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  (DB05707)
Type
Small Molecule
Groups
Approved, Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
AT-101 / NSC-40725
Categories
UNII
WXR179L51S
CAS number
652-67-5
Weight
Average: 146.1412
Monoisotopic: 146.057908808
Chemical Formula
C6H10O4
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]

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UApoptosis regulator Bcl-2Not AvailableHuman
UBcl-2-like protein 1Not AvailableHuman
UInduced myeloid leukemia cell differentiation protein Mcl-1Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Isosorbide.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Isosorbide.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Isosorbide.
AbciximabThe therapeutic efficacy of Abciximab can be increased when used in combination with Isosorbide.
AcemetacinThe therapeutic efficacy of Isosorbide can be decreased when used in combination with Acemetacin.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Isosorbide.
AcetaminophenThe metabolism of Isosorbide can be increased when combined with Acetaminophen.
Acetylsalicylic acidThe therapeutic efficacy of Acetylsalicylic acid can be increased when used in combination with Isosorbide.
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Isosorbide.
AlfentanilThe therapeutic efficacy of Isosorbide can be decreased when used in combination with Alfentanil.
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
12077
ChEBI
6060
ChEMBL
CHEMBL1200660
Wikipedia
Isosorbide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAdult Grade III Lymphomatoid Granulomatosis / Adult Nasal Type Extranodal NK/T-Cell Lymphoma / Contiguous Stage II Adult Burkitt Lymphoma / Contiguous Stage II Adult Diffuse Large Cell Lymphoma / Contiguous Stage II Adult Diffuse Mixed Cell Lymphoma / Contiguous Stage II Adult Diffuse Small Cleaved Cell Lymphoma / Contiguous Stage II Adult Immunoblastic Large Cell Lymphoma / Contiguous Stage II Adult Lymphoblastic Lymphoma / Contiguous Stage II Grade 1 Follicular Lymphoma / Contiguous Stage II Grade 2 Follicular Lymphoma / Contiguous Stage II Grade 3 Follicular Lymphoma / Contiguous Stage II Mantle Cell Lymphoma / Contiguous Stage II Marginal Zone Lymphoma / Contiguous Stage II Small Lymphocytic Lymphoma / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Nodal marginal zone B-cell lymphomas / Noncontiguous Stage II Adult Burkitt Lymphoma / Noncontiguous Stage II Adult Diffuse Large Cell Lymphoma / Noncontiguous Stage II Adult Diffuse Mixed Cell Lymphoma / Noncontiguous Stage II Adult Diffuse Small Cleaved Cell Lymphoma / Noncontiguous Stage II Adult Immunoblastic Large Cell Lymphoma / Noncontiguous Stage II Adult Lymphoblastic Lymphoma / Noncontiguous Stage II Grade 1 Follicular Lymphoma / Noncontiguous Stage II Grade 2 Follicular Lymphoma / Noncontiguous Stage II Grade 3 Follicular Lymphoma / Noncontiguous Stage II Mantle Cell Lymphoma / Noncontiguous Stage II Marginal Zone Lymphoma / Noncontiguous Stage II Small Lymphocytic Lymphoma / Peripheral T-Cell Lymphoma (PTCL) / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Small Lymphocytic Lymphoma / Splenic Marginal Zone Lymphoma / Stage I Adult Burkitt Lymphoma / Stage I Adult Diffuse Large Cell Lymphoma / Stage I Adult Diffuse Mixed Cell Lymphoma / Stage I Adult Diffuse Small Cleaved Cell Lymphoma / Stage I Adult Immunoblastic Large Cell Lymphoma / Stage I Adult Lymphoblastic Lymphoma / Stage I Grade 1 Follicular Lymphoma / Stage I Grade 2 Follicular Lymphoma / Stage I Grade 3 Follicular Lymphoma / Stage I Mantle Cell Lymphoma / Stage I Marginal Zone Lymphoma / Stage I Small Lymphocytic Lymphoma / Stage III Adult Burkitt Lymphoma / Stage III Adult Diffuse Large Cell Lymphoma / Stage III Adult Diffuse Mixed Cell Lymphoma / Stage III Adult Diffuse Small Cleaved Cell Lymphoma / Stage III Adult Immunoblastic Large Cell Lymphoma / Stage III Adult Lymphoblastic Lymphoma / Stage III Grade 1 Follicular Lymphoma / Stage III Grade 2 Follicular Lymphoma / Stage III Grade 3 Follicular Lymphoma / Stage III Mantle Cell Lymphoma / Stage III Marginal Zone Lymphoma / Stage III Small Lymphocytic Lymphoma / Stage IV Adult Burkitt Lymphoma / Stage IV Adult Diffuse Large Cell Lymphoma / Stage IV Adult Diffuse Mixed Cell Lymphoma / Stage IV Adult Diffuse Small Cleaved Cell Lymphoma / Stage IV Adult Immunoblastic Large Cell Lymphoma / Stage IV Adult Lymphoblastic Lymphoma / Stage IV Grade 1 Follicular Lymphoma / Stage IV Grade 2 Follicular Lymphoma / Stage IV Grade 3 Follicular Lymphoma / Stage IV Mantle Cell Lymphoma / Stage IV Marginal Zone Lymphoma / Stage IV Small Lymphocytic Lymphoma / Unspecified Adult Solid Tumor, Protocol Specific / Waldenström's Macroglobulinemia (WM)1
1CompletedTreatmentBrain and Central Nervous System Tumors1
1CompletedTreatmentExtensive Stage Small Cell Lung Cancer / Unspecified Adult Solid Tumor, Protocol Specific1
1, 2CompletedTreatmentHormone Refractory Prostate Cancer1
1, 2CompletedTreatmentLung Cancer Small Cell Lung Cancer (SCLC)1
1, 2CompletedTreatmentProstate Cancer1
1, 2SuspendedTreatmentRecurrent Plasma Cell Myeloma1
1, 2SuspendedTreatmentChronic, recurrent Lymphocytic Leukemia1
1, 2TerminatedTreatmentLocally Advanced Esophageal or GE Junction Cancer1
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 Lymphoma (SLL)1
2CompletedTreatmentExtensive Stage Small Cell Lung Cancer / Refractory Small cell lung cancer1
2CompletedTreatmentFollicular Lymphoma (FL)1
2CompletedTreatmentHormone Refractory Prostate Cancer1
2CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2CompletedTreatmentRecurrent Adrenocortical Carcinoma / Stage III Adrenocortical Carcinoma / Stage IV Adrenocortical Carcinoma1
2TerminatedTreatmentSquamous Cell Carcinoma of the Head and Neck (SCCHN)1
4CompletedTreatmentMyocardial Ischemia / Quality of Life / Stable Angina (SA)1
Not AvailableCompletedHealth Services ResearchBMI >30 kg/m21

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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

Taxonomy

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
Isosorbide / Tetrahydrofuran / Secondary alcohol / Oxacycle / Ether / Dialkyl ether / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Alcohol
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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
Human
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
Human
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 12:10 / Updated on November 02, 2018 07:02