Tirofiban

Structural formula
General
Non-proprietary name	Tirofiban
other names	N - (Butylsulfonyl) -4- [4- (4-piperidyl) butyl] - L -tyrosine (2 S ) -2- (Butylsulfonylamino) -3- [4- (4-piperidyl) butoxy] phenylpropanoic acid ( S ) -2- (Butylsulfonylamino) -3- [4- (4-piperidyl) butoxy] phenylpropanoic acid ( S ) -2- (Butylsulfonylamino) -3- [4- (4-piperidyl) butoxy] phenylpropionic acid
Molecular formula	C 22 H 36 N 2 O 5 S
Brief description	White dust
External identifiers / databases
CAS number 144494-65-5 (Tirofiban) 150915-40-5 (tirofiban hydrochloride · · mono hydrate ) 142373-60-2 ( tirofiban hydrochloride ) EC number 635-682-4 ECHA InfoCard 100.163.548 PubChem 60947 ChemSpider 54912 DrugBank DB00775 Wikidata Q415366
Drug information
ATC code	B01 AC17
Drug class	Antiplatelet drugs
properties
Molar mass	440.60 g mol −1
Physical state	firmly
Melting point	223–225 ° C (Tirofiban)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tirofiban is a drug that is used as a powerful platelet aggregation inhibitor for the treatment of acute coronary syndrome due to its action on thrombocytes (blood platelets) . It is given as an intravenous infusion.

Mode of action

Tirofiban is a synthetic inhibitor of the glycoprotein IIb / IIIa receptor of platelets . This receptor acts as the critical binding site in the process of platelet aggregation, which is the first step in any clotting process. The inhibition by tirofiban is competitive, i.e. reversible.

Indications

Tirofiban is used for unstable angina pectoris and non-ST elevation infarction (NSTEMI). It is also an agent that is used as part of a percutaneous intervention in acute coronary syndromes, especially when blood clots can be displayed in the coronary artery.

unwanted effects

Heavy bleeding rarely occurs with continuous infusion of the drug, while light bleeding is often observed. Headache, nausea, fever and a drop in the platelet count below 100,000 / µl can occur.

Contraindications and interactions

Tirofiban must not be used if the platelet count is below 100,000 / µl, if there is a non-adjustable hypertension, a coagulation disorder or a brain disease that is prone to bleeding. After major operations, injuries or bleeding, you should wait six weeks before the drug can be given. Other substances administered at the same time that also affect the blood coagulation system lead to an increased tendency to bleed.

For regional anesthesia procedures close to the spinal cord ( spinal anesthesia or epidural anesthesia ), Tirofiban should be discontinued eight hours in advance and given again at least four hours after the operation.

marketing

Tirofiban was developed from the disintegrin echistatin , a component of the snake venom of Echis carinatus (sand rattle otter ). Until 2008, the drug was marketed by MSD Sharp & Dohme under the trade name Aggrastat ^® . In January 2008, the rights to the substance were acquired by Iroko Pharmaceuticals (now Correvio International Sàrl). The list price for 250 ml of an infusion solution with 50 µg Tirofiban per ml was € 256.25 in 2017.

Web links

• K. Huber: Tirofiban (Aggrastat®) - an overview of the current publication and study situation. In: Journal of Cardiology. 7 (2), 2000, pp. 84-87. (PDF file; 835 kB)

Individual evidence

1. ↑ ^{a b c} Datasheet Tirofiban at Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
2. ^ The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition. 2006, ISBN 0-911910-00-X , p. 1627.
3. ^ RA O'Rourke: Unstable Angina and Non-ST-Segment Elevation Myocardial Infarction: Clinical Presentation, Diagnostic Evaluation, and Medical Management. In: V. Fuster, W. Alexander, RA O'Rourke (ed.): Hurst's The Heart. 11th edition. McGraw-Hill, New York 2004, ISBN 0-07-142264-1 , p. 1266.
4. ↑ Wiebke Gogarten, Hugo Van Aken: Perioperative thrombosis prophylaxis - platelet aggregation inhibitors - importance for anesthesia. In: AINS - Anesthesiology · Intensive Care Medicine · Emergency Medicine · Pain Therapy. 47, 2012, pp. 242-252, doi: 10.1055 / s-0032-1310414 .
5. ↑ SA Kozek-Langenecker, D. Fries, M. Gütl, N. Hofmann, P. Innerhofer, W. Kneifl, L. Neuner, P. Perger, T. Pernerstorfer, G. Pfanner and others: Locoregional anesthesia with anticoagulant medication. Recommendations of the Perioperative Coagulation Working Group (AGPG) of the Austrian Society for Anaesthesiology and Intensive Care Medicine (ÖGARI). In: The anesthesiologist. Volume 54, Number 5, 2005, pp. 476-484, doi: 10.1007 / s00101-005-0827-0 .
6. ↑ Kastin: Handbook of Biologically Active Peptides , Elsevier, April 28, 2011. ISBN 978-0-12-369442-3 .
7. ↑ Website Correvio International ( Memento of the original from September 17, 2016 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. 
8. ^ Iroko Pharmaceuticals Acquires Rights to Cardiovascular Product from Merck & Co., Inc. at: businesswire.com , January 30, 2008.
9. ↑ Red List 2017, ISBN 978-3-946057-10-9 .

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