IV3
ivosidenib
| Created: | 2023-07-04 |
| Last modified: | 2024-08-28 |
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Chemical Details | |
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| Formal Charge | 0 |
| Atom Count | 63 |
| Chiral Atom Count | 2 |
| Bond Count | 67 |
| Aromatic Bond Count | 18 |
Chemical Component Summary | |
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| Name | ivosidenib |
| Synonyms | N-{(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl}-1-(4-cyanopyridin-2-yl)-N-(5-fluoropyridin-3-yl)-5-oxo-L-prolinamide |
| Systematic Name (OpenEye OEToolkits) | (2~{S})-~{N}-[(1~{S})-2-[[3,3-bis(fluoranyl)cyclobutyl]amino]-1-(2-chlorophenyl)-2-oxidanylidene-ethyl]-1-(4-cyanopyridin-2-yl)-~{N}-(5-fluoranylpyridin-3-yl)-5-oxidanylidene-pyrrolidine-2-carboxamide |
| Formula | C28 H22 Cl F3 N6 O3 |
| Molecular Weight | 582.961 |
| Type | NON-POLYMER |
Chemical Descriptors | |||
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| Type | Program | Version | Descriptor |
| SMILES | ACDLabs | 12.01 | FC1(F)CC(C1)NC(=O)C(c1ccccc1Cl)N(c1cc(F)cnc1)C(=O)C1CCC(=O)N1c1nccc(C#N)c1 |
| SMILES | CACTVS | 3.385 | Fc1cncc(c1)N([CH](C(=O)NC2CC(F)(F)C2)c3ccccc3Cl)C(=O)[CH]4CCC(=O)N4c5cc(ccn5)C#N |
| SMILES | OpenEye OEToolkits | 2.0.7 | c1ccc(c(c1)C(C(=O)NC2CC(C2)(F)F)N(c3cc(cnc3)F)C(=O)C4CCC(=O)N4c5cc(ccn5)C#N)Cl |
| Canonical SMILES | CACTVS | 3.385 | Fc1cncc(c1)N([C@H](C(=O)NC2CC(F)(F)C2)c3ccccc3Cl)C(=O)[C@@H]4CCC(=O)N4c5cc(ccn5)C#N |
| Canonical SMILES | OpenEye OEToolkits | 2.0.7 | c1ccc(c(c1)[C@@H](C(=O)NC2CC(C2)(F)F)N(c3cc(cnc3)F)C(=O)[C@@H]4CCC(=O)N4c5cc(ccn5)C#N)Cl |
| InChI | InChI | 1.06 | InChI=1S/C28H22ClF3N6O3/c29-21-4-2-1-3-20(21)25(26(40)36-18-11-28(31,32)12-18)37(19-10-17(30)14-34-15-19)27(41)22-5-6-24(39)38(22)23-9-16(13-33)7-8-35-23/h1-4,7-10,14-15,18,22,25H,5-6,11-12H2,(H,36,40)/t22-,25-/m0/s1 |
| InChIKey | InChI | 1.06 | WIJZXSAJMHAVGX-DHLKQENFSA-N |
Drug Info: DrugBank
DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
| DrugBank ID | DB14568? |
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| Name | Ivosidenib |
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| Description | Ivosidenib is a first-in-class isocitrate dehydrogenase-1 (IDH1) inhibitor. IDH1 is an enzyme that is often mutated and overexpressed in some cancers, leading to aberrant cell growth and proliferation.[A248750] Ivosidenib inhibits mutated IDH1, blocking the enzymatic activity and further differentiation of cancer cells.[A248745] Ivosidenib was granted accelerated approval by the FDA in July 2018 for the treatment of relapsed of refractory acute myeloid leukemia in adults.[A248745] It is currently approved to also treat newly diagnosed acute myeloid leukemia in older adults in combination [azacitidine] or as monotherapy, as well as locally advanced or metastatic cholangiocarcinoma and relapsed or refractory myelodysplastic syndromes in adults. The drug is only effective in patients with a susceptible IDH1 mutation.[L48781] In February 2023, the EMA's Committee for Medicinal Products for Human Use (CHMP) adopted a positive opinion of ivosidenib and recommended it be granted marketing authorization for the treatment of acute myeloid leukemia and cholangiocarcinoma.[L46287] It was fully approved by the EMA in May 2023.[L46596] |
| Synonyms | Ivosidenib |
| Brand Names | Tibsovo |
| Indication | Ivosidenib is an isocitrate dehydrogenase-1 (IDH1) inhibitor approved for use in the US and Europe. It is indicated for the treatment of patients with a susceptible IDH1 mutation with: - **Newly Diagnosed Acute Myeloid Leukemia (AML)** in combination [azacitidine] or as monotherapy for the treatment of newly diagnosed AML in adults who have comorbidities that preclude the use of intensive induction chemotherapy.[L41870, L46591] this indication is reserved for adults 75 years or older in the US.[L41870] - **Relapsed or refractory AML** in adults in the US.[L41870] - **Locally Advanced or Metastatic Cholangiocarcinoma** in adults who have been previously treated.[L41870, L46591] - **Relapsed or Refractory Myelodysplastic Syndromes** in adults.[L48781] |
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| ATC-Code | L01XX62 |
| CAS number | 1448347-49-6 |
Drug Targets
DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
| Name | Target Sequence | Pharmacological Action | Actions |
|---|---|---|---|
| Isocitrate dehydrogenase [NADP] cytoplasmic | MSKKISGGSVVEMQGDEMTRIIWELIKEKLIFPYVELDLHSYDLGIENRD... | unknown | inhibitor |
| Cytochrome P450 3A4 | MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI... | unknown | substrate,inducer |
| Cytochrome P450 2B6 | MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG... | unknown | inducer |
| Cytochrome P450 2C9 | MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI... | unknown | inducer |
| Cytochrome P450 2C8 | MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI... | unknown | inducer |
| View More | |||
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison
T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS.
Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682
Related Resource References
| Resource Name | Reference |
|---|---|
| Pharos | CHEMBL3989958 |
| PubChem | 71657455 |
| ChEMBL | CHEMBL3989958 |
| ChEBI | CHEBI:145430 |
