Identification

Name
Thalidomide
Accession Number
DB01041  (APRD01251)
Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Description

A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppresive and anti-angiogenic activity. It inhibits release of tumor necrosis factor-alpha from monocytes, and modulates other cytokine action. [PubChem]

Structure
Thumb
Synonyms
  • (+-)-N-(2,6-dioxo-3-Piperidyl)phthalimide
  • (+-)-Thalidomide
  • (±)-N-(2,6-dioxo-3-piperidyl)phthalimide
  • (±)-thalidomide
  • 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline
  • 2,6-dioxo-3-phthalimidopiperidine
  • 3-Phthalimidoglutarimide
  • alpha-(N-Phthalimido)glutarimide
  • alpha-N-Phthalylglutaramide
  • N-(2,6-dioxo-3-piperidyl)phthalimide
  • N-Phthaloylglutamimide
  • N-Phthalyl-glutaminsaeure-imid
  • N-Phthalylglutamic acid imide
  • Talidomida
  • Thalidomidum
  • α-(N-phthalimido)glutarimide
  • α-N-phthalylglutaramide
  • α-phthalimidoglutarimide
External IDs
NSC-527179 / NSC-66847
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Thalidomide CelgeneCapsule50 mgOralCelgene Europe Bv2008-04-16Not applicableEu
ThalomidCapsule50 mgOralCelgene2010-11-01Not applicableCanada
ThalomidCapsule100 mgOralCelgene2011-02-17Not applicableCanada
ThalomidCapsule200 mg/1OralCelgene2003-06-20Not applicableUs
ThalomidCapsule50 mg/1OralCelgene2003-06-20Not applicableUs
ThalomidCapsule150 mgOralCelgeneNot applicableNot applicableCanada
ThalomidCapsule150 mg/1OralCelgene2007-03-20Not applicableUs
ThalomidCapsule200 mgOralCelgene2011-02-17Not applicableCanada
ThalomidCapsule100 mg/1OralCelgene2003-06-20Not applicableUs
International/Other Brands
Contergan / Distaval / K-17 / Pro-ban M / Sedalis / Softenon / Talimol / Thaled
Categories
UNII
4Z8R6ORS6L
CAS number
50-35-1
Weight
Average: 258.2295
Monoisotopic: 258.064056818
Chemical Formula
C13H10N2O4
InChI Key
UEJJHQNACJXSKW-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione
SMILES
O=C1N(C2CCC(=O)NC2=O)C(=O)C2=CC=CC=C12

Pharmacology

Indication

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.

Associated Conditions
Pharmacodynamics

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.

Mechanism of action

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.

TargetActionsOrganism
AProtein cereblon
inhibitor
Human
ATumor necrosis factor
inhibitor
Human
ANuclear factor NF-kappa-B p105 subunit
antagonist
Human
ADNA
intercalation
Human
AFibroblast growth factor receptor 2
antagonist
Human
UProstaglandin G/H synthase 2
antagonist
Human
UNuclear factor kappa-light-chain-enhancer of activated B cells
inhibitor
Human
Ualpha1-acid glycoprotein
binder
Human
Absorption

The absolute bioavailability has not yet been characterized in human subjects due to its poor aqueous solubility. In studies of both healthy volunteers and subjects with Hansen’s disease, the mean time to peak plasma concentrations (Tmax) ranged from 2.9 to 5.7 hours indicating that thalidomide is slowly absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

55% and 66% for the (+)R and (−)S enantiomers, respectively.

Metabolism

Thalidomide itself does not appear to be hepatically metabolized to any large extent, but appears to undergo non-enzymatic hydrolysis in plasma to multiple metabolites. Thalidomide may be metabolized hepatically by enzymes of the cytochrome P450 enzyme system. The end product of metabolism, phthalic acid, is excreted as a glycine conjugate.

Route of elimination

Thalidomide itself has less than 0.7% of the dose excreted in the urine as unchanged drug.

Half life

The mean half-life of elimination ranges from approximately 5 to 7 hours following a single dose and is not altered upon multiple dosing.

Clearance
Not Available
Toxicity

The R-configuration and the S-configuration are more toxic individually than the racemic mixture. The LD50 could not be established in mice for racemic thalidomide, whereas LD50 values for the R and S configurations are reported to be 0.4 to 0.7 g/kg and 0.5 to 1.5 g/kg, respectively.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
7-Nitroindazole7-Nitroindazole may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
AbirateroneThe serum concentration of Thalidomide can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Thalidomide is combined with Acebutolol.
AcepromazineAcepromazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
AceprometazineAceprometazine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Acetyl sulfisoxazoleThe metabolism of Thalidomide can be decreased when combined with Acetyl sulfisoxazole.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Thalidomide.
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Thalidomide.
AdalimumabThe risk or severity of adverse effects can be increased when Thalidomide is combined with Adalimumab.
AdipiplonAdipiplon may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Food Interactions
Not Available

References

Synthesis Reference

Jamshed Shah, "Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs." U.S. Patent US20030139451, issued July 24, 2003.

US20030139451
General References
Not Available
External Links
Human Metabolome Database
HMDB0015175
KEGG Drug
D00754
KEGG Compound
C07910
PubChem Compound
5426
PubChem Substance
46505665
ChemSpider
5233
BindingDB
50070114
ChEBI
74947
ChEMBL
CHEMBL468
Therapeutic Targets Database
DAP000865
PharmGKB
PA451644
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Thalidomide
ATC Codes
L04AX02 — Thalidomide
AHFS Codes
  • 92:20.00 — Immunomodulatory Agents
FDA label
Download (180 KB)
MSDS
Download (58.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentCrohn's Disease (CD)1
0RecruitingTreatmentEwing's Sarcoma (ES) / Gliomas / Neuroectodermal Tumors, Primitive / Retinoblastoma / Rhabdomyosarcomas / Sarcoma, Osteogenic / Wilms' tumor1
0TerminatedTreatmentMultiple Myeloma (MM)1
1Active Not RecruitingTreatmentMultiple Myeloma (MM)1
1CompletedNot AvailableMultiple Myeloma (MM)1
1CompletedTreatmentBrain and Nervous System / Cancers1
1CompletedTreatmentCancers1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare / Tuberculosis, Mycobacterium Infection1
1CompletedTreatmentLeukemias / Malignant Lymphomas1
1CompletedTreatmentMelanoma / Neoplasms, Brain1
1CompletedTreatmentMultiple Myeloma (MM)1
1CompletedTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1RecruitingTreatmentAdvanced Solid Tumors / Advanced/Metastatic Colorectal Cancer1
1RecruitingTreatmentMultiple Myeloma (MM)1
1TerminatedTreatmentEndometriosis1
1TerminatedTreatmentScleroderma, Systemic1
1Unknown StatusTreatmentBrain and Central Nervous System Tumors1
1, 2Active Not RecruitingTreatmentMultiple Myeloma (MM)1
1, 2CompletedTreatmentCancers / Kidney1
1, 2CompletedTreatmentIntraocular Melanoma / Melanoma (Skin)1
1, 2CompletedTreatmentLeukemias1
1, 2CompletedTreatmentMultiple Myeloma (MM)2
1, 2CompletedTreatmentMultiple Myeloma (MM) / Stage I Multiple Myeloma / Stage II Multiple Myeloma / Stage III Multiple Myeloma1
1, 2CompletedTreatmentProstate Cancer1
1, 2CompletedTreatmentRefractory Epilepsy1
1, 2Not Yet RecruitingTreatmentAmyloidosis1
1, 2Unknown StatusTreatmentHepatocellular,Carcinoma1
2Active Not RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL)1
2Active Not RecruitingTreatmentExtramedullary Plasmacytoma / Isolated Plasmacytoma of Bone / Light Chain Deposition Disease / Primary Systemic Amyloidosis / Stage I Multiple Myeloma / Stage II Multiple Myeloma / Stage III Multiple Myeloma1
2Active Not RecruitingTreatmentMultiple Myeloma (MM)2
2Active Not RecruitingTreatmentMultiple Myeloma and Plasma Cell Neoplasm / Neurotoxicity1
2Active Not RecruitingTreatmentRefractory Multiple Myeloma / Stage I Multiple Myeloma / Stage II Multiple Myeloma / Stage III Multiple Myeloma1
2Active Not RecruitingTreatmentRelapsed and/or Refractory Multiple Myeloma1
2CompletedNot AvailableMultiple Myeloma (MM)1
2CompletedDiagnosticNeoplasms1
2CompletedSupportive CareAdvanced Cancers1
2CompletedSupportive CareAnemias / Leukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms1
2CompletedSupportive CareGraft Versus Host Disease (GVHD) / Unspecified Adult Solid Tumor, Protocol Specific / Unspecified Childhood Solid Tumor, Protocol Specific1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Burning Mouth Syndrome / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
2CompletedTreatmentAdult Primary Hepatocellular Carcinoma / Advanced Adult Primary Liver Cancer / Localized Unresectable Adult Primary Liver Cancer1
2CompletedTreatmentAmyloidosis1
2CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2CompletedTreatmentAngiodysplasia / Gastric Antral Vascular Ectasia / Obscure Gastrointestinal Bleeding / Thalidomide1
2CompletedTreatmentAnkylosing Spondylitis (AS)1
2CompletedTreatmentArachnoiditis1
2CompletedTreatmentArteriovenous Malformations / Hematochezia / Hereditary Haemorrhagic Telangiectasia (HHT) / Melena1
2CompletedTreatmentB-Cell Chronic Lymphocytic Leukemia / Chronic Lymphocytic Leukemia (CLL) - Refractory1
2CompletedTreatmentBrain Stem Gliomas1
2CompletedTreatmentBrain Stem Neoplasms, Primary / Neoplasms, Brain Stem1
2CompletedTreatmentBrain and Central Nervous System Tumors4
2CompletedTreatmentBrain and Central Nervous System Tumors / Unspecified Adult Solid Tumor, Protocol Specific1
2CompletedTreatmentCancer of the Ovary2
2CompletedTreatmentCancers / Livers1
2CompletedTreatmentCarcinoid tumour of the gastrointestinal tract / Islet Cell Tumor / Lung Cancers / Neoplastic Syndrome1
2CompletedTreatmentCarcinoma of the Appendix / Colorectal Cancers1
2CompletedTreatmentCentral Nervous System Tumor, Pediatric / Leukemias / Malignant Lymphomas / Neuroblastomas / Sarcomas / Unspecified Childhood Solid Tumor, Protocol Specific1
2CompletedTreatmentCentral Nervous System Tumor, Pediatric / Neuroblastomas1
2CompletedTreatmentChronic Myelomonocytic Leukemia / De Novo Myelodysplastic Syndromes / Previously Treated Myelodysplastic Syndromes / Refractory Anemia / Refractory Anemia With Excess Blasts / Refractory Anemia With Excess Blasts in Transformation / Refractory Anemia With Ringed Sideroblasts / Secondary Myelodysplastic Syndromes1
2CompletedTreatmentChronic Myeloproliferative Disorders / Leukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Diseases1
2CompletedTreatmentChronic Myeloproliferative Disorders / Secondary Myelofibrosis1
2CompletedTreatmentColorectal Adenocarcinoma1
2CompletedTreatmentCrohn's Disease (CD)1
2CompletedTreatmentDiscoid Lupus Erythematosus (DLE)1
2CompletedTreatmentEndometrial Adenoacanthoma / Endometrial Adenocarcinomas / Endometrial Adenosquamous Cell Carcinoma / Endometrial Clear Cell Carcinoma / Endometrial Papillary Serous Carcinoma / Recurrent Endometrial Carcinoma1
2CompletedTreatmentEndometrial Cancers / Sarcomas1
2CompletedTreatmentGlioblastoma Multiforme (GBM) / Gliomas1
2CompletedTreatmentGliomas1
2CompletedTreatmentHIV Wasting Syndrome / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHead and Neck Carcinoma2
2CompletedTreatmentHepatocellular,Carcinoma1
2CompletedTreatmentHereditary Haemorrhagic Telangiectasia (HHT) / Nasal Bleeding1
2CompletedTreatmentHormone-Refractory Prostate Cancer1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Mycobacterium Infections / Tuberculosis1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Stomatitis, Aphthous1
2CompletedTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
2CompletedTreatmentIntraocular Melanoma / Melanoma (Skin)2
2CompletedTreatmentLeukemias1
2CompletedTreatmentLeukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Diseases1
2CompletedTreatmentLeukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms1
2CompletedTreatmentLiver Cancer2
2CompletedTreatmentLung Cancers3
2CompletedTreatmentLymphoplasmacytic Lymphoma / Waldenström's Macroglobulinemia (WM)1
2CompletedTreatmentMALT Lymphoma1
2CompletedTreatmentMalignant Lymphomas1
2CompletedTreatmentMalignant Neoplasm of Pancreas1
2CompletedTreatmentMelanoma (Skin)3
2CompletedTreatmentMultiple Myeloma (MM)16
2CompletedTreatmentMultiple Myeloma (MM) / Plasma Cell Myeloma1
2CompletedTreatmentMultiple Myeloma and Plasma Cell Neoplasm9
2CompletedTreatmentMyelodysplastic Syndromes1
2CompletedTreatmentNeoplasms, Kidney1
2CompletedTreatmentNeuroendocrine Tumors1
2CompletedTreatmentNon Neoplastic Condition / Precancerous Conditions1
2CompletedTreatmentNon-Hodgkin's Lymphoma (NHL)1
2CompletedTreatmentPrimary Myelofibrosis1
2CompletedTreatmentProstate Cancer5
2CompletedTreatmentProstatic Neoplasms2
2CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
2CompletedTreatmentRecurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Small Lymphocytic Lymphoma1
2CompletedTreatmentRecurrent Melanoma / Stage IV Melanoma / Tumors Metastatic to Brain1
2CompletedTreatmentRecurrent Uterine Corpus Sarcoma / Uterine Carcinosarcoma1
2CompletedTreatmentRecurrent Uterine Corpus Sarcoma / Uterine Corpus Leiomyosarcoma1
2CompletedTreatmentRenal Cancers1
2CompletedTreatmentRenal Cell Cancer, Recurrent / Stage IV Renal Cell Cancer1
2CompletedTreatmentSarcomas1
2CompletedTreatmentSjögren's Syndrome / Xerostomia1
2CompletedTreatmentUnspecified Childhood Solid Tumor, Protocol Specific1
2CompletedTreatmentWaldenström's Macroglobulinemia (WM)1
2Not Yet RecruitingTreatmentMultiple Myeloma (MM)1
2RecruitingPreventionMultiple Myeloma (MM)1
2RecruitingTreatmentAdvanced NSCLC1
2RecruitingTreatmentAgnogenic Myeloid Metaplasia1
2RecruitingTreatmentCardiac Amyloidosis1
2RecruitingTreatmentChemotherapy Effect / NSCLC Stage IV1
2RecruitingTreatmentChronic Kidney Disease (CKD) / Multiple Myeloma (MM)1
2RecruitingTreatmentEsophageal Cancers1
2RecruitingTreatmentExtrapancreatic Neuroendocrine Tumor1
2RecruitingTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)1
2RecruitingTreatmentLymphoplasmacytic Lymphoma / Waldenström's Macroglobulinemia (WM)1
2RecruitingTreatmentMedulloblastomas1
2RecruitingTreatmentMetastatic Breast Cancer (MBC)1
2RecruitingTreatmentMulticentric Castleman Disease1
2RecruitingTreatmentMultiple Myeloma (MM)4
2RecruitingTreatmentPlasma Cell Myeloma1
2RecruitingTreatmentRadiation Injuries1
2RecruitingTreatmentRelapse and / or Refractory Myeloma1
2RecruitingTreatmentRelapsed and/or Refractory Multiple Myeloma1
2RecruitingTreatmentThalassaemic disorders2
2TerminatedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2TerminatedTreatmentCancer, Breast1
2TerminatedTreatmentChronic Lymphocytic Leukemia (CLL) - Refractory / Recurrent Small Lymphocytic Lymphoma1
2TerminatedTreatmentChronic Prostatitis (CP) / Pelvic Pain1
2TerminatedTreatmentColorectal Cancers1
2TerminatedTreatmentGraft Versus Host Disease (GVHD) / Vesicular Stomatitis1
2TerminatedTreatmentHodgkins Disease (HD) / Lymphoma, B-Cell1
2TerminatedTreatmentLung Cancers1
2TerminatedTreatmentMelanoma1
2TerminatedTreatmentMultiple Myeloma (MM)3
2TerminatedTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
2TerminatedTreatmentPancreatitis, Chronic1
2TerminatedTreatmentPrimary Sclerosing Cholangitis (PSC)1
2TerminatedTreatmentProstatic Neoplasms1
2TerminatedTreatmentRecurrent Adult Soft Tissue Sarcoma / Stage I Adult Soft Tissue Sarcoma / Stage I Adult Soft Tissue Sarcoma AJCC v7 / Stage II Adult Soft Tissue Sarcoma / Stage II Adult Soft Tissue Sarcoma AJCC v7 / Stage III Adult Soft Tissue Sarcoma / Stage III Adult Soft Tissue Sarcoma AJCC v71
2TerminatedTreatmentRecurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma1
2TerminatedTreatmentWaldenström's Macroglobulinemia (WM)1
2Unknown StatusTreatmentBrain and Central Nervous System Tumors2
2Unknown StatusTreatmentHepatitis C Viral Infection1
2Unknown StatusTreatmentLiver Cancer2
2Unknown StatusTreatmentMalignant Lymphomas1
2Unknown StatusTreatmentMalignant Neoplasm of Colon1
2Unknown StatusTreatmentMelanoma1
2Unknown StatusTreatmentMultiple Myeloma (MM)4
2Unknown StatusTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
2Unknown StatusTreatmentMyelodysplastic Syndrome1
2Unknown StatusTreatmentRenal Cancers1
2Unknown StatusTreatmentSarcomas2
2WithdrawnPreventionMultiple Myeloma (MM)1
2WithdrawnTreatmentGastrointestinal Bleeding of Unknown Origin / Gastrointestinal vascular malformations / Thalidomide Efficiency1
2WithdrawnTreatmentHemorrhage, Gastrointestinal / Vascular Malformations1
2WithdrawnTreatmentImmune Thrombocytopenia1
2WithdrawnTreatmentMalignant Lymphomas1
2WithdrawnTreatmentMelanoma / Neoplasms, Brain1
2WithdrawnTreatmentMultiple Myeloma (MM)1
2WithdrawnTreatmentMultiple Myeloma (MM) / Plasma Cell Myeloma1
2WithdrawnTreatmentRefractory Plasma Cell Neoplasm / Stage I Multiple Myeloma / Stage II Multiple Myeloma / Stage III Multiple Myeloma1
2WithdrawnTreatmentRenal Cancers1
2, 3CompletedTreatmentMultiple Myeloma (MM)2
2, 3Not Yet RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2, 3TerminatedTreatmentOral Cavity Cancer1
2, 3Unknown StatusTreatmentAlzheimer's Disease (AD)1
2, 3Unknown StatusTreatmentHepatocellular,Carcinoma / Liver Cancer1
3Active Not RecruitingTreatmentDS Stage I Plasma Cell Myeloma / DS Stage II Plasma Cell Myeloma / DS Stage III Plasma Cell Myeloma1
3Active Not RecruitingTreatmentMultiple Myeloma (MM)1
3Active Not RecruitingTreatmentPlasma Cell Myeloma / Stage I Multiple Myeloma / Stage II Multiple Myeloma / Stage III Multiple Myeloma1
3CompletedPreventionNeoplasms1
3CompletedTreatmentCoughing / Idiopathic Pulmonary Fibrosis (IPF)1
3CompletedTreatmentCrohn's Disease (CD) / Inflammatory Bowel Diseases (IBD) / Ulcerative Colitis (UC)1
3CompletedTreatmentEffects of Chemotherapy / Multiple Myeloma (MM)1
3CompletedTreatmentFallopian Tube Cancer / Primary Peritoneal Cavity Cancer / Recurrent Ovarian Epithelial Cancer / Stage III Ovarian Epithelial Cancer / Stage IV Ovarian Epithelial Cancer1
3CompletedTreatmentLung Cancers1
3CompletedTreatmentMultiple Myeloma (MM)24
3CompletedTreatmentMultiple Myeloma and Plasma Cell Neoplasm3
3CompletedTreatmentMultiple Myeloma de Novo Treatment1
3CompletedTreatmentMyelodysplastic Syndromes1
3CompletedTreatmentProstate Cancer1
3CompletedTreatmentRenal Cancers1
3CompletedTreatmentSarcoidosis1
3CompletedTreatmentTumors Metastatic to Brain1
3RecruitingTreatmentCrohn's Disease (CD)1
3RecruitingTreatmentExtranodal NK-T-Cell Lymphoma, Nasal and Nasal-Type1
3RecruitingTreatmentGastrointestinal vascular malformations1
3RecruitingTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)1
3RecruitingTreatmentMultiple Myeloma (MM)2
3RecruitingTreatmentRelapsed or Refractory Systemic Light Chain Amyloidosis1
3TerminatedTreatmentHepatocellular,Carcinoma1
3TerminatedTreatmentHypoalbuminemia1
3TerminatedTreatmentLung Cancers1
3TerminatedTreatmentMultiple Myeloma (MM)3
3TerminatedTreatmentNewly Diagnosed, Multiple Myeloma1
3Unknown StatusTreatmentHepatocellular,Carcinoma1
3Unknown StatusTreatmentMultiple Myeloma (MM)3
3Unknown StatusTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
3WithdrawnPreventionHemorrhage, Gastrointestinal / Portal Hypertension1
4Active Not RecruitingTreatmentMultiple Myeloma (MM)1
4CompletedTreatmentMultiple Myeloma (MM)1
4Not Yet RecruitingTreatmentCoronary Artery Disease1
4RecruitingTreatmentCutaneous Lupus / Juvenile SLE / Systemic Lupus Erythematosus (SLE)1
4RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
4RecruitingTreatmentMalignant Neoplasm of Stomach1
4RecruitingTreatmentMantle Cell Lymphoma (MCL)1
4RecruitingTreatmentWaldenström's Macroglobulinemia (WM)1
4TerminatedTreatmentUveitis1
4Unknown StatusTreatmentCongestive Heart Failure (CHF)1
4WithdrawnTreatmentMalnutrition / Peritoneal dialysis therapy1
Not AvailableActive Not RecruitingSupportive CareMantle Cell Lymphoma (MCL) / Non-Hodgkin's Lymphoma (NHL)1
Not AvailableCompletedPreventionBlood Diseases / Graft Versus Host Disease (GVHD) / Hematopoietic Stem Cell Transplantation (HSCT) / Leukemias / Multiple Myeloma (MM) / Myelodysplastic Syndromes / Transplantation, Bone Marrow1
Not AvailableCompletedSupportive CareMultiple Myeloma (MM)1
Not AvailableCompletedTreatmentAdrenoleukodystrophy1
Not AvailableCompletedTreatmentHIV Wasting Syndrome / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableEnrolling by InvitationNot AvailableCrohn's Disease (CD)1
Not AvailableRecruitingPreventionHepatocellular,Carcinoma / Recurrences1
Not AvailableRecruitingPreventionProphylaxis of acute chemotherapy induced nausea and vomiting1
Not AvailableTerminatedTreatmentPlasma Cell Myeloma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Celgene
  • IDT Australia Ltd.
  • Penn Pharmaceutical Services Ltd.
Dosage forms
FormRouteStrength
CapsuleOral100 mg
CapsuleOral100 mg/1
CapsuleOral150 mg/1
CapsuleOral150 mg
CapsuleOral200 mg/1
CapsuleOral200 mg
CapsuleOral50 mg
CapsuleOral50 mg/1
Prices
Unit descriptionCostUnit
Thalomid 28 50 mg capsule Disp Pack4372.47USD disp
Thalomid 200 mg capsule277.5USD capsule
Thalomid 150 mg capsule260.61USD capsule
Thalomid 100 mg capsule243.73USD capsule
Thalomid 50 mg capsule150.15USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6235756No1993-03-012013-03-01Us
CA2505964No2009-07-282023-11-13Canada
CA2157288No2005-11-082014-02-24Canada
US6045501No1998-08-282018-08-28Us
US6315720No2000-10-232020-10-23Us
US6561976No1998-08-282018-08-28Us
US6561977No2000-10-232020-10-23Us
US6755784No2000-10-232020-10-23Us
US6869399No2000-10-232020-10-23Us
US6908432No1998-08-282018-08-28Us
US7141018No2000-10-232020-10-23Us
US7435745No1997-11-032017-11-03Us
US7874984No1998-08-282018-08-28Us
US7959566No2000-10-232020-10-23Us
US8204763No1998-08-282018-08-28Us
US8315886No2000-10-232020-10-23Us
US8626531No2000-10-232020-10-23Us
US8589188No1998-08-282018-08-28Us
US7230012No2003-12-092023-12-09Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)270 °CPhysProp
water solubility545 mg/L (at 25 °C)BUDAVARI,S ET AL. (1996)
logP0.33HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.55 mg/mLALOGPS
logP0.42ALOGPS
logP0.016ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)11.59ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.32 m3·mol-1ChemAxon
Polarizability24.42 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9775
Blood Brain Barrier+0.9382
Caco-2 permeable-0.5651
P-glycoprotein substrateSubstrate0.5301
P-glycoprotein inhibitor INon-inhibitor0.5115
P-glycoprotein inhibitor IINon-inhibitor0.8951
Renal organic cation transporterNon-inhibitor0.8179
CYP450 2C9 substrateNon-substrate0.7904
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5309
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9378
BiodegradationNot ready biodegradable0.8838
Rat acute toxicity3.3039 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9769
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0wba-4900000000-77362eaf27267f59650d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0930000000-e92e8e23d5db87f50f53
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-1940000000-f6d6997d1eaa7a83ec1b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0019-2900000000-ecfd1b7ec17b857ea977

Taxonomy

Description
This compound belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoindoles and derivatives
Sub Class
Isoindolines
Direct Parent
Phthalimides
Alternative Parents
Alpha amino acids and derivatives / Isoindoles / Piperidinediones / Delta lactams / N-substituted carboxylic acid imides / Benzenoids / N-unsubstituted carboxylic acid imides / Dicarboximides / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Phthalimide / Alpha-amino acid or derivatives / Isoindole / Piperidinedione / Delta-lactam / Piperidinone / Benzenoid / Piperidine / Carboxylic acid imide, n-substituted / Carboxylic acid imide
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
piperidones, phthalimides (CHEBI:74947)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Substrate recognition component of a DCX (DDB1-CUL4-X-box) E3 protein ligase complex that mediates the ubiquitination and subsequent proteasomal degradation of target proteins, such as MEIS2. Norma...
Gene Name
CRBN
Uniprot ID
Q96SW2
Uniprot Name
Protein cereblon
Molecular Weight
50545.375 Da
References
  1. Zhu YX, Kortuem KM, Stewart AK: Molecular mechanism of action of immune-modulatory drugs thalidomide, lenalidomide and pomalidomide in multiple myeloma. Leuk Lymphoma. 2013 Apr;54(4):683-7. doi: 10.3109/10428194.2012.728597. Epub 2012 Sep 28. [PubMed:22966948]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Tumor necrosis factor receptor binding
Specific Function
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
Molecular Weight
25644.15 Da
References
  1. Richardson P, Hideshima T, Anderson K: Thalidomide in multiple myeloma. Biomed Pharmacother. 2002 May;56(3):115-28. [PubMed:12046682]
  2. Fu LM, Fu-Liu CS: Thalidomide and tuberculosis. Int J Tuberc Lung Dis. 2002 Jul;6(7):569-72. [PubMed:12102294]
  3. Enomoto N, Takei Y, Hirose M, Ikejima K, Miwa H, Kitamura T, Sato N: Thalidomide prevents alcoholic liver injury in rats through suppression of Kupffer cell sensitization and TNF-alpha production. Gastroenterology. 2002 Jul;123(1):291-300. [PubMed:12105857]
  4. Rajkumar SV: Thalidomide in the treatment of multiple myeloma. Expert Rev Anticancer Ther. 2001 Jun;1(1):20-8. [PubMed:12113124]
  5. Vescovo G, Ravara B, Angelini A, Sandri M, Carraro U, Ceconi C, Dalla Libera L: Effect of thalidomide on the skeletal muscle in experimental heart failure. Eur J Heart Fail. 2002 Aug;4(4):455-60. [PubMed:12167383]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Turk BE, Jiang H, Liu JO: Binding of thalidomide to alpha1-acid glycoprotein may be involved in its inhibition of tumor necrosis factor alpha production. Proc Natl Acad Sci U S A. 1996 Jul 23;93(15):7552-6. [PubMed:8755512]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Transcriptional repressor activity, rna polymerase ii transcription regulatory region sequence-specific binding
Specific Function
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
Gene Name
NFKB1
Uniprot ID
P19838
Uniprot Name
Nuclear factor NF-kappa-B p105 subunit
Molecular Weight
105355.175 Da
References
  1. Yasui K, Kobayashi N, Yamazaki T, Agematsu K: Thalidomide as an immunotherapeutic agent: the effects on neutrophil-mediated inflammation. Curr Pharm Des. 2005;11(3):395-401. [PubMed:15723633]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
4. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
Actions
Intercalation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Stephens TD, Bunde CJ, Fillmore BJ: Mechanism of action in thalidomide teratogenesis. Biochem Pharmacol. 2000 Jun 15;59(12):1489-99. [PubMed:10799645]
  2. Shoji A, Kuwahara M, Ozaki H, Sawai H: Modified DNA aptamer that binds the (R)-isomer of a thalidomide derivative with high enantioselectivity. J Am Chem Soc. 2007 Feb 7;129(5):1456-64. [PubMed:17263432]
  3. Stephens TD, Fillmore BJ: Hypothesis: thalidomide embryopathy-proposed mechanism of action. Teratology. 2000 Mar;61(3):189-95. [PubMed:10661908]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein tyrosine kinase activity
Specific Function
Tyrosine-protein kinase that acts as cell-surface receptor for fibroblast growth factors and plays an essential role in the regulation of cell proliferation, differentiation, migration and apoptosi...
Gene Name
FGFR2
Uniprot ID
P21802
Uniprot Name
Fibroblast growth factor receptor 2
Molecular Weight
92024.29 Da
References
  1. Eichholz A, Merchant S, Gaya AM: Anti-angiogenesis therapies: their potential in cancer management. Onco Targets Ther. 2010 Jun 24;3:69-82. [PubMed:20616958]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Horrobin DF: A low toxicity maintenance regime, using eicosapentaenoic acid and readily available drugs, for mantle cell lymphoma and other malignancies with excess cyclin D1 levels. Med Hypotheses. 2003 May;60(5):615-23. [PubMed:12710892]
  2. Hada M, Mizutari K: [A case report of metastatic pancreatic cancer that responded remarkably to the combination of thalidomide, celecoxib and irinotecan]. Gan To Kagaku Ryoho. 2004 Sep;31(9):1407-10. [PubMed:15446566]
  3. Payvandi F, Wu L, Haley M, Schafer PH, Zhang LH, Chen RS, Muller GW, Stirling DI: Immunomodulatory drugs inhibit expression of cyclooxygenase-2 from TNF-alpha, IL-1beta, and LPS-stimulated human PBMC in a partially IL-10-dependent manner. Cell Immunol. 2004 Aug;230(2):81-8. [PubMed:15598423]
  4. Wiedmann MW, Caca K: Molecularly targeted therapy for gastrointestinal cancer. Curr Cancer Drug Targets. 2005 May;5(3):171-93. [PubMed:15892618]
  5. Du GJ, Lin HH, Xu QT, Wang MW: Thalidomide inhibits growth of tumors through COX-2 degradation independent of antiangiogenesis. Vascul Pharmacol. 2005 Aug;43(2):112-9. [PubMed:15982930]
  6. Kim JH, Scialli AR: Thalidomide: the tragedy of birth defects and the effective treatment of disease. Toxicol Sci. 2011 Jul;122(1):1-6. doi: 10.1093/toxsci/kfr088. Epub 2011 Apr 19. [PubMed:21507989]
7. Nuclear factor kappa-light-chain-enhancer of activated B cells
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
References
  1. Kim JH, Scialli AR: Thalidomide: the tragedy of birth defects and the effective treatment of disease. Toxicol Sci. 2011 Jul;122(1):1-6. doi: 10.1093/toxsci/kfr088. Epub 2011 Apr 19. [PubMed:21507989]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. Turk BE, Jiang H, Liu JO: Binding of thalidomide to alpha1-acid glycoprotein may be involved in its inhibition of tumor necrosis factor alpha production. Proc Natl Acad Sci U S A. 1996 Jul 23;93(15):7552-6. [PubMed:8755512]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Okada Y, Murayama N, Yanagida C, Shimizu M, Guengerich FP, Yamazaki H: Drug interactions of thalidomide with midazolam and cyclosporine A: heterotropic cooperativity of human cytochrome P450 3A5. Drug Metab Dispos. 2009 Jan;37(1):18-23. doi: 10.1124/dmd.108.024679. Epub 2008 Oct 23. [PubMed:18948377]
  4. Ando Y, Fuse E, Figg WD: Thalidomide metabolism by the CYP2C subfamily. Clin Cancer Res. 2002 Jun;8(6):1964-73. [PubMed:12060642]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inducer
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]

Drug created on June 13, 2005 07:24 / Updated on September 24, 2018 10:17