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Identification
- Summary
Isosorbide is a vasodilator used for the prevention and treatment of angina pectoris due to coronary artery disease. It was previously used to reduce intraocular pressure.
- Generic Name
- Isosorbide
- DrugBank Accession Number
- DB09401
- Background
Isosorbide was previously available in an oral formulation for the reduction of intraocular pressure. It was approved by the FDA in 1980, but has since been discontinued. Currently, isosorbide is an organic nitrate currently available in the isosorbide mononitrate and isosorbide dinitrate forms, and is used for the prevention of angina. Refer to these drug entries for more information.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Isosorbide (DB09401)
- Weight
- Average: 146.1412
Monoisotopic: 146.057908808 - Chemical Formula
- C6H10O4
- Synonyms
- Isosorbide
- External IDs
- AT-101
- NSC-40725
Pharmacology
- Indication
Isosorbide was previously indicated for temporary reduction of intraocular pressure and used to interrupt an acute glaucoma attack, however, this is not a currently approved indication.12 Refer to isosorbide mononitrate and isosorbide dinitrate drug entries for more isosorbide indications.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Angina pectoris •••••••••••• •••••• Treatment of Angina pectoris •••••••••••• •••••• - Contraindications & Blackbox Warnings
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Isosorbide reduces intraocular pressure through its effects on ocular blood vessels.8,12 While in the blood, isosorbide promotes redistribution of water toward the circulation, promoting the excretion of urine.12
- Mechanism of action
Isosorbide causes vascular relaxation, reducing systolic ophthalmic artery pressure (SOAP), systolic ocular perfusion pressure (SOPP).8
Target Actions Organism AGuanylate cyclase activatorHumans - Absorption
Isosorbide is rapidly absorbed after oral administration.12 Refer to isosorbide mononitrate for detailed absorption information.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Integrate drug-drug
interactions in your softwareAbacavir Isosorbide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy. Aceclofenac Isosorbide may increase the excretion rate of Aceclofenac which could result in a lower serum level and potentially a reduction in efficacy. Acemetacin The therapeutic efficacy of Isosorbide can be decreased when used in combination with Acemetacin. Acetaminophen Isosorbide may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Isosorbide which could result in a higher serum level. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ismotic Solution 450 mg/1mL Oral ALCON LABORATORIES, INC. 2006-09-26 Not applicable US 
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Furofurans
- Sub Class
- Isosorbides
- Direct Parent
- Isosorbides
- Alternative Parents
- Tetrahydrofurans / Secondary alcohols / Oxacyclic compounds / Dialkyl ethers / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic heteropolycyclic compound / Dialkyl ether / Ether / Hydrocarbon derivative / Isosorbide / Organic oxygen compound / Organooxygen compound / Oxacycle / Secondary alcohol
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- WXR179L51S
- CAS number
- 652-67-5
- InChI Key
- KLDXJTOLSGUMSJ-JGWLITMVSA-N
- InChI
- InChI=1S/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4+,5-,6-/m1/s1
- IUPAC Name
- (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol
- SMILES
- [H][C@]1(O)CO[C@]2([H])[C@]([H])(O)CO[C@]12[H]
References
- Synthesis Reference
Bonnin, I., Mereau, R., Tassaing, T., & De Oliveira Vigier, K. (2020). One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?. Beilstein journal of organic chemistry, 16, 1713–1721. https://doi.org/10.3762/bjoc.16.143
- General References
- Balasubramanian S, Chowdhury YS: Isosorbide . [Article]
- Lee PM, Gerriets V: Nitrates . [Article]
- Chasseaud LF: Isosorbide 5-mononitrate pharmacokinetics. Cardiology. 1987;74 Suppl 1:6-11. doi: 10.1159/000174255. [Article]
- Romanin C, Kukovetz WR: Guanylate cyclase activation by organic nitrates is not mediated via nitrite. J Mol Cell Cardiol. 1988 May;20(5):389-96. doi: 10.1016/s0022-2828(88)80130-5. [Article]
- Schroder H, Noack E: Structure-activity relationship of organic nitrates for activation of guanylate cyclase. Arch Int Pharmacodyn Ther. 1987 Dec;290(2):235-46. [Article]
- Kukovetz WR, Holzmann S, Romanin C: Mechanism of vasodilation by nitrates: role of cyclic GMP. Cardiology. 1987;74 Suppl 1:12-9. doi: 10.1159/000174258. [Article]
- Kulshrestha O.P. and Mittal, R.N.: Isosorbide and intraocular pressure British Journal of Ophthalmology. [Article]
- Hessemer V, Schmidt KG: Influence of the vasodilator drug isosorbide dinitrate on ocular circulation. Arch Ophthalmol. 1997 Mar;115(3):324-7. doi: 10.1001/archopht.1997.01100150326003. [Article]
- FDA Approved Products: Bidil (isosorbide dinitrate and hydralazine hydrochloride) oral tablets [Link]
- FDA Approved Drug Products: Monoket (isosorbide mononitrate) tablets [Link]
- Product monograph: PRO-ISMN-60 (Isosorbide-5-mononitrate ) extended release tablets [Link]
- DailyMed: ISMOTIC (isosorbide) oral solution [Link]
- External Links
- ChemSpider
- 12077
- 6057
- ChEBI
- 6060
- ChEMBL
- CHEMBL1200660
- ZINC
- ZINC000018284778
- Wikipedia
- Isosorbide
- FDA label
- Download (191 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Health Services Research Obesity 1 somestatus stop reason just information to hide Not Available Completed Prevention Portal Hypertension 1 somestatus stop reason just information to hide Not Available Completed Treatment Coronaropathy 1 somestatus stop reason just information to hide 4 Completed Treatment Intrauterine Growth Retardation (IUGR) 1 somestatus stop reason just information to hide 4 Completed Treatment Myocardial Ischemia / Quality of Life (QOL) / Stable Angina (SA) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Oral 450 mg/1mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 60-63 https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1162705.htm boiling point (°C) 175 https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1162705.htm water solubility 29 mg/mL https://www.selleckchem.com/products/isosorbide.html - Predicted Properties
Property Value Source Water Solubility 1210.0 mg/mL ALOGPS logP -1.5 ALOGPS logP -1.4 Chemaxon logS 0.92 ALOGPS pKa (Strongest Acidic) 13.03 Chemaxon pKa (Strongest Basic) -3.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 58.92 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 31.38 m3·mol-1 Chemaxon Polarizability 13.54 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 125.5201148 predictedDarkChem Lite v0.1.0 [M-H]- 125.4845148 predictedDarkChem Lite v0.1.0 [M-H]- 130.77055 predictedDeepCCS 1.0 (2019) [M+H]+ 125.6018148 predictedDarkChem Lite v0.1.0 [M+H]+ 127.5777148 predictedDarkChem Lite v0.1.0 [M+H]+ 133.16623 predictedDeepCCS 1.0 (2019) [M+Na]+ 125.0857148 predictedDarkChem Lite v0.1.0 [M+Na]+ 125.3319148 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.07875 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Activator
- General Function
- Not Available
- Specific Function
- GTP binding
Components:
References
- Kukovetz WR, Holzmann S, Romanin C: Mechanism of vasodilation by nitrates: role of cyclic GMP. Cardiology. 1987;74 Suppl 1:12-9. doi: 10.1159/000174258. [Article]
- Schroder H, Noack E: Structure-activity relationship of organic nitrates for activation of guanylate cyclase. Arch Int Pharmacodyn Ther. 1987 Dec;290(2):235-46. [Article]
- Romanin C, Kukovetz WR: Guanylate cyclase activation by organic nitrates is not mediated via nitrite. J Mol Cell Cardiol. 1988 May;20(5):389-96. doi: 10.1016/s0022-2828(88)80130-5. [Article]
- FDA Approved Products: Bidil (isosorbide dinitrate and hydralazine hydrochloride) oral tablets [Link]
- Product monograph: PRO-ISMN-60 (Isosorbide-5-mononitrate ) extended release tablets [Link]
Drug created at November 30, 2015 19:10 / Updated at May 15, 2021 22:41