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Curcumin sulfate

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

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Identification

Generic Name
Curcumin sulfate
DrugBank Accession Number
DB14635
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 448.44
Monoisotopic: 448.082803398
Chemical Formula
C21H20O9S
Synonyms
  • Curcumin monosulfate
  • Curcumin sulphate
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Pharmacology

Indication

No approved therapeutic indications.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Intravenous application of 25 mg/kg bw curcumin to rats resulted in an increase in bile flow by 80 and 120% 2. In the rat model of inflammation, curcumin was shown to inhibit edema formation. In nude mouse that had been injected subcutaneously with prostate cancer cells, administration of curcumin caused a marked decrease in the extent of cell proliferation, a significant increase of apoptosis and micro-vessel density 2. Curcumin may exert choleretic effects by increasing biliary excretion of bile salts, cholesterol, and bilirubin, as well as increasing bile solubility 2. Curcumin inhibited arachidonic acid-induced platelet aggregation in vitro 2.

Mechanism of action

Curcumin acts as a scavenger of oxygen species, such as hydroxyl radical, superoxide anion, and singlet oxygen and inhibit lipid peroxidation as well as peroxide-induced DNA damage 2. Curcumin mediates potent anti-inflammatory agent and anti-carcinogenic actions via modulating various signalling molecules. It suppresses a number of key elements in cellular signal transduction pathways pertinent to growth, differentiation, and malignant transformation; it was demonstrated in vitro that curcumin inhibits protein kinases, c-Jun/AP-1 activation, prostaglandin biosynthesis, and the activity and expression of the enzyme cyclooxygenase (COX)-2 2.

TargetActionsOrganism
UPeroxisome proliferator-activated receptor gammaNot AvailableHumans
UVitamin D3 receptorNot AvailableHumans
UATP-binding cassette sub-family C member 5Not AvailableHumans
UCarbonyl reductase [NADPH] 1Not AvailableHumans
UGlutathione S-transferase PNot AvailableHumans
Absorption

Curcumin displays poor absorption into the gastrointestinal tract. In a rat study, oral administration of a single dose of 2 g of curcumin resulted in a plasma concentration of less than 5 μg/mL, indicating poor absorption from the gut 2.

Volume of distribution

Following oral administration of radio-labelled curcumin to rats, radioactivity was detected in the liver and kidneys 2.

Protein binding

No pharmacokinetic data available.

Metabolism

Initially, curcumin undergoes rapid intestinal metabolism to form curcumin glucuronide and curcumin sulfate via O-conjugation. Other metabolites formed include tetrahydrocurcumin, hexahydrocurcumin, and hexahydrocurcuminol via reduction 2. Curcumin may also undergo intensive second metabolism in the liver where the major metabolites were glucuronides of tetrahydrocurcumin and hexahydrocurcumin, with dihydroferulic acid and traces of ferulic acid as further metabolites 2. Hepatic metabolites are expected to be excreted in the bile 2. Certain curcumin metabolites, such as tetrahydrocurcumin, retain anti-inflammatory and antioxidant properties 2.

Route of elimination

Following oral administration of curcumin to rats at a dose of 1 g/kg bw, about 75% of dose was excreted in the faeces and only traces of the compound was detected in the urine 2. When a single 400 mg dose of curcumin was administered orally to rats, about 60% was absorbed and 40% was excreted unchanged in the faeces over an period of 5 days 2. Intraperitoneal administration resulted in fecal excretion of 73% and biliary excretion of 11% 2.

Half-life

No pharmacokinetic data available.

Clearance

No pharmacokinetic data available.

Adverse Effects
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Toxicity

In an acute oral toxicity study in mouse, LD50 was >2000 mg/kg MSDS. Single oral doses of curcumin at 1-5 g/kg bw induced no toxic effects in rats 2. There has been no cases of overdose reported 2.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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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
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AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Curcumin sulfate.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Curcumin sulfate.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Curcumin sulfate.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Curcumin sulfate.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Curcumin sulfate.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Diarylheptanoids
Sub Class
Linear diarylheptanoids
Direct Parent
Curcuminoids
Alternative Parents
Hydroxycinnamic acids and derivatives / Phenylsulfates / Methoxyphenols / Anisoles / Styrenes / Phenoxy compounds / Methoxybenzenes / 1-hydroxy-2-unsubstituted benzenoids / Alkyl aryl ethers / Beta-diketones
show 6 more
Substituents
1,3-dicarbonyl compound / 1,3-diketone / 1-hydroxy-2-unsubstituted benzenoid / Acryloyl-group / Alkyl aryl ether / Alpha,beta-unsaturated ketone / Anisole / Aromatic homomonocyclic compound / Arylsulfate / Benzenoid
show 23 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
160DHE331M
CAS number
339286-19-0
InChI Key
NEJVQQBBTRFOHB-FCXRPNKRSA-N
InChI
InChI=1S/C21H20O9S/c1-28-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(21(12-15)29-2)30-31(25,26)27/h3-12,24H,13H2,1-2H3,(H,25,26,27)/b7-3+,8-4+
IUPAC Name
{4-[(1E,6E)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dien-1-yl]-2-methoxyphenyl}oxidanesulfonic acid
SMILES
COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(OS(O)(=O)=O)C(OC)=C2)=CC=C1O

References

General References
  1. Gupta SC, Patchva S, Aggarwal BB: Therapeutic roles of curcumin: lessons learned from clinical trials. AAPS J. 2013 Jan;15(1):195-218. doi: 10.1208/s12248-012-9432-8. Epub 2012 Nov 10. [Article]
  2. EMA Assessment Report: Curcuma xanthorrhiza Roxb. (C. xanthorrhiza D. Dietrich)., rhizoma for oral use [Link]
ChemSpider
34988878
ZINC
ZINC000011524418

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00831 mg/mLALOGPS
logP1.72ALOGPS
logP3.65Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)-2.2Chemaxon
pKa (Strongest Basic)-4.4Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area136.43 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity113.8 m3·mol-1Chemaxon
Polarizability43.54 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-0116900000-43de39295c34708cdef7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-0920300000-22286a818ec286289d52
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0829100000-d0cab8a1115e33171f6d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004s-4984300000-7c1eec610c99bef0c946
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-0912000000-a824a8d63254f36942c3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9721100000-8429fa32c5998debb958
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-214.11319
predicted
DeepCCS 1.0 (2019)
[M+H]+216.0086
predicted
DeepCCS 1.0 (2019)
[M+Na]+222.22267
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peroxisome proliferator-activated receptor gamma
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated pro-inflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of BMAL1 in the blood vessels (By similarity)
Specific Function
alpha-actinin binding
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Nishiyama T, Mae T, Kishida H, Tsukagawa M, Mimaki Y, Kuroda M, Sashida Y, Takahashi K, Kawada T, Nakagawa K, Kitahara M: Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice. J Agric Food Chem. 2005 Feb 23;53(4):959-63. [Article]
Details2. Vitamin D3 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nuclear receptor for calcitriol, the active form of vitamin D3 which mediates the action of this vitamin on cells (PubMed:10678179, PubMed:15728261, PubMed:16913708, PubMed:28698609, PubMed:37478846). Enters the nucleus upon vitamin D3 binding where it forms heterodimers with the retinoid X receptor/RXR (PubMed:28698609). The VDR-RXR heterodimers bind to specific response elements on DNA and activate the transcription of vitamin D3-responsive target genes (PubMed:28698609). Plays a central role in calcium homeostasis (By similarity). Also functions as a receptor for the secondary bile acid lithocholic acid (LCA) and its metabolites (PubMed:12016314, PubMed:32354638)
Specific Function
bile acid nuclear receptor activity
Gene Name
VDR
Uniprot ID
P11473
Uniprot Name
Vitamin D3 receptor
Molecular Weight
48288.64 Da
References
  1. Bartik L, Whitfield GK, Kaczmarska M, Lowmiller CL, Moffet EW, Furmick JK, Hernandez Z, Haussler CA, Haussler MR, Jurutka PW: Curcumin: a novel nutritionally derived ligand of the vitamin D receptor with implications for colon cancer chemoprevention. J Nutr Biochem. 2010 Dec;21(12):1153-61. doi: 10.1016/j.jnutbio.2009.09.012. Epub 2010 Feb 12. [Article]
Details3. ATP-binding cassette sub-family C member 5
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds, and xenobiotics from cells. Mediates ATP-dependent transport of endogenous metabolites such as cAMP and cGMP, folic acid and N-lactoyl-amino acids (in vitro) (PubMed:10893247, PubMed:12637526, PubMed:12695538, PubMed:15899835, PubMed:17229149, PubMed:25964343). Acts also as a general glutamate conjugate and analog transporter that can limit the brain levels of endogenous metabolites, drugs, and toxins (PubMed:26515061). Confers resistance to the antiviral agent PMEA (PubMed:12695538). Able to transport several anticancer drugs including methotrexate, and nucleotide analogs in vitro, however it does with low affinity, thus the exact role of ABCC5 in mediating resistance still needs to be elucidated (PubMed:10840050, PubMed:12435799, PubMed:12695538, PubMed:15899835). Acts as a heme transporter required for the translocation of cytosolic heme to the secretory pathway (PubMed:24836561). May play a role in energy metabolism by regulating the glucagon-like peptide 1 (GLP-1) secretion from enteroendocrine cells (By similarity)
Specific Function
ABC-type xenobiotic transporter activity
Gene Name
ABCC5
Uniprot ID
O15440
Uniprot Name
ATP-binding cassette sub-family C member 5
Molecular Weight
160658.8 Da
References
  1. Prehm P: Curcumin analogue identified as hyaluronan export inhibitor by virtual docking to the ABC transporter MRP5. Food Chem Toxicol. 2013 Dec;62:76-81. doi: 10.1016/j.fct.2013.08.028. Epub 2013 Aug 24. [Article]
Details4. Carbonyl reductase [NADPH] 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Curator comments
Non-competitive inhibitor
General Function
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol (PubMed:15799708, PubMed:17344335, PubMed:17912391, PubMed:18449627, PubMed:18826943, PubMed:1921984, PubMed:7005231). Can convert prostaglandin E to prostaglandin F2-alpha (By similarity). Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione (PubMed:17344335, PubMed:18826943). In addition, participates in the glucocorticoid metabolism by catalyzing the NADPH-dependent cortisol/corticosterone into 20beta-dihydrocortisol (20b-DHF) or 20beta-corticosterone (20b-DHB), which are weak agonists of NR3C1 and NR3C2 in adipose tissue (PubMed:28878267)
Specific Function
15-hydroxyprostaglandin dehydrogenase (NADP+) activity
Gene Name
CBR1
Uniprot ID
P16152
Uniprot Name
Carbonyl reductase [NADPH] 1
Molecular Weight
30374.73 Da
References
  1. Hintzpeter J, Hornung J, Ebert B, Martin HJ, Maser E: Curcumin is a tight-binding inhibitor of the most efficient human daunorubicin reductase--Carbonyl reductase 1. Chem Biol Interact. 2015 Jun 5;234:162-8. doi: 10.1016/j.cbi.2014.12.019. Epub 2014 Dec 22. [Article]
Details5. Glutathione S-transferase P
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Curator comments
Irreversibly inhibits the enzyme via covalent modification at high concentrations. At low concentrations enzyme activity may be modified but not entirely inhibited by covalent binding.
General Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Involved in the formation of glutathione conjugates of both prostaglandin A2 (PGA2) and prostaglandin J2 (PGJ2) (PubMed:9084911). Participates in the formation of novel hepoxilin regioisomers (PubMed:21046276). Negatively regulates CDK5 activity via p25/p35 translocation to prevent neurodegeneration
Specific Function
dinitrosyl-iron complex binding
Gene Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 Da
References
  1. van Iersel ML, Ploemen JP, Lo Bello M, Federici G, van Bladeren PJ: Interactions of alpha, beta-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1. Chem Biol Interact. 1997 Dec 12;108(1-2):67-78. [Article]

Enzymes

Details1. Cytochrome P450 2C19
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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 imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55944.565 Da
References
  1. Volak LP, Ghirmai S, Cashman JR, Court MH: Curcuminoids inhibit multiple human cytochromes P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor. Drug Metab Dispos. 2008 Aug;36(8):1594-605. doi: 10.1124/dmd.108.020552. Epub 2008 May 14. [Article]
Details2. Cytochrome P450 2B6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
Specific Function
anandamide 11,12 epoxidase activity
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Volak LP, Ghirmai S, Cashman JR, Court MH: Curcuminoids inhibit multiple human cytochromes P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor. Drug Metab Dispos. 2008 Aug;36(8):1594-605. doi: 10.1124/dmd.108.020552. Epub 2008 May 14. [Article]
  2. Appiah-Opong R, Commandeur JN, van Vugt-Lussenburg B, Vermeulen NP: Inhibition of human recombinant cytochrome P450s by curcumin and curcumin decomposition products. Toxicology. 2007 Jun 3;235(1-2):83-91. doi: 10.1016/j.tox.2007.03.007. Epub 2007 Mar 15. [Article]
Details3. UDP-glucuronosyltransferases (UGTs) (Protein Group)
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks transferase activity but acts as a negative regulator of isoform 1 (By similarity)
Specific Function
enzyme binding
Components:
NameUniProt ID
UDP-glucuronosyltransferase 1-6P19224
UDP-glucuronosyltransferase 1A1P22309
UDP-glucuronosyltransferase 1A10Q9HAW8
UDP-glucuronosyltransferase 1A3P35503
UDP-glucuronosyltransferase 1A4P22310
UDP-glucuronosyltransferase 1A7Q9HAW7
UDP-glucuronosyltransferase 1A8Q9HAW9
UDP-glucuronosyltransferase 1A9O60656
UDP-glucuronosyltransferase 2B15P54855
UDP-glucuronosyltransferase 2B4P06133
UDP-glucuronosyltransferase 2B7P16662
References
  1. Volak LP, Ghirmai S, Cashman JR, Court MH: Curcuminoids inhibit multiple human cytochromes P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor. Drug Metab Dispos. 2008 Aug;36(8):1594-605. doi: 10.1124/dmd.108.020552. Epub 2008 May 14. [Article]
Details4. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
Curcumin has been shown to inhibit CYP2C9 in studies on rats and in vitro studies. Evidence is contradictory in the literature. Clinical relevance is unknown.
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Volak LP, Ghirmai S, Cashman JR, Court MH: Curcuminoids inhibit multiple human cytochromes P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor. Drug Metab Dispos. 2008 Aug;36(8):1594-605. doi: 10.1124/dmd.108.020552. Epub 2008 May 14. [Article]
  2. Wang Z, Sun W, Huang CK, Wang L, Xia MM, Cui X, Hu GX, Wang ZS: Inhibitory effects of curcumin on activity of cytochrome P450 2C9 enzyme in human and 2C11 in rat liver microsomes. Drug Dev Ind Pharm. 2015 Apr;41(4):613-6. doi: 10.3109/03639045.2014.886697. Epub 2014 Feb 12. [Article]
Details5. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function
1,8-cineole 2-exo-monooxygenase activity
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Volak LP, Ghirmai S, Cashman JR, Court MH: Curcuminoids inhibit multiple human cytochromes P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor. Drug Metab Dispos. 2008 Aug;36(8):1594-605. doi: 10.1124/dmd.108.020552. Epub 2008 May 14. [Article]
Details6. Cytochrome P450 3A5
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
Specific Function
aromatase activity
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Volak LP, Ghirmai S, Cashman JR, Court MH: Curcuminoids inhibit multiple human cytochromes P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor. Drug Metab Dispos. 2008 Aug;36(8):1594-605. doi: 10.1124/dmd.108.020552. Epub 2008 May 14. [Article]
Details7. Cytochrome P450 2D6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
Specific Function
anandamide 11,12 epoxidase activity
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Volak LP, Ghirmai S, Cashman JR, Court MH: Curcuminoids inhibit multiple human cytochromes P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor. Drug Metab Dispos. 2008 Aug;36(8):1594-605. doi: 10.1124/dmd.108.020552. Epub 2008 May 14. [Article]
  2. Al-Jenoobi FI, Al-Thukair AA, Alam MA, Abbas FA, Al-Mohizea AM, Alkharfy KM, Al-Suwayeh SA: Effect of Curcuma longa on CYP2D6- and CYP3A4-mediated metabolism of dextromethorphan in human liver microsomes and healthy human subjects. Eur J Drug Metab Pharmacokinet. 2015 Mar;40(1):61-6. doi: 10.1007/s13318-014-0180-2. Epub 2014 Feb 9. [Article]
Details8. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
Specific Function
aromatase activity
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58406.915 Da
References
  1. Volak LP, Ghirmai S, Cashman JR, Court MH: Curcuminoids inhibit multiple human cytochromes P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor. Drug Metab Dispos. 2008 Aug;36(8):1594-605. doi: 10.1124/dmd.108.020552. Epub 2008 May 14. [Article]
  2. Chen Y, Liu WH, Chen BL, Fan L, Han Y, Wang G, Hu DL, Tan ZR, Zhou G, Cao S, Zhou HH: Plant polyphenol curcumin significantly affects CYP1A2 and CYP2A6 activity in healthy, male Chinese volunteers. Ann Pharmacother. 2010 Jun;44(6):1038-45. doi: 10.1345/aph.1M533. Epub 2010 May 18. [Article]
  3. Appiah-Opong R, Commandeur JN, van Vugt-Lussenburg B, Vermeulen NP: Inhibition of human recombinant cytochrome P450s by curcumin and curcumin decomposition products. Toxicology. 2007 Jun 3;235(1-2):83-91. doi: 10.1016/j.tox.2007.03.007. Epub 2007 Mar 15. [Article]
Details9. Sulfotransferase 1C4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic compounds. Can also sulfonate estrogenic compounds, however, the dietary flavonoids (phytoestrogen) and environmental estrogens, like bisphenol A are better substrates than 17beta-estradiol (E2) (PubMed:17425406, PubMed:26948952, PubMed:28222028, PubMed:9852044). Mediates the sulfation of doxorubicin and its analog epirubicin, two antitumor anthracyclines (PubMed:26948952)
Specific Function
aryl sulfotransferase activity
Gene Name
SULT1C4
Uniprot ID
O75897
Uniprot Name
Sulfotransferase 1C4
Molecular Weight
35519.635 Da
References
  1. Lu X, Jiang K, Han L, Zhang M, Zhou Y, Ma Y, Zhou Y, Meng S: Sulfonation of curcuminoids: characterization and contribution of individual SULT enzymes. Mol Nutr Food Res. 2015 Apr;59(4):634-45. doi: 10.1002/mnfr.201400493. Epub 2015 Feb 11. [Article]
Details10. Sulfotransferase 1A3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs
Specific Function
amine sulfotransferase activity
Gene Name
SULT1A3
Uniprot ID
P0DMM9
Uniprot Name
Sulfotransferase 1A3
Molecular Weight
34195.96 Da
References
  1. Lu X, Jiang K, Han L, Zhang M, Zhou Y, Ma Y, Zhou Y, Meng S: Sulfonation of curcuminoids: characterization and contribution of individual SULT enzymes. Mol Nutr Food Res. 2015 Apr;59(4):634-45. doi: 10.1002/mnfr.201400493. Epub 2015 Feb 11. [Article]
Details11. Sulfotransferase 1E1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone (PubMed:11006110, PubMed:11884392, PubMed:7779757). Is a key enzyme in estrogen homeostasis, the sulfation of estrogens leads to their inactivation. Also sulfates dehydroepiandrosterone (DHEA), pregnenolone, (24S)-hydroxycholesterol and xenobiotic compounds like ethinylestradiol, equalenin, diethyl stilbesterol and 1-naphthol at significantly lower efficiency (PubMed:11006110, PubMed:19589875). Does not sulfonate cortisol, testosterone and dopamine (PubMed:11006110, PubMed:7779757). May play a role in gut microbiota-host metabolic interaction. O-sulfonates 4-ethylphenol (4-EP), a dietary tyrosine-derived metabolite produced by gut bacteria. The product 4-EPS crosses the blood-brain barrier and may negatively regulate oligodendrocyte maturation and myelination, affecting the functional connectivity of different brain regions associated with the limbic system
Specific Function
aryl sulfotransferase activity
Gene Name
SULT1E1
Uniprot ID
P49888
Uniprot Name
Sulfotransferase 1E1
Molecular Weight
35126.185 Da
References
  1. Lu X, Jiang K, Han L, Zhang M, Zhou Y, Ma Y, Zhou Y, Meng S: Sulfonation of curcuminoids: characterization and contribution of individual SULT enzymes. Mol Nutr Food Res. 2015 Apr;59(4):634-45. doi: 10.1002/mnfr.201400493. Epub 2015 Feb 11. [Article]
Details12. Sulfotransferase 1B1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of dopamine, small phenols such as 1-naphthol and p-nitrophenol and thyroid hormones, including 3,3'-diiodothyronine, triidothyronine (T3) and reverse triiodothyronine (rT3) (PubMed:28084139, PubMed:9443824, PubMed:9463486). May play a role in gut microbiota-host metabolic interaction. O-sulfonates 4-ethylphenol (4-EP), a dietary tyrosine-derived metabolite produced by gut bacteria. The product 4-EPS crosses the blood-brain barrier and may negatively regulate oligodendrocyte maturation and myelination, affecting the functional connectivity of different brain regions associated with the limbic system (PubMed:35165440)
Specific Function
aryl sulfotransferase activity
Gene Name
SULT1B1
Uniprot ID
O43704
Uniprot Name
Sulfotransferase 1B1
Molecular Weight
34898.955 Da
References
  1. Lu X, Jiang K, Han L, Zhang M, Zhou Y, Ma Y, Zhou Y, Meng S: Sulfonation of curcuminoids: characterization and contribution of individual SULT enzymes. Mol Nutr Food Res. 2015 Apr;59(4):634-45. doi: 10.1002/mnfr.201400493. Epub 2015 Feb 11. [Article]

Transporters

Details1. ATP-dependent translocase ABCB1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
Specific Function
ABC-type xenobiotic transporter activity
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
ATP-dependent translocase ABCB1
Molecular Weight
141477.255 Da

Drug created at September 01, 2018 18:24 / Updated at May 14, 2021 01:07