Isosorbide

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Isosorbide
Accession Number
DB09401
Description

Isosorbide is an organic nitrate with vasodilatory properties on both arteries and veins.

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

Pharmacology
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Indication

Indicated for the prevention and treatment of angina pectoris due to coronary artery disease. The onset of action of oral isosorbide mononitrate is not sufficiently rapid for this product to be useful in aborting an acute anginal episode.Label

Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UApoptosis regulator Bcl-2Not AvailableHumans
UBcl-2-like protein 1Not AvailableHumans
UInduced myeloid leukemia cell differentiation protein Mcl-1Not AvailableHumans
Absorption
Not Available
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
Medicalerrors
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Toxicity
Not Available
Affected organisms
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.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Isosorbide.
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.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Isosorbide.
AcetaminophenThe metabolism of Isosorbide can be increased when combined with Acetaminophen.
AcetazolamideThe metabolism of Isosorbide can be increased when combined with Acetazolamide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Isosorbide.
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.
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

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

General References
  1. FDA Approved Products: Isordil titradose (isosorbide dinitrate) oral tablets [Link]
  2. FDA Approved Products: Bidil (isosorbide dinitrate and hydralazine hydrochloride) oral tablets [Link]
  3. FDA Approved Drug Products: Monoket (isosorbide mononitrate) tablets [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 Cancer / Hormone-Refractory Prostate Cancer1

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
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

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells. Regulates cell death by controlling the mitochondrial membrane permeability. Appea...
Gene Name
BCL2
Uniprot ID
P10415
Uniprot Name
Apoptosis regulator Bcl-2
Molecular Weight
26265.66 Da
References
  1. Loberg RD, McGregor N, Ying C, Sargent E, Pienta KJ: In vivo evaluation of AT-101 (R-(-)-gossypol acetic acid) in androgen-independent growth of VCaP prostate cancer cells in combination with surgical castration. Neoplasia. 2007 Dec;9(12):1030-7. [PubMed:18084610]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein kinase binding
Specific Function
Potent inhibitor of cell death. Inhibits activation of caspases. Appears to regulate cell death by blocking the voltage-dependent anion channel (VDAC) by binding to it and preventing the release of...
Gene Name
BCL2L1
Uniprot ID
Q07817
Uniprot Name
Bcl-2-like protein 1
Molecular Weight
26048.8 Da
References
  1. Loberg RD, McGregor N, Ying C, Sargent E, Pienta KJ: In vivo evaluation of AT-101 (R-(-)-gossypol acetic acid) in androgen-independent growth of VCaP prostate cancer cells in combination with surgical castration. Neoplasia. 2007 Dec;9(12):1030-7. [PubMed:18084610]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Involved in the regulation of apoptosis versus cell survival, and in the maintenance of viability but not of proliferation. Mediates its effects by interactions with a number of other regulators of...
Gene Name
MCL1
Uniprot ID
Q07820
Uniprot Name
Induced myeloid leukemia cell differentiation protein Mcl-1
Molecular Weight
37336.975 Da
References
  1. Loberg RD, McGregor N, Ying C, Sargent E, Pienta KJ: In vivo evaluation of AT-101 (R-(-)-gossypol acetic acid) in androgen-independent growth of VCaP prostate cancer cells in combination with surgical castration. Neoplasia. 2007 Dec;9(12):1030-7. [PubMed:18084610]

Drug created on November 30, 2015 19:10 / Updated on February 21, 2021 18:52