Drug Information

Drug General Information
Drug ID
D07SDQ
Former ID
DNC006900
Drug Name
Curcumin
Drug Type
Small molecular drug
Indication Cancer [ICD9: 140-229; ICD10:C00-C96] Phase 3 [1], [2]
Structure
Download
2D MOL

3D MOL
Formula
C21H20O6
InChI
InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+
InChIKey
VFLDPWHFBUODDF-FCXRPNKRSA-N
PubChem Compound ID
969516
PubChem Substance ID
91276, 521754, 616319, 806710, 855880, 3139269, 7979963, 8136975, 8145866, 8719722, 10319004, 12013839, 12055808, 14803853, 17389087, 24892408, 24892983, 29203996, 44256039, 46493764, 48184781, 48414613, 48414614, 48423182, 48424998, 49854349, 49856278, 50104137, 50104138, 53788771, 56312449, 56313017, 56422380, 57288615, 57408903, 75735540, 81040856, 81054961, 81093229, 85286188, 85789755, 87565556, 87565557, 88806667, 92126156, 92709887, 93165931, 103961572, 104171337, 105852703
Target and Pathway
Target(s) Carbonic anhydrase II Target Info Inhibitor [3]
Carbonic anhydrase XII Target Info Inhibitor [3]
Carbonic anhydrase VI Target Info Inhibitor [3]
Carbonic anhydrase IX Target Info Inhibitor [3]
Cytochrome P450 3A4 Target Info Inhibitor [4]
Nitric oxide synthase, inducible Target Info Inhibitor [5]
Carbonic anhydrase XIV Target Info Inhibitor [3]
Carbonic anhydrase I Target Info Inhibitor [3]
DNA (cytosine-5)-methyltransferase Target Info Inhibitor [6]
Collagenase 3 Target Info Inhibitor [7]
DNA (cytosine-5)-methyltransferase 3B Target Info Inhibitor [6]
Xanthine dehydrogenase/oxidase Target Info Inhibitor [8]
Prostaglandin G/H synthase 1 Target Info Inhibitor [9]
MMP-9 Target Info Inhibitor [10]
Prostaglandin G/H synthase 2 Target Info Inhibitor [9]
Carbonic anhydrase IV Target Info Inhibitor [3]
Amyloid beta A4 protein Target Info Inhibitor [11]
Carbonic anhydrase Target Info Inhibitor [3]
BioCyc Pathway Citrulline-nitric oxide cyclePWY-6353:Purine nucleotides degradation
Urate biosynthesis/inosine 5'-phosphate degradation
Guanosine nucleotides degradation
Adenosine nucleotides degradation
Retinoate biosynthesis IIPWY66-374:C20 prostanoid biosynthesisPWY66-393:Aspirin-triggered lipoxin biosynthesis
Aspirin triggered resolvin D biosynthesis
C20 prostanoid biosynthesis
Aspirin triggered resolvin E biosynthesis
KEGG Pathway Nitrogen metabolism
Proximal tubule bicarbonate reclamation
Collecting duct acid secretion
Gastric acid secretion
Pancreatic secretion
Bile secretionhsa00910:Nitrogen metabolismhsa00910:Nitrogen metabolismhsa00910:Nitrogen metabolismhsa00140:Steroid hormone biosynthesis
Linoleic acid metabolism
Retinol metabolism
Metabolism of xenobiotics by cytochrome P450
Drug metabolism - cytochrome P450
Drug metabolism - other enzymes
Metabolic pathways
Bile secretion
Chemical carcinogenesishsa00220:Arginine biosynthesis
Arginine and proline metabolism
Calcium signaling pathway
HIF-1 signaling pathway
Peroxisome
Salmonella infection
Pertussis
Leishmaniasis
Chagas disease (American trypanosomiasis)
Toxoplasmosis
Amoebiasis
Tuberculosis
Pathways in cancer
Small cell lung cancerhsa00910:Nitrogen metabolismhsa00910:Nitrogen metabolismhsa00270:Cysteine and methionine metabolism
MicroRNAs in cancerhsa00230:Purine metabolism
Caffeine metabolism
Peroxisomehsa00590:Arachidonic acid metabolism
Platelet activation
Serotonergic synapsehsa04668:TNF signaling pathway
Leukocyte transendothelial migration
Estrogen signaling pathway
Hepatitis B
Transcriptional misregulation in cancer
Proteoglycans in cancer
MicroRNAs in cancer
Bladder cancerhsa00590:Arachidonic acid metabolism
NF-kappa B signaling pathway
VEGF signaling pathway
TNF signaling pathway
Retrograde endocannabinoid signaling
Serotonergic synapse
Ovarian steroidogenesis
Oxytocin signaling pathway
Regulation of lipolysis in adipocytes
Chemical carcinogenesis
Small cell lung cancerhsa00910:Nitrogen metabolism
Proximal tubule bicarbonate reclamationhsa04330:Notch signaling pathway
Alzheimer's disease
NetPath Pathway IL4 Signaling Pathway
EGFR1 Signaling PathwayNetPath_7:TGF_beta_Receptor Signaling PathwayNetPath_13:IL1 Signaling Pathway
IL2 Signaling PathwayNetPath_13:IL1 Signaling PathwayNetPath_7:TGF_beta_Receptor Signaling PathwayNetPath_5:ID Signaling Pathway
TWEAK Signaling Pathway
Leptin Signaling Pathway
TNFalpha Signaling PathwayNetPath_13:IL1 Signaling Pathway
TSH Signaling Pathway
TGF_beta_Receptor Signaling Pathway
IL5 Signaling Pathway
PANTHER Pathway Alzheimer disease-presenilin pathway
Plasminogen activating cascadeP02723:Adenine and hypoxanthine salvage pathway
Purine metabolismP00031:Inflammation mediated by chemokine and cytokine signaling pathwayP00004:Alzheimer disease-presenilin pathway
Plasminogen activating cascade
CCKR signaling map STP00019:Endothelin signaling pathway
Inflammation mediated by chemokine and cytokine signaling pathway
Toll receptor signaling pathway
CCKR signaling map ST
Pathway Interaction Database HIF-1-alpha transcription factor networkil12_2pathway:IL12-mediated signaling events
Alpha9 beta1 integrin signaling events
ATF-2 transcription factor network
IL23-mediated signaling events
Signaling mediated by p38-alpha and p38-beta
HIF-1-alpha transcription factor networkcmyb_pathway:C-MYB transcription factor networkupa_upar_pathway:Urokinase-type plasminogen activator (uPA) and uPAR-mediated signalinglysophospholipid_pathway:LPA receptor mediated events
Plasma membrane estrogen receptor signaling
Osteopontin-mediated events
Validated transcriptional targets of AP1 family members Fra1 and Fra2
Validated targets of C-MYC transcriptional activation
CXCR4-mediated signaling events
amb2 Integrin signaling
Syndecan-4-mediated signaling events
AP-1 transcription factor network
Urokinase-type plasminogen activator (uPA) and uPAR-mediated signaling
Syndecan-1-mediated signaling events
Regulation of nuclear beta catenin signaling and target gene transcription
FGF signaling pathwaynfat_tfpathway:Calcineurin-regulated NFAT-dependent transcription in lymphocytes
S1P1 pathway
C-MYB transcription factor network
Calcium signaling in the CD4+ TCR pathway
PathWhiz Pathway Caffeine Metabolism
Retinol MetabolismPW000565:Gastric Acid ProductionPW000015:Caffeine Metabolism
Purine MetabolismPW000044:Arachidonic Acid MetabolismPW000044:Arachidonic Acid Metabolism
Reactome Erythrocytes take up carbon dioxide and release oxygen
Erythrocytes take up oxygen and release carbon dioxide
Reversible hydration of carbon dioxideR-HSA-1475029:Reversible hydration of carbon dioxideR-HSA-1475029:Reversible hydration of carbon dioxideR-HSA-1234158:Regulation of gene expression by Hypoxia-inducible Factor
Reversible hydration of carbon dioxideR-HSA-211981:Xenobiotics
Aflatoxin activation and detoxificationR-HSA-1222556:ROS production in response to bacteria
Nitric oxide stimulates guanylate cyclaseR-HSA-1475029:Reversible hydration of carbon dioxideR-HSA-1237044:Erythrocytes take up carbon dioxide and release oxygen
Reversible hydration of carbon dioxideR-HSA-1442490:Collagen degradation
Degradation of the extracellular matrix
Activation of Matrix Metalloproteinases
Assembly of collagen fibrils and other multimeric structuresR-HSA-212300:PRC2 methylates histones and DNA
NoRC negatively regulates rRNA expression
DNA methylationR-HSA-74259:Purine catabolismR-HSA-1442490:Collagen degradation
Assembly of collagen fibrils and other multimeric structures
EPH-ephrin mediated repulsion of cellsR-HSA-1237044:Erythrocytes take up carbon dioxide and release oxygen
Reversible hydration of carbon dioxideR-HSA-1251985:Nuclear signaling by ERBB4
Regulated proteolysis of p75NTR
NRIF signals cell death from the nucleus
Activated NOTCH1 Transmits Signal to the Nucleus
Constitutive Signaling by NOTCH1 PEST Domain Mutants
Constitutive Signaling by NOTCH1 HD+PEST Domain Mutants
EPH-ephrin mediated repulsion of cells
WikiPathways Reversible Hydration of Carbon Dioxide
Uptake of Carbon Dioxide and Release of Oxygen by Erythrocytes
Uptake of Oxygen and Release of Carbon Dioxide by ErythrocytesWP2770:Reversible Hydration of Carbon Dioxide
miR-targeted genes in muscle cell - TarBase
miR-targeted genes in leukocytes - TarBase
miR-targeted genes in epithelium - TarBaseWP2770:Reversible Hydration of Carbon DioxideWP2877:Vitamin D Receptor Pathway
Regulation of Hypoxia-inducible Factor (HIF) by OxygenWP702:Metapathway biotransformation
Aflatoxin B1 metabolism
Estrogen metabolism
Benzo(a)pyrene metabolism
Tamoxifen metabolism
Tryptophan metabolism
Oxidation by Cytochrome P450
Nuclear Receptors in Lipid Metabolism and Toxicity
Nuclear Receptors Meta-Pathway
Farnesoid X Receptor Pathway
Vitamin D Receptor Pathway
Felbamate Metabolism
Lidocaine metabolism
Nifedipine Activity
Colchicine Metabolic Pathway
Irinotecan Pathway
Drug Induction of Bile Acid Pathway
Fatty Acid Omega Oxidation
Codeine and Morphine MetabolismWP619:Type II interferon signaling (IFNG)
Spinal Cord Injury
AGE/RAGE pathway
Effects of Nitric OxideWP2770:Reversible Hydration of Carbon DioxideWP2770:Reversible Hydration of Carbon Dioxide
Uptake of Oxygen and Release of Carbon Dioxide by ErythrocytesWP474:Endochondral Ossification
Activation of Matrix Metalloproteinases
Oncostatin M Signaling Pathway
Matrix MetalloproteinasesWP2857:Mesodermal Commitment Pathway
Endoderm Differentiation
Trans-sulfuration and one carbon metabolism
One Carbon Metabolism
miR-targeted genes in lymphocytes - TarBaseWP408:Oxidative Stress
Effects of Nitric Oxide
Metabolism of nucleotides
Selenium Micronutrient NetworkWP98:Prostaglandin Synthesis and Regulation
Arachidonic acid metabolism
Phase 1 - Functionalization of compounds
Eicosanoid Synthesis
Selenium Micronutrient NetworkWP474:Endochondral Ossification
IL1 and megakaryotyces in obesity
Mammary gland development pathway - Involution (Stage 4 of 4)
Degradation of collagen
TWEAK Signaling Pathway
Angiogenesis
Osteopontin Signaling
Matrix MetalloproteinasesWP98:Prostaglandin Synthesis and Regulation
Aryl Hydrocarbon Receptor
Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
Integrated Pancreatic Cancer Pathway
Selenium Micronutrient NetworkWP2770:Reversible Hydration of Carbon Dioxide
Uptake of Oxygen and Release of Carbon Dioxide by ErythrocytesWP61:Notch Signaling Pathway
Signaling by ERBB4
Signaling by NOTCH3
Signaling by NOTCH4
Signaling by NOTCH1
Signaling by NOTCH2
Notch Signaling Pathway
Alzheimers Disease
Signalling by NGF
References
REF 1Nanocurcumin: a promising therapeutic advancement over native curcumin. Crit Rev Ther Drug Carrier Syst. 2013;30(4):331-68.
REF 2(http://www.guidetopharmacology.org/) Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7000).
REF 3Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3. Epub 2010 Jul 13.Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV.
REF 4Eur J Med Chem. 2008 Aug;43(8):1621-31. Epub 2007 Nov 17.Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues.
REF 5Proc Natl Acad Sci U S A. 2007 Dec 18;104(51):20523-8. Epub 2007 Dec 11.A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases.
REF 6Bioorg Med Chem. 2010 Jan 15;18(2):822-9. Epub 2009 Nov 27.Novel and selective DNA methyltransferase inhibitors: Docking-based virtual screening and experimental evaluation.
REF 7Bioorg Med Chem. 2009 Feb 1;17(3):990-1005. Epub 2008 Mar 6.High throughput screening of potentially selective MMP-13 exosite inhibitors utilizing a triple-helical FRET substrate.
REF 8J Nat Prod. 2009 Apr;72(4):725-31.Inhibition studies of bovine xanthine oxidase by luteolin, silibinin, quercetin, and curcumin.
REF 9Bioorg Med Chem Lett. 2005 Apr 1;15(7):1793-7.Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents.
REF 10Bioorg Med Chem. 2009 Feb 1;17(3):1290-6. Epub 2009 Jan 6.Synthesis and biological evaluation of curcuminoid pyrazoles as new therapeutic agents in inflammatory bowel disease: effect on matrix metalloproteinases.
REF 11J Med Chem. 2006 Oct 5;49(20):6111-9.Curcumin and dehydrozingerone derivatives: synthesis, radiolabeling, and evaluation for beta-amyloid plaque imaging.

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