Structure of Propyl pyrazole triol
CAS No.: 263717-53-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Propyl pyrazole triol (PPT) is a selective estrogen receptor alpha (ERα) agonist. The relative binding affinity of Propyl pyrazole triol for ERα (ERα: 49%) around 410 times higher compared with estrogen receptor beta (ERβ: 0.12%). PPT also exerts anti-diabetic effects in mouse models.
Synonyms: PPT
4.5
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CAS No. : | 263717-53-9 |
Formula : | C24H22N2O3 |
M.W : | 386.44 |
SMILES Code : | C(C1C(C2C=CC(=CC=2)O)=NN(C2C=CC(=CC=2)O)C=1C1C=CC(=CC=1)O)CC |
Synonyms : |
PPT
|
MDL No. : | MFCD03453628 |
InChI Key : | IOTXSIGGFRQYKW-UHFFFAOYSA-N |
Pubchem ID : | 5040063 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
HBE33 cells | 1-100 nM | 6 hours | PPT increased Alt Ext-induced IL-33 release in hBE33 cells | Allergy. 2021 Jan;76(1):255-268 |
HaCaT keratinocytes | 10 nM | 4 days | To study the effects of ER-α and ER-β agonists on keratinocyte proliferation and differentiation. Results showed that the ER-β agonist (DPN) increased cell proliferation and keratin-19 expression while decreasing galectin-1 expression. | Int J Mol Med. 2016 Jan;37(1):21-8 |
Endothelial progenitor cells (EPCs) | 100 nM | 4 hours | PPT mimicked the stimulatory effects of estradiol on capillary formation via ER-α | Hypertension. 2010 Sep;56(3):397-404 |
Human dermal fibroblasts | 100 nM | 48 hours | To assess the individual effects of ERα and ERβ on FN expression, PPT significantly increased FN expression | Arthritis Res Ther. 2013 Jan 10;15(1):R10 |
Normal human bronchial epithelial cells (NHBE) | 1-100 nM | 6 hours | PPT increased Alt Ext and HDM-induced IL33 expression in NHBE cells | Allergy. 2021 Jan;76(1):255-268 |
Primary cortical neurons | 10 nM to 1 µM | 6 hours to 48 hours | To investigate the effect of E2 reducing Cav1.2 protein expression through estrogen receptor α (ERα) | Aging Cell. 2019 Aug;18(4):e12961 |
MCF-7 human breast cancer cells | 0.01 nM, 0.1 nM, 1 nM, 3 nM, 10 nM | 7 days | To evaluate the effects of PPT on MCF7 microtissues, including cell count and gene expression changes. PPT treatment increased nuclear counts in a dose-dependent manner with an EC50 of 0.3986 nM. Gene expression analysis showed significant upregulation of PDKZ1 under PPT treatment. | Sci Rep. 2024 Feb 6;14(1):2999 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
Mice | Ovariectomized APP/PS1 mice (Alzheimer's disease model) | Subcutaneous injection | 1 mg/kg | Once daily for two weeks | To investigate the effect of PPT reducing Cav1.2 protein and improving cognitive function through ERα | Aging Cell. 2019 Aug;18(4):e12961 |
Sprague-Dawley rats | Ovariectomized rats | Subcutaneous injection | 1 mg/kg | Once daily for 7 days | To study the effect of ER-β agonist (DPN) on wound healing. Results showed that the ER-β agonist (DPN) accelerated epidermal regeneration. | Int J Mol Med. 2016 Jan;37(1):21-8 |
Female Long-Evans rats | Ovariectomy model | Subcutaneous injection | 10 mg | Single injection, tested 24 hours later | To investigate the effect of PPT on effort-based decision making in female rats. PPT alone increased the choice of the high-reward lever, especially when 10 presses were required. This effect was further enhanced 24 hours post-injection. | Neuropsychopharmacology. 2012 Jan;37(2):390-401 |
Rats | Cocaine self-administration model | Intra-NAc injection | 10 nM | Administered on day 29 and day 30 of withdrawal | Intra-NAc injection of PPT on day 30 of withdrawal significantly decreased cue-induced cocaine seeking. | J Neurosci. 2015 May 27;35(21):8042-58 |
Male C57Bl/6 mice | Cardiac arrest and cardiopulmonary resuscitation model | Intravenous injection and subcutaneous implantation | 2 µg (intravenous) and 50 µg/day (subcutaneous implant) | Single intravenous injection followed by continuous subcutaneous administration for 3 days | To evaluate the effect of ER-α agonist PPT on neuronal survival after cardiac arrest. Results showed that PPT did not significantly reduce neuronal injury in the striatum or hippocampal CA1 region. | J Cereb Blood Flow Metab. 2009 Feb;29(2):277-86 |
Mice | Ovariectomized female mice | Implanted slow-release pellet | 2.5 mg | 60 days | To evaluate the effect of estrogen receptor alpha agonist on the formation of intracranial aneurysms, results showed that PPT (estrogen receptor alpha agonist) did not reduce the incidence of aneurysms in ovariectomized mice. | Neurosurgery. 2014 Dec;75(6):690-5; discussion 695 |
Rats | Hemorrhagic shock model | Subcutaneous injection | 5 μg/kg | Single dose at the onset of resuscitation | To evaluate the effect of PPT on the function of splenic CD4+ T lymphocytes and splenic injury after hemorrhagic shock, results showed that PPT restored the proliferation and cytokine production capacity of CD4+ T lymphocytes and alleviated splenic injury | Sci Rep. 2021 Apr 5;11(1):7508 |
C57BL/6J mice | Gonadectomy model | Intraperitoneal injection | 5.2 µg/25g mouse | Single dose, measured after 24 hours | To investigate the effect of ER alpha agonist on cardiac mitochondrial function in gonadectomized mice. Results showed that ER alpha agonist (PPT) did not modulate State-3 respiration in OVX female or ORX male mice. | Front Endocrinol (Lausanne). 2023 Oct 17;14:1181044 |
Tags: Propyl pyrazole triol | PPTtrogen Receptor/ERR | inhibitor | 263717-53-9 |
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P378 | |
P380 | Evacuate area. |
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P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
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P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
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H411 | Toxic to aquatic life with long-lasting effects |
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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