Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:48 UTC |
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HMDB ID | HMDB0014946 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Indapamide |
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Description | Indapamide is only found in individuals that have used or taken this drug. It is a benzamide-sulfonamide-indole. It is called a thiazide-like diuretic but structure is different enough (lacking the thiazo-ring) so it is not clear that the mechanism is comparable. [PubChem]Indapamide blocks the slow component of delayed rectifier potassium current (IKs) without altering the rapid component (IKr) or the inward rectifier current. Specifically it blocks or antagonizes the action the proteins KCNQ1 and KCNE1. Indapamide is also thought to stimulate the synthesis of the vasodilatory hypotensive prostaglandin PGE2. |
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Structure | CC1CC2=CC=CC=C2N1NC(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O InChI=1S/C16H16ClN3O3S/c1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23/h2-7,9-10H,8H2,1H3,(H,19,21)(H2,18,22,23) |
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Synonyms | Value | Source |
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Indapamida | ChEBI | Indapamidum | ChEBI | Lozol | Kegg | Natrix | Kegg | Metindamide | HMDB |
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Chemical Formula | C16H16ClN3O3S |
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Average Molecular Weight | 365.835 |
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Monoisotopic Molecular Weight | 365.06008979 |
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IUPAC Name | 4-chloro-N-(2-methyl-2,3-dihydro-1H-indol-1-yl)-3-sulfamoylbenzamide |
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Traditional Name | indapamide |
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CAS Registry Number | 26807-65-8 |
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SMILES | CC1CC2=CC=CC=C2N1NC(=O)C1=CC(=C(Cl)C=C1)S(N)(=O)=O |
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InChI Identifier | InChI=1S/C16H16ClN3O3S/c1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23/h2-7,9-10H,8H2,1H3,(H,19,21)(H2,18,22,23) |
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InChI Key | NDDAHWYSQHTHNT-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Benzenesulfonamides |
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Direct Parent | Benzenesulfonamides |
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Alternative Parents | |
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Substituents | - Benzenesulfonamide
- Halobenzoic acid or derivatives
- 4-halobenzoic acid or derivatives
- Benzoic acid or derivatives
- Benzenesulfonyl group
- Indole or derivatives
- Benzoyl
- Chlorobenzene
- Halobenzene
- Aryl chloride
- Aryl halide
- Organosulfonic acid amide
- Aminosulfonyl compound
- Sulfonyl
- Organosulfonic acid or derivatives
- Organic sulfonic acid or derivatives
- Carboxylic acid hydrazide
- Organoheterocyclic compound
- Azacycle
- Carboxylic acid derivative
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Organosulfur compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 161 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.034 g/L | Not Available | LogP | 2.2 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Indapamide,1TMS,isomer #1 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1 | 3206.4 | Semi standard non polar | 33892256 | Indapamide,1TMS,isomer #1 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1 | 3172.0 | Standard non polar | 33892256 | Indapamide,1TMS,isomer #1 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1 | 4145.5 | Standard polar | 33892256 | Indapamide,1TMS,isomer #2 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C | 3072.8 | Semi standard non polar | 33892256 | Indapamide,1TMS,isomer #2 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C | 3157.4 | Standard non polar | 33892256 | Indapamide,1TMS,isomer #2 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C | 4557.2 | Standard polar | 33892256 | Indapamide,2TMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1)[Si](C)(C)C | 3050.4 | Semi standard non polar | 33892256 | Indapamide,2TMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1)[Si](C)(C)C | 3271.8 | Standard non polar | 33892256 | Indapamide,2TMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C)=C1)[Si](C)(C)C | 3918.2 | Standard polar | 33892256 | Indapamide,2TMS,isomer #2 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1 | 3174.8 | Semi standard non polar | 33892256 | Indapamide,2TMS,isomer #2 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1 | 3345.7 | Standard non polar | 33892256 | Indapamide,2TMS,isomer #2 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1 | 4085.0 | Standard polar | 33892256 | Indapamide,3TMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C | 3050.7 | Semi standard non polar | 33892256 | Indapamide,3TMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C | 3457.1 | Standard non polar | 33892256 | Indapamide,3TMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C | 3858.3 | Standard polar | 33892256 | Indapamide,1TBDMS,isomer #1 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1 | 3440.7 | Semi standard non polar | 33892256 | Indapamide,1TBDMS,isomer #1 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1 | 3432.0 | Standard non polar | 33892256 | Indapamide,1TBDMS,isomer #1 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1 | 4167.2 | Standard polar | 33892256 | Indapamide,1TBDMS,isomer #2 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C(C)(C)C | 3307.2 | Semi standard non polar | 33892256 | Indapamide,1TBDMS,isomer #2 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C(C)(C)C | 3392.6 | Standard non polar | 33892256 | Indapamide,1TBDMS,isomer #2 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1)[Si](C)(C)C(C)(C)C | 4581.9 | Standard polar | 33892256 | Indapamide,2TBDMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C | 3446.7 | Semi standard non polar | 33892256 | Indapamide,2TBDMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C | 3778.9 | Standard non polar | 33892256 | Indapamide,2TBDMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C | 3975.2 | Standard polar | 33892256 | Indapamide,2TBDMS,isomer #2 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1 | 3615.9 | Semi standard non polar | 33892256 | Indapamide,2TBDMS,isomer #2 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1 | 3845.6 | Standard non polar | 33892256 | Indapamide,2TBDMS,isomer #2 | CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1 | 4098.8 | Standard polar | 33892256 | Indapamide,3TBDMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C | 3650.0 | Semi standard non polar | 33892256 | Indapamide,3TBDMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C | 4183.5 | Standard non polar | 33892256 | Indapamide,3TBDMS,isomer #1 | CC1CC2=CC=CC=C2N1N(C(=O)C1=CC=C(Cl)C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C | 3934.7 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Indapamide GC-MS (Non-derivatized) - 70eV, Positive | splash10-014i-4593000000-5ea2b9ed9ba04df04bf7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Indapamide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Indapamide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF | splash10-03di-0009000000-ed04e0a5871badc8b166 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF | splash10-03di-1729000000-15aecb441ef4febfe526 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF | splash10-000i-2910000000-b72aeba8db62ebdf9c17 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF | splash10-004r-6900000000-f819fedd1ac654d46dd4 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF | splash10-004i-9300000000-164a2972880c967d2195 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF | splash10-004i-9100000000-d18afa355f919614b652 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF | splash10-01t9-9000000000-9d9e98925e9105738992 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF | splash10-03fr-9000000000-5e7568f4efd1730f47b9 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QFT , negative-QTOF | splash10-03di-9000000000-ecfffadaaa03b447eaf5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 15V, Negative-QTOF | splash10-03di-0009000000-402faf8e93d0dbab4819 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 30V, Negative-QTOF | splash10-03di-1729000000-2c08499116b0b0e83854 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 45V, Negative-QTOF | splash10-000i-2910000000-5bbdb2fc2bcf2e62526d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 75V, Negative-QTOF | splash10-004i-9300000000-19c5630af4462cf388c6 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 60V, Negative-QTOF | splash10-004r-6900000000-bc3ba24dca3e6b592b7a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 60V, Negative-QTOF | splash10-004i-9600000000-a6d3375f1b51366171f6 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 45V, Negative-QTOF | splash10-06w9-5910000000-8452c947868c525522c6 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 15V, Negative-QTOF | splash10-03di-0009000000-741ab6c56008aec37aa6 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 30V, Negative-QTOF | splash10-03e9-3937000000-c64237d0b4aba0c26a1c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 90V, Negative-QTOF | splash10-004i-9100000000-8acae7a494ebb42cc17d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide 75V, Negative-QTOF | splash10-004i-9200000000-ab2306e7db927ef1870a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-qTof , Positive-QTOF | splash10-001i-1900000000-861314def0ccc019ac04 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QTOF , positive-QTOF | splash10-001i-0904000000-530b78f6cae834e11768 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QTOF , positive-QTOF | splash10-001i-0900000000-235673a939e2e7d8c5e3 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QTOF , positive-QTOF | splash10-0159-0900000000-a843660d42ffb01666fe | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Indapamide LC-ESI-QTOF , positive-QTOF | splash10-001i-0900000000-cfee205b361c580e3631 | 2017-09-14 | HMDB team, MONA | View Spectrum |
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