Nitroglycerin (medication)

For the undiluted form used as an explosive, see Nitroglycerin.

Nitroglycerin
Clinical data
Trade namesNitrol, others
Other namesGlyceryl trinitrate
AHFS/Drugs.comMonograph
MedlinePlusa601086
Routes of
administration		Sublingual, transdermal, by mouth, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability<1%
Metabolismliver (rapid), red blood cells, vascular wall
Elimination half-life3 minutes
ExcretionIn urine, in bile
Identifiers
IUPAC name
  • 1,3-dinitrooxypropan-2-yl nitrate; [3-(nitrooxy)-2-[(nitrooxy)methyl]propyl] nitrate; 1,2,3-trinitroxy propane
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC3H5N3O9
Molar mass227.085 g·mol−1
3D model (JSmol)
SMILES
  • C(C(CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]
InChI
  • InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2 Y
  • Key:SNIOPGDIGTZGOP-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Nitroglycerin, also known as glyceryl trinitrate (GTN), is a vasodilator used for heart failure, high blood pressure, anal fissures, painful periods, and to treat and prevent chest pain caused by decreased blood flow to the heart (angina) or due to the recreational use of cocaine.[1][2][3][4] This includes chest pain from a heart attack.[1] It is taken by mouth, under the tongue, applied to the skin, or by injection into a vein.[1]

Common side effects include headache and low blood pressure.[1] The low blood pressure can be severe.[1] It is unclear if use in pregnancy is safe for the fetus.[1] It should not be used together with medications within the PDE5 inhibitor family such as sildenafil due to the risk of low blood pressure.[1] Nitroglycerin is in the nitrate family of medications.[1] While it is not entirely clear how it works, it is believed to function by dilating blood vessels.[1]

Nitroglycerin was written about as early as 1846[5][6] and came into medical use in 1878.[7][8][9] The drug nitroglycerin is a dilute form of the same chemical used as the explosive, nitroglycerin.[9] Dilution makes it non-explosive.[9] In 2022, it was the 196th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[10][11]

  1. ^ a b c d e f g h i "Nitroglycerin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  2. ^ Fenton C, Wellington K, Easthope SE (2006). "0.4% nitroglycerin ointment: in the treatment of chronic anal fissure pain". Drugs. 66 (3): 343–9. doi:10.2165/00003495-200666030-00006. PMID 16526822. S2CID 46984485.
  3. ^ Morgan PJ, Kung R, Tarshis J (May 2002). "Nitroglycerin as a uterine relaxant: a systematic review". Journal of Obstetrics and Gynaecology Canada. 24 (5): 403–9. doi:10.1016/S1701-2163(16)30403-0. PMID 12196860.
  4. ^ O'Leary ME, Hancox JC (May 2010). "Role of voltage-gated sodium, potassium and calcium channels in the development of cocaine-associated cardiac arrhythmias". British Journal of Clinical Pharmacology. 69 (5): 427–42. doi:10.1111/j.1365-2125.2010.03629.x. PMC 2856043. PMID 20573078.
  5. ^ Cite error: The named reference AS1847 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference AS1849 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference WM1879 was invoked but never defined (see the help page).
  8. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 454. ISBN 9783527607495. Archived from the original on 20 December 2016.
  9. ^ a b c Ravina E (2011). The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. p. 153. ISBN 9783527326693. Archived from the original on 20 December 2016.
  10. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  11. ^ "Nitroglycerin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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