Eritrityl tetranitrate - CAS 7297-25-8
Catalog number:
7297-25-8
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C4H6N4O12
Molecular Weight:
302.11
COA:
Inquire
Targets:
Others
Description:
Erythritol tetranitrate is an explosive compound. It is also a vasodilator, and was the active ingredient in the original "sustained release" tablets, made under a process patent in the early 1950s, called "nitroglyn". Ingesting Erythritol tetranitrate or prolonged skin contact can lead to absorption and what is known as a "nitro headache".
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Purity:
98%
Appearance:
Powder
Synonyms:
CHEBI:60072; Eritrityli tetranitras; Tetranitrate d'eritrityle; Tetranitrato de eritritilo; Cardilate; Tetranitrate, Erythrityl; [(2R,3S)-1,3,4-trinitrooxybutan-2-yl] nitrat
Solubility:
Soluble in DMSO
Storage:
-20℃ Freezer
MSDS:
Inquire
Application:
vasodilator
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
InChIKey:
SNFOERUNNSHUGP-ZXZARUISSA-N
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+
Canonical SMILES:
[O-][N+](=O)OC[C@@H](O[N+](=O)[O-])[C@H](CO[N+](=O)[O-])O[N+](=O)[O-]
1.Erythrityl tetranitrate compared with isosorbide dinitrate. Effects on systolic time intervals and nitrate modification of effects of food.
Nakamura Y, Haffty BG, Long RA, Hull HJ, Starbuck RR, Spodick DH. Pharmacotherapy. 1983 Jul-Aug;3(4):230-4.
The pharmacologic effects of erythrityl tetranitrate (ETN) and isosorbide dinitrate (ISDN) were compared to placebo using systolic time intervals (STI) in a randomized, double-blind study in 15 fasted male volunteers. Sublingual doses of ETN 5 mg, ISDN 5 mg, and placebo were administered to each volunteer at weekly intervals, and measurements of heart rate and STI [pre-ejection period (PEP), left ventricular ejection time (LVET), and PEP/LVET ratio] were made serially for up to 6 hours after each dose. STI were determined using ear densitography. Evaluation of the pharmacologic effects of ETN and ISDN were based on placebo-corrected changes from baseline values. Ejection time index (ETI) [LVET corrected for heart rate] was shortened, but the changes were not statistically significant for either drug. However, after ETN and ISDN, statistically significant (p less than 0.05) changes in PEP and PEP/LVET ratio were demonstrated for up to 240 minutes after dosing.
2.Erythrityl tetranitrate; drug efficacy study implementation; revocation of exemption; opportunity for a hearing--FDA. Notice.
Fed Regist. 1998 Jun 23;63(120):34188-90.
The Food and Drug Administration (FDA) is revoking the temporary exemption that has allowed single-entity coronary vasodilator drug products containing erythrityl tetranitrate to remain on the market beyond the time limits scheduled for implementation of the Drug Efficacy Study. FDA is announcing that the products lack substantial evidence of effectiveness and is offering an opportunity for a hearing on a proposal to withdraw approval of any applicable new drug applications (NDA's) or abbreviated new drug applications (ANDA's).
3.Pentaerithrityl tetranitrate and its phase I metabolites are potent activators of cellular cyclic GMP accumulation.
Hinz B1, Kuntze U, Schröder H. Biochem Biophys Res Commun. 1998 Dec 30;253(3):658-61.
Using pig kidney epithelial cells (LLC-PK1), the present study assesses the cyclic GMP stimulatory effect of pentaerithrityl tetranitrate and its metabolites in comparison to other therapeutically used nitric oxide donors. Pentaerithrityl tetranitrate was found to be the most potent activator of cyclic GMP synthesis compared to other clinically relevant organic nitrates (glyceryl trinitrate, isosorbide dinitrate, isosorbide-5-mononitrate). The phase I metabolite pentaerithrityl trinitrate was equipotent with its parent compound in stimulating cyclic GMP. The concentration-response curves of pentaerithrityl dinitrate and isosorbide dinitrate for cyclic GMP accumulation were virtually identical. In contrast, pentaerithrityl mononitrate and the phase II metabolite pentaerithrityl trinitrate glucuronide did not alter basal cyclic GMP levels. It is concluded that the long-term vasodilatory and antiischemic effects of pentaerithrityl tetranitrate are caused to a substantial extent by cyclic GMP-mediated actions of its pharmacologically active phase I metabolites.
4.High-performance liquid chromatographic determination of the nitrate esters isosorbide dinitrate, pentaerythritol tetranitrate, and erythrityl tetranitrate in various tablet forms.
Olsen CS, Scroggins HS. J Pharm Sci. 1984 Sep;73(9):1303-4.
A reliable, sensitive, and specific assay for isosorbide dinitrate pentaerythritol tetranitrate, and erythrityl tetranitrate in sublingual, uncoated, sustained-release, and chewable dosage forms, using high-performance liquid chromatography, is described. The nitrate ester dosage forms were dissolved in methanol, filtered, and injected directly into the liquid chromatograph. A variable-wavelength UV detector, operated at 220 nm, and a reverse-phase C18 microporous silica column were employed. The mobile phase was methanol-water (40:60). The proposed method is quantitative and reproducible.
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CAS 7297-25-8 Eritrityl tetranitrate

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