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

Pharmacology

Indication
Not Available
Structured Indications
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
DrugInteractionDrug group
AcemetacinThe therapeutic efficacy of Isosorbide can be decreased when used in combination with Acemetacin.Approved, Experimental, Investigational
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Isosorbide.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Isosorbide.Experimental
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Isosorbide.Approved, Illicit
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Isosorbide.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Alphaprodine is combined with Isosorbide.Illicit
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Isosorbide.Approved, Investigational, Withdrawn
BevacizumabBevacizumab may increase the cardiotoxic activities of Isosorbide.Approved, Investigational
BezitramideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Isosorbide.Experimental, Illicit, Withdrawn
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Isosorbide.Approved, Illicit, Investigational, Vet Approved
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Isosorbide.Approved, Illicit, Vet Approved
Candesartan cilexetilThe risk or severity of hypotension can be increased when Candesartan cilexetil is combined with Isosorbide.Approved
CarfentanilThe risk or severity of adverse effects can be increased when Carfentanil is combined with Isosorbide.Illicit, Investigational, Vet Approved
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Isosorbide.Approved, Illicit
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Isosorbide.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Isosorbide.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Isosorbide.Approved
DextromoramideThe risk or severity of adverse effects can be increased when Dextromoramide is combined with Isosorbide.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Isosorbide.Approved, Illicit, Investigational, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Dezocine is combined with Isosorbide.Approved, Investigational
DigitoxinDigitoxin may decrease the cardiotoxic activities of Isosorbide.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Isosorbide.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Isosorbide.Approved
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Isosorbide.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Isosorbide.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Dihydromorphine is combined with Isosorbide.Experimental, Illicit
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Isosorbide.Approved, Illicit
DPDPEThe risk or severity of adverse effects can be increased when DPDPE is combined with Isosorbide.Experimental
EthylmorphineThe risk or severity of adverse effects can be increased when Ethylmorphine is combined with Isosorbide.Approved, Illicit
EtorphineThe risk or severity of adverse effects can be increased when Etorphine is combined with Isosorbide.Illicit, Vet Approved
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Isosorbide.Approved, Illicit, Investigational, Vet Approved
GitoformateGitoformate may decrease the cardiotoxic activities of Isosorbide.Experimental
HeroinThe risk or severity of adverse effects can be increased when Heroin is combined with Isosorbide.Approved, Illicit, Investigational
HydrocodoneThe risk or severity of adverse effects can be increased when Hydrocodone is combined with Isosorbide.Approved, Illicit
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Isosorbide.Approved, Illicit
KetobemidoneThe risk or severity of adverse effects can be increased when Ketobemidone is combined with Isosorbide.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Isosorbide.Experimental
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Isosorbide.Approved, Investigational
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Isosorbide.Approved
LofentanilThe risk or severity of adverse effects can be increased when Lofentanil is combined with Isosorbide.Illicit
MeptazinolThe risk or severity of adverse effects can be increased when Meptazinol is combined with Isosorbide.Experimental
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Isosorbide.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Isosorbide.Approved, Illicit
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Isosorbide.Experimental
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Isosorbide.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Isosorbide.Approved
NicomorphineThe risk or severity of adverse effects can be increased when Nicomorphine is combined with Isosorbide.Experimental
NormethadoneThe risk or severity of adverse effects can be increased when Normethadone is combined with Isosorbide.Approved, Illicit
OleandrinOleandrin may decrease the cardiotoxic activities of Isosorbide.Experimental, Investigational
OpiumThe risk or severity of adverse effects can be increased when Opium is combined with Isosorbide.Approved, Illicit
OuabainOuabain may decrease the cardiotoxic activities of Isosorbide.Approved
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Isosorbide.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Isosorbide.Approved, Investigational, Vet Approved
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Isosorbide.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Isosorbide.Experimental
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Isosorbide.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Phenazocine is combined with Isosorbide.Experimental
PhenoperidineThe risk or severity of adverse effects can be increased when Phenoperidine is combined with Isosorbide.Experimental
PiritramideThe risk or severity of adverse effects can be increased when Piritramide is combined with Isosorbide.Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Isosorbide.Experimental
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Isosorbide.Approved
Sodium phosphateIsosorbide may increase the nephrotoxic activities of Sodium phosphate.Approved
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Isosorbide.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Isosorbide.Approved
TilidineThe risk or severity of adverse effects can be increased when Tilidine is combined with Isosorbide.Experimental
TipiracilThe therapeutic efficacy of Isosorbide can be decreased when used in combination with Tipiracil.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Isosorbide.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Isosorbide.Approved, Investigational
Food Interactions
Not Available

References

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

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 / Waldenstrom'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, 2RecruitingTreatmentRecurrent Chronic Lymphocytic Leukemia1
1, 2RecruitingTreatmentRecurrent Plasma Cell Myeloma1
1, 2TerminatedTreatmentLocally Advanced Esophageal or GE Junction 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 / Recurrent 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
2RecruitingTreatmentLaryngeal Cancer1
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 January 05, 2018 16:05