Basic information
- CAS
15421-84-8- Standard SMILES
CCN(CC)c1cc(C)nc2ncnn12- InChIKey
GSNOZLZNQMLSKJ-UHFFFAOYSA-N- Molecular formula
- C10H15N5
- Average molar mass
- 205.26 g/mol
- Monoisotopic mass
- 205.1327455
Overview
Trapidil is a member of triazolopyrimidines.
Names & identifiers
- Preferred name
- Trapidil
- IUPAC
- N,N-diethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
- English name
- 7-(DIETHYLAMINO)-5-METHYL-S-TRIAZOLO[1,5-A]PYRIMIDINE
- Molecular formula
- C10H15N5
- Molecular weight
- 205.26
Names & synonyms
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
Show more names
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)
Database identifiers
- CAS
15421-84-8- PubChem CID
- 5531
- DTXSID
DTXSID0045416- ChEMBL
CHEMBL132767- ChEBI
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 46.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 206
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
Pharmaceutical
LogP1.42
Solubility>30.8 [ug/mL] (The mean of the results at pH 7.4)
Physicochemical properties
- Melting point
- 98 · 98-99.4° (Pfeifer); 102-104° from heptane (Tenor)
- Density
- 1.2 · 1.20±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 2 O: · H2O: ≥15mg/mL
- pka
- 2.79 · pKs = 2.79(at 25℃)
- form
- powder
- color
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (97.4%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Trapidil
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- wgk
- 3
- Toxicity
- LD50 in mice, rats (mg/kg): 115, 76 i.v.; 380, 235 orally; 155, 100 i.p.; 132, 100 s.c. (Fuller)
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
Chemistry & industry
Pharmacology
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.
Uses & manufacturing
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…