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 02:51:53 UTC |
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HMDB ID | HMDB0015149 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Balsalazide |
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Description | Balsalazide is an anti-inflammatory drug used in the treatment of Inflammatory Bowel Disease. It is sold under the name 'Colazal' in the US and 'Colazide' in the UK. The chemical name is (E)-5-[[-4-(2-carboxyethyl) aminocarbonyl] phenyl]azo] -2-hydroxybenzoic acid. It is usually administered as the disodium salt. Balsalazide releases mesalazine, also known as 5-aminosalicylic acid, or 5-ASA, in the large intestine. Its advantage over that drug in the treatment of Ulcerative colitis is believed to be the delivery of the active agent past the small intestine to the large intestine, the active site of ulcerative colitis. |
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Structure | OC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C1=CC=C(O)C(=C1)C(O)=O InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+ |
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Synonyms | Value | Source |
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(e)-5-((4-(((2-Carboxyethyl)amino)carbonyl)phenyl)azo)-2-hydroxybenzoic acid | ChEBI | (e)-5-({p-[(2-carboxyethyl)carbamoyl]phenyl}azo)-2-salicylic acid | ChEBI | 3-(2-{4-[(2-carboxyethyl)carbamoyl]phenyl}hydrazinylidene)-6-oxocyclohexa-1,4-diene-1-carboxylic acid | ChEBI | 5-[4-(2-Carboxy-ethylcarbamoyl)-phenylazo]-2-hydroxy-benzoic acid | ChEBI | Balsalazida | ChEBI | Balsalazido | ChEBI | Balsalazidum | ChEBI | (e)-5-((4-(((2-Carboxyethyl)amino)carbonyl)phenyl)azo)-2-hydroxybenzoate | Generator | (e)-5-({p-[(2-carboxyethyl)carbamoyl]phenyl}azo)-2-salicylate | Generator | 3-(2-{4-[(2-carboxyethyl)carbamoyl]phenyl}hydrazinylidene)-6-oxocyclohexa-1,4-diene-1-carboxylate | Generator | 5-[4-(2-Carboxy-ethylcarbamoyl)-phenylazo]-2-hydroxy-benzoate | Generator | Balsalazide disodium | HMDB |
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Chemical Formula | C17H15N3O6 |
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Average Molecular Weight | 357.3175 |
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Monoisotopic Molecular Weight | 357.096085227 |
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IUPAC Name | 5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxybenzoic acid |
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Traditional Name | balsalazide |
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CAS Registry Number | 80573-04-2 |
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SMILES | OC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C1=CC=C(O)C(=C1)C(O)=O |
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InChI Identifier | InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+ |
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InChI Key | IPOKCKJONYRRHP-FMQUCBEESA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Azobenzenes |
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Sub Class | Not Available |
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Direct Parent | Azobenzenes |
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Alternative Parents | |
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Substituents | - Azobenzene
- Beta amino acid or derivatives
- Hydroxybenzoic acid
- Salicylic acid or derivatives
- Salicylic acid
- Benzoic acid
- Benzoic acid or derivatives
- Benzamide
- Benzoyl
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Dicarboxylic acid or derivatives
- Monocyclic benzene moiety
- Vinylogous acid
- Azo compound
- Secondary carboxylic acid amide
- Carboxamide group
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboxylic acid derivative
- Carboxylic acid
- Carbonyl group
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Organopnictogen compound
- Organonitrogen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | Not Available |
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Role | |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.062 g/L | Not Available | LogP | 1.3 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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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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Balsalazide,1TMS,isomer #1 | C[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1 | 3884.3 | Semi standard non polar | 33892256 | Balsalazide,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)C=C1C(=O)O | 3899.9 | Semi standard non polar | 33892256 | Balsalazide,1TMS,isomer #3 | C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)=CC=C1O | 3881.6 | Semi standard non polar | 33892256 | Balsalazide,1TMS,isomer #4 | C[Si](C)(C)N(CCC(=O)O)C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1 | 3808.7 | Semi standard non polar | 33892256 | Balsalazide,2TMS,isomer #1 | C[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O)=C2)C=C1 | 3847.9 | Semi standard non polar | 33892256 | Balsalazide,2TMS,isomer #2 | C[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C)=C2)C=C1 | 3797.0 | Semi standard non polar | 33892256 | Balsalazide,2TMS,isomer #3 | C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1)[Si](C)(C)C | 3613.8 | Semi standard non polar | 33892256 | Balsalazide,2TMS,isomer #4 | C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)=CC=C1O[Si](C)(C)C | 3859.9 | Semi standard non polar | 33892256 | Balsalazide,2TMS,isomer #5 | C[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C)C=C2)C=C1C(=O)O | 3725.8 | Semi standard non polar | 33892256 | Balsalazide,2TMS,isomer #6 | C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C)C=C2)=CC=C1O | 3621.1 | Semi standard non polar | 33892256 | Balsalazide,3TMS,isomer #1 | C[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)C=C1 | 3783.5 | Semi standard non polar | 33892256 | Balsalazide,3TMS,isomer #2 | C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O)=C2)C=C1)[Si](C)(C)C | 3598.4 | Semi standard non polar | 33892256 | Balsalazide,3TMS,isomer #3 | C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C)=C2)C=C1)[Si](C)(C)C | 3532.0 | Semi standard non polar | 33892256 | Balsalazide,3TMS,isomer #4 | C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C | 3613.3 | Semi standard non polar | 33892256 | Balsalazide,4TMS,isomer #1 | C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)C=C1)[Si](C)(C)C | 3577.8 | Semi standard non polar | 33892256 | Balsalazide,4TMS,isomer #1 | C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)C=C1)[Si](C)(C)C | 3449.0 | Standard non polar | 33892256 | Balsalazide,4TMS,isomer #1 | C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)C=C1)[Si](C)(C)C | 4085.5 | Standard polar | 33892256 | Balsalazide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1 | 4158.0 | Semi standard non polar | 33892256 | Balsalazide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)C=C1C(=O)O | 4198.2 | Semi standard non polar | 33892256 | Balsalazide,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)=CC=C1O | 4172.3 | Semi standard non polar | 33892256 | Balsalazide,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(CCC(=O)O)C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1 | 4093.1 | Semi standard non polar | 33892256 | Balsalazide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2)C=C1 | 4357.5 | Semi standard non polar | 33892256 | Balsalazide,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)C=C1 | 4286.3 | Semi standard non polar | 33892256 | Balsalazide,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1)[Si](C)(C)C(C)(C)C | 4172.8 | Semi standard non polar | 33892256 | Balsalazide,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 4327.4 | Semi standard non polar | 33892256 | Balsalazide,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C)C=C2)C=C1C(=O)O | 4238.4 | Semi standard non polar | 33892256 | Balsalazide,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O | 4146.9 | Semi standard non polar | 33892256 | Balsalazide,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)C=C1 | 4412.4 | Semi standard non polar | 33892256 | Balsalazide,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2)C=C1)[Si](C)(C)C(C)(C)C | 4325.9 | Semi standard non polar | 33892256 | Balsalazide,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)C=C1)[Si](C)(C)C(C)(C)C | 4220.1 | Semi standard non polar | 33892256 | Balsalazide,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C | 4271.8 | Semi standard non polar | 33892256 | Balsalazide,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)C=C1)[Si](C)(C)C(C)(C)C | 4361.2 | Semi standard non polar | 33892256 | Balsalazide,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)C=C1)[Si](C)(C)C(C)(C)C | 4104.3 | Standard non polar | 33892256 | Balsalazide,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)C=C1)[Si](C)(C)C(C)(C)C | 4264.6 | Standard polar | 33892256 |
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Spectra |
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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 - Balsalazide GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ldi-1393000000-af92622c6ce32e802a99 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Balsalazide GC-MS (3 TMS) - 70eV, Positive | splash10-052f-2239460000-dd6d65f067d80197bd6e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Balsalazide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Balsalazide 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 10V, Positive-QTOF | splash10-05mo-1359000000-5ac19318b9222056db99 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 20V, Positive-QTOF | splash10-01b9-4194000000-a389ca20ea5f71b14f1b | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 40V, Positive-QTOF | splash10-00or-9460000000-058a3d277554ae6ad3a0 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 10V, Negative-QTOF | splash10-0r00-0859000000-0815df00a696a3bf2ef9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 20V, Negative-QTOF | splash10-0cdl-1596000000-f30b936242fc2a51a3bc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 40V, Negative-QTOF | splash10-0a4i-1920000000-ab19fc8210a3b9bf159a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 10V, Positive-QTOF | splash10-014i-0090000000-938e67d0a29d75e91560 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 20V, Positive-QTOF | splash10-0297-0094000000-71c0a9165a9dbb26d8ed | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 40V, Positive-QTOF | splash10-0fvi-0590000000-6f84da2d9032ab43467d | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 10V, Negative-QTOF | splash10-0a4i-0019000000-5cde35cdf9191a2d0721 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 20V, Negative-QTOF | splash10-001l-0092000000-e9ef5ce26a4f3979c212 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Balsalazide 40V, Negative-QTOF | splash10-0006-2290000000-1ff988f1dc562e4db92f | 2021-10-11 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01014 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01014 | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB01014 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 10662422 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Balsalazide |
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METLIN ID | Not Available |
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PubChem Compound | Not Available |
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PDB ID | Not Available |
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ChEBI ID | 267413 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. doi: 10.1517/17425250903206996. [PubMed:19743890 ]
- Ragunath K, Williams JG: Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 2001 Oct;15(10):1549-54. [PubMed:11563993 ]
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