Compound: thalidomide
SMILES: O=C1NC(=O)CCC1N2C(=O)c3ccccc3C2=O
InChIKey: UEJJHQNACJXSKW-UHFFFAOYSA-N
Synonyms: thalidomide, 50-35-1, Thalomid, Contergan, Pantosediv, Distaval, Softenon, Kevadon, Calmorex, Neosedyn, Profarmil, Quetimid, Talimol, Telagan, Theophilcholine, Algosediv, Corronarobetin, Ectiluran, Enterosediv, Gastrinide, Nerosedyn, Neurosedin, Neurosedym, Noctosediv, Psycholiquid, Psychotablets, Quietoplex, Sandormin, Sedisperil, Shinnibrol, Telargean, Thalinette, Valgraine, Asmadion, Asmaval, Bonbrain, Calmore, Glutanon, Grippex, Hippuzon, Imidene, Neosydyn, Neurodyn, Nevrodyn, Noxodyn, Sedimide, Sleepan, Softenil, Tensival, Yodomin, Glupan, Isomin, Nibrol, Pangul, Sedin, Slipro, Thalin, Valgis, N-Phthaloylglutamimide, Predni-Sediv, Imida-lab, Sedalis sedi-lab, N-Phthalylglutamic acid imide, Neaufatin, Neurosedyn, Asidon 3, Pro-ban M, 3-Phthalimidoglutarimide, Imidan (peyta), Talidomida, Thaled, alpha-Phthalimidoglutarimide, Sedalis, (+-)-Thalidomide, NSC-66847, 2,6-Dioxo-3-phthalimidopiperidine, N-(2,6-Dioxo-3-piperidyl)phthalimide, Thalidomidum, Pharmion, Talidomide, Celgene, alpha-N-Phthalylglutaramide, Glutarimide, 2-phthalimido-, N-Phthalyl-glutaminsaeure-imid, alpha-(N-Phthalimido)glutarimide, Synovir, Myrin, 1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline, DTXSID9022524, 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-, Phthalimide, N-(2,6-dioxo-3-piperidyl)-, 2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione, 4Z8R6ORS6L, NSC-527179, 2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione, (+-)-N-(2,6-Dioxo-3-piperidyl)phthalimide, NSC66847, DTXCID402524, 2-(6-hydroxy-2-oxo-2,3,4,5-tetrahydropyridin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione, Talidex, Sedoval K-17, RefChem:6298, CHEBI:9513, L04AX02, 2, 6-Dioxo-3-phthalimidopiperidine, 200-031-1, (+/-)-THALIDOMIDE, 2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione, Sedoval, Neufatin, Talargan, Talismol, Shin-naito S, K-17, Bonbrrin, Distaxal, Distoval, Kedavon, Thalidomide Celgene, K 17, .alpha.-Phthalimidoglutarimide, MFCD00153873, N-(2,6-dioxo-3-piperidinyl)phthalimide, .alpha.-N-Phthalylglutaramide, .alpha.-(N-Phthalimido)glutarimide, 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione, CHEMBL468, Thalidomide (soluble form), ENMD 0995, Telargan, Thalomide, 2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione, Pro-Bam M, NCGC00015989-09, Talidomide [DCIT], (+/-)-N-(2,6-dioxo-3-piperidyl)phthalimide, M02554, 1012310-87-0, Talidomida [INN-Spanish], Thalidomidum [INN-Latin], Thalidomine USP26, 2-(2,6-Dioxo-piperidin-3-yl)-isoindole-1,3-dione, Talizer, Phthalimide,6-dioxo-3-piperidyl)-, WLN: T56 BVNVJ C- DT6VMVTJ, Thalomid (TM), Thalomid (TN), Thalidomide Pharmion, Thaled (TN), N-Phthalyl-glutaminsaeure-imid [German], N-Phthalimidoglutamic acid imide, HSDB 3586, 1H-Isoindole-1, 2-(2,6-dioxo-3-piperidinyl)-, SR-01000076184, EINECS 200-031-1, UNII-4Z8R6ORS6L, NSC 527179, BRN 0030233, Talinol, Thalidomide (JAN/USP/INN), AI3-50606, CCRIS 8148, NSC-91730, (y)-Thalidomide, CAS-50-35-1, (?)-Thalidomide, 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione, Nphthaloylglutamimide, Prestwick_463, Thalidomide [USAN:USP:INN:BAN:JAN], (A+/-)-Thalidomide, Pomalidomide Impurity O, Thalidomide (Standard), THALIDOMIDE [MI], (+/-)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione, Prestwick0_000192, Prestwick1_000192, Prestwick2_000192, Prestwick3_000192, Spectrum2_000707, Spectrum3_001715, Spectrum4_001087, Spectrum5_001791, THALIDOMIDE [INN], THALIDOMIDE [JAN], (.+/-.)-Thalidomide, THALIDOMIDE [HSDB], THALIDOMIDE [USAN], UPCMLD-DP139, THALIDOMIDE [VANDF], Thalomid (TN) (Celgene), SCHEMBL7581, NCIOpen2_003188, THALIDOMIDE [MART.], Lopac0_001224, BSPBio_000143, BSPBio_001156, BSPBio_003330, KBioGR_000496, KBioGR_001474, KBioGR_002322, KBioSS_000496, KBioSS_002324, THALIDOMIDE [USP-RS], THALIDOMIDE [WHO-DD], MLS000069353, DivK1c_000051, SPECTRUM1503607, SPBio_000893, SPBio_002064, THALIDOMIDE [EMA EPAR], BPBio1_000159, GTPL7327, orb1310829, SCHEMBL15197560, SCHEMBL23093380, SCHEMBL26641645, UPCMLD-DP139:001, CHEBI:74947, HMS500C13, KBio1_000051, KBio2_000496, KBio2_002322, KBio2_003064, KBio2_004890, KBio2_005632, KBio2_007458, KBio3_000911, KBio3_000912, KBio3_002550, KBio3_002802, THALIDOMIDE [ORANGE BOOK], cMAP_000022, NINDS_000051, Bio1_000387, Bio1_000876, Bio1_001365, Bio2_000418, Bio2_000898, GLXC-07837, HMS1362J17, HMS1568H05, HMS1792J17, HMS1922E12, HMS1990J17, HMS2090O05, HMS2093G15, HMS2095H05, HMS2234C07, HMS3259C22, HMS3263F10, HMS3266F13, HMS3373E06, HMS3373G15, HMS3403J17, HMS3414F19, HMS3654A20, HMS3678F19, HMS3712H05, HMS3884I05, HMS5079O13, Pharmakon1600-01503607, THALIDOMIDE [USP MONOGRAPH], NSC91729, NSC91730, Tox21_110275, Tox21_300580, Tox21_501224, 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-, (+-)-, AC-917, BBL023439, BDBM50070114, CCG-39878, EBC-04403, HY-14658R, MSK157727, NSC527179, NSC758479, STL356025, ( inverted question mark)-Thalidomide, AKOS009529198, Tox21_110275_1, DB01041, FT15648, LP01224, NC00600, NSC-758479, SDCCGSBI-0051191.P004, (+/-)-Thalidomide, >=98%, powder, IDI1_000051, IDI1_002173, (+/-)-Thalidomide - Bio-X trade mark, NCGC00015989-03, NCGC00015989-04, NCGC00015989-05, NCGC00015989-06, NCGC00015989-07, NCGC00015989-08, NCGC00015989-10, NCGC00015989-11, NCGC00015989-12, NCGC00015989-13, NCGC00015989-14, NCGC00015989-16, NCGC00015989-17, NCGC00015989-29, NCGC00015989-32, NCGC00024708-02, NCGC00024708-03, NCGC00024708-04, NCGC00024708-05, NCGC00024708-06, NCGC00024708-07, NCGC00024708-08, NCGC00024708-09, NCGC00024708-10, NCGC00024708-11, NCGC00254343-01, NCGC00261909-01, AS-12367, BP-30256, BT164465, HY-14658, NCI60_023904, SMR000058524, SY052614, WLN: T56 BVNVJ C- DT6VMVTJ -D, WLN: T56 BVNVJ C- DT6VMVTJ -L, SBI-0051191.P003, DB-051759, Phthalimide,6-dioxo-3-piperidyl)-, (+)-, Phthalimide,6-dioxo-3-piperidyl)-, (-)-, AB00052362, EU-0101224, NS00009590, S1193, ST51039042, SW196678-4, T0213, T2524, EN300-60005, Phthalimide,6-dioxo-3-piperidyl)-, D-(+)-, Phthalimide,6-dioxo-3-piperidyl)-, L-(-)-, C07910, D00754, AB00052362-11, AB00052362-12, AB00052362-13, AB00052362_14, AB00052362_15, Thalidomide (Immunoprin, Contergan and Thalomid), Q203174, SR-01000076184-1, SR-01000076184-3, SR-01000076184-5, SR-01000076184-8, Thalidomide N-(2,6-Dioxopiperidin-3-yl)phthalimide, BRD-A93255169-001-04-4, BRD-A93255169-001-06-9, BRD-A93255169-001-24-2, BRD-A93255169-001-27-5, BRD-A93255169-001-28-3, Z905162656, 1H-Isoindole-1, 2-(2,6-dioxo-3-piperidinyl)-, (R)-, 1H-Isoindole-1, 2-(2,6-dioxo-3-piperidinyl)-, (S)-, 2-(2,6-dioxoazaperhydroin-3-yl)benzo[c]azoline-1,3-dione, 2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione #, [(R,S)-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione, Thalidomide, United States Pharmacopeia (USP) Reference Standard, ( inverted question mark)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione, 1H-ISOINDOLE-1,3(2H)-DIONE, 2-(2,6-DIOXO-3-PIPERIDINYL)-, (+/-)-
Theoretical properties:
molecular_formula: C13H10N2O4
molecular_weight: 258.23 g/mol
exact_mass: 258.06405680 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 19
topological_polar_surface_area: 83.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Needles
color: Needles
melting_point: 516 to 520 °F (NTP, 1992)
solubility: less than 1 mg/mL at 72 °F (NTP, 1992)
Descriptions:
{"pubchem": "Thalidomide can cause developmental toxicity according to an independent committee of scientific and health experts.", "chebi": "A dicarboximide that is isoindole-1,3(2<em>H</em>)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group.", "chembl": "THALIDOMIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Thalidomide, sold under the brand names Contergan, Distaval and Thalomid among others, is an oral administered medication used to treat a number of cancers (e.g., multiple myeloma), graft-versus-host disease, and many skin disorders (e.g., complications of leprosy such as skin lesions). Thalidomide has been used to treat conditions associated with HIV: aphthous ulcers, HIV-associated wasting syndrome, diarrhea, and Kaposi's sarcoma, but increases in HIV viral load have been reported.\nCommon side effects include sleepiness, rash, and dizziness. Severe side effects include tumor lysis syndrome, blood clots, and peripheral neuropathy. Thalidomide is a known human teratogen and carries an extremely high risk of severe, life-threatening birth defects if administered or taken during pregnancy. It causes skeletal deformities such as amelia (absence of legs and/or arms), absence of bones, and phocomelia (malformation of the limbs). A single dose of thalidomide, regardless of dosage, is enough to cause teratogenic effects.\nThalidomide was first marketed in 1957 in West Germany, where it was available as an over-the-counter drug. When first released, thalidomide was promoted for anxiety, trouble sleeping, \"tension\", and morning sickness. While it was initially thought to be safe in pregnancy, thalidomide was found to cause birth defects, resulting in its removal from the market in Europe in 1961. The total number of infants severely harmed by thalidomide use during pregnancy is estimated at over 10,000, possibly 20,000, of whom about 40% died around the time of birth. Those who survived had limb, eye, urinary tract, and heart problems. Its initial entry into the US market was prevented by Frances Kelsey, a reviewer at the FDA. The birth defects caused by thalidomide led to the development of greater drug regulation and monitoring in many countries.\nIt was approved in the United States in 1998 for use as a treatment for cancer. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication."}