Indication Type	Indication	Combined Product Details	Approval Level	Patient Characteristics	Dose Form
Prevention of	Angina pectoris		••••••••••••		•••••••• •••••••• •••••••• ••••••
Prevention of	Angina pectoris		••••••••••••		••••••
Used as adjunct in combination to manage	Heart failure	Combination Product in combination with: Hydralazine (DB01275)	••••••••••••	••••••••••••••• •••••	••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Isosorbide Dinitrate is a moderate to long acting oral organic nitrate used for the relief and prophylactic management of angina pectoris. It relaxes the vascular smooth muscle and consequent dilatation of peripheral arteries and veins, especially the latter. Dilatation of the veins promotes peripheral pooling of blood and decreases venous return to the heart, thereby reducing left ventricular end- diastolic pressure and pulmonary capillary wedge pressure (preload). Arteriolar relaxation reduces systemic vascular resistance, systolic arterial pressure, and mean arterial pressure.

Mechanism of action

Isosorbide dinitrate is converted to the active nitric oxide to activate guanylate cyclase. This activation increases levels of cyclic guanosine 3',5'-monophosphate (cGMP). cGMP activates protein kinases and causes a series of phosphorylation reactions which leads to dephosphorylation of myosin light chains of smooth muscle fibres. Finally there is a release of calcium ions which causes smooth muscle relaxation and vasodilation.

Target	Actions	Organism
AAtrial natriuretic peptide receptor 1	agonist	Humans

Absorption

Absorption of isosorbide dinitrate after oral dosing is nearly complete, but bioavailability is highly variable (10% to 90%), with extensive first-pass metabolism in the liver. The average bioavailability of isosorbide dinitrate is about 25%.

Volume of distribution

2 to 4 L/kg

Protein binding

Very low

Metabolism

Hepatic

Route of elimination

Not Available

Half-life

1 hour

Clearance

Not Available

Adverse Effects

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Toxicity

Symptoms of overdose include reduced cardiac output and hypotension.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abaloparatide	The risk or severity of adverse effects can be increased when Isosorbide dinitrate is combined with Abaloparatide.
Acebutolol	The risk or severity of adverse effects can be increased when Isosorbide dinitrate is combined with Acebutolol.
Acetaminophen	Isosorbide dinitrate may increase the hepatotoxic activities of Acetaminophen.
Aldesleukin	The risk or severity of adverse effects can be increased when Aldesleukin is combined with Isosorbide dinitrate.
Aliskiren	The risk or severity of adverse effects can be increased when Isosorbide dinitrate is combined with Aliskiren.

Food Interactions

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Products

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Active Moieties

Name	Kind	UNII	CAS	InChI Key
Isosorbide	unknown	WXR179L51S	652-67-5	KLDXJTOLSGUMSJ-JGWLITMVSA-N

Product Images

International/Other Brands

Carvasin (Ayerst) / Flindix (Vitória) / Isoket (Schwarz) / Isorbid (Armstrong) / Nitrosorbide (Lusofarmaco) / Sorbidilat (Actavis)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Cedocard-SR Srt 20mg	Tablet, extended release	20 mg	Oral	Paladin Labs Inc	1987-12-31	2009-08-07
Cedocard-SR Srt 40mg	Tablet, extended release	40 mg	Oral	Paladin Labs Inc	1995-12-31	2009-08-07
Coradur Tab 20mg	Tablet, extended release	20 mg	Oral	Glaxo Canada Inc	1987-12-31	1997-04-25
Coronex	Tablet	30 mg	Oral	Wyeth Ltd.	1994-12-31	2007-01-08
Coronex	Tablet	10 mg	Oral	Wyeth Ltd.	1994-12-31	2007-01-08

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
IsoDitrate	Tablet, extended release	40 mg/1	Oral	Amedra Pharmaceuticals	2010-04-30	2010-04-30
Isosorbide	Tablet	10 mg/1	Oral	BluePoint Laboratories	2018-11-30	Not applicable
Isosorbide	Tablet	5 mg/1	Oral	Golden State Medical Supply, Inc.	1987-10-26	2017-01-02
Isosorbide	Tablet	10 mg/1	Oral	Med Health Pharma LLC.	2011-03-02	2012-04-15
Isosorbide	Tablet	20 mg/1	Oral	Golden State Medical Supply, Inc.	1987-11-02	2017-01-02

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
BiDil	Isosorbide dinitrate (20 mg/1) + Hydralazine hydrochloride (37.5 mg/1)	Tablet, film coated	Oral	Arbor Pharmaceuticals	2005-06-23	2015-12-31
BiDil	Isosorbide dinitrate (20 mg/1) + Hydralazine hydrochloride (37.5 mg/1)	Tablet, film coated	Oral	Remedy Repack	2013-10-08	2013-10-09
BiDil	Isosorbide dinitrate (20 mg/1) + Hydralazine hydrochloride (37.5 mg/1)	Tablet, film coated	Oral	Azurity	2012-12-05	Not applicable
Isosorbide Dinitrate and Hydralazine Hydrochloride	Isosorbide dinitrate (20 mg/1) + Hydralazine hydrochloride (37.5 mg/1)	Tablet, film coated	Oral	Wilshire Pharmaceuticals	2022-04-15	Not applicable
Isosorbide dinitrate and hydralazine hydrochloride	Isosorbide dinitrate (20 mg/1) + Hydralazine hydrochloride (37.5 mg/1)	Tablet	Oral	Ingenus Pharmaceuticals, LLC	2022-02-12	Not applicable

Chemical Identifiers

UNII: IA7306519N
CAS number: 87-33-2
InChI Key: MOYKHGMNXAOIAT-JGWLITMVSA-N
InChI: InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1
IUPAC Name: (3R,3aS,6S,6aS)-6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl nitrate
SMILES: [H][C@]12OC[C@H](O[N+]([O-])=O)[C@@]1([H])OC[C@H]2O[N+]([O-])=O

References

Synthesis Reference

Gunter Cordes, Ulrich Munch, Ewald Giesselmann, "Supersaturated isosorbide dinitrate solution, process for its production and its use." U.S. Patent US4156736, issued August, 1976.

US4156736

General References

FDA Approved Products: Bidil (isosorbide dinitrate and hydralazine hydrochloride) oral tablets [Link]

External Links

Human Metabolome Database: HMDB0015021
KEGG Drug: D00516
KEGG Compound: C07456
PubChem Compound: 6883
PubChem Substance: 46506412
ChemSpider: 6619
RxNav: 6058
ChEBI: 6061
ChEMBL: CHEMBL6622
ZINC: ZINC000018089317
Therapeutic Targets Database: DAP001057
PharmGKB: PA450125
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Isosorbide_dinitrate

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Post-anesthesia Recovery	1
4	Completed	Prevention	Anesthetics Adverse Reaction / Coronary Artery Atherosclerosis / Insulin resistance syndrome	1
4	Completed	Prevention	Chronic Hemodialysis (ESRD)	1
4	Completed	Treatment	Congestive Heart Failure (CHF)	1
4	Completed	Treatment	Coronary Artery Stenosis / Coronary Heart Disease (CHD)	1

Pharmacoeconomics

Manufacturers

Alcon laboratories inc
Schwarz pharma inc
Wyeth ayerst laboratories
Astrazeneca pharmaceuticals lp
Caraco pharmaceutical laboratories ltd
Corepharma llc
Biovail laboratories inc
Mutual pharmaceutical co inc
Par pharmaceutical inc
Sandoz inc
Superpharm corp
Watson laboratories inc
West ward pharmaceutical corp
West ward inc

Packagers

Amedra Pharmaceuticals LLC
Amerisource Health Services Corp.
Atlantic Biologicals Corporation
Bryant Ranch Prepack
BTA Pharmaceuticals
Caraco Pharmaceutical Labs
Cardinal Health
Consolidated Midland Corp.
Corepharma LLC
Dept Health Central Pharmacy
DHHS Program Support Center Supply Service Center
Direct Dispensing Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
Eon Labs
Forest Pharmaceuticals
Golden State Medical Supply Inc.
H and H Laboratories
Heartland Repack Services LLC
Hikma Pharmaceuticals
Inwood Labs
Kaiser Foundation Hospital
Lake Erie Medical and Surgical Supply
Liberty Pharmaceuticals
Major Pharmaceuticals
Meda AB
Murfreesboro Pharmaceutical Nursing Supply
Neighborcare Repackaging Inc.
Nitromed Inc.
Nucare Pharmaceuticals Inc.
Palmetto Pharmaceuticals Inc.
Par Pharmaceuticals
PCA LLC
PD-Rx Pharmaceuticals Inc.
Pharmedix
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Qualitest
Remedy Repack
Resource Optimization and Innovation LLC
Rising Pharmaceuticals
Sandhills Packaging Inc.
Sandoz
Schwarz Pharma Inc.
Southwood Pharmaceuticals
Talbert Medical Management Corp.
Tya Pharmaceuticals
Va Cmop Dallas
Vangard Labs Inc.
Watson Pharmaceuticals
West-Ward Pharmaceuticals

Dosage Forms

Form	Route	Strength
Solution	Intravenous	50.000 mg
Tablet	Oral	5 mg
Tablet, film coated	Oral
Solution	Intravenous; Parenteral
Tablet, delayed release
Tablet, delayed release		20 mg
Tablet, delayed release		40 mg
Tablet	Oral	40 MG
Tablet	Oral; Sublingual	5 MG
Tablet
Tablet, extended release	Oral
Tablet, extended release	Oral	20 mg
Tablet, extended release	Oral	40 mg
Tablet	Oral	10.000 mg
Tablet	Sublingual	5.000 mg
Capsule	Oral	40 mg/1
Capsule, extended release	Oral	40 mg/1
Capsule	Oral	120 MG
Injection	Intravenous	0.05 %
Injection	Intravenous	0.1 %
Injection, solution, concentrate	Intravenous; Parenteral	1 MG/ML
Tablet	Oral	10 mg
Tablet	Oral	30 mg
Capsule, extended release	Oral	40 mg
Capsule, extended release	Oral	20 MG
Capsule, extended release	Oral	60 MG
Tablet		5 MG
Tablet		20 MG
Tablet		40 MG
Tablet	Oral	1000000 mg
Solution	Buccal	2.510 g
Solution	Intravenous	10.000 mg
Tablet, orally disintegrating	Sublingual	5 MG
Injection	Intracoronary; Intravenous
Capsule, extended release	Oral	120 MG
Capsule, extended release	Oral	80 MG
Capsule, coated pellets	Oral	20 mg
Capsule, coated pellets	Oral	40 mg
Tablet	Sublingual
Injection	Intravenous
Tablet	Oral	5.000 mg
Tablet, extended release	Oral	40 mg/1
Tablet	Oral	2.5 mg/1
Tablet	Oral	40 mg/1
Tablet	Oral	10 mg/1
Tablet	Oral	20 mg/1
Tablet	Oral	5 mg/1
Tablet	Oral
Tablet	Oral	30 mg/1
Tablet	Sublingual	2.5 mg/1
Tablet	Sublingual	5 mg/1
Tablet	Oral
Tablet	Transmucosal	10 mg
Tablet	Transmucosal	5 mg
Capsule	Oral	20 MG
Capsule	Oral	40 MG
Cream		40 G
Injection, solution	Intravenous; Parenteral	5 MG/10ML
Solution	Intravenous	40.00 mg
Injection	Intramuscular	1 mg/100mL
Solution	Parenteral	100.00 mg
Tablet		30 mg
Tablet	Sublingual	5 mg
Tablet		10 mg

Prices

Unit description	Cost	Unit
Isordil Titradose 40 mg tablet	1.7USD	tablet
Isordil 40 mg tablet	1.58USD	tablet
Dilatrate-sr 40 mg capsule	1.48USD	capsule
Isochron 40 mg tablet sa	1.07USD	tablet
Isosorbide Dinitrate CR 40 mg Controlled Release Tabs	0.88USD	tab
Isosorbide Mononitrate 20 mg tablet	0.78USD	tablet
Isosorbide Mononitrate 10 mg tablet	0.74USD	tablet
Isordil Titradose 5 mg tablet	0.68USD	tablet
Isordil 5 mg tablet	0.65USD	tablet
Isosorbide dn 30 mg tablet	0.53USD	tablet
Isordil 10 mg tablet	0.5USD	tablet
Isosorbide Dinitrate 30 mg tablet	0.5USD	tablet
Cedocard-Sr 20 mg Sustained-Release Tablet	0.44USD	tablet
Isosorbide Dinitrate 10 mg tablet	0.43USD	tablet
Isosorbide Dinitrate 20 mg tablet	0.43USD	tablet
Isosorbide Dinitrate 2.5 mg Sublingual Tabs	0.39USD	tab
Isosorbide Dinitrate 5 mg Sublingual Tabs	0.21USD	tab
Isosorbide dn 2.5 mg tablet sl	0.21USD	tablet
Isosorbide dn 5 mg tablet sl	0.21USD	tablet
Isosorbide dn 20 mg tablet	0.2USD	tablet
Isosorbide Dinitrate 5 mg tablet	0.17USD	tablet
Isosorbide dn 10 mg tablet	0.17USD	tablet
Isosorbide dn 5 mg tablet	0.17USD	tablet
Apo-Isdn 30 mg Tablet	0.09USD	tablet
Apo-Isdn 5 mg Sublingual Tablet	0.07USD	tablet
Apo-Isdn 10 mg Tablet	0.04USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US6465463	No	2002-10-15	2020-09-08
US6784177	No	2004-08-31	2020-09-08

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	70 °C	PhysProp
water solubility	550 mg/L (at 25 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	1.31	HANSCH,C ET AL. (1995)
logS	-2.63	ADME Research, USCD

Predicted Properties

Property	Value	Source
Water Solubility	0.938 mg/mL	ALOGPS
logP	0.87	ALOGPS
logP	-0.0096	Chemaxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.2	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	8	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	123.2 Å²	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	42.76 m³·mol^-1	Chemaxon
Polarizability	18.15 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.935
Blood Brain Barrier	+	0.9559
Caco-2 permeable	-	0.5746
P-glycoprotein substrate	Non-substrate	0.8064
P-glycoprotein inhibitor I	Non-inhibitor	0.6173
P-glycoprotein inhibitor II	Non-inhibitor	0.8911
Renal organic cation transporter	Non-inhibitor	0.8453
CYP450 2C9 substrate	Non-substrate	0.9057
CYP450 2D6 substrate	Non-substrate	0.9021
CYP450 3A4 substrate	Substrate	0.5298
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.9534
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9538
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.7116
Biodegradation	Ready biodegradable	0.7633
Rat acute toxicity	2.4849 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.5057
hERG inhibition (predictor II)	Non-inhibitor	0.9381

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-000i-9410000000-92c2931ba576380c836c
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	155.1631312	predicted	DarkChem Lite v0.1.0
[M-H]-	155.3619312	predicted	DarkChem Lite v0.1.0
[M-H]-	131.42505	predicted	DeepCCS 1.0 (2019)
[M+H]+	155.6089312	predicted	DarkChem Lite v0.1.0
[M+H]+	155.7697312	predicted	DarkChem Lite v0.1.0
[M+H]+	133.82115	predicted	DeepCCS 1.0 (2019)
[M+Na]+	155.8224312	predicted	DarkChem Lite v0.1.0
[M+Na]+	156.0861312	predicted	DarkChem Lite v0.1.0
[M+Na]+	139.60342	predicted	DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

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Details1. Atrial natriuretic peptide receptor 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Protein kinase activity
Specific Function: Receptor for the atrial natriuretic peptide NPPA/ANP and the brain natriuretic peptide NPPB/BNP which are potent vasoactive hormones playing a key role in cardiovascular homeostasis. Has guanylate ...
Gene Name: NPR1
Uniprot ID: P16066
Uniprot Name: Atrial natriuretic peptide receptor 1
Molecular Weight: 118918.11 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Villarroya M, Lopez MG, de Pascual R, Garcia AG: Preclinical profile of PF9404C, a nitric oxide donor with beta receptor blocking properties. Cardiovasc Drug Rev. 2005 Summer;23(2):149-60. [Article]
Takabuchi S, Hirota K, Nishi K, Oda S, Oda T, Shingu K, Takabayashi A, Adachi T, Semenza GL, Fukuda K: The inhibitory effect of sodium nitroprusside on HIF-1 activation is not dependent on nitric oxide-soluble guanylyl cyclase pathway. Biochem Biophys Res Commun. 2004 Nov 5;324(1):417-23. [Article]
Beauregard C, Brandt PC, Chiou GC: Nitric oxide and cyclic GMP-mediated protein secretion from cultured lacrimal gland acinar cells. J Ocul Pharmacol Ther. 2002 Oct;18(5):429-43. [Article]

Enzymes

Details1. Cytochrome P450 2E1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name: CYP2E1
Uniprot ID: P05181
Uniprot Name: Cytochrome P450 2E1
Molecular Weight: 56848.42 Da

References

Vuppugalla R, Mehvar R: Selective effects of nitric oxide on the disposition of chlorzoxazone and dextromethorphan in isolated perfused rat livers. Drug Metab Dispos. 2006 Jul;34(7):1160-6. doi: 10.1124/dmd.105.009050. Epub 2006 Apr 18. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Isosorbide dinitrate

Identification

Structure for Isosorbide dinitrate (DB00883)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

Enzymes

References