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

Details

Stereochemistry ACHIRAL
Molecular Formula C23H22ClN5O3
Molecular Weight 451.9063
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETRIXABAN

SMILES

CN(C)C(=N)c1ccc(cc1)C(=O)Nc2ccc(cc2C(=Nc3ccc(cn3)Cl)O)OC

InChI

InChIKey=XHOLNRLADUSQLD-UHFFFAOYSA-N
InChI=1S/C23H22ClN5O3/c1-29(2)21(25)14-4-6-15(7-5-14)22(30)27-19-10-9-17(32-3)12-18(19)23(31)28-20-11-8-16(24)13-26-20/h4-13,25H,1-3H3,(H,27,30)(H,26,28,31)

HIDE SMILES / InChI

Molecular Formula C23H22ClN5O3
Molecular Weight 451.9063
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Betrixaban is an anticoagulant drug which acts as a direct factor Xa inhibitor. Betrixaban is now being developed by Portola Pharmaceuticals. Oral, once-daily Factor Xa inhibitor anticoagulant that directly inhibits the activity of Factor Xa, an important validated target in the blood coagulation pathway, to prevent life-threatening thrombosis. U.S. Food and Drug Administration granted Fast Track designation to betrixaban for extended-duration prevention of venous thromboembolism (VTE; blood clots) in acute medically ill patients (i.e., those who are hospitalized for serious medical conditions, such as heart failure, stroke, infection and pulmonary disease). Has the potential to become the first oral Factor Xa inhibitor anticoagulant approved for hospital-to-home prevention of VTE in acute medically ill patients.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
BEVYXXA

Approved Use

BEVYXXA is indicated for the prophylaxis of venous thromboembolism (VTE) in adult patients hospitalized for an acute medical illness who are at risk for thromboembolic complications due to moderate or severe restricted mobility and other risk factors for VTE.

Launch Date

1.49808965E12
Preventing
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
23.2 ng/mL
40 mg 2 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
73.1 ng/mL
80 mg 2 times / day multiple, oral
dose: 80 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
122 ng/mL
120 mg 2 times / day multiple, oral
dose: 120 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
38 ng/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
58.2 ng/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
9.37 ng/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
179 ng × h/mL
40 mg 2 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
488 ng × h/mL
80 mg 2 times / day multiple, oral
dose: 80 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
821 ng × h/mL
120 mg 2 times / day multiple, oral
dose: 120 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
393 ng × h/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
600 ng × h/mL
120 mg single, oral
dose: 120 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
83.1 ng × h/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
39.7 h
40 mg 2 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
37.3 h
80 mg 2 times / day multiple, oral
dose: 80 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
35.9 h
120 mg 2 times / day multiple, oral
dose: 120 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BETRIXABAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
550 mg 1 times / day single, oral
Highest studied dose
Dose: 550 mg, 1 times / day
Route: oral
Route: single
Dose: 550 mg, 1 times / day
Sources: Page: dexxience-epar-refusal-public-assessment-report_.pdf - p.50
healthy, adult
n = 59
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 59
Sources: Page: dexxience-epar-refusal-public-assessment-report_.pdf - p.50
Other AEs: Electrocardiogram QTc interval prolonged...
Other AEs:
Electrocardiogram QTc interval prolonged (grade 1, 3.4%)
Sources: Page: dexxience-epar-refusal-public-assessment-report_.pdf - p.50
360 mg 1 times / day single, oral
MTD
Dose: 360 mg, 1 times / day
Route: oral
Route: single
Dose: 360 mg, 1 times / day
Sources: Page: dexxience-epar-refusal-public-assessment-report_.pdf - p.50
healthy, adult
n = 59
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 59
Sources: Page: dexxience-epar-refusal-public-assessment-report_.pdf - p.50
Sources: Page: dexxience-epar-refusal-public-assessment-report_.pdf - p.50
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, median age 76.6 years
n = 3716
Health Status: unhealthy
Condition: Venous thromboembolism
Age Group: median age 76.6 years
Sex: M+F
Population Size: 3716
Sources:
Disc. AE: Haemorrhage, Pulmonary embolism...
AEs leading to
discontinuation/dose reduction:
Haemorrhage (2.4%)
Pulmonary embolism
Thrombosis venous deep
Sources:
80 mg 1 times / day steady, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: steady
Dose: 80 mg, 1 times / day
Sources: Page: 208383Orig1s000MedR.pdf - p.76
unhealthy, median age 76.6 years
n = 3716
Health Status: unhealthy
Condition: Venous thromboembolism
Age Group: median age 76.6 years
Sex: M+F
Population Size: 3716
Sources: Page: 208383Orig1s000MedR.pdf - p.76
Other AEs: Gastrointestinal bleeding, Intracranial hemorrhage...
Other AEs:
Gastrointestinal bleeding (major, 19 patients)
Intracranial hemorrhage (major, 2 patients)
Bleeding (grade 5, 1 patient)
Sources: Page: 208383Orig1s000MedR.pdf - p.76
unknown
Other AEs: Epidural hematoma, Spinal hematoma...
Other AEs:
Epidural hematoma
Spinal hematoma
Sources:
AEs

AEs

AESignificanceDosePopulation
Electrocardiogram QTc interval prolonged grade 1, 3.4%
550 mg 1 times / day single, oral
Highest studied dose
Dose: 550 mg, 1 times / day
Route: oral
Route: single
Dose: 550 mg, 1 times / day
Sources: Page: dexxience-epar-refusal-public-assessment-report_.pdf - p.50
healthy, adult
n = 59
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 59
Sources: Page: dexxience-epar-refusal-public-assessment-report_.pdf - p.50
Haemorrhage 2.4%
Disc. AE
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, median age 76.6 years
n = 3716
Health Status: unhealthy
Condition: Venous thromboembolism
Age Group: median age 76.6 years
Sex: M+F
Population Size: 3716
Sources:
Pulmonary embolism Disc. AE
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, median age 76.6 years
n = 3716
Health Status: unhealthy
Condition: Venous thromboembolism
Age Group: median age 76.6 years
Sex: M+F
Population Size: 3716
Sources:
Thrombosis venous deep Disc. AE
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, median age 76.6 years
n = 3716
Health Status: unhealthy
Condition: Venous thromboembolism
Age Group: median age 76.6 years
Sex: M+F
Population Size: 3716
Sources:
Bleeding grade 5, 1 patient
80 mg 1 times / day steady, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: steady
Dose: 80 mg, 1 times / day
Sources: Page: 208383Orig1s000MedR.pdf - p.76
unhealthy, median age 76.6 years
n = 3716
Health Status: unhealthy
Condition: Venous thromboembolism
Age Group: median age 76.6 years
Sex: M+F
Population Size: 3716
Sources: Page: 208383Orig1s000MedR.pdf - p.76
Gastrointestinal bleeding major, 19 patients
80 mg 1 times / day steady, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: steady
Dose: 80 mg, 1 times / day
Sources: Page: 208383Orig1s000MedR.pdf - p.76
unhealthy, median age 76.6 years
n = 3716
Health Status: unhealthy
Condition: Venous thromboembolism
Age Group: median age 76.6 years
Sex: M+F
Population Size: 3716
Sources: Page: 208383Orig1s000MedR.pdf - p.76
Intracranial hemorrhage major, 2 patients
80 mg 1 times / day steady, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: steady
Dose: 80 mg, 1 times / day
Sources: Page: 208383Orig1s000MedR.pdf - p.76
unhealthy, median age 76.6 years
n = 3716
Health Status: unhealthy
Condition: Venous thromboembolism
Age Group: median age 76.6 years
Sex: M+F
Population Size: 3716
Sources: Page: 208383Orig1s000MedR.pdf - p.76
Epidural hematoma
unknown
Spinal hematoma
unknown
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
yes [IC50 11.6 uM]
yes [IC50 11.6 uM]
yes [Inhibition 10 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Emergence of new oral antithrombotics: a critical appraisal of their clinical potential.
2008
New oral anticoagulants in atrial fibrillation.
2008 Jan
Comparative pharmacodynamics and pharmacokinetics of oral direct thrombin and factor xa inhibitors in development.
2009
New anticoagulants for atrial fibrillation.
2009 Jul
Emerging antithrombotic agents for thromboprophylaxis, clinical potential and patient considerations.
2010
New synthetic antithrombotic agents for venous thromboembolism: pentasaccharides, direct thrombin inhibitors, direct Xa inhibitors.
2010 Dec
Novel anticoagulants for stroke prevention in atrial fibrillation: current clinical evidence and future developments.
2010 Dec 14
New anticoagulants for the prevention of venous thromboembolism.
2010 May 25
Role of orally available antagonists of factor Xa in the treatment and prevention of thromboembolic disease: focus on rivaroxaban.
2010 Sep
Patents

Patents

Sample Use Guides

80 mg PO QD for 35 day + 7 days.
Route of Administration: Oral
In a tissue factor-induced thrombin-generation assay, betrixaban, in concentrations ranging between 5 and 25 ng/ml, inhibited thrombin generation to trough and peak levels comparable to those achieved by 2.5 mg of fondaparinux.
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:12:08 UTC 2021
Edited
by admin
on Sat Jun 26 00:12:08 UTC 2021
Record UNII
74RWP7W0J9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BETRIXABAN
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
PRT-054021
Code English
BETRIXABAN [MI]
Common Name English
BETRIXABAN [INN]
Common Name English
N-(5-CHLOROPYRIDIN-2-YL)-2-((4-(N,N-DIMETHYLCARBAMIMIDOYL)BENZOYL)AMINO)-5-METHOXYBENZAMIDE
Systematic Name English
BENZAMIDE, N-(5-CHLORO-2-PYRIDINYL)-2-((4-((DIMETHYLAMINO)IMINOMETHYL)BENZOYL)AMINO)-5-METHOXY-
Systematic Name English
BETRIXABAN [WHO-DD]
Common Name English
BETRIXABAN [USAN]
Common Name English
BETRIXABAN [ORANGE BOOK]
Common Name English
PRT054021
Code English
Classification Tree Code System Code
NCI_THESAURUS C263
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
NDF-RT N0000175637
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL512351
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
RXCUI
1927851
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
LACTMED
Betrixaban
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
MESH
C543086
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
NCI_THESAURUS
C75154
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
INN
8950
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
EVMPD
SUB180756
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
PUBCHEM
10275777
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
DRUG BANK
DB12364
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
CAS
330942-05-7
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
FDA UNII
74RWP7W0J9
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
DRUG CENTRAL
5241
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
MERCK INDEX
M12019
Created by admin on Sat Jun 26 00:12:08 UTC 2021 , Edited by admin on Sat Jun 26 00:12:08 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
COMPETITIVE INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
TARGET -> INHIBITOR
COMPETITIVE INHIBITOR
IC50
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
OFF-TARGET->INHIBITOR
Ki
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE ACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
FOOD EFFECT (CMAX) PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
FOOD EFFECT (AUC) PHARMACOKINETIC
Tmax PHARMACOKINETIC