U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C25H25N5O4
Molecular Weight 459.4971
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APIXABAN

SMILES

COC1=CC=C(C=C1)N2N=C(C(N)=O)C3=C2C(=O)N(CC3)C4=CC=C(C=C4)N5CCCCC5=O

InChI

InChIKey=QNZCBYKSOIHPEH-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C25H25N5O4
Molecular Weight 459.4971
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Apixaban is an orally active inhibitor of coagulation factor Xa with anticoagulant activity. Apixaban directly inhibits factor Xa, thereby interfering with the conversion of prothrombin to thrombin and preventing formation of cross-linked fibrin clots. Apixaban has been available in Europe since May 2012. An FDA decision on apixaban which was expected on June 28, 2012 was initially delayed before final approval on December 28, 2012. On August 21, 2014, Pfizer announced that apixaban was now FDA approved for treatment and secondary prophylaxis of deep vein thrombosis (DVT) and pulmonary embolism (PE). It is being developed in a joint venture by Pfizer and Bristol-Myers Squibb. It has also been used to lower the risk of developing venous thrombosis post-orthopedic surgical procedures.

CNS Activity

CNS Penetrant
2554
Curator's Comment: Apixaban is substrate of p-glycoprotein (p-gp), a ubiquitous transmembrane receptor found in the intestinal wall, as well as various other locations in the body, including the blood-brain barrier. P-gp actively transports molecules with diverse conformations, including drugs, across tissue monolayers.

Originator

Bristol-Myers Squibb
145
Curator's Comment: In 2007, Pfizer and Bristol-Myers Squibb entered into a worldwide collaboration to develop and commercialize apixaban, an oral anticoagulant discovered by Bristol-Myers Squibb. This global alliance combines Bristol-Myers Squibb's long-standing strengths in cardiovascular drug development and commercialization with Pfizer’s global scale and expertise in this field. # Bristol-Myers Squibb

Approval Year

2012
595
Targets

Targets

Primary TargetPharmacologyConditionPotency
Coagulation factor X
20
Target ID: P00742
Gene ID: 2159.0
Gene Symbol: F10
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 0.22 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Approved
8429
ELIQUIS

Approved Use

Indicated to reduce the risk of stroke and systemic embolism in patients with nonvalvular atrial fibrillation; for the prophylaxis of deep vein thrombosis (DVT), which may lead to pulmonary embolism (PE), in patients who have undergone hip or knee replacement surgery; for the treatment of DVT and PE, and for the reduction in the risk of recurrent DVT and PE following initial therapy.

Launch Date

1.35665274E12
Secondary
Approved
8429
ELIQUIS

Approved Use

Indicated to reduce the risk of stroke and systemic embolism in patients with nonvalvular atrial fibrillation; for the prophylaxis of deep vein thrombosis (DVT), which may lead to pulmonary embolism (PE), in patients who have undergone hip or knee replacement surgery; for the treatment of DVT and PE, and for the reduction in the risk of recurrent DVT and PE following initial therapy.

Launch Date

1.35665274E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
207 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23488672/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
APIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2024 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23488672/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
APIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/23488672/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
APIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
50 mg single, oral
Highest studied dose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/30498375
healthy, 20-39 years
n = 23
Health Status: healthy
Age Group: 20-39 years
Sex: M
Population Size: 23
Sources:
https://pubmed.ncbi.nlm.nih.gov/30498375
Sources:
https://pubmed.ncbi.nlm.nih.gov/30498375
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Co-administed with::
digoxin(single 0.75 mg)
Sources:
https://pubmed.ncbi.nlm.nih.gov/33278889
unknown, 23 months
n = 1
Health Status: unknown
Age Group: 23 months
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/33278889
Other AEs: Intoxication...
Other AEs:
Intoxication
Sources:
https://pubmed.ncbi.nlm.nih.gov/33278889
2.5 mg 2 times / day steady, oral
Dose: 2.5 mg, 2 times / day
Route: oral
Route: steady
Dose: 2.5 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
healthy, 27 years (range: 19-39 years)
n = 6
Health Status: healthy
Age Group: 27 years (range: 19-39 years)
Sex: M
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
Disc. AE: Headache, Nausea...
AEs leading to
discontinuation/dose reduction:
Headache (1 patient)
Nausea (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
25 mg 2 times / day steady, oral
Highest studied dose
Dose: 25 mg, 2 times / day
Route: oral
Route: steady
Dose: 25 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
healthy, 27 years (range: 20-41 years)
n = 8
Health Status: healthy
Age Group: 27 years (range: 20-41 years)
Sex: M
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
Other AEs: Haematochezia, Alanine aminotransferase increased...
Other AEs:
Haematochezia (1 patient)
Alanine aminotransferase increased (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
210 mg single, oral
Overdose
Dose: 210 mg
Route: oral
Route: single
Dose: 210 mg
Co-administed with::
levothyroxine(1.5 mg single)
amitriptyline(2.5 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28964584
unknown, 48 years
n = 1
Health Status: unknown
Age Group: 48 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/28964584
Other AEs: Poisoning...
Other AEs:
Poisoning
Sources:
https://pubmed.ncbi.nlm.nih.gov/28964584
2.5 mg 1 times / day steady, oral
Dose: 2.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 2.5 mg, 1 times / day
Co-administed with::
apixaban(oral; 2.5 mg/12h)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30569731
unhealthy, 85 years
n = 1
Health Status: unhealthy
Condition: Auricular fibrillation
Age Group: 85 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/30569731
Disc. AE: Hepatotoxicity...
AEs leading to
discontinuation/dose reduction:
Hepatotoxicity (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30569731
25 mg 2 times / day steady, oral
Overdose
Dose: 25 mg, 2 times / day
Route: oral
Route: steady
Dose: 25 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202155s000lbl.pdf
healthy
Health Status: healthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202155s000lbl.pdf
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202155s000lbl.pdf
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202155s000lbl.pdf
unhealthy
Health Status: unhealthy
Condition: nonvalvular atrial fibrillation
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202155s000lbl.pdf
Other AEs: Thromboembolic event...
Other AEs:
Thromboembolic event
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202155s000lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Intoxication
40 mg single, oral
Overdose
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Co-administed with::
digoxin(single 0.75 mg)
Sources:
https://pubmed.ncbi.nlm.nih.gov/33278889
unknown, 23 months
n = 1
Health Status: unknown
Age Group: 23 months
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/33278889
Headache 1 patient
Disc. AE
2.5 mg 2 times / day steady, oral
Dose: 2.5 mg, 2 times / day
Route: oral
Route: steady
Dose: 2.5 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
healthy, 27 years (range: 19-39 years)
n = 6
Health Status: healthy
Age Group: 27 years (range: 19-39 years)
Sex: M
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
Nausea 1 patient
Disc. AE
2.5 mg 2 times / day steady, oral
Dose: 2.5 mg, 2 times / day
Route: oral
Route: steady
Dose: 2.5 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
healthy, 27 years (range: 19-39 years)
n = 6
Health Status: healthy
Age Group: 27 years (range: 19-39 years)
Sex: M
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
Alanine aminotransferase increased 1 patient
25 mg 2 times / day steady, oral
Highest studied dose
Dose: 25 mg, 2 times / day
Route: oral
Route: steady
Dose: 25 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
healthy, 27 years (range: 20-41 years)
n = 8
Health Status: healthy
Age Group: 27 years (range: 20-41 years)
Sex: M
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
Haematochezia 1 patient
25 mg 2 times / day steady, oral
Highest studied dose
Dose: 25 mg, 2 times / day
Route: oral
Route: steady
Dose: 25 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
healthy, 27 years (range: 20-41 years)
n = 8
Health Status: healthy
Age Group: 27 years (range: 20-41 years)
Sex: M
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/23451769
Poisoning
210 mg single, oral
Overdose
Dose: 210 mg
Route: oral
Route: single
Dose: 210 mg
Co-administed with::
levothyroxine(1.5 mg single)
amitriptyline(2.5 mg, single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28964584
unknown, 48 years
n = 1
Health Status: unknown
Age Group: 48 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/28964584
Hepatotoxicity 1 patient
Disc. AE
2.5 mg 1 times / day steady, oral
Dose: 2.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 2.5 mg, 1 times / day
Co-administed with::
apixaban(oral; 2.5 mg/12h)
Sources:
https://pubmed.ncbi.nlm.nih.gov/30569731
unhealthy, 85 years
n = 1
Health Status: unhealthy
Condition: Auricular fibrillation
Age Group: 85 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/30569731
Thromboembolic event
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202155s000lbl.pdf
unhealthy
Health Status: unhealthy
Condition: nonvalvular atrial fibrillation
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202155s000lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737
substrate
1037

inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2A6
707

CYP2B6
810

CYP2C8
911

CYP3A4/5
278

CYP2C19
1478

P-gp
1461
P-gp
1537

CYP1A2
1054

CYP2C8
693

CYP2C19
991

CYP2J2
56

MRP
7

OATP1B1
406

OATP1B3
350

OATP2B1
104

OAT1
326

OAT3
339

BCRP
561
CYP1A2
701

CYP2B6
547

CYP3A4/5
124
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
1553
 minor [IC50 20 uM]
CYP1A2
1692
 no
CYP1A2
1692
 no
CYP2A6
739
 no
CYP2B6
1001
 no
CYP2B6
1001
 no
CYP2C8
965
 no
CYP2C9
1819
 no
CYP2D6
1891
 no
CYP3A4/5
335
 no
CYP3A4/5
335
 no
P-gp
1650
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1054
 minor
CYP2C19
991
 minor
CYP2C8
693
 minor
CYP2C9
1037
 minor
CYP2J2
56
 minor
MRP
7
 no
OAT1
326
 no
OAT3
339
 no
OATP1B1
406
 no
OATP1B3
350
 no
OATP2B1
104
 no
BCRP
561
 yes
CYP3A4
1737
 yes
yes (co-administration study)
Comment: ketoconazole increased cmax of apixaban 1.5x, auc 2x
Page: 9.0
P-gp
1537
 yes
yes (co-administration study)
Comment: ketoconazole increased cmax of apixaban 1.5x, auc 2x
Page: 9.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:72296
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:72296
ChemicalBook
CB51508586
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB51508586
MolPort
MolPort-006-170-153
https://www.molport.com/shop/molecule-link/MolPort-006-170-153
Selleck Chemicals
Apixaban(BMS-562247-01)
http://www.selleckchem.com/products/Apixaban(BMS-562247-01).html
ZINC
ZINC000011677837
http://zinc15.docking.org/substances/ZINC000011677837
eMolecules
32278100
https://www.emolecules.com/cgi-bin/more?vid=32278100
PubMed

PubMed

TitleDatePubMed
Oral anticoagulants in development: focus on thromboprophylaxis in patients undergoing orthopaedic surgery.
2006
Oral, direct factor Xa inhibitors in development for the prevention and treatment of thromboembolic diseases.
2007 Jun
Discovery of 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (apixaban, BMS-562247), a highly potent, selective, efficacious, and orally bioavailable inhibitor of blood coagulation factor Xa.
2007 Nov 1
Efficacy and safety of the oral direct factor Xa inhibitor apixaban for symptomatic deep vein thrombosis. The Botticelli DVT dose-ranging study.
2008 Aug
Apixaban, an oral direct Factor Xa inhibitor: awaiting the verdict.
2008 Dec
[New anticoagulants].
2008 Feb
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
Controversies in the antiphospholipid syndrome: can we ever stop warfarin?
2008 Nov 11
New developments in anticoagulation for atrial fibrillation.
2008 Sep
Apixaban, an oral, direct inhibitor of activated Factor Xa.
2008 Sep
Use of anticoagulants in elderly patients: practical recommendations.
2009
Comparative pharmacodynamics and pharmacokinetics of oral direct thrombin and factor xa inhibitors in development.
2009
Apixaban, an oral direct factor Xa inhibitor, inhibits human clot-bound factor Xa activity in vitro.
2009 Apr
Recent developments in the use of oral anticoagulants.
2009 Aug
Apixaban or enoxaparin for thromboprophylaxis after knee replacement.
2009 Aug 6
Oral anticoagulation with Factor Xa and thrombin inhibitors: Is there an alternative to warfarin?
2009 Dec
New anticoagulants - towards the development of an "ideal" anticoagulant.
2009 Feb
Apixaban metabolism and pharmacokinetics after oral administration to humans.
2009 Jan
New anticoagulants: focus on venous thromboembolism.
2009 Jul
Apixaban, an oral, direct, selective factor Xa inhibitor, in combination with antiplatelet therapy after acute coronary syndrome: results of the Apixaban for Prevention of Acute Ischemic and Safety Events (APPRAISE) trial.
2009 Jun 9
Rivaroxaban -- an oral, direct Factor Xa inhibitor: lessons from a broad clinical study programme.
2009 May
Gateways to clinical trials.
2009 Nov
Gateways to clinical trials.
2009 Oct
New antithrombotic drugs: potential for use in oncology.
2009 Oct 10
Novel anticoagulant therapy: principle and practice.
2010
New oral anticoagulants in development: potential for improved safety profiles.
2010
VTE prophylaxis for the medical patient: where do we stand? - a focus on cancer patients.
2010 Apr
Antithrombotic and anticoagulant profiles of TAK-442, a novel factor Xa inhibitor, in a rabbit model of venous thrombosis.
2010 Aug
New oral anticoagulants: a practical guide for clinicians.
2010 Feb
Phenyltriazolinones as potent factor Xa inhibitors.
2010 Feb 15
Apixaban: an emerging oral factor Xa inhibitor.
2010 Jan
Drug and dietary interactions of the new and emerging oral anticoagulants.
2010 Jun
Old versus new anticoagulants: focus on pharmacology.
2010 Jun
Rationale and design of AVERROES: apixaban versus acetylsalicylic acid to prevent stroke in atrial fibrillation patients who have failed or are unsuitable for vitamin K antagonist treatment.
2010 Mar
Apixaban for reduction in stroke and other ThromboemboLic events in atrial fibrillation (ARISTOTLE) trial: design and rationale.
2010 Mar
In vitro assessment of metabolic drug-drug interaction potential of apixaban through cytochrome P450 phenotyping, inhibition, and induction studies.
2010 Mar
Forecasting drug utilization and expenditure in a metropolitan health region.
2010 May 17
Novel oral anticoagulants: implications in the perioperative setting.
2010 Sep
Quantification of apixaban's therapeutic utility in prevention of venous thromboembolism: selection of phase III trial dose.
2010 Sep
New antithrombotic agents--insights from clinical trials.
2010 Sep
Role of orally available antagonists of factor Xa in the treatment and prevention of thromboembolic disease: focus on rivaroxaban.
2010 Sep
Patents

Patents

06919451
1
07153960
1
JP2010539945A
2
JP2011502514A
9
JP2011502515A
9

Sample Use Guides

In Vivo Use Guide
The recommended dose is 5 mg orally twice daily. In patients with at least 2 of the following characteristics: age 80 years, body weight 60 kg, or serum creatinine 1.5 mg/dL, the recommended dose is 2.5 mg orally twice daily.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:59:33 UTC 2023
Edited
by admin
on Fri Dec 15 15:59:33 UTC 2023
Record UNII
3Z9Y7UWC1J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APIXABAN
DASH   EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
APIXABAN [EMA EPAR]
Common Name English
APIXABAN [VANDF]
Common Name English
1-(4-METHOXYPHENYL)-7-OXO-6-(4-(2-OXOPIPERIDIN-1-YL)PHENYI)-4,5,6,7-TETRAHYDRO-1H-PYRAZOLO(3,4-C)PYRIDINE-3-CARBOXAMIDE
Common Name English
APIXABAN [JAN]
Common Name English
APIXABAN [MART.]
Common Name English
BMS-562247
Code English
APIXABAN [MI]
Common Name English
BMS-562247-01
Code English
Apixaban [WHO-DD]
Common Name English
APIXABAN [ORANGE BOOK]
Common Name English
1H-PYRAZOLO(3,4-C)PYRIDINE-3-CARBOXAMIDE, 4,5,6,7-TETRAHYDRO-1-( 4-METHOXYPHENYL)-7-OXO-6-(4-(2-OXO-1-PIPERIDINYL)PHENYL)-
Common Name English
ELIQUIS
Brand Name English
apixaban [INN]
Common Name English
APIXABAN [USAN]
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548281
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
WHO-ATC B01AF02
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
NCI_THESAURUS C263
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
EMA ASSESSMENT REPORTS ELIQUIS (AUTHORIZED: ARTHROPLASTY)
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
LOINC 74214-8
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
WHO-VATC QB01AF02
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
EMA ASSESSMENT REPORTS ELIQUIS (AUTHORIZED: VENOUS THROMBOEMBOLISM)
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
NDF-RT N0000175637
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
Code System Code Type Description
SMS_ID
100000091294
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
IUPHAR
6390
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
FDA UNII
3Z9Y7UWC1J
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
EVMPD
SUB25425
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
INN
8626
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
JAPANESE REVIEW
ELIQUIS
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY APPROVED DECEMBER 2012
MESH
C522181
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL231779
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
MERCK INDEX
m1993
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY Merck Index
CAS
503612-47-3
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
DAILYMED
3Z9Y7UWC1J
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
LACTMED
Apixaban
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
CHEBI
72296
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
HSDB
8223
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
PUBCHEM
10182969
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
WIKIPEDIA
APIXABAN
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
RXCUI
1364430
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB06605
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
USAN
QQ-78
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
NCI_THESAURUS
C61308
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID80436500
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
DRUG CENTRAL
4298
Created by admin on Fri Dec 15 15:59:33 UTC 2023 , Edited by admin on Fri Dec 15 15:59:33 UTC 2023
PRIMARY
Related Record Type Details
Structure of APIXABAN
EXCRETED UNCHANGED
URINE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
COAGULATION FACTOR X HUMAN
TARGET -> INHIBITOR
Ki
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
FACTOR XA
TARGET -> INHIBITOR
Structure of APIXABAN
EXCRETED UNCHANGED
FECAL
Related Record Type Details
Structure of O-DEMETHYL APIXABAN
METABOLITE -> PARENT
MINOR
Structure of O-DEMETHYL APIXABAN SULFATE
METABOLITE -> PARENT
MAJOR
PLASMA
Related Record Type Details
Structure of Ethyl 1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
IMPURITY -> PARENT
Structure of 3,3-Dichloro-1-(4-nitrophenyl)piperidin-2-one
IMPURITY -> PARENT
Structure of Ethyl 6-[4-[(5-bromo-1-oxopentyl)amino]phenyl]-4,5,6,7-tetrahydro-1-(4-methoxyphenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
IMPURITY -> PARENT
Structure of Apixaban acid
IMPURITY -> PARENT
Structure of Methyl 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
IMPURITY -> PARENT
Structure of Chloroapixaban
IMPURITY -> PARENT
Structure of Apixaban open ring amide
IMPURITY -> PARENT
Structure of Apixaban open ring acid
IMPURITY -> PARENT
Structure of Apixaban ethyl ester
IMPURITY -> PARENT
Structure of N-Formyl-1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide
IMPURITY -> PARENT
Structure of Ethyl 6-[4-(5-chloropentanamido)phenyl]-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
IMPURITY -> PARENT
Related Record Type Details
Structure of APIXABAN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Volume of Distribution PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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