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Betrixaban

Betrixaban structure

CAS No:
330942-05-7
Formula:
C23H22ClN5O3
Chemical Name:
Betrixaban
Synonyms:
Benzamide,N-(5-chloro-2-pyridinyl)-2-[[4-[(dimethylamino)iminomethyl]benzoyl]amino]-5-methoxy-;N-(5-Chloro-2-pyridinyl)-2-[[4-[(dimethylamino)iminomethyl]benzoyl]amino]-5-methoxybenzamide;Betrixaban;PRT 054021;Bevyxxa
Categories:
Active Pharmaceutical Ingredients > Other Chemical Drugs

Description

Betrixaban is a highly potent, selective, and orally efficacious factor Xa (fXa) inhibitor with IC50 of 1.5 nM.

Betrixaban is a secondary carboxamide obtained by formal condensation of the carboxy group of 4-(N,N-dimethylcarbamimidoyl)benzoic acid with the amino group of 2-amino-N-(5-chloropyridin-2-yl)-5-methoxybenzamide. A synthetic anticoagulant compound that targets activated factor Xa in the coagulation cascade. It has a role as an anticoagulant and an EC 3.4.21.6 (coagulation factor Xa) inhibitor. It is a member of guanidines, a member of benzamides, a secondary carboxamide, a monochloropyridine and a monomethoxybenzene.|Betrixaban is a non-vitamin K oral anticoagulant whose action is driven by the competitive and reversible inhibition of the factor Xa. It was selected among all lead compounds due to its low hERG channel affinity while sustaining its factor Xa inhibition capacity. Betrixaban, now developed by Portola Pharmaceuticals Inc., is prescribed as a venous thromboembolism (VTE) prophylactic for adult patients with moderate to severe restricted motility or with other risks for VTE. VTE can be manifested as deep vein thrombosis or pulmonary embolism and it is a leading cause of preventable death in hospitalized patients.|Betrixaban is a Factor Xa Inhibitor. The mechanism of action of betrixaban is as a Factor Xa Inhibitor.|Betrixaban is an oral anticoagulant and direct inhibitor of factor Xa which is used to decrease the risk of deep vein thrombosis and pulmonary embolus in hospitalized patients at high risk for venous thromboses. Betrixaban has been linked to a low rate of serum aminotransferase elevations during therapy, but has not been linked to instances of clinically apparent liver injury.|Betrixaban is an orally active inhibitor of coagulation factor Xa (activated factor X) with anticoagulant activity. Betrixaban is primarily excreted unchanged in the bile and has a half life of about 19 hours.

Betrixaban Basic Attributes

Molecular Weight：

451.90548

Exact Mass：

451.91

UNII：

74RWP7W0J9

NCI Thesaurus Code：

C75154

ATC Code：

B01AF|B - Blood and blood forming organs

Characteristics

PSA：

107

XLogP3：

3.6

Density：

1.3±0.1 g/cm3

Melting Point：

200-212 ºC

Refractive Index：

1.629

Water Solubility：

H2O: 2.5-2.7 mg/ml

Safety Information

Packing level：

Ⅲ

Transport codes：

2811

hazard class code：

6.1

Precautionary statement(s)：

P260, P264, P270, P301+P312, P314, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P301+P312, P314, P330, and P501|Aggregated GHS information provided by 36 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Betrixaban presents a minimal hepatotoxicity, which is the main adverse effect found in this class of drugs. Some of the major adverse effects of Betrixaban are bleeding or hypersensitivity.

Hepatotoxicity：

In prelicensing studies, serum aminotransferase elevations of greater than 3 times the upper limit of normal (ULN) occurred in 1% to 2% of betrixaban-treated patients and in a similar proportion of control subjects treated with enoxaparin. Similarly, aminotransferase levels rose to above 5 times ULN in 0.6% of betrixaban and 0.4% of enoxaparin treated control subjects. Aminotransferase elevations with jaundice arose in

Protein Binding：

Betrixaban is reported to be present a proteing binding of about 60%.

Drug Information

Drug Indication：

Betrixaban is indicated for prophylaxis of venous thromboembolism (VTE) in conditions of moderate to severe restricted mobility or in patients that qualify as in risk of VTE.|FDA Label|Prevention of venous thromboembolism

LiverTox Summary：

Betrixaban is an oral anticoagulant and direct inhibitor of factor Xa which is used to decrease the risk of deep vein thrombosis and pulmonary embolus in hospitalized patients at high risk for venous thromboses. Betrixaban has been linked to a low rate of serum aminotransferase elevations during therapy, but has not been linked to instances of clinically apparent liver injury.

Drug Classes：

Antithrombotic Agents

Pharmacology：

Betrixaban is an oral anticoagulant that excerts its action by preventing thrombin generation without having a direct effect on platelet aggregation.

MeSH：

Endogenous factors and drugs that inhibit or block the activity of FACTOR XA. (See all compounds classified as Factor Xa Inhibitors.)

Absorption：

Betrixaban presents a rapid absorption at a dose of 80 mg. Its peak plasma concentration is registered within 3-4 hours after oral administration in healthy humans. The oral bioavailability is 34%, and it can be reduced with the consumption of food. Specifically, the C_max and AUC is reduced by an average of 70% and 61% with a low-fat meal, and 50% and 48% with a high-fat meal compared to the fasted state, an effect which is apparent up to six hours following food intake.|Betrixaban is reported to present mainly a gastrointestinal elimination route, it has been shown that even 85% of it gets disposed in the feces and only 11% of it can be found in the urine.|The apparent volume of distribution os 32 L/kg.|Betrixaban presents a minimal renal clearance (being 5-7% of the administered dose).

Metabolism/Metabolites：

One of the major characteristics of Betrixaban is its minimal hepatic metabolism (< 1%), preventing potential accumulation with liver impariment. Unchanged Betrixaban is the main form found in human plasma, followed by two hydolitic CYP-independent inactive metabolites (15-18%). The minimal hepatic metabolism produces an unlikely drug-to-drug interaction with inhibitors or agonists of CYP450.

Biological Half-Life：

Betrixaban presents a long half-life of between 19-27 hours.

Mechanism of Action：

Betrixaban is a cofactor-independent direct inhibitor of the Factor Xa and inhibits free and prothrombinase-bound Factor Xa.

MeSH Entry Terms：

betrixaban

Betrixaban Use and Manufacturing

Uses

A novelanticoagulant. An oral direct inhibitor of factor Xa (FXa) for use in the prevention of venous thromboembolism (VTE).

Use Classification：

Human drugs -> Dexxience -> EMA Drug Category|Antithrombotic agents -> Human pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:451.9
XLogP3:3.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:451.1411173
Monoisotopic Mass:451.1411173
Topological Polar Surface Area:107
Heavy Atom Count:32
Complexity:668
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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330942-05-7 N-(5-chloropyridin-2-yl)-2-[[4-(N,N-dimethylcarbamimidoyl)benzoyl]amino]-5-methoxybenzamide

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