Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C13H10N2O4 |
| Molecular Weight | 258.23 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1N(C2CCC(=O)NC2=O)C(=O)C3=CC=CC=C13
InChI
InChIKey=UEJJHQNACJXSKW-UHFFFAOYSA-N
InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)
| Molecular Formula | C13H10N2O4 |
| Molecular Weight | 258.23 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB01041Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020785s051lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01041
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020785s051lbl.pdf
Thalidomide is an immunomodulatory agent with a spectrum of activity that is not fully characterized. Thalidomide is racemic — it contains both left and right-handed isomers in equal amounts: one enantiomer is effective against morning sickness, and the other is teratogenic. The enantiomers are converted to each other in vivo. That is, if a human is given D-thalidomide or L-thalidomide, both isomers can be found in the serum. Hence, administering only one enantiomer will not prevent the teratogenic effect in humans. In patients with erythema nodosum leprosum (ENL) the mechanism of action is not fully understood. Available data from in vitro studies and preliminary clinical trials suggest that the immunologic effects of this compound can vary substantially under different conditions, but may be related to suppression of excessive tumor necrosis factor-alpha (TNF-a) production and down-modulation of selected cell surface adhesion molecules involved in leukocyte migration. For example, administration of thalidomide has been reported to decrease circulating levels of TNF-a in patients with ENL, however, it has also been shown to increase plasma TNF-a levels in HIV-seropositive patients. As a cancer treatment, the drug may act as a VEGF inhibitor. Thalidomide is used for the acute treatment of the cutaneous manifestations of moderate to severe erythema nodosum leprosum (ENL). Also for use as maintenance therapy for prevention and suppression of the cutaneous manifestations of ENL recurrence. Thalidomide is sold under the brand name Immunoprin, among others.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22650377
Curator's Comment: Thalidomide, an inhibitor of TNF-α protein synthesis is readily capable of crossing the blood-brain barrier
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q96SW2 Gene ID: 51185.0 Gene Symbol: CRBN Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB01041 |
|||
Target ID: CHEMBL1825 Sources: http://www.drugbank.ca/drugs/DB01041 |
200.0 µM [IC50] | ||
Target ID: CHEMBL3251 Sources: http://www.drugbank.ca/drugs/DB01041 |
|||
Target ID: CHEMBL4142 Sources: http://www.drugbank.ca/drugs/DB01041 |
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Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11909713 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | THALOMID Approved UseTHALOMID in combination with dexamethasone is indicated for the treatment of patients with newly diagnosed multiple myeloma (MM).
THALOMID is indicated for the acute treatment of the cutaneous manifestations of moderate to severe erythema nodosum leprosum (ENL).
THALOMID is not indicated as monotherapy for such ENL treatment in the presence of moderate to severe neuritis.
THALOMID is also indicated as maintenance therapy for prevention and suppression of the cutaneous manifestations of ENL recurrence. Launch Date1998 |
|||
| Primary | THALOMID Approved UseTHALOMID in combination with dexamethasone is indicated for the treatment of patients with newly diagnosed multiple myeloma (MM).
THALOMID is indicated for the acute treatment of the cutaneous manifestations of moderate to severe erythema nodosum leprosum (ENL).
THALOMID is not indicated as monotherapy for such ENL treatment in the presence of moderate to severe neuritis.
THALOMID is also indicated as maintenance therapy for prevention and suppression of the cutaneous manifestations of ENL recurrence. Launch Date1998 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.82 μg/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
2 mg/L |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
36.4 μg × h/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
19.8 mg × h/L |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.29 h |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
6.17 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
45% |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
40% |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
THALIDOMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
400 mg/m2 1 times / day multiple, oral MTD Dose: 400 mg/m2, 1 times / day Route: oral Route: multiple Dose: 400 mg/m2, 1 times / day Sources: |
unhealthy, 11 Health Status: unhealthy Age Group: 11 Sex: M+F Food Status: UNKNOWN Sources: |
DLT: Somnolence... |
400 mg/m2 1 times / day multiple, oral MTD Dose: 400 mg/m2, 1 times / day Route: oral Route: multiple Dose: 400 mg/m2, 1 times / day Sources: |
unhealthy, 11 Health Status: unhealthy Age Group: 11 Sex: M+F Food Status: UNKNOWN Sources: |
DLT: Ataxia... |
200 mg 2 times / day multiple, oral Studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 57 Health Status: unhealthy Age Group: 57 Sex: M+F Food Status: UNKNOWN Sources: |
DLT: Dyspnea... |
150 mg 2 times / day multiple, oral MTD Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, UNKNOWN Health Status: unhealthy Age Group: UNKNOWN Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Fetal damage, Deep vein thrombosis... AEs leading to discontinuation/dose reduction: Fetal damage Sources: Deep vein thrombosis Pulmonary embolism |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Somnolence | 20% DLT |
400 mg/m2 1 times / day multiple, oral MTD Dose: 400 mg/m2, 1 times / day Route: oral Route: multiple Dose: 400 mg/m2, 1 times / day Sources: |
unhealthy, 11 Health Status: unhealthy Age Group: 11 Sex: M+F Food Status: UNKNOWN Sources: |
| Ataxia | 16.7% DLT |
400 mg/m2 1 times / day multiple, oral MTD Dose: 400 mg/m2, 1 times / day Route: oral Route: multiple Dose: 400 mg/m2, 1 times / day Sources: |
unhealthy, 11 Health Status: unhealthy Age Group: 11 Sex: M+F Food Status: UNKNOWN Sources: |
| Dyspnea | 50% DLT |
200 mg 2 times / day multiple, oral Studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy, 57 Health Status: unhealthy Age Group: 57 Sex: M+F Food Status: UNKNOWN Sources: |
| Deep vein thrombosis | Disc. AE | 400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, UNKNOWN Health Status: unhealthy Age Group: UNKNOWN Sex: M+F Food Status: UNKNOWN Sources: |
| Fetal damage | Disc. AE | 400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, UNKNOWN Health Status: unhealthy Age Group: UNKNOWN Sex: M+F Food Status: UNKNOWN Sources: |
| Pulmonary embolism | Disc. AE | 400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, UNKNOWN Health Status: unhealthy Age Group: UNKNOWN Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Extended survival in advanced and refractory multiple myeloma after single-agent thalidomide: identification of prognostic factors in a phase 2 study of 169 patients. | 2001-07-15 |
|
| Thalidomide and immunomodulatory derivatives augment natural killer cell cytotoxicity in multiple myeloma. | 2001-07-01 |
|
| Clinical aspects and management of AIDS-related Kaposi's sarcoma. | 2001-07 |
|
| [Comparative treatment between thalidomide and transfer factor in severe atopic dermatitis]. | 2001-06-26 |
|
| Neurobehavioral teratogenic effects of thalidomide in rats. | 2001-06-22 |
|
| Deep venous thrombosis and thalidomide therapy for multiple myeloma. | 2001-06-21 |
|
| Pilot study using the combination of methotrexate and thalidomide in the treatment of rheumatoid arthritis. | 2001-06-16 |
|
| Thalidomide and prednisolone inhibit growth factor-induced human retinal pigment epithelium cell proliferation in vitro. | 2001-06-16 |
|
| [New concepts about atopic dermatitis]. | 2001-06-12 |
|
| [Thalidomide and thrombosis: three observations]. | 2001-06-09 |
|
| Thalidomide-induced amenorrhoea: two cases. | 2001-06 |
|
| [Thalidomide and cancer--revival of a drug]. | 2001-06 |
|
| Alpha-glucosidase inhibitors with a 4,5,6,7-tetrachlorophthalimide skeleton pendanted with a cycloalkyl or dicarba-closo-dodecaborane group. | 2001-06 |
|
| Disease controlling antirheumatic therapy in spondyloarthropathy. | 2001-06 |
|
| Thalidomide dose proportionality assessment following single doses to healthy subjects. | 2001-06 |
|
| Color Doppler ultrasonography of the superior mesenteric artery for prenatal ultrasonographic diagnosis of a left-sided congenital diaphragmatic hernia. | 2001-06 |
|
| Effectors of inflammation in actinic prurigo. | 2001-06 |
|
| Successful thalidomide treatment of severe infantile Behçet disease. | 2001-05-19 |
|
| [Sarcoidosis: thalidomide treatment in ten patients]. | 2001-05 |
|
| Possible role of adjunctive thalidomide therapy in the resolution of a massive intracranial tuberculous abscess. | 2001-05 |
|
| Enantioseparation of aminoglutethimide and thalidomide by high performance liquid chromatography or supercritical fluid chromatography on mono-2 and mono-6-O-pentenyl-beta-cyclodextrin-based chiral stationary phases. | 2001-05 |
|
| Is infliximab effective for induction of remission in patients with ulcerative colitis? | 2001-05 |
|
| Thalidomide in multiple myeloma: lack of response of soft-tissue plasmacytomas. | 2001-05 |
|
| Transcending conventional therapies: the role of biologic and other novel therapies. | 2001-05 |
|
| Approach to corticosteroid-dependent and corticosteroid-refractory Crohn's disease. | 2001-05 |
|
| Synthesis and immunological activity of water-soluble thalidomide prodrugs. | 2001-05 |
|
| Thalidomide and its dermatologic uses. | 2001-05 |
|
| Intractable insomnia after cessation of treatment with thalidomide. | 2001-05 |
|
| Novel approaches to the treatment of chronic graft-versus-host disease. | 2001-05 |
|
| Aza analogues of thalidomide: synthesis and evaluation as inhibitors of tumor necrosis factor-alpha production in vitro. | 2001-04 |
|
| A cybernetic theory of morality and moral autonomy. | 2001-04 |
|
| Current management of cancer-associated anorexia and weight loss. | 2001-04 |
|
| In vitro and in vivo kinetic interactions of the antitumour agent 5,6-dimethylxanthenone-4-acetic acid with thalidomide and diclofenac. | 2001-04 |
|
| Thalidomide use: past history and current implications for practice. | 2001-04 |
|
| The irreplaceable image. Thalidomide in refractory myeloma patients: early changes in bone marrow cellularity. | 2001-04 |
|
| Salvage therapy with thalidomide in multiple myeloma patients relapsing after autologous peripheral blood stem cell transplantation. | 2001-04 |
|
| Thalidomide treatment of resistant or relapsed multiple myeloma patients. | 2001-04 |
|
| Low-dose thalidomide plus dexamethasone is an effective salvage therapy for advanced myeloma. | 2001-04 |
|
| Thalidomide: near complete regression of extramedullary bulk in refractory multiple myeloma. | 2001-03-10 |
|
| [Management of severe skin disorders in sarcoidosis]. | 2001-03 |
|
| Thalidomide-induced sensory neuropathy. | 2001-03 |
|
| Targeting of vasculature in cancer and other angiogenic diseases. | 2001-03 |
|
| [Teratology, 40 years after the thalidomide tragedy]. | 2001-02 |
|
| Pharmacotherapeutic options in inflammatory bowel disease: an update. | 2001-02 |
|
| Scleroderma. | 2001-02 |
|
| Differential effect of thalidomide and dexamethasone on the transcription factor NF-kappa B. | 2001-01 |
|
| Thalidomide as an anti-angiogenic agent in relapsed gliomas. | 2001-01 |
|
| Randomized clinical trial of thalidomide, cyclosporine, and prednisone versus cyclosporine and prednisone as initial therapy for chronic graft-versus-host disease. | 2001 |
|
| Thalidomide in gastrointestinal disorders. | 2001 |
|
| Managing cancer-related anorexia/cachexia. | 2001 |
Sample Use Guides
MM: 200 mg orally once daily. The recommended dose of
dexamethasone is 40 mg/day on days 1-4, 9-12, and 17-20
every 28 days.
• ENL: 100 to 300 mg/day for an episode of cutaneous ENL.
Up to 400 mg/day for severe cutaneous ENL.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22011961
The minimum dose of thalidomide used (1 uM) inhibited TNF-α production in HTLV-1-infected subjects in vitro.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:21:32 GMT 2025
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on
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| Record UNII |
4Z8R6ORS6L
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| Record Status |
FAILED
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| Record Version |
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
43890
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FDA ORPHAN DRUG |
80194
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FDA ORPHAN DRUG |
30788
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WHO-ATC |
L04AX02
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FDA ORPHAN DRUG |
115598
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FDA ORPHAN DRUG |
43790
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NDF-RT |
N0000008663
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WHO-VATC |
QL04AX02
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FDA ORPHAN DRUG |
90795
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EU-Orphan Drug |
EU/3/01/067
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NDF-RT |
N0000008663
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FDA ORPHAN DRUG |
585417
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FDA ORPHAN DRUG |
110197
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FDA ORPHAN DRUG |
72092
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NCI_THESAURUS |
C129820
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FDA ORPHAN DRUG |
114998
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NCI_THESAURUS |
C1742
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FDA ORPHAN DRUG |
121898
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FDA ORPHAN DRUG |
187204
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FDA ORPHAN DRUG |
94995
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NCI_THESAURUS |
C574
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FDA ORPHAN DRUG |
32188
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EMA ASSESSMENT REPORTS |
THALIDOMIDE CELGENE (AUTHORIZED: MUTIPLE MYELOMA)
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NCI_THESAURUS |
C54677
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FDA ORPHAN DRUG |
82594
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LIVERTOX |
NBK548371
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527179
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10432
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4Z8R6ORS6L
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DTXSID9022524
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100000089194
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1652500
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4Z8R6ORS6L
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74947
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D013792
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66847
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DB01041
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7327
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CHEMBL468
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THALIDOMIDE
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SUB10958MIG
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9513
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C870
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200-031-1
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762
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2616
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m10673
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3586
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TARGET -> INHIBITOR |
Kd
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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TARGET -> INHIBITOR |
BINDING
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TARGET -> INHIBITOR |
Dose-dependent interaction with the CRBN-DDB1 complex
IC50
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
CYP2C9 and CYP1A2 were also mediators in this reaction.
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
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