Tirofiban

Aggrastat · MK-383 · C07965 · CS-584 · irofiban · TIROFIBAN · Tirofiban(L700462 · Tirofiban USP/EP/BP

https://huagongshe.com/ko/chemical/60947

식별자 및 물리적 특성

CAS No.	144494-65-5
분자식	C22H36N2O5S
평균 분자량	440.6 g/mol
단동위원소 질량	440.23449325 g/mol
SMILES	CCCCS(=O)(=O)N[C@@H](Cc1ccc(OCCCCC2CCNCC2)cc1)C(=O)O
InChIKey	COKMIXFXJJXBQG-NRFANRHFSA-N
PubChem CID	60947
ChEMBL	CHEMBL916
ChEBI	CHEBI:9605
EC No.	635-682-4
DTXSID	DTXSID20162730

화학 및 물리적 성질

XLogP	1.4
극성 표면적	113
수소 결합 공여자 수	3
수소 결합 수용자 수	7
회전 가능 결합 수	14
무거운 원자 수	30
형식 전하	0
복잡도	579
의약품	Pharmaceuticals -> Listed in ZINC15
LogP(분배 계수)	log Kow = 1.4 /Estimated/
Color/Form	White solid
용해도	Very slightly soluble3.17e-03 g/LLimited solubility
Human Drugs	Breast FeedingLactationMilk, HumanFibrinolytic AgentsPlatelet Aggregation Inhibitors
녹는점	223-225 °C223-225°
증기압	5.2X10-16 mmHg at 25 °C /Estimated/
헨리 상수	Henry's Law constant = 7.4X10-15 atm-cu m/mole at 25 °C /Estimated/1.3×109 mol/(m3Pa) at 25℃, HSDB (2015)
Physical Description	Solid
Dissociation Constants	pKa = 3.3 (carboxylic acid)pKa = 10.5 (amine) /Estimated/
Other Experimental Properties	White to off-white, non-hygroscopic, free-flowing powderMW: 495.08very slightly soluble in water. /Tirofiban hydrochloride salt mono hydrate/Hydroxyl radical reaction rate constant = 1.6X10-10 cu cm/molec-sec at 25 °C /Estimated/
끓는 점	611.7±65.0 °C(Predicted)
밀도	1.154±0.06 g/cm3(Predicted)
저장 조건	Keep in dark place,Sealed in dry,Store in freezer, under -20°C
물리적 상태	Solid
pKa(산도 계수)	3.37±0.10(Predicted)
색상	White to off-white
BRN	6182267
InChI	1S/C22H36N2O5S/c1-2-3-16-30(27,28)24-21(22(25)26)17-19-7-9-20(10-8-19)29-15-5-4-6-18-11-13-23-14-12-18/h7-10,18,21,23-24H,2-6,11-17H2,1H3,(H,25,26)/t21-/m0/s1
InChIKey	COKMIXFXJJXBQG-NRFANRHFSA-N
SMILES	CCCCS(=O)(=O)N[C@@H](Cc1ccc(OCCCCC2CCNCC2)cc1)C(O)=O

화학적 성질

Tirofiban is an Off-White to Pale Yellow Solid. It is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide, which should be purged with an inert gas. The solubility of tirofiban in these solvents is approximately 30 mg/ml.

안전 및 규제

GHS 분류	WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
FDA 요건	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl tirofiban hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Tirofiban Hydrochloride/
Hazard Classes and Categories	Skin Irrit. 2 (100%)
처리 방법	SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
상호 작용	Concurrent use /with other platelet aggregation inhibitors (especially inhibitors of platelet receptor GP IIb/IIIa) is not recommended.Data from a large clinical study indicate that concomitant administration of tirofiban and levothyroxine or omeprazole was associated with a higher clearance of tirofibanthe clinical importance of this effect is not known.
환경 거동	TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 40,000(SRC), determined from a structure estimation method(2), indicates that tirofiban is expected to be immobile in soil(SRC). Volatilization of tirofiban from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.4X10-15 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Estimated pKa values of 3.3 (carboxylic acid group) and 10.5 (amino group)(4) indicate that tirofiban will exist as a zwitterion at pH values of 5 to 9 and therefore volatilization from moist soil is not expected to be an important fate process. Tirofiban is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.2X10-16 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2005).

용도

Tirofiban (Aggrastatt, MK-0383; L-700,462) is a parenteral, highly specific, and potent GPIIb/IIIa antagonist that was approved for patient use in 1998 for the treatment of unstable angina and non-Q-wave myocardial infarction.Tirofiban is a nonpeptide GP IIb/IIIa antagonist that binds reversibly to IIb/IIIa receptors. Tirofiban is a non-peptide reversible antagonist of the platelet integrin glycoprotein (GP) IIbIIIa receptor used as an antiplatelet drug.Tirofiban is a small molecule inhibitor of the protein-protein interaction between fibrinogen and the platelet integrin receptor GP IIb/IIIa and is the first drug candidate whose origins can be traced to a pharmacophore-based virtual screening lead.

일반 설명

Tirofiban is a nonpeptide that appears unrelatedchemically to eptifibatide, but actually has many similarities.The chemical architecture incorporates a systemthat is mimicking the RGD moiety that is present in eptifibatide.This can be seen in the distance between the nitrogenof the piperidine ring, which mimics the basic nitrogen ofarginine in the RGD sequence, and the carboxylic acid,which mimics the acid of aspartate in the RGD sequence.The basic nitrogen and the carboxylic acid of tirofiban areseparated by approximately 15 to 17 (16–18 atoms). Thisis the optimum distance seen in the RGD sequence of theplatelet receptor. Tirofiban is useful in treating non–Q wavemyocardial infarction and unstable angina.