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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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

TargetActionsOrganism
AGuanylate cyclase
activator
Humans
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
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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.
DrugInteraction
AbacavirIsosorbide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
AceclofenacIsosorbide may increase the excretion rate of Aceclofenac which could result in a lower serum level and potentially a reduction in efficacy.
AcemetacinThe therapeutic efficacy of Isosorbide can be decreased when used in combination with Acemetacin.
AcetaminophenIsosorbide may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Isosorbide which could result in a higher serum level.
AclidiniumIsosorbide may increase the excretion rate of Aclidinium which could result in a lower serum level and potentially a reduction in efficacy.
AcrivastineIsosorbide may increase the excretion rate of Acrivastine which could result in a lower serum level and potentially a reduction in efficacy.
AcyclovirIsosorbide may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy.
Albutrepenonacog alfaIsosorbide may increase the excretion rate of Albutrepenonacog alfa which could result in a lower serum level and potentially a reduction in efficacy.
AlclofenacIsosorbide may increase the excretion rate of Alclofenac which could result in a lower serum level and potentially a reduction in efficacy.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
IsmoticSolution450 mg/1mLOralALCON LABORATORIES, INC.2006-09-26Not applicableUS flag

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
  1. Balasubramanian S, Chowdhury YS: Isosorbide . [Article]
  2. Lee PM, Gerriets V: Nitrates . [Article]
  3. Chasseaud LF: Isosorbide 5-mononitrate pharmacokinetics. Cardiology. 1987;74 Suppl 1:6-11. doi: 10.1159/000174255. [Article]
  4. 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]
  5. 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]
  6. 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]
  7. Kulshrestha O.P. and Mittal, R.N.: Isosorbide and intraocular pressure British Journal of Ophthalmology. [Article]
  8. 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]
  9. FDA Approved Products: Bidil (isosorbide dinitrate and hydralazine hydrochloride) oral tablets [Link]
  10. FDA Approved Drug Products: Monoket (isosorbide mononitrate) tablets [Link]
  11. Product monograph: PRO-ISMN-60 (Isosorbide-5-mononitrate ) extended release tablets [Link]
  12. DailyMed: ISMOTIC (isosorbide) oral solution [Link]
ChemSpider
12077
RxNav
6057
ChEBI
6060
ChEMBL
CHEMBL1200660
ZINC
ZINC000018284778
Wikipedia
Isosorbide
FDA label
Download (191 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentMyocardial Ischemia / Quality of Life / Stable Angina (SA)1
3CompletedSupportive CareInduction of Labor Affected Fetus / Newborn / Rupture of Membranes Prior to Onset of Labor1
2Active Not RecruitingTreatmentLaryngeal Cancer1
2CompletedTreatmentAdenocarcinoma of the Prostate / Stage IV Prostate Cancer1
2CompletedTreatmentAdult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Recurrent Adult Brain Tumor1
2CompletedTreatmentChronic Lymphocytic Leukaemia (CLL)1
2CompletedTreatmentChronic Lymphocytic Leukaemia (CLL) / Diffuse Large Cell Lymphoma / Follicular Lymphoma ( FL) / Mantle Cell Lymphoma (MCL) / Small Lymphocytic Lymphoma1
2CompletedTreatmentExtensive Stage Small Cell Lung Cancer / Refractory Small cell lung cancer1
2CompletedTreatmentFollicular Lymphoma ( FL)1
2CompletedTreatmentHormone Refractory Prostate Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral450 mg/1mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)60-63https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1162705.htm
boiling point (°C)175https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1162705.htm
water solubility29 mg/mLhttps://www.selleckchem.com/products/isosorbide.html
Predicted Properties
PropertyValueSource
Water Solubility1210.0 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.4ChemAxon
logS0.92ALOGPS
pKa (Strongest Acidic)13.03ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.38 m3·mol-1ChemAxon
Polarizability13.54 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0gb9-1900000000-7677c061f75035fcbd24
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Activator
General Function
Not Available
Specific Function
Gtp binding

Components:
References
  1. 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]
  2. 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]
  3. 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]
  4. FDA Approved Products: Bidil (isosorbide dinitrate and hydralazine hydrochloride) oral tablets [Link]
  5. 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