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Details

Stereochemistry ACHIRAL
Molecular Formula C5H8N4O12
Molecular Weight 316.1366
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTAERYTHRITOL TETRANITRATE

SMILES

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

InChI

InChIKey=TZRXHJWUDPFEEY-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C5H8N4O12
Molecular Weight 316.1366
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Sources: www.ncbi.nlm.nih.gov/pubmed/24071762
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pubmed/13106442

Pentaerythritol tetranitrate is an organic nitrate that has been used for the treatment of angina pectoris. Upon administration, the drug undergoes exstensive metabolism to NO which causes vasodilation and the relaxation of smooth muscle cells. The compound belongs to a familiy of explosive substances and may be used accordingly.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2111348
Sources: www.ncbi.nlm.nih.gov/pubmed/18574453
0.1 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PERITRATE

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
35 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENTAERYTHRITOL MONONITRATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
79 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENTAERYTHRITOL MONONITRATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
17 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENTAERYTHRITOL DINITRATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
7.5 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENTAERYTHRITOL DINITRATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.5 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENTAERYTHRITOL MONONITRATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
10.5 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENTAERYTHRITOL MONONITRATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4.5 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENTAERYTHRITOL DINITRATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4.5 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENTAERYTHRITOL DINITRATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
The nitric oxide donor pentaerythritol tetranitrate can preserve endothelial function in established atherosclerosis.
2001 Apr
Ca2+-induced phosphoethanolamine transfer to the outer 3-deoxy-D-manno-octulosonic acid moiety of Escherichia coli lipopolysaccharide. A novel membrane enzyme dependent upon phosphatidylethanolamine.
2001 Jan 12
Heme oxygenase-1 induction may explain the antioxidant profile of pentaerythrityl trinitrate.
2002 Feb 8
[Atherosclerosis progression and standard in coronary disease. Nitrate with special talents: PETN (pentaerythritol tetranitrate) is vasoprotective].
2002 Nov 7
Lack of oxidative stress during sustained therapy with isosorbide dinitrate and pentaerythrityl tetranitrate in healthy humans: a randomized, double-blind crossover study.
2003 Feb
Structural characterization of a novel branching pattern in the lipopolysaccharide from nontypeable Haemophilus influenzae.
2003 Jul
Comparison of the effects of pentaerythritol tetranitrate and nitroglycerin on endothelium-dependent vasorelaxation in male volunteers.
2003 Jun 1
In silico identification and experimental validation of PmrAB targets in Salmonella typhimurium by regulatory motif detection.
2004
Coupling capillary electrophoresis and high-field asymmetric waveform ion mobility spectrometry mass spectrometry for the analysis of complex lipopolysaccharides.
2004 Aug 15
Periplasmic cleavage and modification of the 1-phosphate group of Helicobacter pylori lipid A.
2004 Dec 31
Atomic resolution structures and solution behavior of enzyme-substrate complexes of Enterobacter cloacae PB2 pentaerythritol tetranitrate reductase. Multiple conformational states and implications for the mechanism of nitroaromatic explosive degradation.
2004 Jul 16
Phylogeny of Panax using chloroplast trnC-trnD intergenic region and the utility of trnC-trnD in interspecific studies of plants.
2004 Jun
Secondary electrospray ionization-ion mobility spectrometry for explosive vapor detection.
2004 May 15
Nitroester drug's effects and their antagonistic effects against morphine on human sphincter of Oddi motility.
2005 Apr 21
[Comparison of the effect of nitroglycerine and pentaerithritol compositum on exercise time restricted by anginal pain or objective parameters of ischaemia in patients with stable angina].
2005 Aug
Acetylcholine and bradykinin enhance hypotension and affect the function of remodeled conduit arteries in SHR and SHR treated with nitric oxide donors.
2005 Jun
Anharmonic vibrational properties of explosives from temperature-dependent Raman.
2005 Nov 10
Raman scattering studies of the high-pressure stability of pentaerythritol tetranitrate, C(CH2ONO2)4.
2005 Oct 20
NO-donors, part X [1] : investigations on the stability of pentaerythrityl tetranitrate (PETN) by HPLC-chemoluminescence-N-detection (CLND) versus UV-detection in HPLC.
2006 Mar 18
Prediction of heat of formation and related parameters of high energy materials.
2006 May 20
Mitochondrial oxidative stress and nitrate tolerance--comparison of nitroglycerin and pentaerithrityl tetranitrate in Mn-SOD+/- mice.
2006 Nov 8
Number of nitrate groups determines reactivity and potency of organic nitrates: a proof of concept study in ALDH-2-/- mice.
2007 Feb
PetG and PetN, but not PetL, are essential subunits of the cytochrome b6f complex from Synechocystis PCC 6803.
2007 Jan-Feb
On-line strategies for determining trace levels of nitroaromatic explosives and related compounds in water.
2007 Jun 15

Sample Use Guides

1 tablet (80 mg) before breakfast and one before the evening meal (sustained action).
Route of Administration: Oral
In Vitro Use Guide
Sources: www.ncbi.nlm.nih.gov/pubmed/25928879
The number of adhering platelets to fibrinogen coated glass slides was significantly reduced by 30 minute in vitro pre-incubation of PRP with pentaerythritol tetranitrate (5ug/mL) as compared to control samples which were pre-incubated with the solvent DMSO.
Substance Class Chemical
Created
by admin
on Fri Dec 16 16:07:03 UTC 2022
Edited
by admin
on Fri Dec 16 16:07:03 UTC 2022
Record UNII
10L39TRG1Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENTAERYTHRITOL TETRANITRATE
HSDB   JAN   MI   VANDF  
Systematic Name English
PENTAERYTHRITOL TETRANITRATE [VANDF]
Common Name English
2,2-Bis(hydroxymethyl)-1,3-propanediol tetranitrate
Systematic Name English
PENTAERYTHRITOL TETRANITRATE [JAN]
Common Name English
PENTAERYTHRITOL TETRANITRATE [HSDB]
Common Name English
PENTAERYTHRITYL TETRANITRATE
Common Name English
Pentaerithrityl tetranitrate [WHO-DD]
Common Name English
1,3-PROPANEDIOL, 2,2-BIS((NITROOXY)METHYL)-, DINITRATE (ESTER)
Common Name English
PENTRITOL TEMPULES
Brand Name English
PENTAERITHRITYL TETRANITRATE [MART.]
Common Name English
PENTAERYTHRITOL TETRANITRATE [MI]
Common Name English
PENTALONG
Brand Name English
pentaerithrityl tetranitrate [INN]
Common Name English
PERITRATE
Brand Name English
PENTAERITHRITYL TETRANITRATE
INN   MART.   WHO-DD  
INN  
Official Name English
Classification Tree Code System Code
WHO-VATC QC01DA05
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
WHO-VATC QC01DA55
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
NCI_THESAURUS C29707
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
WHO-ATC C01DA05
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
CFR 21 CFR 250.102
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
WHO-ATC C01DA55
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
WHO-ATC C01DA20
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
Code System Code Type Description
EPA CompTox
DTXSID2023430
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
CHEBI
17553
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
NCI_THESAURUS
C47660
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
ECHA (EC/EINECS)
201-084-3
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
ChEMBL
CHEMBL466659
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
MESH
D010417
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
HSDB
6313
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
RXCUI
7992
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY RxNorm
WIKIPEDIA
PENTAERYTHRITOL TETRANITRATE
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
CAS
78-11-5
Created by admin on Fri Dec 16 16:07:03 UTC 2022 , Edited by admin on Fri Dec 16 16:07:03 UTC 2022
PRIMARY
MERCK INDEX
M8492
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY Merck Index
PUBCHEM
6518
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
CHEBI
25879
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
EVMPD
SUB09676MIG
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
FDA UNII
10L39TRG1Z
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
DRUG BANK
DB06154
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
INN
1455
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
DRUG CENTRAL
2087
Created by admin on Fri Dec 16 16:07:04 UTC 2022 , Edited by admin on Fri Dec 16 16:07:04 UTC 2022
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG