Nitroglycerin

Details

Stereochemistry	ACHIRAL
Molecular Formula	C3H5N3O9
Molecular Weight	227.0865
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=SNIOPGDIGTZGOP-UHFFFAOYSA-N

InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2

HIDE SMILES / InChI

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
liberation of NO 18	Activator 1,430
Soluble guanylate cyclase 34	Activator 1,430	0.1 µM [EC50]
Soluble guanylate cyclase 34	Activator 1,430
Atrial natriuretic peptide receptor A 19	Activator 1,430
Soluble guanylate cyclase 34	Activator 1,430
Soluble guanylate cyclase 34	Activator 1,430
Soluble guanylate cyclase 34	Activator 1,430

Conditions

Condition	Modality	Highest Phase	Product
Hypertensive crises 18	Primary	Approved 8,429	NIPRIDE
Heart failure 103	Primary	Approved 8,429	NIPRIDE
Pulmonary hypertension 30	Palliative	Approved 8,429	INOMAX
Angina pectoris 106	Primary	Approved 8,429	DILATRATE-SR
Angina pectoris 106	Primary	Approved 8,429	MONOKET
Angina pectoris 106	Primary	Approved 8,429	Unknown
Coronary heart disease 41	Primary	Basic research	Unknown
Angina 32	Primary	Approved 8,429	NITROSTAT
Myocardial infarction 121	Primary	Approved 8,429	NITROGLYCERIN
Hypertension 567	Primary	Approved 8,429	NITROGLYCERIN
Heart failure 103	Primary	Approved 8,429	NITROGLYCERIN
Angina pectoris 106	Primary	Approved 8,429	Metamine
Angina pectoris 106	Primary	Approved 8,429	PERITRATE

C_max

Value	Dose	Analyte	Population
35 ng/mL	100 mg single, oral	PENTAERYTHRITOL MONONITRATE plasma	Homo sapiens
79 ng/mL	100 mg single, oral	PENTAERYTHRITOL MONONITRATE plasma	Homo sapiens
1151 ng/mL	120 mg 1 times / day steady-state, oral	ISOSORBIDE MONONITRATE plasma	Homo sapiens
557 ng/mL	60 mg 1 times / day steady-state, oral	ISOSORBIDE MONONITRATE plasma	Homo sapiens
388 ng/mL	20 mg single, oral	ISOSORBIDE MONONITRATE plasma	Homo sapiens
356 ng/mL	20 mg single, intravenous	ISOSORBIDE MONONITRATE plasma	Homo sapiens
1.7 pg/mL	800 μg single, sublingual	NITROGLYCERIN plasma	Homo sapiens
17 ng/mL	100 mg single, oral	PENTAERYTHRITOL DINITRATE plasma	Homo sapiens
7.5 ng/mL	100 mg single, oral	PENTAERYTHRITOL DINITRATE plasma	Homo sapiens
187 ng/mL	20 mg single, oral	ISOSORBIDE DINITRATE plasma	Homo sapiens
84 ng/mL	13 mg single, oral	GLYCERYL 1,2-DINITRATE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
14241 ng × h/mL	120 mg 1 times / day steady-state, oral	ISOSORBIDE MONONITRATE plasma	Homo sapiens
6979 ng × h/mL	60 mg 1 times / day steady-state, oral	ISOSORBIDE MONONITRATE plasma	Homo sapiens
2524 ng × h/mL	20 mg single, oral	ISOSORBIDE MONONITRATE plasma	Homo sapiens
2647 ng × h/mL	20 mg single, intravenous	ISOSORBIDE MONONITRATE plasma	Homo sapiens
12.3 pg × min/mL	800 μg single, sublingual	NITROGLYCERIN plasma	Homo sapiens
1458 ng × h/mL	20 mg single, oral	ISOSORBIDE DINITRATE plasma	Homo sapiens
3380 ng × min/mL	13 mg single, oral	GLYCERYL 1,2-DINITRATE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
2 min	single, intravenous	NITROPRUSSIDE plasma	Rattus norvegicus
10.5 h	100 mg single, oral	PENTAERYTHRITOL MONONITRATE plasma	Homo sapiens
10.5 h	100 mg single, oral	PENTAERYTHRITOL MONONITRATE plasma	Homo sapiens
6.2 h	120 mg 1 times / day steady-state, oral	ISOSORBIDE MONONITRATE plasma	Homo sapiens
6.2 h	60 mg 1 times / day steady-state, oral	ISOSORBIDE MONONITRATE plasma	Homo sapiens
4 h	20 mg single, oral	ISOSORBIDE MONONITRATE plasma	Homo sapiens
4 h	20 mg single, intravenous	ISOSORBIDE MONONITRATE plasma	Homo sapiens
40 min	800 μg single, sublingual	NITROGLYCERIN plasma	Homo sapiens
4.5 h	100 mg single, oral	PENTAERYTHRITOL DINITRATE plasma	Homo sapiens
4.5 h	100 mg single, oral	PENTAERYTHRITOL DINITRATE plasma	Homo sapiens
303 min	20 mg single, oral	ISOSORBIDE DINITRATE plasma	Homo sapiens
50 min	13 mg single, oral	GLYCERYL 1,2-DINITRATE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
100%			ISOSORBIDE DINITRATE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
75 mg 3 times / day multiple, oral Recommended\|MTD	unhealthy, mean age 57 years n = 517	Other AEs: Headache, Dizziness...
75 mg 3 times / day multiple, oral Recommended\|MTD	unhealthy, mean age 57 years n = 517	Disc. AE: Chest pain, Heart arrest...
75 mg 3 times / day multiple, oral Recommended\|MTD	unhealthy, mean age 57 years n = 517	Other AEs: Neurolysis, Ophthalmitis...
75 mg 3 times / day multiple, oral Recommended\|MTD	unhealthy, mean age 57 years n = 517	Disc. AE: Asthenia, Headache...
240 mg 1 times / day steady, oral Highest studied dose	unhealthy, adult n = 312	Other AEs: Headache...

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AEs

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AE	Significance	Dose	Population
Nausea	10%	75 mg 3 times / day multiple, oral Recommended\|MTD	unhealthy, mean age 57 years n = 517
Asthenia	14%	75 mg 3 times / day multiple, oral Recommended\|MTD	unhealthy, mean age 57 years n = 517
Tachycardia	2%	75 mg 3 times / day multiple, oral Recommended\|MTD	unhealthy, mean age 57 years n = 517
Amblyopia	3%	75 mg 3 times / day multiple, oral Recommended\|MTD	unhealthy, mean age 57 years n = 517
Hyperlipidemia	3%	75 mg 3 times / day multiple, oral Recommended\|MTD	unhealthy, mean age 57 years n = 517

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	substrate 1,037	substrate 1,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
ALDH2 19 P-gp 1,461 MRP2 383 K+ channels 70 Ca2+ channels 57	ALDH2 19 CYP1A2 1,054 CYP2A6 543 CYP2E1 667 CYP4A11 119	OCT1 35

Drug as perpetrator

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Target	Modality	Activity
ALDH2 19	inhibitor 3,277	no
K+ channels 70	inhibitor 3,277	no
Ca2+ channels 60	inhibitor 3,277	yes
MRP2 475	inhibitor 3,277	yes
OCT1 543	inducer 1,573	yes

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Drug as victim

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Target	Modality	Activity
CYP3A4 1,737	substrate 3,367	major
CYP1A2 1,054	substrate 3,367	minor
CYP2A6 543	substrate 3,367	minor
CYP2C9 1,037	substrate 3,367	minor
CYP2D6 1,217	substrate 3,367	minor

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-4956	http://www.3bsc.com/index/pro_info.php?id=79896
3B Scientific (Wuhan) Corp	3B3-046180	http://www.3bsc.com/index/pro_info.php?id=82779
AA Blocks	AA00ILEO	https://www.aablocks.com/goods/Goods/detail?id=AA00ILEO
ABI Chem	AC1L1MPG
ABI Chem	AC1Q21X4

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PubMed

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Title	Date	PubMed
[The classic anti-anginal agents and molsidomine].	1983 Feb	6407452
Prostaglandin I2 and the nitric oxide donor molsidomine have synergistic effects on thromboresistance in man.	1992 Mar	1576049
Nitric oxide donors antagonize N-nitro-L-arginine and haloperidol catalepsy: potential implication for the treatment of Parkinsonism?	1997 Aug	9437770
Nitric oxide (NO) pathway and locomotor hyperactivity towards dopaminomimetics in rats.	1997 Sep-Oct	9566027
[The effect of nitric oxide administration on pateints with pulmonary hypertension: a dose-response study].	1998 Feb	10923418

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Sample Use Guides

In Vivo Use Guide

twice-daily 8-mg tablet

Route of Administration: Intravenous

In Vitro Use Guide

Was studied the action of the biologically active metabolite of molsidomine, N-morpholino-N-nitrosoamino-acetonitrile (SIN), on eicosanoid formation and functional behavior of bovine coronary arteries and human platelets in vitro. Molsidomine itself was inactive

Show entries

Name

Type

Language

Nitroglycerin

Systematic Name

English

NITRO-DUR

Brand Name

English

RECTIV

Brand Name

English

NITRO IV

Brand Name

English

GLYCERIN TRINITRATE

Systematic Name

English

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Classification Tree

Code System

Code

Muscle relaxants

WHO-VATC

QC05AE01

Organic nitrates

WHO-VATC

QC01DA02

CFR

21 CFR 250.102

NDF-RT

N0000007647

NDF-RT

N0000007647

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Code System

Code

Type

Description

WIKIPEDIA

Nitroglycerin (medication)

PRIMARY

ECHA (EC/EINECS)

200-240-8

PRIMARY

FDA UNII

G59M7S0WS3

PRIMARY

DAILYMED

G59M7S0WS3

PRIMARY

PUBCHEM

4510

PRIMARY

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ACTIVE MOIETY


					31C4KY9ESH

NITRIC OXIDE

METABOLITE (PARENT)


					8542I4GE54

GLYCERYL 1,2-DINITRATE

METABOLITE (PARENT)


					3P3G498O9T

GLYCERYL 1,3-DINITRATE

METABOLITE (PARENT)


					212452MD4J

GLYCERYL 1-NITRATE

SUBSTANCE RECORD


					G59M7S0WS3

Nitroglycerin

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator