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Identification
NameMenadione
Accession NumberDB00170  (NUTR00062)
TypeSmall Molecule
GroupsApproved, Nutraceutical
DescriptionA synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. [PubChem]
Structure
Thumb
Synonyms
2-Methyl-1,4-Naphthalenedione
2-Methyl-1,4-naphthochinon
2-Methyl-1,4-naphthoquinone
Menadione
Vitamin K3
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
SynkaviteNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Menadiol diphosphate
ThumbNot applicableDBSALT000878
Categories
UNII723JX6CXY5
CAS number58-27-5
WeightAverage: 172.18
Monoisotopic: 172.0524295
Chemical FormulaC11H8O2
InChI KeyMJVAVZPDRWSRRC-UHFFFAOYSA-N
InChI
InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
IUPAC Name
2-methyl-1,4-dihydronaphthalene-1,4-dione
SMILES
CC1=CC(=O)C2=CC=CC=C2C1=O
Pharmacology
IndicationThe primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.
Structured Indications Not Available
PharmacodynamicsMenadione (Vitamin K3) is a fat-soluble vitamin precursor that is converted into menaquinone in the liver. Vitamin K1 and K2 are the naturally occurring types of vitamin K. The former, which is also known as phylloquinone, is synthesized by plants and can be found in such foods as spinach, broccoli, lettuce, and soybeans. The latter, sometimes alternatively referred to as menaquinone, is primarily produced by bacteria in the anterior part of the gut and the intestines. Vitamin K3, on the other hand, is one of the many manmade versions of vitamin K. Also called menadione, this yellowish, synthetic crystalline substance is converted into the active form of the K2 vitamin inside of the animal body. While a vitamin K deficiency can be dangerous, especially to infants that may easily suffer from extensive hemorrhaging, an overdose can be as equally detrimental. Newborns that are administered too great a dosage of vitamin K3 can suffer from kernicterus, a form of severe brain damage that may produce decreased movement, loss of appetite, seizures, deafness, mental retardation, and even death. This condition is associated with an abnormally high concentration of bilirubin, a bile pigment, in the tissues of the brain, which can be caused by the presence of K3. For this reason, K3 is less often utilized medically than it was in former times.
Mechanism of actionMenadione (vitamin K3) is involved as a cofactor in the posttranslational gamma-carboxylation of glutamic acid residues of certain proteins in the body. These proteins include the vitamin K-dependent coagulation factors II (prothrombin), VII (proconvertin), IX (Christmas factor), X (Stuart factor), protein C, protein S, protein Zv and a growth-arrest-specific factor (Gas6). In contrast to the other vitamin K-dependent proteins in the blood coagulation cascade, protein C and protein S serve anticoagulant roles. The two vitamin K-dependent proteins found in bone are osteocalcin, also known as bone G1a (gamma-carboxyglutamate) protein or BGP, and the matrix G1a protein or MGP. Gamma-carboxylation is catalyzed by the vitamin K-dependent gamma-carboxylases. The reduced form of vitamin K, vitamin K hydroquinone, is the actual cofactor for the gamma-carboxylases. Proteins containing gamma-carboxyglutamate are called G1a proteins.
TargetKindPharmacological actionActionsOrganismUniProt ID
Vitamin K-dependent gamma-carboxylaseProteinyes
cofactor
HumanP38435 details
Vitamin K epoxide reductase complex subunit 1Proteinyes
cofactor
HumanQ9BQB6 details
Vitamin K epoxide reductase complex subunit 1-like protein 1Proteinyes
cofactor
HumanQ8N0U8 details
ProthrombinProteinunknown
activator
HumanP00734 details
Coagulation factor VIIProteinunknown
activator
HumanP08709 details
Coagulation factor IXProteinunknown
activator
HumanP00740 details
Coagulation factor XProteinunknown
activator
HumanP00742 details
Vitamin K-dependent protein CProteinunknown
activator
HumanP04070 details
Vitamin K-dependent protein SProteinunknown
activator
HumanP07225 details
Vitamin K-dependent protein ZProteinunknown
activator
HumanP22891 details
Ribosyldihydronicotinamide dehydrogenase [quinone]ProteinunknownNot AvailableHumanP16083 details
NAD(P)H dehydrogenase [quinone] 1ProteinunknownNot AvailableHumanP15559 details
OsteocalcinProteinunknown
agonist
HumanP02818 details
Related Articles
AbsorptionVariable and ranges from 10% to 80%
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityMenadione (vitamin K3), which is not used as a nutritional supplemental form of vitamin K for humans, has been reported to cause adverse reactions, including hemolytic anemia. Large doses have also been reported to cause brain damage.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Menadione can be increased when it is combined with Abiraterone.Approved
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Menadione resulting in a loss in efficacy.Approved
AzithromycinThe metabolism of Menadione can be decreased when combined with Azithromycin.Approved
BortezomibThe metabolism of Menadione can be decreased when combined with Bortezomib.Approved, Investigational
CaffeineThe metabolism of Menadione can be decreased when combined with Caffeine.Approved
CarbamazepineThe metabolism of Menadione can be increased when combined with Carbamazepine.Approved, Investigational
CitalopramThe metabolism of Menadione can be decreased when combined with Citalopram.Approved
ClotrimazoleThe metabolism of Menadione can be decreased when combined with Clotrimazole.Approved, Vet Approved
Cyproterone acetateThe serum concentration of Menadione can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DeferasiroxThe serum concentration of Menadione can be increased when it is combined with Deferasirox.Approved, Investigational
DisulfiramThe metabolism of Menadione can be decreased when combined with Disulfiram.Approved
Fibrinogen Concentrate (Human)The risk or severity of adverse effects can be increased when Menadione is combined with Fibrinogen Concentrate (Human).Approved
FluvoxamineThe metabolism of Menadione can be decreased when combined with Fluvoxamine.Approved, Investigational
IsoniazidThe metabolism of Menadione can be decreased when combined with Isoniazid.Approved
LidocaineThe metabolism of Menadione can be decreased when combined with Lidocaine.Approved, Vet Approved
MexiletineThe metabolism of Menadione can be decreased when combined with Mexiletine.Approved
NevirapineThe metabolism of Menadione can be decreased when combined with Nevirapine.Approved
NicotineThe metabolism of Menadione can be decreased when combined with Nicotine.Approved
OsimertinibThe serum concentration of Menadione can be decreased when it is combined with Osimertinib.Approved
Peginterferon alfa-2bThe serum concentration of Menadione can be increased when it is combined with Peginterferon alfa-2b.Approved
PhenobarbitalThe metabolism of Menadione can be increased when combined with Phenobarbital.Approved
PrimidoneThe metabolism of Menadione can be increased when combined with Primidone.Approved, Vet Approved
RifampicinThe metabolism of Menadione can be increased when combined with Rifampicin.Approved
RopiniroleThe metabolism of Menadione can be decreased when combined with Ropinirole.Approved, Investigational
SimeprevirThe metabolism of Menadione can be decreased when combined with Simeprevir.Approved
TenofovirThe metabolism of Menadione can be decreased when combined with Tenofovir.Approved, Investigational
TeriflunomideThe serum concentration of Menadione can be decreased when it is combined with Teriflunomide.Approved
TheophyllineThe metabolism of Menadione can be decreased when combined with Theophylline.Approved
TiclopidineThe metabolism of Menadione can be decreased when combined with Ticlopidine.Approved
TretinoinTretinoin may increase the thrombogenic activities of Menadione.Approved, Investigational, Nutraceutical
VemurafenibThe serum concentration of Menadione can be increased when it is combined with Vemurafenib.Approved
Food InteractionsNot Available
References
Synthesis Reference

Joachim U. Schneider, Hans Kiefer, “Menadione choline bisulfite adduct, its preparation and antihemorrhagic compositions.” U.S. Patent US4735969, issued January, 1980.

US4735969
General ReferencesNot Available
External Links
ATC CodesB02BA02
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (52.9 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8265
Caco-2 permeable+0.8641
P-glycoprotein substrateNon-substrate0.5245
P-glycoprotein inhibitor IInhibitor0.7375
P-glycoprotein inhibitor IINon-inhibitor0.8743
Renal organic cation transporterNon-inhibitor0.8027
CYP450 2C9 substrateNon-substrate0.7596
CYP450 2D6 substrateNon-substrate0.8924
CYP450 3A4 substrateNon-substrate0.5705
CYP450 1A2 substrateInhibitor0.934
CYP450 2C9 inhibitorInhibitor0.9165
CYP450 2D6 inhibitorInhibitor0.7999
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.7529
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8612
Ames testAMES toxic0.9108
CarcinogenicityNon-carcinogens0.9137
BiodegradationNot ready biodegradable0.7581
Rat acute toxicity2.7195 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.778
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Menadione powder5.59USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point107 °CPhysProp
water solubility160 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.20HANSCH,C ET AL. (1995)
logS-3.03ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.504 mg/mLALOGPS
logP1.91ALOGPS
logP1.89ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.94ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.54 m3·mol-1ChemAxon
Polarizability17.64 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.97 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-0gk9-3900000000-ad6c0e599173ba802f73View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0ufr-2910000000-bbd6cf78055e623046a6View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0ufr-2910000000-5db665917b8c152a80b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-074j-1900000000-a62dd17c23ac6e7fa95dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0aor-1900000000-ce35b89eaf766c9398e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-65a9c21d7aa7be21de3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0g4i-6900000000-0c6c7737ff416205089cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ea17be197704c13eba82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-2d0b65ea01fe9dd6b4feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-7900000000-509fb00927321d93a529View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-252f2831b39763f805b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-cea08e3f258cdd275a55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-6900000000-b84149529316a1f0987fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0gk9-5900000000-48fb5ac08ce624a689ccView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthoquinones
Direct ParentNaphthoquinones
Alternative Parents
Substituents
  • Naphthoquinone
  • Aryl ketone
  • Quinone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
cofactor
General Function:
Gamma-glutamyl carboxylase activity
Specific Function:
Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vitamin K to vitamin K epoxide.
Gene Name:
GGCX
Uniprot ID:
P38435
Molecular Weight:
87560.065 Da
References
  1. Wang Z, Wang M, Finn F, Carr BI: The growth inhibitory effects of vitamins K and their actions on gene expression. Hepatology. 1995 Sep;22(3):876-82. [PubMed:7657295 ]
  2. Stafford DW: The vitamin K cycle. J Thromb Haemost. 2005 Aug;3(8):1873-8. [PubMed:16102054 ]
  3. Presnell SR, Stafford DW: The vitamin K-dependent carboxylase. Thromb Haemost. 2002 Jun;87(6):937-46. [PubMed:12083499 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
cofactor
General Function:
Vitamin-k-epoxide reductase (warfarin-sensitive) activity
Specific Function:
Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K. Vitamin K is required for the gamma-carboxylation of various proteins, including clotting factors, and is required for normal blood coagulation, but also for normal bone development.
Gene Name:
VKORC1
Uniprot ID:
Q9BQB6
Molecular Weight:
18234.3 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Oldenburg J, Bevans CG, Muller CR, Watzka M: Vitamin K epoxide reductase complex subunit 1 (VKORC1): the key protein of the vitamin K cycle. Antioxid Redox Signal. 2006 Mar-Apr;8(3-4):347-53. [PubMed:16677080 ]
  4. Stafford DW: The vitamin K cycle. J Thromb Haemost. 2005 Aug;3(8):1873-8. [PubMed:16102054 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
cofactor
General Function:
Vitamin-k-epoxide reductase (warfarin-sensitive) activity
Specific Function:
Involved in vitamin K metabolism. Can reduce inactive vitamin K 2,3-epoxide to active vitamin K (in vitro), and may contribute to vitamin K-mediated protection against oxidative stress. Plays a role in vitamin K-dependent gamma-carboxylation of Glu residues in target proteins.
Gene Name:
VKORC1L1
Uniprot ID:
Q8N0U8
Molecular Weight:
19835.425 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Oldenburg J, Bevans CG, Muller CR, Watzka M: Vitamin K epoxide reductase complex subunit 1 (VKORC1): the key protein of the vitamin K cycle. Antioxid Redox Signal. 2006 Mar-Apr;8(3-4):347-53. [PubMed:16677080 ]
  4. Stafford DW: The vitamin K cycle. J Thromb Haemost. 2005 Aug;3(8):1873-8. [PubMed:16102054 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Thrombospondin receptor activity
Specific Function:
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostasis, inflammation and wound healing.
Gene Name:
F2
Uniprot ID:
P00734
Molecular Weight:
70036.295 Da
References
  1. Lee SK, Lee JY, Lee MY, Chung SM, Chung JH: Advantages of calcium green-1 over other fluorescent dyes in measuring cytosolic calcium in platelets. Anal Biochem. 1999 Sep 10;273(2):186-91. [PubMed:10469489 ]
  2. Casper HH, Alstad AD, Tacke DB, Johnson LJ, Lloyd WE: Evaluation of vitamin K3 feed additive for prevention of sweet clover disease. J Vet Diagn Invest. 1989 Apr;1(2):116-9. [PubMed:2484931 ]
  3. McCarthy DJ, Lindamood C 3rd, Gundberg CM, Hill DL: Retinoid-induced hemorrhaging and bone toxicity in rats fed diets deficient in vitamin K. Toxicol Appl Pharmacol. 1989 Feb;97(2):300-10. [PubMed:2922761 ]
  4. Szejtli J, Bolla-Pusztai E, Tardy-Lengyel M, Szabo P, Ferenczy T: Preparation, properties and biological activity of beta-cyclodextrin inclusion complex of menadione. Pharmazie. 1983 Mar;38(3):189-93. [PubMed:6867080 ]
  5. Wang Z, Wang M, Finn F, Carr BI: The growth inhibitory effects of vitamins K and their actions on gene expression. Hepatology. 1995 Sep;22(3):876-82. [PubMed:7657295 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Serine-type peptidase activity
Specific Function:
Initiates the extrinsic pathway of blood coagulation. Serine protease that circulates in the blood in a zymogen form. Factor VII is converted to factor VIIa by factor Xa, factor XIIa, factor IXa, or thrombin by minor proteolysis. In the presence of tissue factor and calcium ions, factor VIIa then converts factor X to factor Xa by limited proteolysis. Factor VIIa will also convert factor IX to f...
Gene Name:
F7
Uniprot ID:
P08709
Molecular Weight:
51593.465 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Serine-type endopeptidase activity
Specific Function:
Factor IX is a vitamin K-dependent plasma protein that participates in the intrinsic pathway of blood coagulation by converting factor X to its active form in the presence of Ca(2+) ions, phospholipids, and factor VIIIa.
Gene Name:
F9
Uniprot ID:
P00740
Molecular Weight:
51778.11 Da
References
  1. Berkessel A, Guixa M, Schmidt F, Neudorfl JM, Lex J: Highly enantioselective epoxidation of 2-methylnaphthoquinone (vitamin K3) mediated by new cinchona alkaloid phase-transfer catalysts. Chemistry. 2007;13(16):4483-98. [PubMed:17348045 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Serine-type endopeptidase activity
Specific Function:
Factor Xa is a vitamin K-dependent glycoprotein that converts prothrombin to thrombin in the presence of factor Va, calcium and phospholipid during blood clotting.
Gene Name:
F10
Uniprot ID:
P00742
Molecular Weight:
54731.255 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Serine-type endopeptidase activity
Specific Function:
Protein C is a vitamin K-dependent serine protease that regulates blood coagulation by inactivating factors Va and VIIIa in the presence of calcium ions and phospholipids (PubMed:25618265). Exerts a protective effect on the endothelial cell barrier function (PubMed:25651845).
Gene Name:
PROC
Uniprot ID:
P04070
Molecular Weight:
52070.82 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Milgrom E, Diab H, Middleton F, Kane PM: Loss of vacuolar proton-translocating ATPase activity in yeast results in chronic oxidative stress. J Biol Chem. 2007 Mar 9;282(10):7125-36. Epub 2007 Jan 10. [PubMed:17215245 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Endopeptidase inhibitor activity
Specific Function:
Anticoagulant plasma protein; it is a cofactor to activated protein C in the degradation of coagulation factors Va and VIIIa. It helps to prevent coagulation and stimulating fibrinolysis.
Gene Name:
PROS1
Uniprot ID:
P07225
Molecular Weight:
75121.905 Da
References
  1. Chai YC, Hendrich S, Thomas JA: Protein S-thiolation in hepatocytes stimulated by t-butyl hydroperoxide, menadione, and neutrophils. Arch Biochem Biophys. 1994 Apr;310(1):264-72. [PubMed:8161215 ]
  2. Mallis RJ, Hamann MJ, Zhao W, Zhang T, Hendrich S, Thomas JA: Irreversible thiol oxidation in carbonic anhydrase III: protection by S-glutathiolation and detection in aging rats. Biol Chem. 2002 Mar-Apr;383(3-4):649-62. [PubMed:12033454 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
activator
General Function:
Serine-type endopeptidase activity
Specific Function:
Appears to assist hemostasis by binding thrombin and promoting its association with phospholipid vesicles. Inhibits activity of the coagulation protease factor Xa in the presence of SERPINA10, calcium and phospholipids.
Gene Name:
PROZ
Uniprot ID:
P22891
Molecular Weight:
44743.605 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Nadph dehydrogenase (quinone) activity
Specific Function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO2
Uniprot ID:
P16083
Molecular Weight:
25918.4 Da
References
  1. Long DJ 2nd, Iskander K, Gaikwad A, Arin M, Roop DR, Knox R, Barrios R, Jaiswal AK: Disruption of dihydronicotinamide riboside:quinone oxidoreductase 2 (NQO2) leads to myeloid hyperplasia of bone marrow and decreased sensitivity to menadione toxicity. J Biol Chem. 2002 Nov 29;277(48):46131-9. Epub 2002 Sep 25. [PubMed:12351651 ]
  2. Kwiek JJ, Haystead TA, Rudolph J: Kinetic mechanism of quinone oxidoreductase 2 and its inhibition by the antimalarial quinolines. Biochemistry. 2004 Apr 20;43(15):4538-47. [PubMed:15078100 ]
  3. Foster CE, Bianchet MA, Talalay P, Zhao Q, Amzel LM: Crystal structure of human quinone reductase type 2, a metalloflavoprotein. Biochemistry. 1999 Aug 3;38(31):9881-6. [PubMed:10433694 ]
  4. Celli CM, Tran N, Knox R, Jaiswal AK: NRH:quinone oxidoreductase 2 (NQO2) catalyzes metabolic activation of quinones and anti-tumor drugs. Biochem Pharmacol. 2006 Jul 28;72(3):366-76. Epub 2006 May 4. [PubMed:16765324 ]
  5. Boutin JA, Chatelain-Egger F, Vella F, Delagrange P, Ferry G: Quinone reductase 2 substrate specificity and inhibition pharmacology. Chem Biol Interact. 2005 Feb 10;151(3):213-28. [PubMed:15733542 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Superoxide dismutase activity
Specific Function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO1
Uniprot ID:
P15559
Molecular Weight:
30867.405 Da
References
  1. Munday R, Smith BL, Munday CM: Effect of butylated hydroxyanisole on the toxicity of 2-hydroxy-1,4-naphthoquinone to rats. Chem Biol Interact. 1999 Feb 12;117(3):241-56. [PubMed:10190578 ]
  2. Chiou TJ, Wang YT, Tzeng WF: DT-diaphorase protects against menadione-induced oxidative stress. Toxicology. 1999 Nov 29;139(1-2):103-10. [PubMed:10614691 ]
  3. Munday R, Smith BL, Munday CM: Effect of inducers of DT-diaphorase on the toxicity of 2-methyl- and 2-hydroxy-1,4-naphthoquinone to rats. Chem Biol Interact. 1999 Dec 15;123(3):219-37. [PubMed:10654840 ]
  4. Ip SP, Yiu HY, Ko KM: Schisandrin B protects against menadione-induced hepatotoxicity by enhancing DT-diaphorase activity. Mol Cell Biochem. 2000 May;208(1-2):151-5. [PubMed:10939639 ]
  5. Kishi T, Takahashi T, Mizobuchi S, Mori K, Okamoto T: Effect of dicumarol, a Nad(P)h: quinone acceptor oxidoreductase 1 (DT-diaphorase) inhibitor on ubiquinone redox cycling in cultured rat hepatocytes. Free Radic Res. 2002 Apr;36(4):413-9. [PubMed:12069105 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Structural molecule activity
Specific Function:
Constitutes 1-2% of the total bone protein. It binds strongly to apatite and calcium.
Gene Name:
BGLAP
Uniprot ID:
P02818
Molecular Weight:
10962.445 Da
References
  1. Price PA: Role of vitamin-K-dependent proteins in bone metabolism. Annu Rev Nutr. 1988;8:565-83. [PubMed:3060178 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xanthine oxidase activity
Specific Function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular Weight:
146422.99 Da
References
  1. Yee SB, Pritsos CA: Comparison of oxygen radical generation from the reductive activation of doxorubicin, streptonigrin, and menadione by xanthine oxidase and xanthine dehydrogenase. Arch Biochem Biophys. 1997 Nov 15;347(2):235-41. [PubMed:9367530 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xanthine dehydrogenase activity
Specific Function:
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide and N-methylphthalazinium, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Participates in the bioactivation of prodrugs such as famciclovir, catalyz...
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular Weight:
147916.735 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein complex binding
Specific Function:
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name:
MTHFR
Uniprot ID:
P42898
Molecular Weight:
74595.895 Da
References
  1. Vanoni MA, Ballou DP, Matthews RG: Methylenetetrahydrofolate reductase. Steady state and rapid reaction studies on the NADPH-methylenetetrahydrofolate, NADPH-menadione, and methyltetrahydrofolate-menadione oxidoreductase activities of the enzyme. J Biol Chem. 1983 Oct 10;258(19):11510-4. [PubMed:6352699 ]
  2. Clark JE, Ljungdahl LG: Purification and properties of 5,10-methylenetetrahydrofolate reductase, an iron-sulfur flavoprotein from Clostridium formicoaceticum. J Biol Chem. 1984 Sep 10;259(17):10845-9. [PubMed:6381490 ]
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 or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinducer
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinducer
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular Weight:
56501.005 Da
References
  1. 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23