Trapidil
Grundinformationen
- CAS
15421-84-8- Standard-SMILES
CCN(CC)c1cc(C)nc2ncnn12- InChIKey
GSNOZLZNQMLSKJ-UHFFFAOYSA-N- Summenformel
- C10H15N5
- Durchschnittliche Molmasse
- 205,26 g/mol
- Monoisotopische Masse
- 205,1327455
Überblick
Trapidil is a member of triazolopyrimidines.
Namen und Bezeichner
- Bevorzugter Name
- Trapidil
- IUPAC
- N,N-diethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
- Lokaler Name
- Trapidil
- Englischer Name
- 7-(DIETHYLAMINO)-5-METHYL-S-TRIAZOLO[1,5-A]PYRIMIDINE
- Summenformel
- C10H15N5
- Molmasse
- 205.26
Namen und Synonyme
trapidil15421-84-8RocornalTrapyminN,N-diethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amineAR 12008TrapidilumDTXSID0045416AR-12008(1,2,4)Triazolo(1,5-a)pyrimidin-7-amine, N,N-diethyl-5-methyl-EYG5Y6355EDTXCID8025416
Weitere Namen anzeigen
ar12008AvantrinTrapymineTrapidil CRSTrapidil (AR12008)Trapidil >=98% (HPLC)Trapidil, 10 mM in DMSO
[1,2,4]Triazolo[1,5-a]pyrimidin-7-amine, N,N-diethyl-5-methyl-N,N-diethyl-5-methyl-(1,2,4)triazolo(1,5-a)pyrimidin-7-amineRefChem:389337C01DX117-Diethylamino-5-methyl(1,2,4)triazolo(1,5-a)pyrimidine239-434-2MFCD00193104Rocornal (TN)
Datenbank-Bezeichner
- CAS
15421-84-8- PubChem CID
- 5531
- DTXSID
DTXSID0045416- ChEMBL
CHEMBL132767
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,7
- Polarare Oberfläche (TPSA)
- 46,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 206
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
Pharmaceutical
LogP1.42
Solubility>30.8 [ug/mL] (The mean of the results at pH 7.4)
Physikochemische Eigenschaften
- Schmelzpunkt
- 98 · 98-99.4° (Pfeifer); 102-104° from heptane (Tenor)
- Dichte
- 1.2 · 1.20±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- Löslichkeit
- 2 O: · H2O: ≥15mg/mL
- pka
- 2.79 · pKs = 2.79(at 25℃)
- Aggregatzustand
- powder
- Farbe
- white to tan
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1S/C10H15N5/c1-4-14(5-2)9-6-8(3)13-10-11-7-12-15(9)10/h6-7H,4-5H2,1-3H3
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H315 (97.4%): 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.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Irrit. 2 (97.4%)
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Trapidil
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- wgk
- 3
- risk_code
- 36/37/38
- Toxizität
- LD50 in mice, rats (mg/kg): 115, 76 i.v.; 380, 235 orally; 155, 100 i.p.; 132, 100 s.c. (Fuller)
- hazard_code
- Xi
- safety_code
- 26
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
PharmacodynamicsTrapidil exerts vasodilatory and antiplatelet effects. It also inhibits the activity of platelet derived growth factor (PDGF).
Mechanism of Action
Trapidil is thought to inhibit cyclic adenosine monophosphate (cAMP) phosphodiesterase enzymes. The resultant increase in cAMP potentiates the inhibition of platelets by adenosine. The reduction in platelet activation is likely responsible for the decrease in thromboxane A2 generation seen with trapidil. The increase in cAMP is also likely responsible for the vasdilatory action of trapidil. The increase in protein kinase A activity due to increased cAMP activated L-type calcium channels in the heart leading to increased depolarization and a positive inotropic effect. Lastly, PKA inactivates Raf-1, an activator of mitogen activated protein kinase (MAPK), which leads to a reduction in MAPK activation. This reduction in MAPK prevents mitogenesis due to PDGF binding to PDGF receptors.
Biological Half-LifeThe half life of elimination is 1.31 h for a single dose and 1.14 h for steady state dosing.
MeSH Pharmacological Classification
Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
Drugs used to cause dilation of the blood vessels.
Absorption, Distribution and Excretion
Trapidil has a Tmax of 1 h.
The apparent clearance is 179 mL/min for a single dose and 273 mL/min for steady state dosing.
Verwendung und Herstellung
Zugehörige Reaktionen
0
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Notizen zur Verbindung
Wird geladen…