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Eptifibatide

Product Name
Eptifibatide
CAS No.
188627-80-7
Chemical Name
Eptifibatide
Synonyms
Intrifiban;INTEGRELIN;Eptifibatide;Eptifitatide;Eptifibatide USP/EP/BP;Eptifibatide (free base);Integrilin(Eptifibatide);Eptifibatide acetate salt;MAP-LYS-GLY-ASP-TRP-PRO-CYS-NH2;3-Mercaptopropionyl-HoMoarg-Gly-Asp-Trp-Pro-Cys-NH2
CBNumber
CB0416566
Molecular Formula
C35H49N11O9S2
Formula Weight
831.97
MOL File
188627-80-7.mol
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Eptifibatide Property

Density 
1.60±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
DMF: 30 mg/ml,DMSO: 14 mg/ml,Ethanol: 5 mg/ml,PBS (pH 7.2): 5 mg/ml
form 
A crystalline solid
pka
4.01±0.10(Predicted)
color 
White to off-white
Water Solubility 
Soluble to 5 mg/ml in water
InChI
InChI=1/C35H49N11O9S2/c36-30(51)25-18-57-56-13-10-27(47)42-22(8-3-4-11-39-35(37)38)31(52)41-17-28(48)43-23(15-29(49)50)32(53)44-24(14-19-16-40-21-7-2-1-6-20(19)21)34(55)46-12-5-9-26(46)33(54)45-25/h1-2,6-7,16,22-26,40H,3-5,8-15,17-18H2,(H2,36,51)(H,41,52)(H,42,47)(H,43,48)(H,44,53)(H,45,54)(H,49,50)(H4,37,38,39)/t22-,23-,24-,25-,26-/s3
InChIKey
CZKPOZZJODAYPZ-ITVGJGJRNA-N
SMILES
N12CCC[C@H]1C(=O)N[C@@H](CSSCCC(=O)N[C@@H](CCCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1C3C=CC=CC=3NC=1)C2=O)C(N)=O |&1:4,8,17,33,41,r|
CAS DataBase Reference
188627-80-7
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Safety

HS Code 
2933299090
Hazardous Substances Data
188627-80-7(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

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

P314Get medical advice/attention if you feel unwell.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
21578
Product name
Eptifibatide
Purity
≥95%
Packaging
5mg
Price
$47
Updated
2024/03/01
Cayman Chemical
Product number
21578
Product name
Eptifibatide
Purity
≥95%
Packaging
10mg
Price
$87
Updated
2024/03/01
Cayman Chemical
Product number
21578
Product name
Eptifibatide
Purity
≥95%
Packaging
25mg
Price
$206
Updated
2024/03/01
Cayman Chemical
Product number
21578
Product name
Eptifibatide
Purity
≥95%
Packaging
50mg
Price
$360
Updated
2024/03/01
Tocris
Product number
4725
Product name
Eptifibatide
Packaging
1
Price
$85
Updated
2021/12/16
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Eptifibatide Chemical Properties,Usage,Production

Description

Eptifibatide is a reversible antagonist of the glycoprotein llb/llla complex, a specific platelet adhesion receptor that plays a central role in the cascade of thrombus formation by allowing mediators such as fibrinogen or von Willbrand factor to cross-link adjacent platelets and to give rise to aggregation. In diverse animal experimental models of arterial thrombosis, treatment with Eptifibatide resulted in an enhanced lysis of occlusive thrombus and a restoration of arterial blood flow. In clinical trials involving patients with acute coronary syndromes, Eptifibatide demonstrated a significant decrease in the incidence of death or nonfatal myocardial infarction at 30 days. In other trials in patients undergoing percutaneous coronary intervention (PCI), it showed a positive trend. Eptifibatide has the advantage of being short acting, its antiplatelet effect being rapidly reversible.

Originator

Cor Therapeutics (US)

Uses

Eptifibatide is a cyclical heptapeptide with anticoagulant activity. Eptifibatide selectively and reversibly binds to and blocks the platelet glycoprotein IIb/IIIa receptor. This prevents the binding of fibrinogen, von Willebrand factor, and other adhesive ligands and leads to an inhibition of platelet aggregation and prevents thrombus development. It is an efficient peptide drug to reduce the risk of cardiac ischemic events, however has a short half-life. Therefore, antithrombotic agents like eptifibatide are required to become improved with a protected and targeted delivery system such as using nano-liposomes to the site of thrombus.

Definition

ChEBI: Eptifibatide is a synthetic homodetic cyclic peptide comprising N(alpha)-(3-sulfanylpropanoyl)homoarginyl, glycyl, aspartyl, tryptophyl, prolyl and cysteinamide residues connected in sequence and cyclised via a disulfide bond. Derived from a protein found in the venom of the southeastern pygmy rattlesnake, Sistrurus miliarus barbouri, eptifibatide is an anti-coagulant that inhibits platelet aggregation by selectively blocking the platelet glycoprotein IIb/IIIa receptor, so preventing the binding of fibrinogen, von Willebrand factor, and other adhesive ligands. It is used in the management of unstable angina and in patients undergoing coronary angioplasty and stenting procedures. It has a role as a platelet aggregation inhibitor and an anticoagulant. It is an organic disulfide, a macrocycle and a homodetic cyclic peptide.

brand name

Integrilin

General Description

Eptifibatide (188627-80-7) is a syntheticcyclic heptapeptide that acts as a GPIIb/IIIa receptor antagonist,thus causing inhibition of platelet aggregation. Itsstructure is based on the natural product barbourin, a peptideisolated from the venom of a pygmy rattlesnake (Sistrurusmilarud barbouri). As part of the structure, there is a sequenceRGD that can bind to the RGD receptor found onplatelets and block its ability to bind with fibrinogen. Thisagent is used in the treatment of unstable angina and for angioplasticcoronary interventions.

Biological Activity

Eptifibatide is a potent glycoprotein IIb/IIIa antagonist (GPIIb/IIIa; Kd = 120 nM) that inhibits platelet aggregation. Eptifibatide prevents binding of the adhesion proteins fibrinogen and von Willebrand factor to GPIIb/IIIa on the surface of activated platelets to prevent aggregation and thrombus formation. It inhibits ADP-induced citrated blood aggregation (IC50 = 0.11-0.22 μg/ml) in vitro and in vivo (IC50 = 52 μg/ml in porcine plasma). Formulations containing eptifibatide have been used to reduce risk of thrombolysis in myocardial infarction in patients undergoing percutaneous coronary intervention.

Mechanism of action

Eptifibatide reversibly inhibits platelet aggregation by preventing the binding of fibrinogen, von Willebrand factor and other adhesive ligands to the glycoprotein (GP) IIb/IIIa receptors. When administered intravenously, eptifibatide inhibits ex vivo platelet aggregation in a dose- and concentration-dependent manner.
www.accessdata.fda.gov

Clinical Use

Eptifibatide is a cyclic heptapeptide composed of six amino acids and one mercaptopropionyl residue. The cyclization is completed via a disulfide linkage between the cysteine and the mercaptopropionyl moieties. The lysine-glycine-aspartate component of eptifibatide is highly specific for the GPIIb/IIIa receptor, with low binding affinity, as indicated by the rapid dissociation constant. Because of this, eptifibatide is a reversible, parenterally administered antagonist of platelet aggregation.

Drug interactions

Potentially hazardous interactions with other drugs Iloprost: increased risk of bleeding.

Metabolism

Renal excretion accounts for approximately 50% of total body clearance of eptifibatide; approximately 50% of the amount cleared is excreted unchanged in the urine.

storage

Store at -20°C

Eptifibatide Preparation Products And Raw materials

Raw materials

Preparation Products

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Eptifibatide Suppliers

Toronto Research Chemicals
Tel
--
Fax
--
Email
info@trc-canada.com
Country
Canada
ProdList
6038
Advantage
71
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View Lastest Price from Eptifibatide manufacturers

Shandong Huizhihan Supply Chain Co., Ltd
Product
Eptifibatide 188627-80-7
Price
US $0.00-0.00/BOX
Min. Order
1BOX
Purity
99%
Supply Ability
20T
Release date
2024-11-12
Shandong Huizhihan Supply Chain Co., Ltd
Product
Eptifibatide 188627-80-7
Price
US $0.00-0.00/box
Min. Order
1box
Purity
99%
Supply Ability
2000
Release date
2024-10-29
Shanghai Affida new material science and technology center
Product
Eptifibatide 188627-80-7
Price
US $0.00-0.00/Box
Min. Order
1Box
Purity
99
Supply Ability
50000KG/month
Release date
2024-04-12

188627-80-7, EptifibatideRelated Search:


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  • 3-Mercaptopropionyl-HoMoarg-Gly-Asp-Trp-Pro-Cys-NH2
  • Eptifibatide,MPA-HAR-Gly-Asp-Trp-Pro-Cys-NH2,{MPA}{HAR}GDWPC-NH2
  • L-Cysteinamide, N6-(aminoiminomethyl)-N2-(3-mercapto-1-oxopropyl)-L-lysylglycyl-L-α-aspartyl-L-tryptophyl-L-prolyl-, cyclic (1→6)-disulfide
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  • 2-((3R,11S,17S,20S,25aS)-20-((1H-Indol-3-yl)methyl)-3-carbamoyl-11-(4-guanidinobutyl)-1,9,12,15,18,21-hexaoxodocosahydro-1H-pyrrolo[2,1-g][1,2,5,8,11,14,17,20]dithiahexaazacyclotricosin-17-yl)acetic acid
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  • 2-[(3R,11S,17S,20S,25aS)-11-(4-carbamimidamidobutyl)-3-carbamoyl-20-[(1H-indol-3-yl)methyl]-1,9,12,15,18,21-hexaoxo-docosahydro-1H-pyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-17-yl]acetic acid
  • deamino-Cys(1)-D-hArg-Gly-D-Asp-Trp-Pro-D-Cys(1)-NH2
  • 188627-80-7
  • C35H49N11O9S2
  • Intermediates & Fine Chemicals
  • Peptides
  • Pharmaceuticals
  • GMP
  • 188627-80-7