Record Information |
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Version | 1.0 |
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Creation Date | 2016-06-03 13:31:30 UTC |
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Update Date | 2016-11-09 01:23:22 UTC |
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Accession Number | CHEM045629 |
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Identification |
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Common Name | irrinotecan |
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Class | Small Molecule |
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Description | A member of the class of pyranoindolizinoquinolines that is the carbamate ester obtained by formal condensation of the carboxy group of [1,4'-bipiperidine]-1'-carboxylic acid with the phenolic hydroxy group of (4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2- hydrochloride]quinoline-3,14-dione. Used (in the form of its hydrochloride salt trihydrate) in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine-based therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active. |
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Contaminant Sources | - HMDB Contaminants - Urine
- STOFF IDENT Compounds
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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(+)-Irinotecan | ChEBI | HSDB 7607 | ChEBI | Irinophore C | ChEBI | Irinotecan lactone | ChEBI | Irinotecan mylan | ChEBI | Irinotecanum | ChEBI | Biotecan | Kegg | Irinotecan hydrochloride trihydrate | HMDB | CPT-11 | HMDB | sn38 CPD | HMDB | 7-Ethyl-10-hydroxycamptothecin | HMDB | Camptosar | HMDB | Irrinotecan | HMDB | Camptothecin-11 | HMDB | Irinotecan hydrochloride | HMDB | NK012 Compound | HMDB | sn-38 | HMDB | CPT 11 | HMDB | sn 38 | HMDB | 7 Ethyl 10 hydroxycamptothecin | HMDB | CPT11 | HMDB | Camptothecin 11 | HMDB |
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Chemical Formula | C33H38N4O6 |
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Average Molecular Mass | 586.678 g/mol |
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Monoisotopic Mass | 586.279 g/mol |
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CAS Registry Number | 97682-44-5 |
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IUPAC Name | (19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate |
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Traditional Name | irinotecan |
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SMILES | CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2 |
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InChI Identifier | InChI=1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1 |
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InChI Key | UWKQSNNFCGGAFS-XIFFEERXSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring). |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Camptothecins |
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Sub Class | Not Available |
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Direct Parent | Camptothecins |
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Alternative Parents | |
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Substituents | - Camptothecin
- Pyranopyridine
- Quinoline
- Piperidinecarboxylic acid
- 4-aminopiperidine
- Pyridinone
- Piperidine
- Pyridine
- Benzenoid
- Carbamic acid ester
- Tertiary alcohol
- Heteroaromatic compound
- Amino acid or derivatives
- Tertiary aliphatic amine
- Tertiary amine
- Carboxylic acid ester
- Lactam
- Lactone
- Carbonic acid derivative
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organopnictogen compound
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organic nitrogen compound
- Organic oxide
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS ("Irinotecan,1TMS,#1" TMS) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0006-0091000000-b15811b1af58e71b3ec6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0006-0091000000-b15811b1af58e71b3ec6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-000i-0101190000-eed1a0e57a719811aa8e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-000i-0200090000-b02dc01510d13cf037e7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0006-0000090000-f8b88d90efcda01ed933 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kr-0711190000-017c476dfdce0a695ded | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014j-1913030000-900f8f5bcd9d41c35513 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-4900000000-2609623f4a3366568329 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000l-0301190000-9348778de404f9c838c4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-2915280000-3ff569c46ef34dfc85a4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03xr-3973100000-fa1a14e54424adaa488b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000090000-5a234f897e3e4b6515a3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0100190000-7b0ab4e5fa02d64ba15a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-02gk-4900010000-b6eab61080ef0a9d3fc8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0000090000-ada5e1406bd27c1d2b44 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0000290000-fe55b707040cb6e249f1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001r-0312290000-ba4e4f01f6849a926d64 | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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External Links |
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DrugBank ID | DB00762 |
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HMDB ID | HMDB0014900 |
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FooDB ID | Not Available |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | C00052324 |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | CP0 |
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Wikipedia Link | Irinotecan |
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Chemspider ID | 54825 |
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ChEBI ID | 80630 |
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PubChem Compound ID | 60838 |
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Kegg Compound ID | C16641 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. https://www.ncbi.nlm.nih.gov/pubmed/?term=26081596 | 2. https://www.ncbi.nlm.nih.gov/pubmed/?term=26352218 | 3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26381420 | 4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26487578 | 5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26503200 | 6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26526067 | 7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26541586 | 8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26574999 | 9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26580826 | 10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26739304 | 11. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. | 12. Innocenti F, Undevia SD, Iyer L, Chen PX, Das S, Kocherginsky M, Karrison T, Janisch L, Ramirez J, Rudin CM, Vokes EE, Ratain MJ: Genetic variants in the UDP-glucuronosyltransferase 1A1 gene predict the risk of severe neutropenia of irinotecan. J Clin Oncol. 2004 Apr 15;22(8):1382-8. Epub 2004 Mar 8. | 13. O'Dwyer PJ, Catalano RB: Uridine diphosphate glucuronosyltransferase (UGT) 1A1 and irinotecan: practical pharmacogenomics arrives in cancer therapy. J Clin Oncol. 2006 Oct 1;24(28):4534-8. | 14. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. | 15. FDA label |
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