Clopidogrel
(S)-Clopidogrel · methyl (2s)-2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetate · Thieno[3,2-c]pyridine-5(4H)-acetic acid, α-(2-chlorophenyl)-6,7-dihydro-, methyl ester, (αS)- · CLOPIDOGREL · Chlopidogrel · ClopidogrelHcl · Clopidogrel–d4 · Clopidogrel API
Identifikatoren & physikalische Daten
| CAS No. | 113665-84-2 |
|---|---|
| Summenformel | C16H16ClNO2S |
| Durchschnittliche Molmasse | 321,8 g/mol |
| Monoisotopische Masse | 321,0590276 g/mol |
| SMILES | COC(=O)[C@H](c1ccccc1Cl)N1CCc2sccc2C1 |
| InChIKey | GKTWGGQPFAXNFI-HNNXBMFYSA-N |
| PubChem CID | 60606 |
| ChEMBL | CHEMBL1771 |
| ChEBI | CHEBI:37941 |
| EC No. | 601-269-2 |
| DTXSID | DTXSID6022848 |
Chemische & physikalische Eigenschaften
| XLogP | 3,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 57,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 21 |
| Formalladung | 0 |
| Komplexität | 381 |
| Color/Form | Colorless oil |
| Löslichkeit | 15.1 [ug/mL] (The mean of the results at pH 7.4)DMSO: 50mg/ml in DMSO |
| Schmelzpunkt | 158 |
| Optical Rotation | Mol wt 419.90. White crystals. mp 184 °C. Specific optical rotation at 20 °C for D (sodium) line = +55.10 deg (c = 1.891 in methanol). Soluble in water, methanol /Clopidogrel hydrogen sulfate/Specific optical rotation at 25 °C for D (sodium) line = +55.10 deg (c = 1.61 in methanol) |
| Physical Description | Solid |
| Collision Cross Section | 166.53 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]168.65 Ų [M+H]+ |
| Siedepunkt | 423.7±45.0 °C(Predicted) |
| Dichte | 1.317±0.06 g/cm3(Predicted) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Oil |
| pKa (Säurekonstante) | 4.56±0.20(Predicted) |
| Farbe | Colorless to light yellow |
| Henry-Konstante | 4.5×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | InChI=1/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/s3 |
| InChIKey | GKTWGGQPFAXNFI-UJHUVDBMNA-N |
| SMILES | [C@@H](C1C=CC=CC=1Cl)(N1CCC2SC=CC=2C1)C(=O)OC |&1:0,r| |
| CAS Datenbank | 113665-84-2(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | H362 (100%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]P203, P260, P263, P264, P270, and P318 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including clopidogrel bisulfate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Clopidogrel bisulfate/ |
| Hazard Classes and Categories | Lact. (100%) |
| Entsorgungsverfahren | SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash. |
| Wechselwirkungen | Aspirin has not been found to modify the clopidogrel mediated inhibition of ADP-induced platelet aggregation, nor has it been found to increase the prolongation of bleeding time induced by clopidogrelhowever, clopidogrel potentiated the effect of aspirin on collagen-induced platelet aggregation.Coadministration of Plavix and nonsteroidal anti-inflammatory drugs (NSAIDs) increases the risk of gastrointestinal bleeding.Potential pharmacokinetic interaction (decreased plasma concentrations of active metabolite of clopidogrel) and pharmacodynamic interaction (reduced antiplatelet effects) with certain proton-pump inhibitors. Because clopidogrel is a prodrug that is dependent on its activation to an active metabolite principally by CYP2C19, concurrent use of drugs such as omeprazole that inhibit CYP2C19 reduces plasma concentrations of the active metabolite and potentially could reduce clinical efficacy. |
Anwendungen & Verwendung
Beschreibung
Clopidogrel was launched in the US as a potent inhibitor of platelet aggregation for the preventive management of secondary ischemic events, including MI, stroke and vascular deaths. Clopidogrel can be synthesized in 4 steps (including an optical resolution to the S active enantiomer) from 2-(2- ch1orophenyl)-glycine, the key step being the cyclization to thienopyridine with formaldehyde and acetic acid. Clopidogrel belongs to the original chemical class of Ticlopidine, but shows fewer side effects (in particular, bone-marrowsuppressing effects) at the dosage generally used. Like Ticlopidine, it is an Adenosine diphosphate (ADP) antagonist acting at the purinergic P2y receptor. In in vivo experiments with rabbits, Clopidogrel shows a maximal antiaggregant effect at 20mg/kg po, reducing adhesion of platelets to the vascular subendothelium ; moreover, it reduces myointimal thickening occuring after endothelial injury of rat carotid artery. Clopigrel does not affect platelet aggregation in vitro ; actually, its in vivo activity is highly dependent on hepatic metabolism. The results of a CAPRIE trial (Clopidogrel versus Aspirin in patients at risk of ischemic events) demonstrated that Clopidogrel was well tolerated and more effective than aspirin.
History
Clopidogrel, sold under the brand name Plavix among others, is an antiplatelet medication used to reduce the risk of heart disease and stroke in those at high risk. Clopidogrel was discovered by Dr Fernand Eloy, it was patented in 1982, and approved for medical use in 1997. It is on the World Health Organization's List of Essential Medicines.
Verwenden
anthelmintic, antiparasitic, antimite