action: yes
Actions: agonist

Receptor for atrial natriuretic peptide (ANP), brain natriuretic peptide (BNP), and C-type natriuretic peptide (CNP). Has guanylate cyclase activity on binding of ligand. The activation order seems to be CNP > BNP > ANP

Organism class: human
UniProt ID: P20594 Link_out
Gene: NPR2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Drug created on August 29, 2007 14:04 / Updated on February 08, 2013 16:20