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Compound Detail

CHEMBL730

NITROGLYCERIN
💊 Approved Drug
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💊 Approved Drug
O=[N+]([O-])OCC(CO[N+](=O)[O-])O[N+](=O)[O-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL730
Name NITROGLYCERIN
Phase Approved
Structure Type MOL
InChI Key SNIOPGDIGTZGOP-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1200689

Known Names

C01DA02 Chlormethine oxide hydrochloride Coro-nitro Deponit 10 Deponit 5 Diluted nitroglycerin Glonoinum Glyceryl trinitrate Glyceryl trinitrate solution Glytrin Gonitro Imx-150 +18 more
7
Targets
19
Activities
2
Assay Types
0
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

227.1
MW (Da)
-1.02
ALogP
9
HBA
0
HBD
157.1
PSA (Ų)
0.37
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral Topical

Flags

Black Box Warning Natural Product Prodrug

Extended Properties

Molecular Formula C3H5N3O9
MW 227.08
Aromatic Rings 0
Heavy Atoms 15
NP-Likeness -0.04

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Soluble guanylate cyclase activator ACTIVATOR Soluble guanylate cyclase ✓ ✓

Indications

Angina Pectoris Cardiovascular Diseases Coronary Artery Disease Heart Failure Heart Failure Hemorrhoids Hypertension Myocardial Infarction Pain Anus Diseases Arthritis, Rheumatoid Bone Diseases, Metabolic Heart Diseases Muscle Cramp Myocardial Ischemia Osteoporosis Raynaud Disease Reperfusion Injury Scleroderma, Localized Stroke

ATC Classification

C01DA02
glyceryl trinitrate
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY
C01DA52
glyceryl trinitrate, combinations
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY
C05AE01
glyceryl trinitrate
Level 1: CARDIOVASCULAR SYSTEM
Level 2: VASOPROTECTIVES

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

EC50 13 meas. best 8.15
IC50 6 meas. best 8.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Saphenous artery
CHEMBL4845615
 IC50 8.72 8.37 1.9 2
Canis familiaris
CHEMBL373
 EC50 8.15 8.075 7.0 2
Oryctolagus cuniculus
CHEMBL374
 IC50 7.8 7.8 16.0 1
Rattus norvegicus
CHEMBL376
 EC50 7.66 6.6725 22.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.57 7.57 27.0 1
Aorta
CHEMBL613606
 EC50 7.54 6.3275 29.0 4
Molecular identity unknown
CHEMBL612546
 EC50 7.45 7.45 35.6 1
Aorta
CHEMBL613606
 IC50 7.23 7.01 58.9 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Saphenous artery IC50 = 1.9 nM 8.72 Vasorelaxant activity in normal Chinchilla rabbit saphenous artery ring administ... 28557445
Canis familiaris EC50 = 7.0 nM 8.15 In vitro vascular relaxation in canine mesenteric veins precontracted with pheny... 1654425
Saphenous artery IC50 = 9.6 nM 8.02 Vasorelaxant activity in nirate-tolerant Chinchilla rabbit saphenous artery ring... 28557445
Canis familiaris EC50 = 10.0 nM 8.0 In vitro vascular relaxation in canine coronary arteries precontracted with pros... 1654425
Oryctolagus cuniculus IC50 = 16.0 nM 7.8 Vasorelaxation activity in the isolated endothelium-denuded rabbit aorta 7837224
Rattus norvegicus EC50 = 22.0 nM 7.66 Capacity to increase [Ca2+] entry into the vascular smooth muscle was evaluated ... 15115410
Rattus norvegicus EC50 = 22.4 nM 7.65 Relaxation of endothelium denucleated strips of rat aorta precontracted with nor... 9046336
NON-PROTEIN TARGET EC50 = 27.0 nM 7.57 Vasorelaxant activity in pig pulmonary artery by organ bath experiment 19406636
Aorta EC50 = 29.0 nM 7.54 Vasodilatory activity in Wistar rat endothelium-denuded thoracic aortic ring ass... 19438239
Molecular identity unknown EC50 = 35.6 nM 7.45 Vasodilatory effect in pig pulmonary artery assessed as inhibition of PGF2-alpha... 17855086
Aorta IC50 = 58.88 nM 7.23 Vasorelaxant activity in endothelium-denuded Wistar rat thoracic aortic ring ass... 19595600
Aorta IC50 = 125.89 nM 6.9 Vasorelaxant activity in Wistar rat endothelium-removed thoracic aortic rings as... 23534442
Aorta IC50 = 125.89 nM 6.9 Vasorelaxation activity against KCl-induced contraction in isolated Wistar rat t... 21992176
Aorta EC50 = 420.0 nM 6.38 Vasodilatory activity in Wistar rat endothelium-denuded thoracic aortic ring ass... 19438239
Aorta EC50 = 940.0 nM 6.03 Vasodilatory activity in Wistar rat endothelium-denuded thoracic aortic ring ass... 19438239
Rattus norvegicus EC50 = 1900.0 nM 5.72 Effective concentration for relaxation of isolated rat aortic strips, submaximal... 12270164
Rattus norvegicus EC50 = 2200.0 nM 5.66 Compound was tested for its vasodilator effects on endothelium-denuded strips of... 7996554
Aorta EC50 = 4400.0 nM 5.36 Vasodilatory activity in Wistar rat endothelium-denuded cross tolerant thoracic ... 19438239

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
1654425 10.1021/jm00113a002 Canis familiaris 11
19438239 10.1021/jm9002236 Aorta 8
12699747 10.1016/s0960-894x(03)00199-9 Canis familiaris 4
7837224 10.1021/jm00001a018 Rattus norvegicus 4
20014752 10.1021/tx900326k Hepatotoxicity 3
1654425 10.1021/jm00113a002 Unchecked 2
7996554 10.1021/jm00051a020 Rattus norvegicus 2
14695839 10.1021/jm030333h Cavia porcellus 2
10498219 10.1016/s0960-894x(99)00445-x Cavia porcellus 2
20097072 10.1016/j.bmcl.2010.01.014 No relevant target 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
21992176 10.1021/jm200715n Aorta 2
11831908 10.1021/jm010394k Cavia porcellus 2
19595600 10.1016/j.bmc.2009.06.049 Aorta 2
9046336 10.1021/jm960379t Molecular identity unknown 2
17855086 10.1016/j.bmcl.2007.08.046 Molecular identity unknown 2
19419861 10.1016/j.bmcl.2009.04.059 No relevant target 2
18096394 10.1016/j.bmc.2007.12.006 Unchecked 2
18295489 10.1016/j.bmc.2007.11.029 Rattus norvegicus 2

Data from ChEMBL 36 via Core Engine