Identification

Name
Thalidomide
Accession Number
DB01041
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A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects.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]

Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Structure
Thumb
Weight
Average: 258.2295
Monoisotopic: 258.064056818
Chemical Formula
C13H10N2O4
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
  • Thalidomide
  • Thalidomidum
  • α-(N-phthalimido)glutarimide
  • α-N-phthalylglutaramide
  • α-phthalimidoglutarimide
External IDs
  • NSC-527179
  • NSC-66847

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
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
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
Humans
ATumor necrosis factor
inhibitor
Humans
ANuclear factor NF-kappa-B p105 subunit
antagonist
Humans
ADNA
intercalation
Humans
AFibroblast growth factor receptor 2
antagonist
Humans
UProstaglandin G/H synthase 2
antagonist
Humans
Ualpha1-acid glycoprotein
binder
Humans
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.

Hover over products below to view reaction partners

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
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe metabolism of Thalidomide can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Thalidomide.
AbirateroneThe metabolism of Thalidomide can be decreased when combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Thalidomide is combined with Acebutolol.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Thalidomide.
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
AcetohexamideThe metabolism of Thalidomide can be decreased when combined with Acetohexamide.
AcetophenazineAcetophenazine 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.
Additional Data Available
  • Extended Description
    Extended Description
    Available for Purchase

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity
    Available for Purchase

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level
    Available for Purchase

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action
    Available for Purchase

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Avoid alcohol. Ingesting alcohol may increase the drowsiness caused by thalidomide.
  • Take after a meal. Wait at least 1 hour after eating before taking thalidomide.

Products

Purchasing individual compounds or compound libraries for your research?
Learn More
International/Other Brands
Contergan / Distaval / K-17 / Pro-ban M / Sedalis / Softenon / Talimol / Thaled
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Thalidomide CelgeneCapsule50 mgOralCelgene Europe Bv2008-04-16Not applicableEU flag
ThalomidCapsule100 mgOralCelgene2011-02-17Not applicableCanada flag
ThalomidCapsule150 mgOralCelgeneNot applicableNot applicableCanada flag
ThalomidCapsule100 mg/1OralCelgene Corporation2003-06-20Not applicableUS flag
ThalomidCapsule200 mg/1OralCelgene Corporation2003-06-20Not applicableUS flag
ThalomidCapsule50 mg/1OralCelgene Corporation2003-06-20Not applicableUS flag
ThalomidCapsule200 mgOralCelgene2011-02-17Not applicableCanada flag
ThalomidCapsule150 mg/1OralCelgene Corporation2007-03-20Not applicableUS flag
ThalomidCapsule50 mgOralCelgene2010-11-01Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more

Categories

ATC Codes
L04AX02 — Thalidomide
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid imide / Carboxylic acid imide, n-substituted / Carboxylic acid imide, n-unsubstituted / Delta-lactam
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
piperidones, phthalimides (CHEBI:74947)

Chemical Identifiers

UNII
4Z8R6ORS6L
CAS number
50-35-1
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

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
Human Metabolome Database
HMDB0015175
KEGG Drug
D00754
KEGG Compound
C07910
PubChem Compound
5426
PubChem Substance
46505665
ChemSpider
5233
BindingDB
50070114
RxNav
10432
ChEBI
74947
ChEMBL
CHEMBL468
Therapeutic Targets Database
DAP000865
PharmGKB
PA451644
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Thalidomide
AHFS Codes
  • 92:20.00 — Immunomodulatory Agents
FDA label
Download (180 KB)
MSDS
Download (58.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentMultiple Myeloma (MM)1
4Not Yet RecruitingTreatmentCancer, Therapy-Related1
4RecruitingTreatmentCutaneous Lupus / Juvenile SLE / Systemic Lupus Erythematosus (SLE)1
4RecruitingTreatmentImmunoglobulin Light-Chain Amyloidosis1
4TerminatedTreatmentUveitis1
4Unknown StatusTreatmentCongestive Heart Failure (CHF)1
4Unknown StatusTreatmentCoronary Artery Disease (CAD)1
4Unknown StatusTreatmentMalignant Neoplasm of Stomach1
4Unknown StatusTreatmentMantle Cell Lymphoma (MCL)1
4Unknown StatusTreatmentMultiple Myeloma (MM)2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Celgene
  • IDT Australia Ltd.
  • Penn Pharmaceutical Services Ltd.
Dosage Forms
FormRouteStrength
CapsuleOral50 mg
CapsuleOral100 mg/1
CapsuleOral100 mg
CapsuleOral150 mg/1
CapsuleOral150 mg
CapsuleOral200 mg/1
CapsuleOral200 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)Region
US6235756No2001-05-222013-03-01US flag
CA2505964No2009-07-282023-11-13Canada flag
CA2157288No2005-11-082014-02-24Canada flag
US6045501No2000-04-042018-08-28US flag
US6315720No2001-11-132020-10-23US flag
US6561976No2003-05-132018-08-28US flag
US6561977No2003-05-132020-10-23US flag
US6755784No2004-06-292020-10-23US flag
US6869399No2005-03-222020-10-23US flag
US6908432No2005-06-212018-08-28US flag
US7141018No2006-11-282020-10-23US flag
US7435745No2008-10-142017-11-03US flag
US7874984No2011-01-252018-08-28US flag
US7959566No2011-06-142020-10-23US flag
US8204763No2012-06-192018-08-28US flag
US8315886No2012-11-202020-10-23US flag
US8626531No2014-01-072020-10-23US flag
US8589188No2013-11-192018-08-28US flag
US7230012No2007-06-122023-12-09US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

    Learn more

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

Targets

Kind
Protein
Organism
Humans
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
Humans
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
Humans
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]
Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Intercalation
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
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
Humans
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
Humans
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]
Kind
Protein group
Organism
Humans
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
Humans
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. 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]
  2. Ando Y, Fuse E, Figg WD: Thalidomide metabolism by the CYP2C subfamily. Clin Cancer Res. 2002 Jun;8(6):1964-73. [PubMed:12060642]
  3. Li Y, Jiang Z, Xiao Y, Li L, Gao Y: Metabolism of thalidomide by human liver microsome cytochrome CYP2C19 is required for its antimyeloma and antiangiogenic activities in vitro. Hematol Oncol. 2012 Mar;30(1):13-21. doi: 10.1002/hon.992. Epub 2011 Jun 3. [PubMed:21638302]
  4. Ando Y, Price DK, Dahut WL, Cox MC, Reed E, Figg WD: Pharmacogenetic associations of CYP2C19 genotype with in vivo metabolisms and pharmacological effects of thalidomide. Cancer Biol Ther. 2002 Nov-Dec;1(6):669-73. doi: 10.4161/cbt.318. [PubMed:12642692]
Kind
Protein
Organism
Humans
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
Humans
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
Humans
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]
  2. 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
Humans
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
Humans
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
Humans
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 November 30, 2020 13:38

Pm 5