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*This document is like a lab demo—an example Certificate of Analysis (COA) that showcases what a COA looks like but may not match the latest batch in all its glory. Think of it as a chemistry experiment: close, but not quite the final reaction!
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Bulk Quote| IUPAC name | 3-(7-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione |
| inchi | InChI=1S/C13H13N3O3/c14-9-3-1-2-7-8(9)6-16(13(7)19)10-4-5-11(17)15-12(10)18/h1-3,10H,4-6,14H2,(H,15,17,18) |
| inchi key | GOTYRUGSSMKFNF-UHFFFAOYSA-N |
| molecular formula | C13H13N3O3 |
| synonyms | |
| Compound Description |
| Molecular Weight: | 259.26 g/mol |
| XLogP3: | -0.5 |
| Hydrogen Bond Donor Count: | 2 |
| Hydrogen Bond Acceptor Count: | 4 |
| Rotatable Bond Count: | 1 |
| Exact Mass: | 259.09569129 g/mol |
| Monoisotopic Mass: | 259.09569129 g/mol |
| Topological Polar Surface Area: | 92.5 Ų |
| Heavy Atom Count: | 19 |
| Formal Charge: | 0 |
| Complexity: | 437 |
| Isotope Atom Count: | 0 |
| Defined Atom Stereocenter Count: | 0 |
| Undefined Atom Stereocenter Count: | 1 |
| Defined Bond Stereocenter Count: | 0 |
| Undefined Bond Stereocenter Count: | 0 |
| Covalently-Bonded Unit Count: | 1 |
| Compound Is Canonicalized: | Yes |
| hazard signal | Danger |
| hazard classes and categories | |
| precautionary statement codes | P203, P260, P261, P264, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P318, P319, P321, P330, P362+P364, P405, and P501 |
| hazard statements |
| toxicity summary | IDENTIFICATION AND USE: Lenalidomide is off-white to pale-yellow solid powder. Lenalidomide, a thalidomide analog, is an immunomodulatory agent with antineoplastic and antiangiogenic activity. Lenalidomide is used for the treatment of patients with transfusion-dependent anemia due to low- or intermediate-1-risk myelodysplastic syndromes associated with a deletion 5q cytogenetic abnormality with or without additional cytogenetic abnormalities. It is also used for the treatment of patients with mantle cell lymphoma whose disease has relapsed or progressed after two prior therapies, one of which included bortezomib. It is used in combination with dexamethasone for the treatment of patients with multiple myeloma who have received at least one prior therapy. HUMAN EXPOSURE AND TOXICITY: Lenalidomide can cause fetal harm when administered to a pregnant female. Limb abnormalities were seen in the offspring of monkeys that were dosed with lenalidomide during organogenesis. This effect was seen at all doses tested. Due to the results of this developmental monkey study, and lenalidomide's structural similarities to thalidomide, a known human teratogen, lenalidomide is contraindicated in females who are pregnant. Lenalidomide has demonstrated a significantly increased risk of deep vein thrombosis and pulmonary embolism , as well as risk of myocardial infarction and stroke in patients with multiple myeloma who were treated with lenalidomide and dexamethasone therapy. Hepatic failure, including fatal cases, has occurred in patients treated with lenalidomide in combination with dexamethasone. Patients with multiple myeloma treated with lenalidomide in studies including melphalan and stem cell transplantation had a higher incidence of second primary malignancies, particularly acute myelogenous leukemia and Hodgkin lymphoma, compared to patients in the control arms who received similar therapy but did not receive lenalidomide. Lenalidomide can cause significant neutropenia and thrombocytopenia. Fatal instances of tumor lysis syndrome have been reported during treatment with lenalidomide. The patients at risk of tumor lysis syndrome are those with high tumor burden prior to treatment. Angioedema and serious dermatologic reactions, including Stevens-Johnson syndrome and toxic epidermal necrolysis, have been reported in lenalidomide-treated patients. These reactions can be fatal. ANIMAL STUDIES: Acute administration of lenalidomide to rats and mice via intravenous and oral administration did not result in mortality. However, repeated oral administration of 4 and 6 mg/kg/day to monkeys for up to 20 weeks produced mortality and significant toxicity. The embryotoxic and teratogenic potential of lenalidomide was studied in rats, rabbits and monkeys. A pre- and post-natal development study in rats revealed few adverse effects in the offspring of female rats treated with lenalidomide at doses up to 500 mg/kg. In rabbits, no limb abnormalities were attributable to lenalidomide in the offspring of females administered 3, 10 and 20 mg/kg/day orally. Developmental toxicity at the 10 and 20 mg/kg/day dose levels was characterized by slightly reduced fetal body weights, increased incidences of post implantation loss , and gross external findings in the fetuses associated with morbidity and pharmacotoxic effects of lenalidomide . An absence of the intermediate lobe of the lung was observed at 10 and 20 mg/kg/day with dose dependence and displaced kidneys were observed at 20 mg/kg/day. Soft tissue and skeletal variations in the fetuses were also observed at 10 and 20 mg/kg/day. These included minor variations in skull ossification and small delays in ossification of the metacarpals, associated with the reduced fetal body weights. In monkeys, malformations were observed in the offspring of female monkeys who received lenalidomide doses as low as 0.5 mg/kg/day during pregnancy. The observed malformations ranged from stiff and slightly malrotated hindlimbs at 0.5 mg/kg/day of lenalidomide up to severe external malformations, such as bent, shortened, malformed, malrotated, and/or absent part of the extremities, oligo- or polydactyly at 4 mg/kg/day of lenalidomide. Lenalidomide was not mutagenic in the bacterial reverse mutation assay and did not induce chromosome aberrations in cultured human peripheral blood lymphocytes, or mutations at the thymidine kinase locus of mouse lymphoma L5178Y cells. Lenalidomide did not increase morphological transformation in Syrian Hamster Embryo assay or induce micronuclei in the polychromatic erythrocytes of the bone marrow of male rats. |
| symptoms |
