Pentaerythritol Tetranitrate

Identification

Name
Pentaerythritol Tetranitrate
Accession Number
DB06154
Type
Small Molecule
Groups
Approved
Description

Pentaerythritol tetranitrate is the nitrate ester of pentaerythritol that possesses explosive properties. When mixed with a plasticizer, this chemical forms a plastic explosive. It is recognized by the FDA to be a coronary vasodilator in the treatment of heart conditions such as angina [9].

It is a pentaerythritol nitrate in which all four hydroxy groups of pentaerythritol have been converted to the corresponding nitrate ester. It is a vasodilator with properties that are quite similar to those of glyceryl trinitrate, however, with a more prolonged duration of action. It is also one of the most powerful high explosives known and is a component of the plastic explosive known as Semtex [7].

PETN has the chemical formula C5H8N4O12. It is formed by reacting pentaerythritol (C5H12O4), an alcohol commonly used in paints and varnishes, with nitric acid (HNO2). The reacting solution is chilled to precipitate the PETN. It is then filtered out, washed, dried, and recrystallized to produce a colorless crystalline material that is stored and shipped as a mixture with water and alcohol [8].

Interestingly, this drug was studied for potential benefits in chronic ischemic heart failure patients. PETN targeting reactive oxygen species generation halted the changes of mitochondrial antioxidant enzymes and progressive fibrotic remodeling, leading to amelioration of cardiac functional performance in rats with ischemic heart failure [4].

Structure
Thumb
Synonyms
  • corpent
  • PENT
  • PENTA
  • Pentaerithrityl tetranitrate
  • pentaerithrityli tetranitras
  • penthrite
  • TEN
  • tetranitrate de pentaerithrityle
  • tetranitrato de pentaeritritilo
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Peritrate Sa 80mg TabTablet, extended release80 mgOralParke Davis Division, Warner Lambert Canada Inc.1961-12-311998-09-14Canada
Peritrate Tab 10mgTablet10 mgOralParke Davis Division, Warner Lambert Canada Inc.1961-12-311997-08-11Canada
Peritrate Tab 20mgTablet20 mgOralParke Davis Division, Warner Lambert Canada Inc.1961-12-311998-09-14Canada
Categories
UNII
10L39TRG1Z
CAS number
78-11-5
Weight
Average: 316.1366
Monoisotopic: 316.01387174
Chemical Formula
C5H8N4O12
InChI Key
TZRXHJWUDPFEEY-UHFFFAOYSA-N
InChI
InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2
IUPAC Name
3-(nitrooxy)-2,2-bis[(nitrooxy)methyl]propyl nitrate
SMILES
[O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O

Pharmacology

Indication

Used for the treatment of angina pectoris [7].

Structured Indications
Not Available
Pharmacodynamics

Organic nitrate which causes systemic vasodilation, decreasing cardiovascular preload [15].

Nitrate enters vascular smooth muscle and converted to nitric oxide (NO) which acts as a cellular messenger, leading to activation of cyclic GMP and, therefore, vasodilation [15].

The nitrovasodilator group of drugs relaxes most smooth muscles in the body, including those in the walls of arteries and veins, and selectively dilate large coronary vessels [12]. Lower doses of nitrates increase coronary blood flow without significantly affecting systemic arterial pressure. Higher doses, especially if repeated frequently, decrease systolic and diastolic blood pressure as well as cardiac output, which can result in a headache, weakness, dizziness, and the activation of compensatory sympathetic reflexes, including tachycardia and peripheral arteriolar vasoconstriction [5].

Smooth muscles in the bronchi, biliary tract, gastrointestinal tract, ureters, and uterus also can be relaxed by nitrovasodilators. PETN seems to be unique among the long-acting nitrovasodilators in that patients do not demonstrate tolerance to treatment, which results in sustained vasodilation in humans with continuous PETN treatment [14].

Important to note is that this drug is devoid of induction of oxidative stress and related side-effects such as endothelial dysfunction or tolerance to nitrates. Some of these effects are related to special pharmacokinetics of PETN, but upon chronic administration, PETN also induces antioxidative pathways at the genomic level, resulting in increased expression of heme oxygenase-1 (HO-1) and ferritin, both possessing highly protective properties. There is good experimental evidence that at least part of the beneficial profile of long-term treatment with this drug is based on the activation of the heme oxygenase-1/ferritin system [16].

Mechanism of action

Pentaerythritol tetranitrate is the lipid soluble polyol ester of nitric acid belonging to the family of nitro-vasodilators. Pentaerythritol tetranitrate releases free nitric oxide (NO) after the denitration reaction, which triggers NO-dependent signaling transduction involving soluble guanylate cyclase (sGC). Nitric oxide binds reversibly to the ferrous-heme center of sGC, causing conformational change and activating the enzyme. This enzyme activation results in increased cellular concentrations of _cyclic guanosine monophosphate _(cGMP) within the vascular smooth muscle, resulting in vasodilation mediated by cGMP-dependent protein kinases. Additionally, this agent causes dose-dependent arterial and venous bed [7].

TargetActionsOrganism
AHemoglobin subunit alpha
agonist
Human
AHemoglobin subunit beta
agonist
Human
NFree radicals
antagonist
Human
Absorption
Not Available
Volume of distribution

The steady-state volume of distribution was 4.2 +/- 1.1 L/kg (n = 6) in rats given this drug by the intra-arterial route [1].

Protein binding
Not Available
Metabolism

Extensively metabolized in the liver [15].

Metabolites: pentaerythritol trinitrate, pentaerythritol dinitrate, pentaerythritol mononitrate, & pentaerythritol (inactive)[15]

Route of elimination

Mainly the urine [15].

Half life

The elimination half-life in plasma from male volunteers given an oral 100-mg dose of the tetranitrate was reported to be 4-5 hours [9].

Clearance

In a pharmacokinetic study of rats after intra-arterial administration of this drug, the clearance was measured to be 0.61 +/- 0.16 L/min/kg [1].

Toxicity

The toxicity of nitrate drugs are the result of nitrate conversion to nitrite in the body. Nitrite leads to the autocatalytic oxidation of oxyhemoglobin to both hydrogen peroxide and methemoglobin. This increase in methemoglobin levels is a condition known as methemoglobinemia and is manifested by tissue hypoxia, as methemoglobin is unable to bind oxygen [17].

Dizziness, redness of the skin (due to vasodilatation), skin irritation and headache are common adverse effects of this drug. Postural hypotension can also occur, especially if this drug is taken at higher doses or while standing [9].

PETN - Oral LD50 (mouse) = 25,000 mg/kg [MSDS]

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
(4R)-limonene(4R)-limonene may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
AbciximabAbciximab may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
AceclofenacAceclofenac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
AcemetacinThe risk or severity of bleeding can be increased when Pentaerythritol Tetranitrate is combined with Acemetacin.Approved, Experimental, Investigational
AcenocoumarolAcenocoumarol may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved
AdapaleneAdapalene may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
AlclofenacAlclofenac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Withdrawn
AllylestrenolThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Allylestrenol.Approved
AlminoprofenAlminoprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
AloxiprinAloxiprin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
AlprostadilAlprostadil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
AlteplaseAlteplase may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
AltrenogestThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Altrenogest.Vet Approved
Aminosalicylic AcidAminosalicylic Acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
AnagrelideAnagrelide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
AncrodAncrod may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
AndrographolideAndrographolide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
AnisodamineAnisodamine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
AnistreplaseAnistreplase may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
AntipyrineAntipyrine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Antithrombin III humanPentaerythritol Tetranitrate may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanApixaban may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
ApocyninApocynin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
ApremilastApremilast may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
AprotininThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Aprotinin.Approved, Investigational, Withdrawn
ArdeparinArdeparin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Withdrawn
ArgatrobanArgatroban may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
AstaxanthinAstaxanthin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
AvanafilAvanafil may increase the vasodilatory activities of Pentaerythritol Tetranitrate.Approved
AzapropazoneAzapropazone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Withdrawn
AzelastineAzelastine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Azficel-TThe risk or severity of adverse effects can be increased when Pentaerythritol Tetranitrate is combined with Azficel-T.Approved, Investigational
BalsalazideBalsalazide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
BatroxobinBatroxobin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
BecaplerminBecaplermin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
BemiparinBemiparin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
BendazacBendazac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
BenorilateBenorilate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
BenoxaprofenBenoxaprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Withdrawn
BenzydamineBenzydamine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
BeraprostBeraprost may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
BevoniumBevonium may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
BivalirudinBivalirudin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
BrinaseBrinase may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
BromfenacBromfenac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
BucillamineBucillamine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
BufexamacBufexamac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Experimental
BuflomedilBuflomedil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
BumadizoneBumadizone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
ButylphthalideButylphthalide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
CangrelorCangrelor may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
CaplacizumabCaplacizumab may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
Carbaspirin calciumCarbaspirin calcium may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental, Investigational
CarprofenCarprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
CelecoxibCelecoxib may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
CertoparinPentaerythritol Tetranitrate may increase the anticoagulant activities of Certoparin.Approved, Investigational
ChloroquineChloroquine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Vet Approved
ChlorotrianiseneChlorotrianisene may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational, Withdrawn
Choline magnesium trisalicylateCholine magnesium trisalicylate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
CilostazolCilostazol may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Citric AcidCitric Acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Nutraceutical, Vet Approved
ClonixinClonixin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
ClopidogrelClopidogrel may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
CloricromenCloricromen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
ClorindioneClorindione may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Pentaerythritol Tetranitrate is combined with Collagenase clostridium histolyticum.Approved, Investigational
Conjugated estrogensConjugated estrogens may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
CurcuminCurcumin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
DaidzeinDaidzein may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
DalteparinPentaerythritol Tetranitrate may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidPentaerythritol Tetranitrate may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Pentaerythritol Tetranitrate.Investigational
DarexabanPentaerythritol Tetranitrate may increase the anticoagulant activities of Darexaban.Investigational
DasatinibDasatinib may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
DeferasiroxThe risk or severity of adverse effects can be increased when Pentaerythritol Tetranitrate is combined with Deferasirox.Approved, Investigational
DefibrotideDefibrotide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
DemegestoneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Demegestone.Experimental
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Pentaerythritol Tetranitrate is combined with Deoxycholic Acid.Approved
DersalazineDersalazine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
DesirudinPentaerythritol Tetranitrate may increase the anticoagulant activities of Desirudin.Approved
DesmoteplaseDesmoteplase may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
DesogestrelThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Desogestrel.Approved
DextranPentaerythritol Tetranitrate may increase the anticoagulant activities of Dextran.Approved, Investigational, Vet Approved
DiclofenacDiclofenac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved
DicoumarolDicoumarol may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
DienestrolDienestrol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
DienogestThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Dienogest.Approved
DiethylstilbestrolDiethylstilbestrol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
DifenpiramideDifenpiramide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
DiflunisalDiflunisal may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
DiphenadioneDiphenadione may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
DipyridamoleDipyridamole may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
DitazoleDitazole may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Withdrawn
Drotrecogin alfaDrotrecogin alfa may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Withdrawn
DroxicamDroxicam may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Withdrawn
DuvelisibDuvelisib may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
DydrogesteroneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Dydrogesterone.Approved, Investigational, Withdrawn
E-6201E-6201 may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
Edetic AcidEdetic Acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved
EdoxabanEdoxaban may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
EnoxaparinEnoxaparin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
EpimestrolEpimestrol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
EpinastineEpinastine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
EpirizoleEpirizole may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
EplivanserinEplivanserin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
eplivanserineeplivanserine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
EpoprostenolEpoprostenol may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
EptifibatideEptifibatide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
EquolEquol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
EstradiolEstradiol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Vet Approved
Estradiol acetateEstradiol acetate may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Vet Approved
Estradiol cypionateEstradiol cypionate may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Vet Approved
Estradiol valerateEstradiol valerate may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Vet Approved
EstriolEstriol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Vet Approved
Estrogens, esterifiedEstrogens, esterified may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
EstroneEstrone may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
EtanerceptEtanercept may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
EthanolEthanol may increase the vasodilatory activities of Pentaerythritol Tetranitrate.Approved
EthenzamideEthenzamide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Ethyl biscoumacetatePentaerythritol Tetranitrate may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EthynodiolThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Ethynodiol.Experimental
EtodolacEtodolac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
EtonogestrelThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Etonogestrel.Approved, Investigational
EtoricoxibEtoricoxib may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Evening primrose oilEvening primrose oil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
ExisulindExisulind may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
FelbinacFelbinac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
FenbufenFenbufen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
FenoprofenFenoprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
FentiazacFentiazac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
FeprazoneFeprazone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
Ferulic acidFerulic acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
FibrinolysinFibrinolysin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
FloctafenineFloctafenine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Withdrawn
FluindionePentaerythritol Tetranitrate may increase the anticoagulant activities of Fluindione.Approved, Investigational
FlunixinFlunixin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Vet Approved
FlunoxaprofenFlunoxaprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
FondaparinuxPentaerythritol Tetranitrate may increase the anticoagulant activities of Fondaparinux.Approved, Investigational
Fondaparinux sodiumFondaparinux sodium may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
GabexatePentaerythritol Tetranitrate may increase the anticoagulant activities of Gabexate.Investigational
GenisteinGenistein may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
GestodeneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Gestodene.Approved, Investigational
GestonoroneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Gestonorone.Experimental
GestrinoneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Gestrinone.Approved
GuacetisalGuacetisal may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
HeminHemin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Hemoglobin crosfumarilHemoglobin crosfumaril may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
HeparinHeparin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
HexestrolHexestrol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Withdrawn
HigenamineHigenamine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
Hydroxyprogesterone caproateThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
HydroxytyrosolHydroxytyrosol may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Pentaerythritol Tetranitrate is combined with Ibritumomab tiuxetan.Approved, Investigational
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Pentaerythritol Tetranitrate.Approved
IbudilastIbudilast may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
IbuprofenIbuprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
IbuproxamIbuproxam may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Withdrawn
IcatibantIcatibant may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Nutraceutical
IdraparinuxPentaerythritol Tetranitrate may increase the anticoagulant activities of Idraparinux.Investigational
IfenprodilIfenprodil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Withdrawn
IfetrobanIfetroban may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
IloprostIloprost may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Imidazole salicylateImidazole salicylate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
IndobufenIndobufen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
IndomethacinIndomethacin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
IndoprofenIndoprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Withdrawn
IsoxicamIsoxicam may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Withdrawn
KebuzoneKebuzone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
KetanserinKetanserin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
KetoprofenKetoprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved
KetorolacKetorolac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
LeflunomideLeflunomide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
LepirudinLepirudin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
LetaxabanPentaerythritol Tetranitrate may increase the anticoagulant activities of Letaxaban.Investigational
LevonorgestrelThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Levonorgestrel.Approved, Investigational
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Pentaerythritol Tetranitrate.Approved, Investigational
LinsidomineLinsidomine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
LisofyllineLisofylline may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
LonazolacLonazolac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
LornoxicamLornoxicam may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
LoxoprofenLoxoprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
LumiracoxibLumiracoxib may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Magnesium salicylateMagnesium salicylate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
MasoprocolMasoprocol may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Meclofenamic acidMeclofenamic acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved
MedrogestoneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Medrogestone.Approved
Medroxyprogesterone acetateThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Medroxyprogesterone acetate.Approved, Investigational
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Megestrol acetateThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Megestrol acetate.Approved, Investigational, Vet Approved
MelagatranPentaerythritol Tetranitrate may increase the anticoagulant activities of Melagatran.Experimental
MeloxicamMeloxicam may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved
MesalazineMesalazine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
MestranolMestranol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
MetamizoleMetamizole may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Withdrawn
MethallenestrilMethallenestril may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
Methyl salicylateMethyl salicylate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved
MethylestrenoloneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Methylestrenolone.Experimental
MilrinoneMilrinone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
MirodenafilMirodenafil may increase the vasodilatory activities of Pentaerythritol Tetranitrate.Investigational
MizoribineMizoribine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
MofebutazoneMofebutazone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
MolsidomineMolsidomine may increase the hypotensive activities of Pentaerythritol Tetranitrate.Approved, Investigational
MoxestrolMoxestrol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
Mycophenolate mofetilMycophenolate mofetil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Mycophenolic acidMycophenolic acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
NabumetoneNabumetone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
NadroparinPentaerythritol Tetranitrate may increase the anticoagulant activities of Nadroparin.Approved, Investigational
NafamostatNafamostat may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
NaftifineNaftifine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
NaftopidilNaftopidil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
NaproxenNaproxen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved
NepafenacNepafenac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
NifenazoneNifenazone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
Niflumic AcidNiflumic Acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
NimesulideNimesulide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Withdrawn
NintedanibThe risk or severity of adverse effects can be increased when Pentaerythritol Tetranitrate is combined with Nintedanib.Approved
NitroaspirinNitroaspirin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
NomegestrolThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Nomegestrol.Approved
NorethisteroneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Norethisterone.Approved
NorgestrienoneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Norgestrienone.Experimental
ObinutuzumabThe risk or severity of adverse effects can be increased when Pentaerythritol Tetranitrate is combined with Obinutuzumab.Approved, Investigational
OlopatadineOlopatadine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
OlsalazineOlsalazine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Omacetaxine mepesuccinateThe risk or severity of bleeding can be increased when Pentaerythritol Tetranitrate is combined with Omacetaxine mepesuccinate.Approved, Investigational
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Nutraceutical
Omega-3-carboxylic acidsThe therapeutic efficacy of Pentaerythritol Tetranitrate can be increased when used in combination with Omega-3-carboxylic acids.Approved, Investigational
OrgoteinOrgotein may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Vet Approved
OtamixabanPentaerythritol Tetranitrate may increase the anticoagulant activities of Otamixaban.Investigational
OxaprozinOxaprozin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
OxyphenbutazoneOxyphenbutazone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Withdrawn
OzagrelOzagrel may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
ParecoxibParecoxib may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
ParnaparinParnaparin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
ParthenolideParthenolide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
PentoxifyllinePentoxifylline may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
PhenindionePhenindione may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
PhenprocoumonPhenprocoumon may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
Phenyl aminosalicylatePhenyl aminosalicylate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
PhenylbutazonePhenylbutazone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved
PicotamidePicotamide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
PimecrolimusPimecrolimus may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
PirfenidonePirfenidone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
PiroxicamPiroxicam may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
PirprofenPirprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
Polyestradiol phosphatePolyestradiol phosphate may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
PranoprofenPranoprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental, Investigational
PrasugrelPrasugrel may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
ProgesteroneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Progesterone.Approved, Vet Approved
ProglumetacinProglumetacin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
PromegestoneThe therapeutic efficacy of Pentaerythritol Tetranitrate can be decreased when used in combination with Promegestone.Experimental
PromestrienePromestriene may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
PropacetamolPropacetamol may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
PropyphenazonePropyphenazone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
ProquazoneProquazone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
Protein CPentaerythritol Tetranitrate may increase the anticoagulant activities of Protein C.Approved
Protein S humanPentaerythritol Tetranitrate may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydePentaerythritol Tetranitrate may increase the anticoagulant activities of Protocatechualdehyde.Approved
PTC299PTC299 may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
QuinestrolQuinestrol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
RamatrobanRamatroban may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
RelcovaptanRelcovaptan may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
ResveratrolResveratrol may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Experimental, Investigational
ReteplaseReteplase may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
ReviparinPentaerythritol Tetranitrate may increase the anticoagulant activities of Reviparin.Approved, Investigational
RidogrelRidogrel may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
RiociguatPentaerythritol Tetranitrate may increase the hypotensive activities of Riociguat.Approved
RivaroxabanPentaerythritol Tetranitrate may increase the anticoagulant activities of Rivaroxaban.Approved
RofecoxibRofecoxib may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Withdrawn
RosiglitazoneThe risk or severity of adverse effects can be increased when Pentaerythritol Tetranitrate is combined with Rosiglitazone.Approved, Investigational
SalicylamideSalicylamide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Salicylic acidSalicylic acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Vet Approved
SalsalateSalsalate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
SarpogrelateSarpogrelate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
SaruplaseSaruplase may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
SecoisolariciresinolSecoisolariciresinol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
SelexipagSelexipag may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
SemapimodSemapimod may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
SeratrodastSeratrodast may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
SerrapeptaseSerrapeptase may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
SevofluraneSevoflurane may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Vet Approved
SildenafilSildenafil may increase the vasodilatory activities of Pentaerythritol Tetranitrate.Approved, Investigational
SRT501SRT501 may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
StreptokinaseStreptokinase may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
SugammadexSugammadex may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
SulfasalazineSulfasalazine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
SulindacSulindac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
SulodexidePentaerythritol Tetranitrate may increase the anticoagulant activities of Sulodexide.Approved, Investigational
SuprofenSuprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Withdrawn
SuxibuzoneSuxibuzone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
Synthetic Conjugated Estrogens, ASynthetic Conjugated Estrogens, A may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Synthetic Conjugated Estrogens, BSynthetic Conjugated Estrogens, B may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TadalafilTadalafil may increase the vasodilatory activities of Pentaerythritol Tetranitrate.Approved, Investigational
TarenflurbilTarenflurbil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
TenecteplaseTenecteplase may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TenidapTenidap may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
TenoxicamTenoxicam may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TepoxalinTepoxalin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Vet Approved
TeriflunomideTeriflunomide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TesmilifeneTesmilifene may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
Testosterone cypionateThe therapeutic efficacy of Pentaerythritol Tetranitrate can be increased when used in combination with Testosterone cypionate.Approved
Testosterone enanthateThe therapeutic efficacy of Pentaerythritol Tetranitrate can be increased when used in combination with Testosterone enanthate.Approved
Testosterone undecanoateThe therapeutic efficacy of Pentaerythritol Tetranitrate can be increased when used in combination with Testosterone undecanoate.Approved, Investigational
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TiboloneTibolone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
TicagrelorTicagrelor may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TiclopidineTiclopidine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TinoridineTinoridine may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
TinzaparinTinzaparin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TioclomarolTioclomarol may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
TipranavirTipranavir may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
TirofibanTirofiban may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Tolfenamic AcidTolfenamic Acid may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
TolmetinTolmetin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TositumomabThe risk or severity of adverse effects can be increased when Pentaerythritol Tetranitrate is combined with Tositumomab.Approved, Investigational
TranilastTranilast may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
TrapidilTrapidil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TreprostinilTreprostinil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
TribenosideTribenoside may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Experimental
TriflusalTriflusal may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
TriptolideTriptolide may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Investigational
Trolamine salicylateTrolamine salicylate may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
TroxerutinPentaerythritol Tetranitrate may increase the anticoagulant activities of Troxerutin.Investigational
UdenafilUdenafil may increase the vasodilatory activities of Pentaerythritol Tetranitrate.Approved, Investigational
UrokinaseUrokinase may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Withdrawn
ValdecoxibValdecoxib may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Withdrawn
VardenafilVardenafil may increase the vasodilatory activities of Pentaerythritol Tetranitrate.Approved
Vitamin EVitamin E may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Nutraceutical, Vet Approved
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Pentaerythritol Tetranitrate.Approved
WarfarinWarfarin may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
XimelagatranXimelagatran may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Withdrawn
ZaltoprofenZaltoprofen may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational
ZeranolZeranol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Vet Approved
ZileutonZileuton may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved, Investigational, Withdrawn
ZomepiracZomepirac may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Withdrawn
Food Interactions
  • Take without regard to meals, taking it with food will dealy the onset on action.

References

General References
  1. King SY, Fung HL: Pharmacokinetics of pentaerythritol tetranitrate following intra-arterial and oral dosing in the rat. J Pharm Sci. 1986 Mar;75(3):247-50. [PubMed:3701607]
  2. Jurt U, Gori T, Ravandi A, Babaei S, Zeman P, Parker JD: Differential effects of pentaerythritol tetranitrate and nitroglycerin on the development of tolerance and evidence of lipid peroxidation: a human in vivo study. J Am Coll Cardiol. 2001 Sep;38(3):854-9. [PubMed:11527645]
  3. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [PubMed:23611293]
  4. Fraccarollo D, Galuppo P, Neuser J, Bauersachs J, Widder JD: Pentaerythritol Tetranitrate Targeting Myocardial Reactive Oxygen Species Production Improves Left Ventricular Remodeling and Function in Rats With Ischemic Heart Failure. Hypertension. 2015 Nov;66(5):978-87. doi: 10.1161/HYPERTENSIONAHA.115.05931. Epub 2015 Sep 8. [PubMed:26351025]
  5. Abrams J: Hemodynamic effects of nitroglycerin and long-acting nitrates. Am Heart J. 1985 Jul;110(1 Pt 2):216-24. [PubMed:3925741]
  6. Pentaerythritol tetranitrate [Link]
  7. CheBi - Pentaerythritol [Link]
  8. PETN [Link]
  9. OSHA document [Link]
  10. Pentaerythritol tetra nitrate [Link]
  11. Determination of Pentaerythritol Tetranitrate in Pharmaceuticals by High Performance Liquid Chromatography [Link]
  12. Pentaerythrityl tetranitrate (PETN): a better nitrate? [Link]
  13. Pentaerythritol tetranitrate [Link]
  14. Pentaerythritol tetranitrate [Link]
  15. Medscape- Pentaerythritol tetra nitrate [Link]
  16. Characterization of the Antioxidant Properties of Pentaerithrityl Tetranitrate (PETN)-Induction of the Intrinsic Antioxidative System Heme Oxygenase-1 (HO-1) [Link]
  17. Pentaerythritol tetranitrate [Link]
  18. Pentaerythritoltetranitrate (PETN) EPA document [Link]
  19. PENTAERYTHRITE TETRANITRATE [Link]
  20. Pentaerithrityl tetranitrate improves angiotensin II induced vascular dysfunction via induction of heme oxygenase-1 [Link]
External Links
KEGG Drug
D01721
PubChem Compound
6518
PubChem Substance
347827759
ChemSpider
6271
ChEBI
25879
ChEMBL
CHEMBL466659
Wikipedia
Pentaerythritol_tetranitrate
ATC Codes
C01DA05 — Pentaerithrityl tetranitrateC01DA55 — Pentaerithrityl tetranitrate, combinations
MSDS
Download (40.9 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Tablet, extended releaseOral80 mg
TabletOral10 mg
TabletOral20 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)140MSDS
water solubility0.133 mg/mLL2402
Predicted Properties
PropertyValueSource
Water Solubility0.133 mg/mLALOGPS
logP1.62ALOGPS
logP0.055ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area209.48 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity54.49 m3·mol-1ChemAxon
Polarizability22.79 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-004j-9000000000-14fe59ae096adb8f0c17
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as alkyl nitrates. These are organic compounds containing a nitrate that is O-linked to an alkyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organic oxoanionic compounds
Sub Class
Organic nitrates
Direct Parent
Alkyl nitrates
Alternative Parents
Organic nitro compounds / Organic nitric acids and derivatives / Organooxygen compounds / Organic oxides / Organic nitrogen compounds / Hydrocarbon derivatives
Substituents
Alkyl nitrate / Organic nitro compound / Organic nitric acid or derivatives / Organic 1,3-dipolar compound / Allyl-type 1,3-dipolar organic compound / Organic nitrogen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
pentaerythritol nitrate (CHEBI:25879)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Oxygen transporter activity
Specific Function
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name
HBA1
Uniprot ID
P69905
Uniprot Name
Hemoglobin subunit alpha
Molecular Weight
15257.405 Da
References
  1. Pentaerythritol tetranitrate [Link]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Oxygen transporter activity
Specific Function
Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an...
Gene Name
HBB
Uniprot ID
P68871
Uniprot Name
Hemoglobin subunit beta
Molecular Weight
15998.34 Da
References
  1. Pentaerythritol tetranitrate [Link]
3. Free radicals
Kind
Group
Organism
Human
Pharmacological action
No
Actions
Antagonist
References
  1. Fraccarollo D, Galuppo P, Neuser J, Bauersachs J, Widder JD: Pentaerythritol Tetranitrate Targeting Myocardial Reactive Oxygen Species Production Improves Left Ventricular Remodeling and Function in Rats With Ischemic Heart Failure. Hypertension. 2015 Nov;66(5):978-87. doi: 10.1161/HYPERTENSIONAHA.115.05931. Epub 2015 Sep 8. [PubMed:26351025]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inducer
General Function
Heme binding
Specific Function
Has guanylyl cyclase on binding to the beta-1 subunit.Isoform 2 acts as a negative regulator of guanylyl cyclase activity as it forms non-functional heterodimers with the beta subunits.
Gene Name
GUCY1A2
Uniprot ID
P33402
Uniprot Name
Guanylate cyclase soluble subunit alpha-2
Molecular Weight
81749.185 Da
References
  1. Pentaerythritol tetranitrate [Link]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inducer
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induce...
Gene Name
NOS3
Uniprot ID
P29474
Uniprot Name
Nitric oxide synthase, endothelial
Molecular Weight
133287.62 Da
References
  1. CheBi - Pentaerythritol [Link]
  2. Nitrate Reduction to Nitrite, Nitric Oxide and Ammonia by Gut Bacteria under Physiological Conditions [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Electron carrier activity
Specific Function
Not Available
Gene Name
ALDH2
Uniprot ID
P05091
Uniprot Name
Aldehyde dehydrogenase, mitochondrial
Molecular Weight
56380.93 Da
References
  1. OSHA document [Link]

Drug created on January 30, 2008 07:45 / Updated on May 01, 2018 23:18