Home Other Building Blocks Indisulam

Indisulam

CAS No.:
165668-41-7
Catalog Number:
AG001W9L
Molecular Formula:
C14H12ClN3O4S2
Molecular Weight:
385.8458
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$91
- +
5mg
≥98%
1 week
United States
$187
- +
10mg
≥98%
1 week
United States
$300
- +
25mg
≥98%
1 week
United States
$621
- +
Product Description
Catalog Number:
AG001W9L
Chemical Name:
Indisulam
CAS Number:
165668-41-7
Molecular Formula:
C14H12ClN3O4S2
Molecular Weight:
385.8458
MDL Number:
MFCD00945325
IUPAC Name:
4-N-(3-chloro-1H-indol-7-yl)benzene-1,4-disulfonamide
InChI:
InChI=1S/C14H12ClN3O4S2/c15-12-8-17-14-11(12)2-1-3-13(14)18-24(21,22)10-6-4-9(5-7-10)23(16,19)20/h1-8,17-18H,(H2,16,19,20)
InChI Key:
SETFNECMODOHTO-UHFFFAOYSA-N
SMILES:
Clc1c[nH]c2c1cccc2NS(=O)(=O)c1ccc(cc1)S(=O)(=O)N
UNII:
WJ98J3NM90
Properties
Complexity:
651  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
384.996g/mol
Formal Charge:
0
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
385.837g/mol
Monoisotopic Mass:
384.996g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
139A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.8  
Literature
Title Journal
Carbonic anhydrase inhibitors: synthesis and inhibition of the human carbonic anhydrase isoforms I, II, VII, IX and XII with benzene sulfonamides incorporating 4,5,6,7-tetrabromophthalimide moiety. Bioorganic & medicinal chemistry 20131001
Therapeutic potential and molecular mechanism of a novel sulfonamide anticancer drug, indisulam (E7070) in combination with CPT-11 for cancer treatment. Cancer chemotherapy and pharmacology 20120501
Molecular cloning, characterization, and inhibition studies of a β-carbonic anhydrase from Malassezia globosa, a potential antidandruff target. Journal of medicinal chemistry 20120412
Cloning, characterization and sulfonamide inhibition studies of an α-carbonic anhydrase from the living fossil sponge Astrosclera willeyana. Bioorganic & medicinal chemistry 20120215
Predictive ability of a semi-mechanistic model for neutropenia in the development of novel anti-cancer agents: two case studies. Investigational new drugs 20111001
Carbonic anhydrase inhibitors. Synthesis, molecular structures, and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with novel 3-pyridinesulfonamide derivatives. European journal of medicinal chemistry 20110901
Inhibition studies of the β-carbonic anhydrases from the bacterial pathogen Salmonella enterica serovar Typhimurium with sulfonamides and sulfamates. Bioorganic & medicinal chemistry 20110815
A new β-carbonic anhydrase from Brucella suis, its cloning, characterization, and inhibition with sulfonamides and sulfamates, leading to impaired pathogen growth. Bioorganic & medicinal chemistry 20110201
Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata. Bioorganic & medicinal chemistry letters 20110115
Carbonic anhydrase inhibitors. Regioselective synthesis of novel 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the human cytosolic isozymes I and II and transmembrane cancer-associated isozymes IX and XII. European journal of medicinal chemistry 20100901
New hydroxypyrimidinone-containing sulfonamides as carbonic anhydrase inhibitors also acting as MMP inhibitors. Bioorganic & medicinal chemistry letters 20100615
Carbonic anhydrase inhibitors: synthesis and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with 4-substituted 3-pyridinesulfonamides. European journal of medicinal chemistry 20100601
Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from Brucella suis. Journal of medicinal chemistry 20100311
Two-stage model-based clinical trial design to optimize phase I development of novel anticancer agents. Investigational new drugs 20100201
Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from Mycobacterium tuberculosis, Rv3588c. Bioorganic & medicinal chemistry letters 20091201
Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorganic & medicinal chemistry 20090715
Discovery of low nanomolar and subnanomolar inhibitors of the mycobacterial beta-carbonic anhydrases Rv1284 and Rv3273. Journal of medicinal chemistry 20090709
Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal beta-carbonic anhydrase from Candida albicans with sulfonamides. Bioorganic & medicinal chemistry 20090701
Self-associated indisulam in phospholipid-based nanomicelles: a potential nanomedicine for cancer. Nanomedicine : nanotechnology, biology, and medicine 20090601
Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis. Journal of medicinal chemistry 20090514
Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate. Journal of medicinal chemistry 20090423
Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates. Bioorganic & medicinal chemistry 20090201
Covariate-based dose individualization of the cytotoxic drug indisulam to reduce the risk of severe myelosuppression. Journal of pharmacokinetics and pharmacodynamics 20090201
Population pharmacokinetic and pharmacodynamic analysis to support treatment optimization of combination chemotherapy with indisulam and carboplatin. British journal of clinical pharmacology 20081001
Carbonic anhydrase inhibitors: design of spin-labeled sulfonamides incorporating TEMPO moieties as probes for cytosolic or transmembrane isozymes. Bioorganic & medicinal chemistry letters 20080615
Carbonic anhydrase inhibitors: bioreductive nitro-containing sulfonamides with selectivity for targeting the tumor associated isoforms IX and XII. Journal of medicinal chemistry 20080612
PK/PD model of indisulam and capecitabine: interaction causes excessive myelosuppression. Clinical pharmacology and therapeutics 20080601
Development of small molecule carbonic anhydrase IX inhibitors. BJU international 20080601
A dose-escalation study of indisulam in combination with capecitabine (Xeloda) in patients with solid tumours. British journal of cancer 20080422
Carbonic anhydrase inhibitors: inhibition of human cytosolic isozymes I and II and tumor-associated isozymes IX and XII with S-substituted 4-chloro-2-mercapto-5-methyl-benzenesulfonamides. Bioorganic & medicinal chemistry 20080401
Inhibition of carbonic anhydrases with glycosyltriazole benzene sulfonamides. Journal of medicinal chemistry 20080327
Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorganic & medicinal chemistry 20071201
Clinical complete long-term remission of a patient with metastatic malignant melanoma under therapy with indisulam (E7070). Melanoma research 20071001
Carbonic anhydrase inhibitors: the beta-carbonic anhydrase from Helicobacter pylori is a new target for sulfonamide and sulfamate inhibitors. Bioorganic & medicinal chemistry letters 20070701
CYP2C9 and CYP2C19 polymorphic forms are related to increased indisulam exposure and higher risk of severe hematologic toxicity. Clinical cancer research : an official journal of the American Association for Cancer Research 20070515
Carbonic anhydrase inhibitors: inhibition of isozymes I, II, and IX with triazole-linked O-glycosides of benzene sulfonamides. Journal of medicinal chemistry 20070405
Carbonic anhydrase inhibitors: inhibition of cytosolic/tumor-associated isoforms I, II, and IX with iminodiacetic carboxylates/hydroxamates also incorporating benzenesulfonamide moieties. Bioorganic & medicinal chemistry letters 20070315
A randomized phase II pharmacokinetic and pharmacodynamic study of indisulam as second-line therapy in patients with advanced non-small cell lung cancer. Clinical cancer research : an official journal of the American Association for Cancer Research 20070315
A phase I and pharmacokinetic study of indisulam in combination with carboplatin. British journal of cancer 20070226
Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. Journal of medicinal chemistry 20070125
A novel class of carbonic anhydrase inhibitors: glycoconjugate benzene sulfonamides prepared by 'click-tailing'. Journal of medicinal chemistry 20061102
Targeting tumor-associated carbonic anhydrase IX in cancer therapy. Trends in pharmacological sciences 20061101
A semi-physiological population pharmacokinetic model describing the non-linear disposition of indisulam. Journal of pharmacokinetics and pharmacodynamics 20061001
Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX. Journal of medicinal chemistry 20060907
Saturable binding of indisulam to plasma proteins and distribution to human erythrocytes. Drug metabolism and disposition: the biological fate of chemicals 20060601
Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori. Bioorganic & medicinal chemistry letters 20060415
Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs. Journal of medicinal chemistry 20060323
Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors. Journal of medicinal chemistry 20051201
Carbonic anhydrase inhibitors: inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with benzo[b]thiophene 1,1-dioxide sulfonamides. Bioorganic & medicinal chemistry letters 20051101
Phase I pharmacokinetic and pharmacogenomic study of E7070 administered once every 21 days. Cancer science 20051001
Carbonic anhydrase inhibitors: stacking with Phe131 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II. Journal of medicinal chemistry 20050908
Human metabolism of [(14)C]indisulam following i.v. infusion in cancer patients. Investigational new drugs 20050801
Carbonic anhydrase inhibitors. Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-mediated acidification of hypoxic tumors. Journal of medicinal chemistry 20050728
Carbonic anhydrase inhibitors: novel sulfonamides incorporating 1,3,5-triazine moieties as inhibitors of the cytosolic and tumour-associated carbonic anhydrase isozymes I, II and IX. Bioorganic & medicinal chemistry letters 20050615
Carbonic anhydrase inhibitors. Inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, IX, and XII with Schiff's bases incorporating chromone and aromatic sulfonamide moieties, and their zinc complexes. Bioorganic & medicinal chemistry letters 20050615
Semi-physiological model describing the hematological toxicity of the anti-cancer agent indisulam. Investigational new drugs 20050601
Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating thioureido-sulfanilyl scaffolds. Bioorganic & medicinal chemistry letters 20050502
Drugging cell cycle kinases in cancer therapy. Current drug targets 20050501
Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with bis-sulfamates. Bioorganic & medicinal chemistry letters 20050201
Phase II study of E7070 in patients with metastatic melanoma. Annals of oncology : official journal of the European Society for Medical Oncology 20050101
Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides derived from 4-isothiocyanato-benzolamide. Bioorganic & medicinal chemistry letters 20041206
Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating 1,2,4-triazine moieties. Bioorganic & medicinal chemistry letters 20041101
A phase II clinical and pharmacodynamic study of E7070 in patients with metastatic, recurrent, or refractory squamous cell carcinoma of the head and neck: modulation of retinoblastoma protein phosphorylation by a novel chloroindolyl sulfonamide cell cycle inhibitor. Clinical cancer research : an official journal of the American Association for Cancer Research 20040715
Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with fluorine-containing sulfonamides. The first subnanomolar CA IX inhibitor discovered. Bioorganic & medicinal chemistry letters 20040503
Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX. Journal of medicinal chemistry 20040422
Pharmacokinetic drug-drug interaction of the novel anticancer agent E7070 and acenocoumarol. Investigational new drugs 20040401
Carbonic anhydrase inhibitors: the first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX. Bioorganic & medicinal chemistry letters 20040223
Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride. Bioorganic & medicinal chemistry letters 20040119
Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX. Bioorganic & medicinal chemistry letters 20040105
Quantitative determination of the novel anticancer drug E7070 (indisulam) and its metabolite (1,4-benzenedisulphonamide) in human plasma, urine and faeces by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Rapid communications in mass spectrometry : RCM 20040101
Phase I and pharmacokinetic study of E7070, a chloroindolyl-sulfonamide anticancer agent, administered on a weekly schedule to patients with solid tumors. Clinical cancer research : an official journal of the American Association for Cancer Research 20031101
In vitro pharmacokinetic study of the novel anticancer agent E7070: red blood cell and plasma protein binding in human blood. Anti-cancer drugs 20030701
Quantitative chemical proteomics for identifying candidate drug targets. Analytical chemistry 20030501
Phase I clinical and pharmacokinetic study of E7070, a novel sulfonamide given as a 5-day continuous infusion repeated every 3 weeks in patients with solid tumours. A study by the EORTC Early Clinical Study Group (ECSG). European journal of cancer (Oxford, England : 1990) 20030501
New analogues of the anticancer E7070: synthesis and pharmacology. Journal of enzyme inhibition and medicinal chemistry 20030401
Indisulam: an anticancer sulfonamide in clinical development. Expert opinion on investigational drugs 20030201
E7070: a novel synthetic sulfonamide targeting the cell cycle progression for the treatment of cancer. Anti-cancer drugs 20021101
Development and validation of limited sampling strategies for prediction of the systemic exposure to the novel anticancer agent E7070 (N-(3-chloro-7-indolyl)-1,4-benzenedisulphonamide). British journal of clinical pharmacology 20021101
Array-based structure and gene expression relationship study of antitumor sulfonamides including N-[2-[(4-hydroxyphenyl)amino]-3-pyridinyl]-4-methoxybenzenesulfonamide and N-(3-chloro-7-indolyl)-1,4-benzenedisulfonamide. Journal of medicinal chemistry 20021024
Population pharmacokinetics of the novel anticancer agent E7070 during four phase I studies: model building and validation. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20021001
An excretion balance and pharmacokinetic study of the novel anticancer agent E7070 in cancer patients. Anti-cancer drugs 20020901
Phase I and pharmacokinetic study of E7070, a novel chloroindolyl sulfonamide cell-cycle inhibitor, administered as a one-hour infusion every three weeks in patients with advanced cancer. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020815
Anticancer agent E7070 inhibits amino acid and uracil transport in fission yeast. Molecular pharmacology 20011201
E7070, a novel sulphonamide agent with potent antitumour activity in vitro and in vivo. European journal of cancer (Oxford, England : 1990) 20011101
Phase I and pharmacokinetic study of E7070, a novel sulfonamide, given at a daily times five schedule in patients with solid tumors. A study by the EORTC-early clinical studies group (ECSG). Annals of oncology : official journal of the European Society for Medical Oncology 20010901
Mechanisms of action of the novel sulfonamide anticancer agent E7070 on cell cycle progression in human non-small cell lung cancer cells. Investigational new drugs 20010101
Properties