NAV

2-chloro-5-[(1S)-1-hydroxy-3-oxo-2H-isoindol-1-yl]benzenesulfonamide

Identification

Generic Name
2-chloro-5-[(1S)-1-hydroxy-3-oxo-2H-isoindol-1-yl]benzenesulfonamide
DrugBank Accession Number
DB08046
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 338.766
Monoisotopic: 338.012805247
Chemical Formula
C14H11ClN2O4S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCarbonic anhydrase 2Not 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
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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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoindoles and derivatives
Sub Class
Isoindolines
Direct Parent
Isoindolones
Alternative Parents
Benzenesulfonamides / Benzenesulfonyl compounds / Isoindoles / Chlorobenzenes / Aryl chlorides / Organosulfonamides / Aminosulfonyl compounds / Lactams / Secondary carboxylic acid amides / Alkanolamines
show 6 more
Substituents
Alkanolamine / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Carboxamide group
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
0953RA202M
CAS number
1441368-51-9
InChI Key
JIVPVXMEBJLZRO-AWEZNQCLSA-N
InChI
InChI=1S/C14H11ClN2O4S/c15-11-6-5-8(7-12(11)22(16,20)21)14(19)10-4-2-1-3-9(10)13(18)17-14/h1-7,19H,(H,17,18)(H2,16,20,21)/t14-/m0/s1
IUPAC Name
2-chloro-5-[(1S)-1-hydroxy-3-oxo-2,3-dihydro-1H-isoindol-1-yl]benzene-1-sulfonamide
SMILES
NS(=O)(=O)C1=C(Cl)C=CC(=C1)[C@@]1(O)NC(=O)C2=C1C=CC=C2

References

General References
Not Available
PubChem Compound
688424
PubChem Substance
99444517
ChemSpider
599888
ChEMBL
CHEMBL402262
ZINC
ZINC000000057255
PDBe Ligand
KLT
PDB Entries
3f4x

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0528 mg/mLALOGPS
logP1.27ALOGPS
logP1.6Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.76Chemaxon
pKa (Strongest Basic)-2.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area109.49 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity81.3 m3·mol-1Chemaxon
Polarizability30.88 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.5447
Caco-2 permeable-0.6272
P-glycoprotein substrateNon-substrate0.767
P-glycoprotein inhibitor INon-inhibitor0.9603
P-glycoprotein inhibitor IINon-inhibitor0.9573
Renal organic cation transporterNon-inhibitor0.891
CYP450 2C9 substrateNon-substrate0.6403
CYP450 2D6 substrateNon-substrate0.822
CYP450 3A4 substrateNon-substrate0.6369
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9299
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8193
Ames testNon AMES toxic0.7277
CarcinogenicityNon-carcinogens0.5752
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8623 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9968
hERG inhibition (predictor II)Non-inhibitor0.8914
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0592-2933000000-812ab55054ce38e3ff28
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-a259f9e96638aa9b6f34
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000l-0059000000-508a39caa2f290b026bc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-d8a4b40348e48435343d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000l-0049000000-4fd6b5bddf28690f938d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0920000000-8f29b2a820fe80622606
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-9400000000-ca3adf766e73fef793c5
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-164.54515
predicted
DeepCCS 1.0 (2019)
[M+H]+166.90315
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.56673
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Carbonic anhydrase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:28 / Updated at June 12, 2020 16:52