Indications and Usage Mechanisms of Action Clinical Research Drug Interactions Warnings and Precautions
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Apixaban

Indications and Usage Mechanisms of Action Clinical Research Drug Interactions Warnings and Precautions
Product Name
Apixaban
CAS No.
503612-47-3
Chemical Name
Apixaban
Synonyms
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;CS-343;pixaban;BMS562247;1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-1H,4H,5H,6H,7H-pyrazolo[3,4-c]pyridine-3-carboxamide;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]-;xaban;Apixaba;Apxaban;Apixaban
CBNumber
CB51508586
Molecular Formula
C25H25N5O4
Formula Weight
459.5
MOL File
503612-47-3.mol
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Apixaban Property

Melting point:
235-238°C
Boiling point:
770.5±60.0 °C(Predicted)
Density 
1.42
storage temp. 
Refrigerator
solubility 
DMSO (Slightly, Heated), Methanol (Slightly)
pka
15.01±0.20(Predicted)
form 
Solid
color 
White to Off-White
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)
InChIKey
QNZCBYKSOIHPEH-UHFFFAOYSA-N
SMILES
C1(=O)N(C2=CC=C(N3CCCCC3=O)C=C2)CCC2C(C(N)=O)=NN(C3=CC=C(OC)C=C3)C1=2
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Safety

Hazardous Substances Data
503612-47-3(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
15427
Product name
Apixaban
Purity
≥98%
Packaging
1mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
15427
Product name
Apixaban
Purity
≥98%
Packaging
5mg
Price
$202
Updated
2024/03/01
Cayman Chemical
Product number
15427
Product name
Apixaban
Purity
≥98%
Packaging
10mg
Price
$356
Updated
2024/03/01
Cayman Chemical
Product number
15427
Product name
Apixaban
Purity
≥98%
Packaging
50mg
Price
$711
Updated
2024/03/01
TRC
Product number
A726700
Product name
Apixaban
Packaging
500mg
Price
$525
Updated
2021/12/16
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Apixaban Chemical Properties,Usage,Production

Indications and Usage

Apixaban is a new form of oral anticoagulant drug developed by Bristol Myers Squibb and Pfizer. It is a new form of oral Xa factor inhibitor, and its commercial name is Eliquis. Apixaban is used to treat adult patients undergoing elective hip or knee replacement surgery to prevent venous thromboembolism (VTE)

Mechanisms of Action

Apixaban(503612-47-3) is an oral selective activated Xa factor inhibitor and can prevent thrombin generation and thrombosis.

Clinical Research

Apixaban(503612-47-3) is the third new oral anticoagulant to go on sale, following dabigatran and rivaroxaban, and it has already been approved in Europe for preventing venous thromboembolism in patients undergoing elective hip or knee replacement surgery. Out of these three oral anticoagulants approved in Europe, compared to the current standard preventative treatment against venous thromboembolism, enoxaparin, rivaroxaban excelled in the record experiment, and apixaban excelled in the advance experiment. Rivaroxaban’s curative effects were slightly superior, but it caused more severe bleeding than apixaban. Researchers attributed these differences to medication time, as rivaroxaban was taken 6-8 hours after surgery in the record experiment, while apixaban was used 18 hours after surgery in the advance experiment. These drugs have better curative effect when used closer to time of surgery, but also have an increased bleeding risk. Clinical research showed that compared to a daily subdermal injection of 40mg enoxaparin, 2 oral 2.5mg dosages of apixaban had better preventative effects against venous thromboembolism following hip or knee replacement surgery and did not increase bleeding risk.

Drug Interactions

1.A double inhibitor of strong CYP3A4 and P-gp increases apixaban’s blood levels: decrease Eliquis dosage to 2.5mg or avoid simultaneous usage.
2.A inductor of strong CYP3A4 and P-gp can decrease apixaban’s blood levels: avoid simultaneous usage.

Warnings and Precautions

  • Breastfeeding mothers should stop usage or stop breastfeeding.
  • Use during pregnancy is not advised.
  • Use while experiencing severe liver damage is not advised.

Description

Eliquis (apixaban), a direct inhibitor of factor Xa (FXa), was approved by the European Commission on May 18, 2011 for prevention of venous thromboembolic events (VTE) in adult patients who have undergone elective hip or knee replacement surgery. The discovery of apixaban was the culmination of a succession of novel and innovative medicinal chemistry discoveries starting with the identification of nonpeptide leads, rational drug design using computer-aided and X-ray crystallographic information, and the building of drug-like properties through the systematic replacement of basic groups with neutral moieties. Apixaban arose from modifications to razaxaban by constraining a pyrazole amide to form a bicyclic pyrazolo-pyridinone scaffold. Optimization of the P1 group resulted in the identification of the nonbasic methoxy phenyl group, while a P4 piperidinone improved the balance of potency and pharmacokinetics with low Vdss. The synthesis of apixaban begins with the generation of a hydrazone of 4-methoxyaniline which is then used in a 3+2 cycloaddition with a dihydropiperidinone to form a bicyclic pyrazolo-pyridinone scaffold. The distal piperidinone group is installed using an Ullmann coupling reaction followed by aminolysis of an ethyl ester on the pyrazole ring to complete the synthesis of apixaban.

Description

Apixaban is an orally bioavailable, selective inhibitor of both free and prothrombinase-bound factor Xa (Kis = 0.8 nM). In vivo, apixaban has antithrombotic effects in a rabbit model of venous thrombosis. Apixaban (357.5 mg) also prevents thrombus formation without inducing adverse bleeding events in a porcine model of aortic heterotopic valve replacement. Formulations containing apixaban have been used to prevent blood clot formation in patients with atrial fibrillation.

Originator

Bristol Myers Squibb Company (United States)

Uses

Apixaban is a highly selective, reversible inhibitor of Factor Xa with Ki of 0.08 nM and 0.17 nM in human and rabbit, respectively.

Definition

ChEBI: A pyrazolopyridine that is 7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide substituted at position 1 by a 4-methoxyphenyl group and at position 6 by a 4-(2-oxopiperidin-1-yl)phenyl group. It is used for the prevention and treatment of thromboembolic diseases.

brand name

Eliquis

Pharmacokinetics

The maximum plasma concentration (Cmax) of apixaban occurs 3–4 h after oral administration. The absorption of apixaban appears to occur primarily in the small intestine and decreases progressively throughout the gastrointestinal tract. Compared with oral administration, the bioavailability of 2.5 mg of apixaban solution was approximately 60% and 84% lower when released in the distal small bowel and ascending colon, respectively. For oral doses up to 10 mg, the absolute bioavailability of apixaban is~50%, resulting from the incomplete absorption and first-pass metabolism in the gut and liver[1].

Clinical Use

Apixaban is an oral anticoagulant with highly selective inhibition of factor Xa. It was approved by the European Medicines Agency (EMA) for the treatment of venous thromboembolic events and first marketed in Germany under the brand name Eliquis in June 2011. Apixaban was co-developed by Bristol-Myers Squibb and Pfizer and represents the first approved drug for this indication since warfarin over 50 years ago.

Side effects

Possible side effects of Apixaban are: bleeding gums, nosebleeds, heavy vaginal bleeding , red, pink, or brown urine; red or black, tarry stools; coughing or spitting up blood or a substance that looks like coffee grounds; swelling or joint pain, headache, rash, chest pain or tightness in the chest, swelling of the face or tongue, trouble breathing, wheezing. Feeling dizzy or fainting.Apixaban prevents your blood from clotting properly, so if you get a cut or injury, it may take longer than usual for the bleeding to stop. This medication may also cause you to bruise or bleed more easily.

Synthesis

Although several convenient preparations of apixaban (BMS-562247) have been reported, the most likely process-scale route is described in the scheme. The starting material 4-iodoaniline (14) was acylated with 5-bromovaleryl chloride (15) and triethylamine followed by cyclization under basic conditions to give lactam 16 in 49% yield. Intermediate 16 was then reacted with phosphorus pentachloride to provide the a,a-dichlorinated lactam 17 in 87% yield.30 This dichloride was reacted with excess morpholine to affect an alkylation¨Celimination sequence to afford enaminolactam 18 in 86% yield. N-Arylation of this iodide with valerolactam 19 using a copper (I) catalyst resulted in a 77% yield of the desired p-bispiperidone 20. Interestingly, sequential exposure of 20 to a nitrile imine generated from the treatment of ethyl 2-chloro-2-(2,4-methoxyphenyl)-hydrazono) acetate 21 with base resulted in a [3+2] dipolarcycloadditon reaction. Upon acidification with 4 N HCl, pyrazole 22 was furnished in 67% over two steps. Conversion of the ester within 22 to the corresponding amide was achieved via a mixture of formamide and sodium methoxide to give apixaban (III) in 71% yield. It is important to note that intermediate 21 was prepared from commercially available 4-methoxyaniline (23) by sequential diazotization and condensation with ethyl 2-chloroacetoacetate (24).

in vitro

apixabanhas exhibited a high degree of potency, selectivity, and efficacy on factor xa with ki of 0.08 nm and 0.17 nm for human factor xa and rabbit factor xa, respectively [1]. apixaban prolonged the clotting times of normal human plasma with the concentrations (ec2x) of 3.6, 0.37, 7.4 and 0.4 μm, which are required respectively to double the prothrombin time (pt), modified prothrombin time (mpt), activated partial thromboplastin time (aptt) and heptest. besides, apixaban showed the highest potency in human and rabbit plasma, but less potency in rat and dog plasma in both the pt and aptt assays [3].

in vivo

apixaban exihibited the excellent pharmacokinetics with very low clearance (cl: 0.02 l kg-1h-1), and low volume of distribution (vdss: 0.2 l/kg) in the dog. besides, apixaban also showed a moderate half-life with t1/2 of 5.8 hours and good oral bioavailability (f: 58%) [1]. in the arteriovenous-shunt thrombosis (avst), venous thrombosis (vt) and electrically mediated carotid arterial thrombosis (ecat) rabbit models, apixaban produced antithrombotic effects with ec50 of 270 nm, 110 nm and 70 nm in a dose-dependent manner[3]. apixaban significantly inhibited factor xa activity with an ic50 of 0.22 μm in rabbit ex vivo[4]. in chimpanzee, apixaban also showed small volume of distribution (vdss: 0.17 l kg-1), low systemic clearance (cl: 0.018 l kg-1h-1), and good oral bioavailability (f: 59%) [5].

Drug interactions

Potentially hazardous interactions with other drugs
Analgesics: increased risk of haemorrhage with IV diclofenac and ketorolac - avoid.
Antibacterials: avoid with clarithromycin and telithromycin; concentration possibly reduced by rifampicin - avoid if treating DVT/PE.
Anticoagulants: increased risk of haemorrhage with other anticoagulants - avoid.
Antidepressants: concentration possibly reduced by St John’s wort - avoid if treating DVT/PE.
Antiepileptics: concentration possibly reduced by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidone - avoid if treating DVT/ PE with carbamazepine.
Antifungals: concentration increased by ketoconazole - avoid; avoid with itraconazole, posaconazole and voriconazole.
Antivirals: avoid with atazanavir, boceprevir, darunavir, fosamprenavir, indinavir, lopinavir, ritonavir, saquinavir, telaprevir and tipranavir.
Cobicistat: avoid concomitant use.

Metabolism

Apixaban is metabolised in the liver mainly via the P450 cytochromes CYP3A4 and CYP3A5.
Apixaban has multiple routes of elimination. Of the administered apixaban dose in humans, approximately 25% was recovered as metabolites, with the majority recovered in faeces. Renal excretion of apixaban accounts for approximately 27% of total clearance. There are also additional contributions from biliary and direct intestinal excretion.

References

https://en.wikipedia.org/wiki/Apixaban
https://www.drugbank.ca/drugs/DB06605
[1] Wonkyung Byon. “Apixaban: A Clinical Pharmacokinetic and Pharmacodynamic Review.” Clinical Pharmacokinetics 58 10 (2019): 1265–1279.

Apixaban Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Apixaban manufacturers

hebei hongtan Biotechnology Co., Ltd
Product
Apixaban 503612-47-3
Price
US $15.00-1.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
500
Release date
2024-05-14
hebei hongtan Biotechnology Co., Ltd
Product
Apixaban 503612-47-3
Price
US $30.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000kg
Release date
2024-05-16
hebei hongtan Biotechnology Co., Ltd
Product
Apixaban 503612-47-3
Price
US $50.00-30.00/kg
Min. Order
1kg
Purity
99.99%
Supply Ability
1000
Release date
2024-05-16

503612-47-3, ApixabanRelated Search:


  • Apixaban
  • Apixaban, BMS 562247-01
  • 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]-
  • 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
  • BMS562247
  • BMS 562247-01
  • 1-(4-Methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid aMide
  • 1-(4-Methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4, 5-dihydropyrazolo[3,4-c]pyridine-3-carboxaMide
  • Nilotinib and its interMediate
  • Apixaban ,ELIQUIS
  • 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
  • Apixaban 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 ,ELIQUIS,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 API
  • Apixaban, >=99%
  • 1-(4-Methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidi
  • Apixaban extra pure
  • CS-343
  • Apixaba
  • BMS-562247-01; BMS 562247-01; BMS562247-01
  • 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-1H,4H,5H,6H,7H-pyrazolo[3,4-c]pyridine-3-carboxamide
  • 4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxo-1-piperidinyl) phenyl]-1H-pyrazolo[3,4-c]pyridine-3-carboxamide
  • Apixaban USP/EP/BP
  • pixaban
  • Apixaban (10mM in DMSO)
  • xaban
  • Apixaban Working Std.
  • 1-(4-Methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-...
  • Apixaban-amorphous
  • ApixabanQ: What is Apixaban Q: What is the CAS Number of Apixaban Q: What is the storage condition of Apixaban Q: What are the applications of Apixaban
  • Apxaban
  • 2-Butenoicacid,2-cyano-9-methyl-,ethylester
  • Benzeneethanol,10-amino-β,β-dimethyl-
  • Apishaban
  • Apixabar
  • 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-1H,4H,5H,6H,7H-pyrazolo[3,4-c]pyridine-3-carboxamide Apixaban
  • 1-(4-Methoxyphenyl)-7-oxo-6-[4-(2-oxo-1-piperidyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide
  • Apaisaban
  • Apixaban CRS(BMS-562247-01 CRS)
  • Apixaban Reference Standard
  • Apixaban CAS
  • apixaban high purity
  • Apashaban
  • 503612-47-3
  • C25H25N5O4
  • Inhibitors
  • Inhibitor
  • API
  • 503612-47-3