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 15:16:51 UTC |
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Update Date | 2022-03-07 02:51:49 UTC |
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HMDB ID | HMDB0015018 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Chlorothiazide |
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Description | Chlorothiazide is only found in individuals that have used or taken this drug. It is a thiazide diuretic with actions and uses similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p812)As a diuretic, chlorothiazide inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like chlorothiazide also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of chlorothiazide is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle. |
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Structure | NS(=O)(=O)C1=C(Cl)C=C2NC=NS(=O)(=O)C2=C1 InChI=1S/C7H6ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-3H,(H,10,11)(H2,9,12,13) |
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Synonyms | Value | Source |
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6-Chloro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[1,2,4]thiadiazine-7-sulfonic acid amide | ChEBI | 6-Chloro-7-sulfamoyl-2H-1,2,4-benzothiadiazine 1,1-dioxide | ChEBI | Chlorothiazidum | ChEBI | Clorotiazida | ChEBI | Diuril | Kegg | 6-Chloro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[1,2,4]thiadiazine-7-sulfonate amide | Generator | 6-Chloro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[1,2,4]thiadiazine-7-sulphonate amide | Generator | 6-Chloro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[1,2,4]thiadiazine-7-sulphonic acid amide | Generator | 6-Chloro-7-sulphamoyl-2H-1,2,4-benzothiadiazine 1,1-dioxide | Generator | Chlorothiazid | HMDB | Chlorthiazide | HMDB | Chlortiazid | HMDB |
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Chemical Formula | C7H6ClN3O4S2 |
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Average Molecular Weight | 295.723 |
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Monoisotopic Molecular Weight | 294.948824782 |
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IUPAC Name | 6-chloro-1,1-dioxo-4H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide |
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Traditional Name | microzide |
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CAS Registry Number | 58-94-6 |
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SMILES | NS(=O)(=O)C1=C(Cl)C=C2NC=NS(=O)(=O)C2=C1 |
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InChI Identifier | InChI=1S/C7H6ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-3H,(H,10,11)(H2,9,12,13) |
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InChI Key | JBMKAUGHUNFTOL-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1,2,4-benzothiadiazine-1,1-dioxides. These are aromatic heterocyclic compounds containing a 1,2,4-benzothiadiazine ring system with two S=O bonds at the 1-position. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Thiadiazines |
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Sub Class | Benzothiadiazines |
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Direct Parent | 1,2,4-benzothiadiazine-1,1-dioxides |
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Alternative Parents | |
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Substituents | - 1,2,4-benzothiadiazine-1,1-dioxide
- Aryl chloride
- Aryl halide
- Organosulfonic acid amide
- Benzenoid
- Organic sulfonic acid or derivatives
- Organosulfonic acid or derivatives
- Sulfonyl
- Aminosulfonyl compound
- Propargyl-type 1,3-dipolar organic compound
- Formamidine
- Amidine
- Organic 1,3-dipolar compound
- Azacycle
- Organopnictogen compound
- Organic nitrogen compound
- Organic oxygen compound
- Organosulfur compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Hydrocarbon derivative
- Organic oxide
- 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 | |
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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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Chlorothiazide,1TMS,isomer #1 | C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 2806.1 | Semi standard non polar | 33892256 | Chlorothiazide,1TMS,isomer #1 | C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 2738.9 | Standard non polar | 33892256 | Chlorothiazide,1TMS,isomer #1 | C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 4170.7 | Standard polar | 33892256 | Chlorothiazide,1TMS,isomer #2 | C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21 | 2765.1 | Semi standard non polar | 33892256 | Chlorothiazide,1TMS,isomer #2 | C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21 | 2977.5 | Standard non polar | 33892256 | Chlorothiazide,1TMS,isomer #2 | C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21 | 4277.9 | Standard polar | 33892256 | Chlorothiazide,2TMS,isomer #1 | C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 2697.6 | Semi standard non polar | 33892256 | Chlorothiazide,2TMS,isomer #1 | C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 2907.5 | Standard non polar | 33892256 | Chlorothiazide,2TMS,isomer #1 | C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 4114.0 | Standard polar | 33892256 | Chlorothiazide,2TMS,isomer #2 | C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=NS2(=O)=O | 2763.8 | Semi standard non polar | 33892256 | Chlorothiazide,2TMS,isomer #2 | C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=NS2(=O)=O | 2971.6 | Standard non polar | 33892256 | Chlorothiazide,2TMS,isomer #2 | C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C=NS2(=O)=O | 3751.4 | Standard polar | 33892256 | Chlorothiazide,3TMS,isomer #1 | C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C21 | 2712.9 | Semi standard non polar | 33892256 | Chlorothiazide,3TMS,isomer #1 | C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C21 | 3299.3 | Standard non polar | 33892256 | Chlorothiazide,3TMS,isomer #1 | C[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C21 | 3829.4 | Standard polar | 33892256 | Chlorothiazide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 3064.3 | Semi standard non polar | 33892256 | Chlorothiazide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 2995.4 | Standard non polar | 33892256 | Chlorothiazide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 4224.8 | Standard polar | 33892256 | Chlorothiazide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21 | 3051.4 | Semi standard non polar | 33892256 | Chlorothiazide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21 | 3229.7 | Standard non polar | 33892256 | Chlorothiazide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C21 | 4460.4 | Standard polar | 33892256 | Chlorothiazide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 3205.8 | Semi standard non polar | 33892256 | Chlorothiazide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 3398.8 | Standard non polar | 33892256 | Chlorothiazide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC=NS2(=O)=O | 4127.4 | Standard polar | 33892256 | Chlorothiazide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=NS2(=O)=O | 3226.1 | Semi standard non polar | 33892256 | Chlorothiazide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=NS2(=O)=O | 3416.2 | Standard non polar | 33892256 | Chlorothiazide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C=NS2(=O)=O | 3853.5 | Standard polar | 33892256 | Chlorothiazide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C21 | 3436.7 | Semi standard non polar | 33892256 | Chlorothiazide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C21 | 4034.0 | Standard non polar | 33892256 | Chlorothiazide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=NS(=O)(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C21 | 3936.2 | 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 - Chlorothiazide GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fvi-3390000000-4907b28333e017912f33 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Chlorothiazide 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 - Chlorothiazide LC-ESI-QFT , negative-QTOF | splash10-0006-0090000000-e74dd6446e0284a7f0aa | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF | splash10-0006-0090000000-baf93e639a13c39dc1d6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF | splash10-01ox-0090000000-473477518be3f6c8ddcd | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF | splash10-03di-0290000000-0e599c26917ade291ca0 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF | splash10-03di-0890000000-ad270ef1247ce9a114ad | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF | splash10-004i-0920000000-3c4bb920bb8316022718 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF | splash10-004i-2900000000-eca13dbca70054de3470 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF | splash10-02vr-9700000000-9261e1bf4e212aee7d84 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , negative-QTOF | splash10-0i09-9100000000-491baf01fc6ef9ca39e1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF | splash10-0002-0090000000-388cb4ff11dc0a41ad99 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF | splash10-002b-0090000000-5645eee512f78cd689a7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF | splash10-0udi-0390000000-a39ffe78224ed4cacc13 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF | splash10-0pbl-0920000000-eb979e3c4ecd1f12fb71 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF | splash10-059f-2900000000-4c2eb27958fba0102431 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF | splash10-05tk-5900000000-b42b446bc2b9f6216af1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF | splash10-00kk-9400000000-b4b975e3c1fabe09f4a7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF | splash10-03di-9100000000-f8f80586b12a43c2a667 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide LC-ESI-QFT , positive-QTOF | splash10-03di-9000000000-9d41a0f061f998097c17 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Chlorothiazide 60V, Negative-QTOF | splash10-03di-0190000000-b4aa6830cd5272c0d44b | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlorothiazide 10V, Positive-QTOF | splash10-0002-0090000000-6500ac39cf672b42f75d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlorothiazide 20V, Positive-QTOF | splash10-014i-0090000000-80ebd93be346579a63b3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlorothiazide 40V, Positive-QTOF | splash10-0uxr-0790000000-2156a2679d57dbda9635 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlorothiazide 10V, Negative-QTOF | splash10-0006-0090000000-d2924827db1564ab2598 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlorothiazide 20V, Negative-QTOF | splash10-0006-1090000000-5218745f5848fdcbeb08 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chlorothiazide 40V, Negative-QTOF | splash10-004i-9020000000-8cc5eabcbcc35fa29dbc | 2016-08-03 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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