Isosorbide
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
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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- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
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
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our 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. Aclidinium Isosorbide may increase the excretion rate of Aclidinium which could result in a lower serum level and potentially a reduction in efficacy. Acrivastine Isosorbide may increase the excretion rate of Acrivastine which could result in a lower serum level and potentially a reduction in efficacy. Acyclovir Isosorbide may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Albutrepenonacog alfa Isosorbide may increase the excretion rate of Albutrepenonacog alfa which could result in a lower serum level and potentially a reduction in efficacy. Alclofenac Isosorbide may increase the excretion rate of Alclofenac which could result in a lower serum level and potentially a reduction in efficacy. 
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- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- 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
Phase Status Purpose Conditions Count 4 Completed Treatment Myocardial Ischemia / Quality of Life / Stable Angina (SA) 1 3 Completed Supportive Care Induction of Labor Affected Fetus / Newborn / Rupture of Membranes Prior to Onset of Labor 1 2 Active Not Recruiting Treatment Laryngeal Cancer 1 2 Completed Treatment Adenocarcinoma of the Prostate / Stage IV Prostate Cancer 1 2 Completed Treatment Adult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Recurrent Adult Brain Tumor 1 2 Completed Treatment Chronic Lymphocytic Leukaemia (CLL) 1 2 Completed Treatment Chronic Lymphocytic Leukaemia (CLL) / Diffuse Large Cell Lymphoma / Follicular Lymphoma ( FL) / Mantle Cell Lymphoma (MCL) / Small Lymphocytic Lymphoma 1 2 Completed Treatment Extensive Stage Small Cell Lung Cancer / Refractory Small cell lung cancer 1 2 Completed Treatment Follicular Lymphoma ( FL) 1 2 Completed Treatment Hormone Refractory Prostate Cancer 1
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
Spectrum Spectrum Type Splash Key GC-MS Spectrum - GC-MS (2 TMS) GC-MS splash10-0gb9-1900000000-7677c061f75035fcbd24 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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with our fully connected ADMET & drug target dataset.
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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 on November 30, 2015 19:10 / Updated on May 15, 2021 22:41