Identification

Name
Apixaban
Accession Number
DB06605  (DB07828)
Type
Small Molecule
Groups
Approved
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
  • apixabán
  • apixabanum
External IDs
BMS 562247-01 / BMS-562247 / BMS-562247-01
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EliquisTablet, film coated2.5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
EliquisTablet, film coated2.5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
EliquisTablet, film coated5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
EliquisTablet2.5 mgOralBristol Myers Squibb2012-02-01Not applicableCanada
EliquisTablet, film coated5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
EliquisTablet, film coated5 mg/1Oralbryant ranch prepack2012-12-28Not applicableUs
EliquisTablet, film coated5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
EliquisTablet, film coated2.5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
EliquisTablet, film coated5 mg/1OralA-S Medication Solutions2012-12-28Not applicableUs50090 143720180907 15195 1xwl117
EliquisTablet, film coated2.5 mgOralBristol Myers Squibb / Pfizer Eeig2011-05-18Not applicableEu
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ELIQUIS 30-Day Starter PackApixaban (5 mg/1) + Apixaban (5 mg/1)KitE.R. Squibb & Sons, L.L.C.2017-11-29Not applicableUs
ELIQUIS 30-Day Starter PackApixaban (5 mg/1) + Apixaban (5 mg/1)KitE.R. Squibb & Sons, L.L.C.2017-11-29Not applicableUs
Categories
UNII
3Z9Y7UWC1J
CAS number
503612-47-3
Weight
Average: 459.4971
Monoisotopic: 459.190654313
Chemical Formula
C25H25N5O4
InChI Key
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

Pharmacology

Indication

Apixaban 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.

Associated Conditions
Pharmacodynamics

Apixaban 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 action

Apixaban acts by directly inhibiting, in a reversible manner, free and clot-bound factor Xa to inhibit coagulation.

TargetActionsOrganism
ACoagulation factor X
inhibitor
Human
Absorption

Apixaban 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 binding

Apixaban 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 elimination

25% 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 life

If 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.

Toxicity

Major bleeding events.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(1,2,6,7-3H)TestosteroneThe therapeutic efficacy of Apixaban can be increased when used in combination with (1,2,6,7-3H)Testosterone.
(R)-warfarinApixaban may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinApixaban may increase the anticoagulant activities of (S)-Warfarin.
1-TestosteroneThe therapeutic efficacy of Apixaban can be increased when used in combination with 1-Testosterone.
18-methyl-19-nortestosteroneThe therapeutic efficacy of Apixaban can be increased when used in combination with 18-methyl-19-nortestosterone.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Apixaban.
4-hydroxycoumarinApixaban may increase the anticoagulant activities of 4-hydroxycoumarin.
4-HydroxytestosteroneThe therapeutic efficacy of Apixaban can be increased when used in combination with 4-Hydroxytestosterone.
5-androstenedioneThe metabolism of Apixaban can be decreased when combined with 5-androstenedione.
5beta-dihydrotestosteroneThe therapeutic efficacy of Apixaban can be increased when used in combination with 5beta-dihydrotestosterone.
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.

References

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
KEGG Drug
D03213
PubChem Compound
10182969
PubChem Substance
175427077
ChemSpider
8358471
BindingDB
19023
ChEBI
72296
ChEMBL
CHEMBL231779
PharmGKB
PA166163740
HET
GG2
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Apixaban
ATC Codes
B01AF02 — Apixaban
AHFS Codes
  • 20:12.04.14 — Direct Factor Xa Inhibitors
PDB Entries
2p16
FDA label
Download (655 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableEnd Stage Renal Disease (ESRD)1
1CompletedNot AvailableThrombotic events1
1CompletedBasic ScienceAnticoagulation1
1CompletedBasic ScienceHealthy Volunteers3
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics / Venous Thromboembolism (VTE)1
1CompletedBasic ScienceN/A - Healthy Subjects2
1CompletedBasic ScienceVenous Thromboembolism (VTE)1
1CompletedBasic ScienceThrombotic events1
1CompletedTreatmentAcute Coronary Syndromes (ACS) / Nonvalvular Atrial Fibrillation1
1CompletedTreatmentHaemorrhage1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentThrombotic events1
1RecruitingOtherGlomerulonephritis minimal lesion / Proteinuria1
1RecruitingOtherThromboembolism1
1RecruitingTreatmentCombination of Oral Anticoagulation Therapy and Sildenafil / Intermediate-high Risk / Pulmonary Embolism (PE)1
1TerminatedOtherVenous Thromboembolism (VTE)1
2Active Not RecruitingPreventionKnee Arthroplasty, Total1
2Active Not RecruitingPreventionVTE Prophylaxis With Anticoagulation After Total Knee Replacement Surgery1
2CompletedPreventionAcute Coronary Syndromes (ACS)1
2CompletedPreventionMalignancies / Pulmonary Embolism (PE) / Thrombotic events1
2CompletedTreatmentAnticoagulant Toxicity / ESRD1
2CompletedTreatmentDeep Vein Thrombosis (DVT)1
2CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentNonvalvular Atrial Fibrillation1
2Not Yet RecruitingTreatmentCardiac surgery, heparin-induced thrombocytopenia and thrombosis syndrome / Heparin-induced Thrombocytopenia and Thrombosis1
2RecruitingPreventionAnti-Xa Activity1
2RecruitingPreventionGynecologic Cancers / Venous Thromboembolism (VTE)1
2RecruitingPreventionMalignancies / Venous Thromboembolism (VTE)1
2RecruitingPreventionSpinal Cord Injuries (SCI) / Venous Thromboembolism (VTE)1
2RecruitingTreatmentHaemorrhage1
2RecruitingTreatmentIntracerebral Hemorrhage / Nonvalvular Atrial Fibrillation1
2RecruitingTreatmentThrombotic events1
2TerminatedTreatmentAcute Coronary Syndromes (ACS)1
2WithdrawnNot AvailableNonvalvular Atrial Fibrillation1
2WithdrawnBasic ScienceNonvalvular Atrial Fibrillation1
2WithdrawnPreventionCardiac Implantable Electronic Device / Patent Foramen Ovale (PFO)1
2, 3CompletedPreventionPulmonary Embolism (PE) / Thrombosis, Venous1
2, 3RecruitingPreventionCoronary Artery Bypass Graft Surgery Patients / Deep Venous Thrombosis / Postoperative Atrial Fibrilation / Strokes / Systemic Embolism1
2, 3RecruitingTreatmentMenstruation / Venous Thromboembolism (VTE)1
2, 3Unknown StatusTreatmentStroke, Ischemic / Transient Ischaemic Attack (TIA)1
3Active Not RecruitingSupportive CareCerebral Vein Thrombosis / Deep Vein Thrombosis (DVT) / Gonadal Thrombosis / Hepatic Thrombosis / Mesenteric Thrombosis / Metastatic Malignant Neoplasm / Neoplasms, Malignant / Portal Vein Thrombosis / Pulmonary Embolism (PE) / Renal Vein Thrombosis / Splenic thrombosis / Venous Thromboembolism (VTE)1
3CompletedPreventionAtrial Flutter / Nonvalvular Atrial Fibrillation1
3CompletedPreventionDeep Vein Thrombosis (DVT) / Pulmonary Embolism (PE)2
3CompletedPreventionNonvalvular Atrial Fibrillation1
3CompletedPreventionPulmonary Embolism (PE) / Thrombosis, Venous1
3CompletedPreventionReduction in Hospitalizations / Sickle Cell Disorders / Vaso-Occlusive Crises1
3CompletedTreatmentDeep Vein Thrombosis (DVT) / Pulmonary Embolism (PE)2
3CompletedTreatmentHematoma1
3CompletedTreatmentThrombosis, Venous2
3Not Yet RecruitingPreventionIntracerebral Hemorrhage / Microhaemorrhage / Nonvalvular Atrial Fibrillation1
3Not Yet RecruitingTreatmentAcute Myocardial Infarction (AMI) / Anticoagulants and Bleeding Disorders / Left Ventricular Thrombosis1
3Not Yet RecruitingTreatmentCancer-associated Thrombosis1
3Not Yet RecruitingTreatmentEnd-Stage Kidney Disease / Nonvalvular Atrial Fibrillation1
3Not Yet RecruitingTreatmentVenous Thromboembolism (VTE)1
3RecruitingPreventionAcute Lymphoblastic Leukaemias (ALL) / Malignant Lymphomas1
3RecruitingPreventionAtrial Flutter / Intracranial Hemorrhage, Hypertensive / Intracranial Hemorrhages / Intraventricular Hemorrhage / Microhaemorrhage / Nonvalvular Atrial Fibrillation / Small Vessel Cerebrovascular Disease / Subarachnoid Hemorrhage / Subdural haematoma1
3RecruitingPreventionCerebral Vein Thrombosis / Deep Vein Thrombosis (DVT) / Metastatic Malignant Neoplasm / Neoplasms, Malignant / Pulmonary Embolism (PE) / Splanchnic Vein Thrombosis1
3RecruitingPreventionNonvalvular Atrial Fibrillation / Strokes / Transient Ischaemic Attack (TIA)1
3RecruitingPreventionStrokes1
3RecruitingTreatmentEligible for Transcatheter Aortic Valve Replacement / Symptomatic Aortic Stenosis1
3RecruitingTreatmentEmbolic Stroke1
3RecruitingTreatmentImpaired Renal Function1
3RecruitingTreatmentLeft Ventricular Thrombosis1
3RecruitingTreatmentPlasma Cell Myeloma / Venous Thromboembolism (VTE)1
3RecruitingTreatmentVenous Thromboembolism (VTE)1
3TerminatedPreventionAcute Coronary Syndromes (ACS)1
4Active Not RecruitingOtherAcute Coronary Syndromes (ACS)1
4Active Not RecruitingPreventionMultiple Myeloma (MM) / Venous Thromboembolism (VTE)1
4CompletedNot AvailableEnd-Stage Renal Disease (ESRD) / ESRD1
4CompletedNot AvailableNon-valvular Atrial Fibrillation (NVAF)1
4CompletedPreventionNonvalvular Atrial Fibrillation1
4CompletedSupportive CareNonvalvular Atrial Fibrillation1
4CompletedTreatmentNeoplasms / Thrombosis, Venous1
4CompletedTreatmentNonvalvular Atrial Fibrillation2
4CompletedTreatmentVenous Thromboembolism (VTE)1
4Not Yet RecruitingTreatmentDeep Vein Thrombosis (DVT)1
4RecruitingBasic ScienceBMI >30 kg/m2 / Post-gastrointestinal bypass surgery1
4RecruitingPreventionAnticoagulants / Venous Thromboembolism (VTE)1
4RecruitingPreventionAntiphospholipid Syndrome / Thrombotic events1
4RecruitingPreventionNonvalvular Atrial Fibrillation2
4RecruitingPreventionNonvalvular Atrial Fibrillation / Strokes1
4RecruitingTreatmentAnticoagulation1
4RecruitingTreatmentDeep Vein Thrombosis (DVT) / Deep Venous Thrombosis / Thromboembolism / Upper Extremity Deep Venous Thrombosis / Venous Thromboembolism (VTE)1
4RecruitingTreatmentDeep Vein Thrombosis (DVT) / Pulmonary Embolism (PE)1
4RecruitingTreatmentDiabetes Mellitus (DM)1
4RecruitingTreatmentEnd Stage Renal Disease (ESRD) / Nonvalvular Atrial Fibrillation1
4RecruitingTreatmentNonvalvular Atrial Fibrillation1
4RecruitingTreatmentVenous Thromboembolism (VTE)2
4TerminatedPreventionVentricular Tachycardia (VT)1
Not AvailableActive Not RecruitingNot AvailableAnticoagulation1
Not AvailableActive Not RecruitingNot AvailableMajor Bleeding / Myocardial Infarction / Nonvalvular Atrial Fibrillation / Stroke, Ischemic / Systemic Embolization / The Mortality Rate1
Not AvailableActive Not RecruitingNot AvailableNonvalvular Atrial Fibrillation4
Not AvailableCompletedNot AvailableAnticoagulation1
Not AvailableCompletedNot AvailableDeep Vein Thrombosis (DVT) / Pulmonary Embolism (PE)1
Not AvailableCompletedNot AvailableMajor Bleeding / Myocardial Infarction / Nonvalvular Atrial Fibrillation / Stroke, Ischemic / Systemic Embolization / The Mortality Rate1
Not AvailableCompletedNot AvailableMajor Bleeding / Venous Thromboembolism (VTE)1
Not AvailableCompletedNot AvailableNonvalvular Atrial Fibrillation7
Not AvailableCompletedNot AvailableStroke, Ischemic1
Not AvailableCompletedNot AvailableStrokes1
Not AvailableCompletedNot AvailableUnsuspected Pulmonary Embolism1
Not AvailableCompletedNot AvailableVenous Thromboembolism (VTE)1
Not AvailableEnrolling by InvitationTreatmentAcute DVT of Lower Extremity1
Not AvailableNot Yet RecruitingNot AvailableNon-valvular Atrial Fibrillation (NVAF)1
Not AvailableNot Yet RecruitingNot AvailableStroke, Ischemic1
Not AvailableRecruitingNot AvailableAnticoagulants and Bleeding Disorders / Venous Thromboembolism (VTE)1
Not AvailableRecruitingNot AvailableCancer Patients / Central Venous Catheter Thrombosis / Upper Extremity Thrombosis1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingNot AvailableVenous Thromboembolism (VTE)2
Not AvailableRecruitingHealth Services ResearchNeoplasms / Thrombosis, Venous1
Not AvailableRecruitingPreventionNonvalvular Atrial Fibrillation / Strokes1
Not AvailableRecruitingScreeningCoagulation Disorders / Non Valvular Atrial Fibrillation1
Not AvailableRecruitingSupportive CareHemorrhage / Nonvalvular Atrial Fibrillation / Periodontal Diseases1
Not AvailableRecruitingTreatmentBlood Clots / Deep Vein Thrombosis (DVT) / Malignancies / Pulmonary Embolism (PE) / Venous Thromboembolism (VTE)1
Not AvailableRecruitingTreatmentPersistent Atrial Fibrillation1
Not AvailableWithdrawnNot AvailableNon-valvular Atrial Fibrillation (NVAF)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral2.5 mg
TabletOral5.0 mg
Tablet, film coatedOral2.5 mg/1
Tablet, film coatedOral2.5 mg
Tablet, film coatedOral5 mg/1
Tablet, film coatedOral5 mg
Kit
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2349330No2009-09-292019-12-17Canada
CA2461202No2011-07-122022-09-17Canada
US6413980No1999-12-222019-12-22Us
US6967208No2003-02-032023-02-03Us
US9326945No2011-02-242031-02-24Us

Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0210900000-941cd1e773f20ff3a0d7

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Phenylpyrazoles / Pyridinecarboxamides / Methoxyanilines / 2-heteroaryl carboxamides / Pyrazole-5-carboxamides / Anisoles / Phenoxy compounds / Methoxybenzenes / Alkyl aryl ethers / Delta lactams
show 10 more
Substituents
Phenylpiperidine / Phenylpyrazole / Methoxyaniline / Pyridinecarboxamide / 2-heteroaryl carboxamide / Phenoxy compound / Anisole / Pyrazole-5-carboxamide / Phenol ether / Methoxybenzene
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aromatic ether, lactam, piperidones, pyrazolopyridine (CHEBI:72296)

Targets

Details
1. Coagulation factor X
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
Uniprot Name
Coagulation factor X
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Cada DJ, Levien TL, Baker DE: Apixaban. Hosp Pharm. 2013 Jun;48(6):494-509. doi: 10.1310/hpj4806-494. [PubMed:24421512]
  2. Apixaban FDA label [File]
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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Cada DJ, Levien TL, Baker DE: Apixaban. Hosp Pharm. 2013 Jun;48(6):494-509. doi: 10.1310/hpj4806-494. [PubMed:24421512]
  2. Budovich A, Zargarova O, Nogid A: Role of apixaban (eliquis) in the treatment and prevention of thromboembolic disease. P T. 2013 Apr;38(4):206-31. [PubMed:23785225]
  3. Wu Z, Lee D, Joo J, Shin JH, Kang W, Oh S, Lee do Y, Lee SJ, Yea SS, Lee HS, Lee T, Liu KH: CYP2J2 and CYP2C19 are the major enzymes responsible for metabolism of albendazole and fenbendazole in human liver microsomes and recombinant P450 assay systems. Antimicrob Agents Chemother. 2013 Nov;57(11):5448-56. doi: 10.1128/AAC.00843-13. Epub 2013 Aug 19. [PubMed:23959307]
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 f...
Gene Name
CYP2J2
Uniprot ID
P51589
Uniprot Name
Cytochrome P450 2J2
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
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
Uniprot Name
Multidrug resistance protein 1
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 fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da

Drug created on March 19, 2008 10:40 / Updated on November 14, 2018 12:54