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SML0071

Sigma-Aldrich

Trapidil

≥98% (HPLC)

Synonym(s):

AR 12008, Avantrin, N,N-diethyl-5-methyl-[1,2,4]Triazolo[1,5-a]pyrimidin-7-amine, Rocornal, Trapymin, Trapymine

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About This Item

Empirical Formula (Hill Notation):
C10H15N5
CAS Number:
15421-84-8
Molecular Weight:
205.26
EC Number:
239-434-2
MDL number:
MFCD00193104
UNSPSC Code:
41116107
PubChem Substance ID:
329825135
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

H2O: ≥15 mg/mL

storage temp.

room temp

SMILES string

CCN(CC)c1cc(C)nc2ncnn12

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

InChI key

GSNOZLZNQMLSKJ-UHFFFAOYSA-N

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Application

Trapidil was used to study the mechanism of osteoclastogenesis and bone loss in mice.

Biochem/physiol Actions

Trapidil is an antiplatelet agent that acts in part as a phosphodiesterase inhibitor and as a competitive inhibitor of the platelet-derived growth factor (PDGF) receptor. Trapidil, with its vasodilator and NO releasing effect may have some potential to diminish the tissue injury. Trapidil suppresses platelet-derived growth factor (PDGF)-induced vascular smooth muscle cell (VSMC) proliferation by inhibiting Raf-1/extracellular signal-regulated kinase (ERK) via cAMP/protein kinase A (PKA). In addn. to cAMP/PKA activation, trapidil inhibits RhoA/ROCK activation.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Phosphodiesterases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Russell T Turner et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 25(7), 1637-1649 (2010-03-05)
Chronic hyperparathyroidism (HPT) is a common cause of metabolic bone disease. These studies investigated the underlying cellular and molecular mechanisms responsible for the detrimental actions of elevated parathyroid hormone (PTH) on the skeleton. Bone biopsies from hyperparathyroid patients revealed an
Salih Somuncu et al.
Pediatric surgery international, 24(3), 315-318 (2007-12-07)
We aimed to detect the protective effect of trapidil in ischemia-reperfusion (IR) injury due to ovarian torsion and detorsion. Thirty-two pubertal New Zealand albino rabbits were used. Adnexal torsion was created by rotating the left adnexa including the tubal and
Salih Somuncu et al.
International journal of urology : official journal of the Japanese Urological Association, 13(5), 601-605 (2006-06-15)
We aimed to detect the preventive effects of trapidil in ischemia-reperfusion (IR) injury due to testicular torsion and detorsion. Forty prepubertal albino rats were used. In the IR group, torsion was created by rotating the left testis over 2 h
W Sziegoleit et al.
International journal of clinical pharmacology and therapeutics, 45(1), 10-15 (2007-01-30)
In this study the effect of locally administered trapidil on human hand veins was examined. 10 healthy male volunteers aged 20 - 30 years were included. The dorsal hand vein compliance technique was used. In a crossover design the influence
Jodie M Dodd et al.
The Cochrane database of systematic reviews, (6)(6), CD006780-CD006780 (2010-06-18)
Pregnancy complications such as pre-eclampsia and eclampsia, intrauterine growth restriction and placental abruption are thought to have a common origin related to abnormalities in the development and function of the placenta. To compare, using the best available evidence, the benefits
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Articles

Phosphodiesterases

Cyclic nucleotide phosphodiesterases (PDEs) catalyze the hydrolysis of cAMP and/or cGMP. There are 11 different mammalian PDE families.

Related Content

Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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