Trapidil - 10mM in DMSO , CAS No.15421-84-8

CAS: 15421-84-8 Cat. No.: T421833 Molecular Weight: 205.26 EC Number: 239-434-2 PubChem CID: 5531

GRADE & PURITY 10mM in DMSO

Synonyms

trapidil|15421-84-8|Rocornal|Trapymin|Avantrin|Trapymine|N,N-diethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine|AR 12008|AR-12008|(1,2,4)Triazolo(1,5-a)pyrimidin-7-amine, N,N-diethyl-5-methyl-|7-Diethylamino-5-methyl-s-triazolo(1,5-a)pyrimidine|MLS0

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Trapidil Trapidil (Rocornal, Trapymin, Avantrin, Trapymine) is a PDGF antagonist that can inhibit the proliferation of the PDGF-producing glioma cells.

Targets

PDGF

In vitro

Trapidil interrupts the autocrine loop at the PDGF and PDGF-receptor level.Trapidil has proved to possess a significant antiproliferative activity. The addition of 100 to 400 μg/ml trapidil significantly reduced cell proliferation induced by different growth factors (FCS, PDGF-BB, bFGF, EGF), the highest inhibitory effect being on PDGF-BB stimulated Mesangial cell(MC) growth. The effect of the drug was dose-dependent and seemingly specific. Trapidil is an anti-platelet drug active against various aggregating agents, such as collagen, ADP, arachidonic acid, PAF and calcium ionophore. It exerts its action by blocking the biosynthesis of thromboxane A2 and antagonizing its effect at the receptor level, and by stimulating the synthesis and release of prostacyclin. Trapidil strongly inhibited osteoclast formation in co-cultures of bone marrow cells and osteoblasts without affecting receptor activator of NF-κB ligand (RANKL) or osteoprotegerin expression in osteoblasts. In addition, trapidil suppressed RANKL-induced osteoclast formation from osteoclast precursors. Trapidil reduced RANKL-induced expression of nuclear factor of activated T cells, cytoplasmic 1 (NFATc1), a master transcription factor for osteoclastogenesis, without affecting the expression of c-Fos that functions as a key upstream activator of NFATc1 during osteoclastogenesis. Trapidil has also been reported to inhibit phosphodiesterase, thromboxane A2, and CD40 signaling and activate protein kinase A.

In vivo

Trapidil is an antiplatelet drug with specific platelet-derived growth factor antagonism and antiproliferative effects in the rat and rabbit models after balloon angioplasty. Trapidil had a potent inhibitory effect on osteoclast formation and bone resorption induced by interleukin-1 in an animal model. No abnormal symptoms, such as changes in body weight, diarrhea, high fever, and convulsion, were observed after intraperitoneal injections of trapidil.

Cell Research(from reference)

Cell lines：Human Mesangial cell lines 

Concentrations：100 μg/ml 

Incubation Time：96 h 

Specifications

Synonyms

trapidil | 15421-84-8 | Rocornal | Trapymin | Avantrin | Trapymine | N, N-diethyl-5-methyl-[1, 2, 4]triazolo[1, 5-a]pyrimidin-7-amine | AR 12008 | AR-12008 | (1, 2, 4)Triazolo(1, 5-a)pyrimidin-7-amine, N, N-diethyl-5-methyl- | 7-Diethylamino-5-methyl-s-triazolo(1, 5-a)pyrimidine | MLS0

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Trapidil (Rocornal, Trapymin, Avantrin, Trapymine) is a PDGF antagonist that can inhibit the proliferation of the PDGF-producing glioma cells.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Product Properties

• ALogP: 1.922
• Rotatable Bond: 3

Names and Identifiers

• Pubchem Sid: 528773201
• Canonical Smiles: CCN(CC)C1=CC(=NC2=NC=NN12)C
• IUPAC Name: N,N-diethyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
• InChIKey: GSNOZLZNQMLSKJ-UHFFFAOYSA-N
• 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
• Isomeric SMILES: CCN(CC)C1=CC(=NC2=NC=NN12)C
• PubChem CID: 5531
• Molecular Weight: 205.26

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Triazolopyrimidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Triazolopyrimidines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Triazolopyrimidines
• Alternative Parents: Dialkylarylamines Aminopyrimidines and derivatives Triazoles Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Triazolopyrimidine - Dialkylarylamine - Aminopyrimidine - Pyrimidine - Heteroaromatic compound - 1,2,4-triazole - Triazole - Azole - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triazolopyrimidines. These are polycyclic aromatic compounds containing triazole ring fused to a pyrimidine ring. Triazole is a five-membered ring consisting of two carbon atoms and three nitrogen atoms. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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PDE3B Tclin Phosphodiesterase 3B (312 Activities)

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Homo sapiens (32628 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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GMNN Tbio Geminin (128009 Activities)

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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Associated Targets(non-human)

Mapk1 MAP kinase ERK2 (650 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Plasmodium falciparum (966862 Activities)

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Cavia porcellus (23802 Activities)

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Canis familiaris (36305 Activities)

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Rattus norvegicus (775804 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• DMSO(mg / mL) Max Solubility: 41
• DMSO(mM) Max Solubility: 199.7466628
• Water(mg / mL) Max Solubility: 41
• Water(mM) Max Solubility: 199.7466628
• Molecular Weight: 205.260 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 205.133 Da
• Monoisotopic Mass: 205.133 Da
• Topological Polar Surface Area: 46.300 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 206.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1