DrugBank: Erythrityl Tetranitrate (DB01613)

targets (2)

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

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]

Brand names

Cardilate
Cardiloid
Cardivell
Cardiwell
Tetranitrin
Tetranitrol

Brand name 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-UHFFFAOYSA-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

Plain Text

IUPAC Name

2,3,4-tris(nitrooxy)butyl nitrate

SMILES

[O-][N+](=O)OCC(O[N+]([O-])=O)C(CO[N+]([O-])=O)O[N+]([O-])=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Glycerol and Derivatives

Substructures

Glycerol and Derivatives
Oxoazaniums
Esters
Nitrates

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

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

Melting point

61 oC

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	1.95e-01 g/l	ALOGPS
logP	1.68	ALOGPS
logP	1.23	ChemAxon Molconvert
logS	-3.19	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	12	ChemAxon Molconvert
hydrogen donor count	0	ChemAxon Molconvert
polar surface area	220.20	ChemAxon Molconvert
rotatable bond count	11	ChemAxon Molconvert
refractivity	53.25	ChemAxon Molconvert
polarizability	20.37	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	23723
PubChem Substance	46508990
ChemSpider	22183
ChEBI	60072
ChEMBL	60072
Therapeutic Targets Database	DAP001060
PharmGKB	PA449492
Drug Product Database	0

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

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 Gene: NPR1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 Gene: NPR2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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

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:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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 April 19, 2011 15:10

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.