Iodophthalein is an organic compound that was formerly used as a diagnostic agent for various medical conditions. It is a derivative of phthalic anhydride, with iodine atoms attached to the aromatic ring. It is synthesized through a multi-step process involving the reaction of phthalic anhydride with iodine and potassium iodide in the presence of an oxidizing agent. Iodophthalein was used as a contrast agent for X-ray imaging of the gallbladder and other organs. However, its use has been largely replaced by safer and more effective alternatives due to its potential toxicity and side effects. Despite its past clinical use, iodophthalein is still studied for its potential applications in other areas, such as in the development of new diagnostic tools and for its unique chemical properties. The compound has shown some potential for use in antimicrobial and antifungal applications. Research into its potential uses continues. '
iodophthalein: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 75195 |
| CHEMBL ID | 1160008 |
| SCHEMBL ID | 867056 |
| MeSH ID | M0062294 |
| PubMed CID | 67846 |
| CHEMBL ID | 1325961 |
| SCHEMBL ID | 2833068 |
| MeSH ID | M0062294 |
| Synonym |
|---|
| 2-((3,5-diiodo-4-oxo-2,5-cyclohexadien-1-ylidene)(4-hydroxy-3,5-diiodophenyl)methyl)benzoic acid |
| phthalein der. |
| 3',3'',5',5''-tetraiodophenophthalein |
| 2-[(3,5-diiodo-4-oxo-cyclohexa-2,5-dien-1-ylidene)-(4-hydroxy-3,5-diiodo-phenyl)methyl]benzoic acid |
| nsc-164900 |
| CHEMBL1160008 |
| dtxsid7048291 , |
| dtxcid8028266 |
| cas-386-17-4 |
| tox21_113639 |
| SCHEMBL867056 |
| nsc4904 |
| nsc-4904 |
| 561-28-4 |
| jodphthaleinum |
| iodophthalein |
| brn 0351654 |
| 3,3-bis(4-hydroxy-3,5-diiodophenyl)phthalide |
| phenolphthalein, 3',3'',5',5''-tetraiodo- |
| iodophthalein sodium free acid |
| einecs 206-857-9 |
| iodophene |
| 3',3'',5',5''-tetraiodophenolphthalein |
| tetraiodophenolphthalein |
| 1(3h)-isobenzofuranone, 3,3-bis(4-hydroxy-3,5-diiodophenyl)- |
| 3,3-bis(4-hydroxy-3,5-diiodophenyl)-1(3h)-isobenzofuranone |
| UPCMLD-DP078:001 |
| UPCMLD-DP078 |
| 3,3-bis(4-hydroxy-3,5-diiodophenyl)-2-benzofuran-1-one |
| 3,3-bis(4-hydroxy-3,5-diiodophenyl)-2-benzofuran-1(3h)-one |
| tetraiodophthalein |
| 386-17-4 |
| T0126 |
| AKOS001044034 |
| unii-r2cc46ua50 |
| r2cc46ua50 , |
| 4-18-00-01949 (beilstein handbook reference) |
| smr002529480 |
| MLS004773975 |
| CHEMBL1325961 |
| 3,3',5,5'-tetraiodophenolphthalein |
| iodophthalein sodium free acid [mi] |
| SCHEMBL2833068 |
| 3,3-bis(4-hydroxy-3,5-diiodo-phenyl)isobenzofuran-1-one |
| mfcd00001614 |
| AS-58248 |
| 3,3-bis(4-hydroxy-3,5-diiodophenyl)-1,3-dihydro-2-benzofuran-1-one |
| 3,3-bis(4-hydroxy-3,5-diiodophenyl)isobenzofuran-1(3h)-one |
| Q19286247 |
| DTXSID10971479 |
| bdbm50530710 |
| CS-0147266 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE | Homo sapiens (human) | Potency | 22.3872 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
| TDP1 protein | Homo sapiens (human) | Potency | 27.3171 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| AR protein | Homo sapiens (human) | Potency | 28.0795 | 0.0002 | 21.2231 | 8,912.5098 | AID743035; AID743042; AID743063 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 9.9499 | 0.0002 | 14.3764 | 60.0339 | AID720691; AID720692; AID720719 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 13.5457 | 0.0002 | 29.3054 | 16,493.5996 | AID743069; AID743075; AID743078 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 2.1314 | 0.0010 | 19.4141 | 70.9645 | AID743140 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 19.4135 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743066; AID743067 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 10.5909 | 0.0023 | 19.5956 | 74.0614 | AID651631; AID720552 |
| Chain A, ATP-DEPENDENT DNA HELICASE Q1 | Homo sapiens (human) | Potency | 8.9125 | 0.1259 | 19.1169 | 125.8920 | AID2549 |
| Luciferase | Photinus pyralis (common eastern firefly) | Potency | 32.1968 | 0.0072 | 15.7588 | 89.3584 | AID624030 |
| phosphopantetheinyl transferase | Bacillus subtilis | Potency | 39.8107 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
| GLS protein | Homo sapiens (human) | Potency | 25.1189 | 0.3548 | 7.9355 | 39.8107 | AID624170 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 17.4882 | 0.1800 | 13.5574 | 39.8107 | AID1460; AID1468 |
| euchromatic histone-lysine N-methyltransferase 2 | Homo sapiens (human) | Potency | 7.0795 | 0.0355 | 20.9770 | 89.1251 | AID504332 |
| Bloom syndrome protein isoform 1 | Homo sapiens (human) | Potency | 35.4813 | 0.5406 | 17.6392 | 96.1227 | AID2528 |
| polyunsaturated fatty acid lipoxygenase ALOX12 | Homo sapiens (human) | Potency | 11.2202 | 1.0000 | 12.2326 | 31.6228 | AID1452 |
| 15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1 | Homo sapiens (human) | Potency | 11.2202 | 0.0018 | 15.6638 | 39.8107 | AID894 |
| vitamin D3 receptor isoform VDRA | Homo sapiens (human) | Potency | 19.9526 | 0.3548 | 28.0659 | 89.1251 | AID504847 |
| thyroid hormone receptor beta isoform a | Homo sapiens (human) | Potency | 50.1187 | 0.0100 | 39.5371 | 1,122.0200 | AID1479 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 35.4813 | 0.0079 | 8.2332 | 1,122.0200 | AID2546 |
| DNA polymerase kappa isoform 1 | Homo sapiens (human) | Potency | 3.5481 | 0.0316 | 22.3146 | 100.0000 | AID588579 |
| histone acetyltransferase KAT2A isoform 1 | Homo sapiens (human) | Potency | 8.9125 | 0.2512 | 15.8432 | 39.8107 | AID504327 |
| Polyunsaturated fatty acid lipoxygenase ALOX15B | Homo sapiens (human) | Potency | 8.9125 | 0.3162 | 12.7657 | 31.6228 | AID881 |
| Histamine H2 receptor | Cavia porcellus (domestic guinea pig) | Potency | 8.9125 | 0.0063 | 8.2350 | 39.8107 | AID881 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| B2 bradykinin receptor | Cavia porcellus (domestic guinea pig) | IC50 (µMol) | 3.0000 | 0.0011 | 2.5864 | 8.0000 | AID43124; AID43125 |
| Dihydrofolate reductase | Gallus gallus (chicken) | IC50 (µMol) | 20.0000 | 0.0000 | 0.1273 | 0.4000 | AID56466 |
| Beta-lactamase | Escherichia coli K-12 | IC50 (µMol) | 3.0000 | 0.0150 | 2.4657 | 8.0000 | AID218575; AID218680; AID218681; AID218682; AID43124; AID43125 |
| Malate dehydrogenase | Thermus thermophilus | IC50 (µMol) | 25.0000 | 0.7000 | 4.9000 | 8.0000 | AID106657 |
| Chymotrypsinogen B | Homo sapiens (human) | IC50 (µMol) | 11.0000 | 10.0000 | 10.0000 | 10.0000 | AID52462 |
| 5-hydroxytryptamine receptor 1A | Rattus norvegicus (Norway rat) | IC50 (µMol) | 3.0000 | 0.0003 | 1.3833 | 8.4000 | AID43124 |
| Beta-lactamase TEM | Escherichia coli | IC50 (µMol) | 4.5000 | 0.0019 | 1.7618 | 10.0000 | AID43245; AID43246; AID43247 |
| Beta-lactamase TEM | Escherichia coli | IC50 (µMol) | 3.4000 | 0.0019 | 1.7618 | 10.0000 | AID1616742 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID43246 | Inhibitory activity against TEM-1 Beta-lactamase mutant G238A at 42 degree Centigrade | 2003 | Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20 | A specific mechanism of nonspecific inhibition. |
| AID106657 | Inhibitory activity against malate dehydrogenase (MDH) from Thermus flavus | 2003 | Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8 | Kinase inhibitors: not just for kinases anymore. |
| AID218575 | Inhibitory activity against beta-lactamase | 2002 | Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8 | A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. |
| AID43251 | Percentage inhibition against beta-Lactamase in the absence of detergent Triton X-100 was determined at a concentration of 10 uM | 2003 | Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20 | A specific mechanism of nonspecific inhibition. |
| AID218680 | Inhibitory activity against beta-lactamase in the presence of 500 mMKPi concentration of buffer | 2002 | Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8 | A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. |
| AID43247 | Inhibitory activity against TEM-1 Beta-lactamase mutant M182T at 42 degree Centigrade | 2003 | Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20 | A specific mechanism of nonspecific inhibition. |
| AID43245 | Inhibitory activity against TEM-1 Beta-lactamase mutant G238A at 24 degree Centigrade | 2003 | Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20 | A specific mechanism of nonspecific inhibition. |
| AID218566 | Preincubated with beta-lactamase, inhibitory activity expressed as fold decrease in IC50(ie. improved activity) | 2002 | Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8 | A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. |
| AID52780 | Inhibitory activity against chymotrypsinogen | 2002 | Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8 | A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. |
| AID218679 | Inhibition of beta-lactamase from Escherichia coli | 2003 | Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8 | Kinase inhibitors: not just for kinases anymore. |
| AID43125 | Inhibitory activity against Beta-lactamase from DMSO stock was determined | 2003 | Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20 | A specific mechanism of nonspecific inhibition. |
| AID40277 | Inhibition of Beta-galactosidase | 2002 | Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8 | A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. |
| AID56466 | Inhibitory activity against cloned Dihydrofolate reductase (cDHFR) | 2002 | Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8 | A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. |
| AID218689 | The effect of 10-fold increase in enzyme concentration on beta-lactamase inhibition. | 2002 | Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8 | A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. |
| AID228517 | Aggregates forming ability by dynamic light scattering(DLS). | 2002 | Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8 | A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. |
| AID43124 | Inhibitory activity against Amp C beta-Lactamase | 2003 | Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20 | A specific mechanism of nonspecific inhibition. |
| AID218681 | Inhibitory activity against beta-lactamase in the presence of 50 mM KPi concentration of buffer | 2002 | Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8 | A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. |
| AID43259 | Percentage inhibition against beta-Lactamase in the presence of detergent 0.01% Triton X-100 was determined at a concentration of 10 uM | 2003 | Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20 | A specific mechanism of nonspecific inhibition. |
| AID52462 | Inhibitory activity against Chymotrypsinogen from Thermus flavus | 2003 | Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8 | Kinase inhibitors: not just for kinases anymore. |
| AID43266 | Percentage inhibition of Beta-lactamase at KPi (Potassium Phosphate) stock concentration of 10 uM | 2003 | Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20 | A specific mechanism of nonspecific inhibition. |
| AID218682 | Inhibitory activity against beta-lactamase in the presence of 5 mM KPi concentration of buffer | 2002 | Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8 | A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. |
| AID1616743 | Inhibition of bacterial Beta-lactamase TEM-1 R164S mutant pre-incubated for 5 mins before addition of chromogenic beta-lactamase substrate CENTA by spectrophotometry | 2019 | Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21 | Protein Stability Effects in Aggregate-Based Enzyme Inhibition. |
| AID1616740 | Inhibition of bacterial Beta-lactamase TEM-1 M182T mutant pre-incubated for 5 mins before addition of chromogenic beta-lactamase substrate CENTA by spectrophotometry | 2019 | Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21 | Protein Stability Effects in Aggregate-Based Enzyme Inhibition. |
| AID1616741 | Inhibition of bacterial Beta-lactamase TEM-1 M182T/G238S mutant pre-incubated for 5 mins before addition of chromogenic beta-lactamase substrate CENTA by spectrophotometry | 2019 | Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21 | Protein Stability Effects in Aggregate-Based Enzyme Inhibition. |
| AID1616744 | Inhibition of bacterial Beta-lactamase TEM-1 G238S mutant pre-incubated for 5 mins before addition of chromogenic beta-lactamase substrate CENTA by spectrophotometry | 2019 | Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21 | Protein Stability Effects in Aggregate-Based Enzyme Inhibition. |
| AID1616742 | Inhibition of bacterial wild type Beta-lactamase TEM-1 pre-incubated for 5 mins before addition of chromogenic beta-lactamase substrate CENTA by spectrophotometry | 2019 | Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21 | Protein Stability Effects in Aggregate-Based Enzyme Inhibition. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 7 (41.18) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 5 (29.41) | 29.6817 |
| 2010's | 3 (17.65) | 24.3611 |
| 2020's | 2 (11.76) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (11.84) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 6 (100.00%) | 84.16% |
| Other | 11 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||