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Identification
NameApixaban
Accession NumberDB06605  (DB07828)
TypeSmall Molecule
GroupsApproved
Description

Apixaban is an oral, direct, and highly selective factor Xa (FXa) inhibitor (of both free and prothrombinase-bound FXa independently of antithrombin III) for the prevention and treatment of thromboembolic diseases. It is marketed under the name Eliquis. FDA approved on December 28, 2012.

Structure
Thumb
Synonyms
Apixabanum
BMS 562247-01
BMS-562247
BMS-562247-01
Eliquis
External Identifiers
  • BMS-562247
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Eliquistablet, film coated2.5 mg/1oralE.R. Squibb & Sons, L.L.C.2012-12-28Not applicableUs
Eliquistablet5.0 mgoralBristol Myers Squibb Canada2012-12-21Not applicableCanada
Eliquistablet2.5 mgoralBristol Myers Squibb Canada2012-02-01Not applicableCanada
Eliquistablet, film coated2.5 mg/1oralCardinal Health2012-12-28Not applicableUs
Eliquistablet, film coated5 mg/1oralE.R. Squibb & Sons, L.L.C.2012-12-28Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII3Z9Y7UWC1J
CAS number503612-47-3
WeightAverage: 459.4971
Monoisotopic: 459.190654313
Chemical FormulaC25H25N5O4
InChI KeyInChIKey=QNZCBYKSOIHPEH-UHFFFAOYSA-N
InChI
InChI=1S/C25H25N5O4/c1-34-19-11-9-18(10-12-19)30-23-20(22(27-30)24(26)32)13-15-29(25(23)33)17-7-5-16(6-8-17)28-14-3-2-4-21(28)31/h5-12H,2-4,13-15H2,1H3,(H2,26,32)
IUPAC Name
1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-1H,4H,5H,6H,7H-pyrazolo[3,4-c]pyridine-3-carboxamide
SMILES
COC1=CC=C(C=C1)N1N=C(C(N)=O)C2=C1C(=O)N(CC2)C1=CC=C(C=C1)N1CCCCC1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPhenylpiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • Phenylpyrazole
  • Methoxyaniline
  • Pyridinecarboxamide
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Piperidinone
  • Delta-lactam
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Pyrazole
  • Azole
  • Tertiary amine
  • Primary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationApixaban is to reduce the risk of stroke and systemic embolism in patients with nonvalvular atrial fibrillation. It has also been used to lower the risk of developing venous thrombosis post-orthopedic surgical procedures.
PharmacodynamicsApixaban acts by inhibiting coagulation, and thus prevents development of blood clots. As a result of FXa inhibition, apixaban prolongs clotting tests such as prothrombin time (PT), INR, and activated partial thromboplastin time (aPTT). Changes observed in these clotting tests at the expected therapeutic dose, however, are small, subject to a high degree of variability, and not useful in monitoring the anticoagulation effect of apixaban. The Rotachrom® Heparin chromogenic assay is not recommended for assessing the anticoagulant effect of apixaban.
Mechanism of actionApixaban acts by directly inhibiting, in a reversible manner, free and clot-bound factor Xa to inhibit coagulation.
Related Articles
AbsorptionApixaban is absorbed in the stomach and small intestine. For doses up to 10 mg, the absolute bioavailability is about 50%. For oral administration, absorption is not affected by the presence of food, and it takes about 3-4 hours to achieve maximum plasma concentrations. For large oral doses equal or greater than 25 mg, absorption is dissolution limited and bioavailability is decreased. Most of the absorption occurs in the distal small intestine and the ascending colon.
Volume of distribution

The steady state volume of distribution is 21 L.

Protein bindingApixaban is about 87% plasma protein bound.
Metabolism

Apixaban mainly undergoes o-demethylation and hydroxylation to metabolites. The major site of biotransformation is at the 3-oxopiperidinyl moiety. The main enzyme responsible for metabolism is CYP3A4/5 while CYP1A2, 2C8, 2C9, 2C19, and 2J2 are minor metabolic enzymes. There are no active metabolites and unchanged apixaban is the primary circulating entity.

Route of elimination25% of the administered dose is eliminated in the feces and urine. For elimination in the feces, it is excreted by the intestine and bile to the feces.
Half lifeIf administered orally, the half life is 12 hours (due to prolonged absorption). If administerd by I.V., the half-life is about 5 hours.
Clearance

About 27% of total apixaban is renally cleared.

ToxicityMajor bleeding events.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9974
Blood Brain Barrier+0.9329
Caco-2 permeable-0.5308
P-glycoprotein substrateSubstrate0.6144
P-glycoprotein inhibitor IInhibitor0.6804
P-glycoprotein inhibitor IIInhibitor0.594
Renal organic cation transporterNon-inhibitor0.5628
CYP450 2C9 substrateNon-substrate0.8528
CYP450 2D6 substrateNon-substrate0.811
CYP450 3A4 substrateSubstrate0.764
CYP450 1A2 substrateNon-inhibitor0.9271
CYP450 2C9 inhibitorInhibitor0.5555
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorInhibitor0.5
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6447
Ames testNon AMES toxic0.5062
CarcinogenicityNon-carcinogens0.8796
BiodegradationNot ready biodegradable0.9965
Rat acute toxicity2.3038 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8351
hERG inhibition (predictor II)Inhibitor0.6205
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tabletoral2.5 mg
Tabletoral5.0 mg
Tablet, film coatedoral2.5 mg/1
Tablet, film coatedoral5 mg/1
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2349330 No2009-09-292019-12-17Canada
CA2461202 No2011-07-122022-09-17Canada
US6413980 No1999-12-222019-12-22Us
US6967208 No2003-02-032023-02-03Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityAqueous solubility: 40-50 μg/ml in 0.9% saline solutionNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0679 mg/mLALOGPS
logP2.22ALOGPS
logP1.83ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)13.12ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area110.76 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.9 m3·mol-1ChemAxon
Polarizability49.62 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. Granger CB, Alexander JH, McMurray JJ, Lopes RD, Hylek EM, Hanna M, Al-Khalidi HR, Ansell J, Atar D, Avezum A, Bahit MC, Diaz R, Easton JD, Ezekowitz JA, Flaker G, Garcia D, Geraldes M, Gersh BJ, Golitsyn S, Goto S, Hermosillo AG, Hohnloser SH, Horowitz J, Mohan P, Jansky P, Lewis BS, Lopez-Sendon JL, Pais P, Parkhomenko A, Verheugt FW, Zhu J, Wallentin L: Apixaban versus warfarin in patients with atrial fibrillation. N Engl J Med. 2011 Sep 15;365(11):981-92. doi: 10.1056/NEJMoa1107039. Epub 2011 Aug 27. [PubMed:21870978 ]
  2. de Souza Brito F, Lopes RD, Alexander JH: The safety and efficacy of apixaban : where do we stand in 2013? Expert Opin Drug Saf. 2013 Jul;12(4):559-67. doi: 10.1517/14740338.2013.799663. Epub 2013 May 10. [PubMed:23662974 ]
External Links
ATC CodesB01AF02
AHFS Codes
  • 20:12.04.14
PDB EntriesNot Available
FDA labelDownload (655 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Apixaban.
AcenocoumarolApixaban may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Apixaban.
AlteplaseAlteplase may increase the anticoagulant activities of Apixaban.
AnagrelideThe risk or severity of adverse effects can be increased when Anagrelide is combined with Apixaban.
AnistreplaseAnistreplase may increase the anticoagulant activities of Apixaban.
AprepitantThe serum concentration of Apixaban can be increased when it is combined with Aprepitant.
ArgatrobanApixaban may increase the anticoagulant activities of Argatroban.
AtazanavirThe serum concentration of Apixaban can be increased when it is combined with Atazanavir.
BexaroteneThe serum concentration of Apixaban can be decreased when it is combined with Bexarotene.
BivalirudinApixaban may increase the anticoagulant activities of Bivalirudin.
BoceprevirThe serum concentration of Apixaban can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Apixaban can be decreased when it is combined with Bosentan.
CangrelorThe risk or severity of adverse effects can be increased when Cangrelor is combined with Apixaban.
CarbamazepineThe serum concentration of Apixaban can be decreased when it is combined with Carbamazepine.
CeritinibThe serum concentration of Apixaban can be increased when it is combined with Ceritinib.
ChlorotrianiseneChlorotrianisene may decrease the anticoagulant activities of Apixaban.
CilostazolThe risk or severity of adverse effects can be increased when Cilostazol is combined with Apixaban.
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Apixaban.
Citric AcidApixaban may increase the anticoagulant activities of Citric Acid.
ClarithromycinThe serum concentration of Apixaban can be increased when it is combined with Clarithromycin.
ClopidogrelThe risk or severity of adverse effects can be increased when Clopidogrel is combined with Apixaban.
CobicistatThe serum concentration of Apixaban can be increased when it is combined with Cobicistat.
CollagenaseThe risk or severity of adverse effects can be increased when Apixaban is combined with Collagenase.
ConivaptanThe serum concentration of Apixaban can be increased when it is combined with Conivaptan.
CrizotinibThe serum concentration of Apixaban can be increased when it is combined with Crizotinib.
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Apixaban.
DabrafenibThe serum concentration of Apixaban can be decreased when it is combined with Dabrafenib.
DalteparinApixaban may increase the anticoagulant activities of Dalteparin.
DanaparoidApixaban may increase the anticoagulant activities of Danaparoid.
DarunavirThe serum concentration of Apixaban can be increased when it is combined with Darunavir.
DasatinibDasatinib may increase the anticoagulant activities of Apixaban.
DeferasiroxThe serum concentration of Apixaban can be decreased when it is combined with Deferasirox.
DelavirdineThe serum concentration of Apixaban can be increased when it is combined with Delavirdine.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Apixaban is combined with Deoxycholic Acid.
DesirudinApixaban may increase the anticoagulant activities of Desirudin.
DesogestrelThe therapeutic efficacy of Apixaban can be decreased when used in combination with Desogestrel.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Apixaban.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Apixaban.
DicoumarolApixaban may increase the anticoagulant activities of Dicoumarol.
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Apixaban.
DiltiazemThe serum concentration of Apixaban can be increased when it is combined with Diltiazem.
DipyridamoleThe risk or severity of adverse effects can be increased when Dipyridamole is combined with Apixaban.
DronedaroneThe serum concentration of Apixaban can be increased when it is combined with Dronedarone.
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Apixaban.
DydrogesteroneThe therapeutic efficacy of Apixaban can be decreased when used in combination with Dydrogesterone.
Edetic AcidApixaban may increase the anticoagulant activities of Edetic Acid.
EdoxabanEdoxaban may increase the anticoagulant activities of Apixaban.
EnoxaparinApixaban may increase the anticoagulant activities of Enoxaparin.
EnzalutamideThe serum concentration of Apixaban can be decreased when it is combined with Enzalutamide.
EptifibatideThe risk or severity of adverse effects can be increased when Eptifibatide is combined with Apixaban.
ErythromycinThe serum concentration of Apixaban can be increased when it is combined with Erythromycin.
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Apixaban.
Ethyl biscoumacetateApixaban may increase the anticoagulant activities of Ethyl biscoumacetate.
EtodolacThe risk or severity of adverse effects can be increased when Etodolac is combined with Apixaban.
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Apixaban.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Apixaban.
FluconazoleThe serum concentration of Apixaban can be increased when it is combined with Fluconazole.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Apixaban.
FlurbiprofenThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Apixaban.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Apixaban.
Fondaparinux sodiumApixaban may increase the anticoagulant activities of Fondaparinux sodium.
FosamprenavirThe serum concentration of Apixaban can be increased when it is combined with Fosamprenavir.
FosphenytoinThe serum concentration of Apixaban can be decreased when it is combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Apixaban can be increased when it is combined with Fusidic Acid.
GestodeneThe therapeutic efficacy of Apixaban can be decreased when used in combination with Gestodene.
HeparinApixaban may increase the anticoagulant activities of Heparin.
HomoharringtonineThe risk or severity of adverse effects can be increased when Apixaban is combined with Homoharringtonine.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Apixaban is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Apixaban.
IbuprofenThe risk or severity of adverse effects can be increased when Ibuprofen is combined with Apixaban.
IdelalisibThe serum concentration of Apixaban can be increased when it is combined with Idelalisib.
ImatinibThe serum concentration of Apixaban can be increased when it is combined with Imatinib.
IndinavirThe serum concentration of Apixaban can be increased when it is combined with Indinavir.
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Apixaban.
InfliximabInfliximab may increase the anticoagulant activities of Apixaban.
IsavuconazoniumThe serum concentration of Apixaban can be increased when it is combined with Isavuconazonium.
ItraconazoleThe serum concentration of Apixaban can be increased when it is combined with Itraconazole.
KetoconazoleThe serum concentration of Apixaban can be increased when it is combined with Ketoconazole.
KetoprofenThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Apixaban.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Apixaban.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Apixaban.
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Apixaban.
Mefenamic acidThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Apixaban.
MeloxicamThe risk or severity of adverse effects can be increased when Meloxicam is combined with Apixaban.
MifepristoneThe serum concentration of Apixaban can be increased when it is combined with Mifepristone.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Apixaban.
MitotaneThe serum concentration of Apixaban can be decreased when it is combined with Mitotane.
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with Apixaban.
NadroparinApixaban may increase the anticoagulant activities of Nadroparin.
NaproxenThe risk or severity of adverse effects can be increased when Naproxen is combined with Apixaban.
NefazodoneThe serum concentration of Apixaban can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Apixaban can be increased when it is combined with Nelfinavir.
NilotinibThe serum concentration of Apixaban can be increased when it is combined with Nilotinib.
NintedanibThe risk or severity of adverse effects can be increased when Apixaban is combined with Nintedanib.
ObinutuzumabThe risk or severity of adverse effects can be increased when Apixaban is combined with Obinutuzumab.
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Apixaban.
OxaprozinThe risk or severity of adverse effects can be increased when Oxaprozin is combined with Apixaban.
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Apixaban.
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Apixaban.
PhenindioneApixaban may increase the anticoagulant activities of Phenindione.
PhenobarbitalThe serum concentration of Apixaban can be decreased when it is combined with Phenobarbital.
PhenprocoumonApixaban may increase the anticoagulant activities of Phenprocoumon.
PhenytoinThe serum concentration of Apixaban can be decreased when it is combined with Phenytoin.
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Apixaban.
PosaconazoleThe serum concentration of Apixaban can be increased when it is combined with Posaconazole.
PrasugrelThe risk or severity of adverse effects can be increased when Prasugrel is combined with Apixaban.
PrimidoneThe serum concentration of Apixaban can be decreased when it is combined with Primidone.
ProgesteroneThe therapeutic efficacy of Apixaban can be decreased when used in combination with Progesterone.
ReteplaseReteplase may increase the anticoagulant activities of Apixaban.
RidogrelRidogrel may increase the anticoagulant activities of Apixaban.
RifabutinThe serum concentration of Apixaban can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Apixaban can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Apixaban can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of Apixaban can be increased when it is combined with Ritonavir.
RivaroxabanApixaban may increase the anticoagulant activities of Rivaroxaban.
SaquinavirThe serum concentration of Apixaban can be increased when it is combined with Saquinavir.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Apixaban.
SiltuximabThe serum concentration of Apixaban can be decreased when it is combined with Siltuximab.
St. John's WortThe serum concentration of Apixaban can be decreased when it is combined with St. John's Wort.
StreptokinaseStreptokinase may increase the anticoagulant activities of Apixaban.
SugammadexSugammadex may increase the anticoagulant activities of Apixaban.
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Apixaban.
SulodexideApixaban may increase the anticoagulant activities of Sulodexide.
TelaprevirThe serum concentration of Apixaban can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Apixaban can be increased when it is combined with Telithromycin.
TenecteplaseTenecteplase may increase the anticoagulant activities of Apixaban.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Apixaban.
TiboloneTibolone may increase the anticoagulant activities of Apixaban.
TicagrelorThe risk or severity of adverse effects can be increased when Ticagrelor is combined with Apixaban.
TiclopidineThe risk or severity of adverse effects can be increased when Ticlopidine is combined with Apixaban.
TinzaparinApixaban may increase the anticoagulant activities of Tinzaparin.
TipranavirTipranavir may increase the anticoagulant activities of Apixaban.
TirofibanThe risk or severity of adverse effects can be increased when Tirofiban is combined with Apixaban.
TocilizumabThe serum concentration of Apixaban can be decreased when it is combined with Tocilizumab.
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Apixaban.
TositumomabThe risk or severity of adverse effects can be increased when Apixaban is combined with Tositumomab.
TreprostinilApixaban may increase the anticoagulant activities of Treprostinil.
UrokinaseUrokinase may increase the anticoagulant activities of Apixaban.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Apixaban.
VerapamilThe serum concentration of Apixaban can be increased when it is combined with Verapamil.
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Apixaban.
Vitamin EVitamin E may increase the anticoagulant activities of Apixaban.
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Apixaban.
VoriconazoleThe serum concentration of Apixaban can be increased when it is combined with Voriconazole.
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Apixaban.
WarfarinApixaban may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Alfalfa, Anise, Bilberry may increase the adverse effects of apixaban.
  • Grapefruit juice may increase apixaban serum concentration.
  • St. John's wort will likely decrease apixaban serum concentration. Avoid combination if possible.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
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. Spyropoulos AC: Investigational treatments of venous thromboembolism. Expert Opin Investig Drugs. 2007 Apr;16(4):431-40. [PubMed:17371192 ]
  2. Harenberg J, Wehling M: Current and future prospects for anticoagulant therapy: inhibitors of factor Xa and factor IIa. Semin Thromb Hemost. 2008 Feb;34(1):39-57. doi: 10.1055/s-2008-1066023. [PubMed:18393142 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
no
Actions
substrate
General Function:
Vitamin d3 25-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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Wang L, Zhang D, Raghavan N, Yao M, Ma L, Frost CE, Maxwell BD, Chen SY, He K, Goosen TC, Humphreys WG, Grossman SJ: In vitro assessment of metabolic drug-drug interaction potential of apixaban through cytochrome P450 phenotyping, inhibition, and induction studies. Drug Metab Dispos. 2010 Mar;38(3):448-58. doi: 10.1124/dmd.109.029694. Epub 2009 Nov 25. [PubMed:19940026 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:
CYP2J2
Uniprot ID:
P51589
Molecular Weight:
57610.165 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. de Souza Brito F, Lopes RD, Alexander JH: The safety and efficacy of apixaban : where do we stand in 2013? Expert Opin Drug Saf. 2013 Jul;12(4):559-67. doi: 10.1517/14740338.2013.799663. Epub 2013 May 10. [PubMed:23662974 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular Weight:
72313.47 Da
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Drug created on March 19, 2008 10:40 / Updated on July 28, 2016 01:52