P7C3-A20
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MedKoo CAT#: 510283

CAS#: 1235481-90-9 (free base)

Description: P7C3-A20 is an analogue of P7C3, and is a proneurogenic, neuroprotective agent. P7C3-A20 displayed increased activity and an improved toxicity profile compared to P7C3. P7C3-A20 demonstrated greater proneurogenic efficacy than a wide spectrum of currently marketed antidepressant drugs. P7C3-A20 showed neuroprotective properties in rodent models of Parkinson's disease, amyotrophic lateral sclerosis, traumatic brain injury and age-related cognitive decline.


Chemical Structure

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P7C3-A20
CAS# 1235481-90-9 (free base)

Theoretical Analysis

MedKoo Cat#: 510283
Name: P7C3-A20
CAS#: 1235481-90-9 (free base)
Chemical Formula: C22H19Br2FN2O
Exact Mass: 503.98482
Molecular Weight: 506.21
Elemental Analysis: C, 52.20; H, 3.78; Br, 31.57; F, 3.75; N, 5.53; O, 3.16

Price and Availability

Size Price Availability Quantity
10.0mg USD 90.0 Ready to ship
25.0mg USD 150.0 Ready to ship
50.0mg USD 250.0 Ready to ship
100.0mg USD 450.0 Ready to ship
200.0mg USD 750.0 Ready to ship
500.0mg USD 1650.0 Ready to ship
1.0g USD 2950.0 Ready to ship
2.0g USD 5250.0 Ready to ship
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Related CAS #: 1235481-90-9 (free base)   1485572-67-5 (HCl)    

Synonym: P7C3-A20; P7C3A20; P7C3 A20

IUPAC/Chemical Name: N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyaniline

InChi Key: XNLTWMQBJFWQOU-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H19Br2FN2O/c1-28-18-4-2-3-17(11-18)26-12-16(25)13-27-21-7-5-14(23)9-19(21)20-10-15(24)6-8-22(20)27/h2-11,16,26H,12-13H2,1H3

SMILES Code: COC1=CC(NCC(F)CN2C3=C(C4=C2C=CC(Br)=C4)C=C(Br)C=C3)=CC=C1

Appearance: Light yellow solid to semi-solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: 1. Literature method: P7C3A20 were dissolved in 5% dextrose (pH 7.0) with 2.5% DMSO and 10% Cremaphor EL (Sigma; C5135). (Ref: Proc Natl Acad Sci U S A. 2012 Oct 16;109(42):17010-5). 2. This drug may be formulated in DMSO 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: P7C3-A20 is a derivative of P7C3 with potent proneurogenic and neuroprotective activity. P7C3-A20 exerts an antidepressant-like effect. P7C3-A20 can cross the blood-brain barrier and therefore has the potential for brain injury treatment
In vitro activity: The aim of this study was to investigate the effect of a potential NAMPT activator, P7C3-A20, an aminopropyl carbazole derivative, on ischemic stroke. In vitro study, neuron protection effect of P7C3-A20 was investigated by co-incubation with primary neurons subjected to oxygen-glucose deprivation (OGD) or oxygen-glucose deprivation/reperfusion (OGD/R) injury. In order to explore the role of P7C3‐A20 in cerebral ischemia, we cultured primary cortical neurons and established neuronal OGD model to mimic in vitro ischemic stress. Primary cortical neurons were exposed to OGD condition for 1.5 and 12 h, respectively. We found that neuronal injuries were growing worse following prolonged duration of OGD. Prolonged administration of P7C3‐A20 may have positive effects for the recovery of chronic stroke. Furthermore, P7C3‐A20 may benefit poststroke recovery because of its role in neurogenesis, given evidence that P7C3‐A20 could rescue NPAS3−/−‐induced loss of hippocampal neurogenesis, and augment hippocampal neurogenesis. CNS Neurosci Ther. 2016 Sep; 22(9): 782–788. Published online 2016 Jun 23. doi: 10.1111/cns.12576 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6492790/
In vivo activity: This laboratory model produces neurodegeneration and neurobehavioral deficits reminiscent of TBI in people. Mice were treated and analyzed beginning 1 y after a single injury, as outlined in Fig. 1A. Two-month-old mice were subjected to TBI or sham-TBI and housed under standard conditions for 1 y. Mice were then administered either vehicle (TBI-Veh, Sham-Veh) or P7C3-A20 (10 mg⋅kg−1⋅day−1 intraperitoneally [IP]; TBI-P7C3-A20) for 4 wk. Animals were then housed under standard conditions with no treatment for four additional months (Fig. 1A). At 19 mo of age (17 mo postinjury), TBI-Veh mice exhibited impaired learning (Fig. 1B) and memory (Fig. 1C) whereas TBI-P7C3-A20 mice again performed as well as Sham-Veh animals. P7C3-A20 directly protects brain microvascular endothelial cells in vivo in mice and in cultured human cells. Taken together, the results suggest that BBB deterioration may be a major contributor to chronic neurodegeneration after remote TBI and that its repair may halt this pathology. Proc Natl Acad Sci U S A. 2020 Nov 3; 117(44): 27667–27675. Published online 2020 Oct 21. doi: 10.1073/pnas.2010430117 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7959512/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 5.1 10.1

Preparing Stock Solutions

The following data is based on the product molecular weight 506.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Vázquez-Rosa E, Shin MK, Dhar M, Chaubey K, Cintrón-Pérez CJ, Tang X, Liao X, Miller E, Koh Y, Barker S, Franke K, Crosby DR, Schroeder R, Emery J, Yin TC, Fujioka H, Reynolds JD, Harper MM, Jain MK, Pieper AA. P7C3-A20 treatment one year after TBI in mice repairs the blood-brain barrier, arrests chronic neurodegeneration, and restores cognition. Proc Natl Acad Sci U S A. 2020 Nov 3;117(44):27667-27675. doi: 10.1073/pnas.2010430117. Epub 2020 Oct 21. PMID: 33087571; PMCID: PMC7959512. 2. Hill CS, Menon DK, Coleman MP. P7C3-A20 neuroprotection is independent of Wallerian degeneration in primary neuronal culture. Neuroreport. 2018 Dec 12;29(18):1544-1549. doi: 10.1097/WNR.0000000000001146. PMID: 30334859; PMCID: PMC6250284. 3.Wang SN, Xu TY, Wang X, Guan YF, Zhang SL, Wang P, Miao CY. Neuroprotective Efficacy of an Aminopropyl Carbazole Derivative P7C3-A20 in Ischemic Stroke. CNS Neurosci Ther. 2016 Sep;22(9):782-8. doi: 10.1111/cns.12576. Epub 2016 Jun 23. PMID: 27333812; PMCID: PMC6492790.
In vitro protocol: 1.Wang SN, Xu TY, Wang X, Guan YF, Zhang SL, Wang P, Miao CY. Neuroprotective Efficacy of an Aminopropyl Carbazole Derivative P7C3-A20 in Ischemic Stroke. CNS Neurosci Ther. 2016 Sep;22(9):782-8. doi: 10.1111/cns.12576. Epub 2016 Jun 23. PMID: 27333812; PMCID: PMC6492790.
In vivo protocol: 1. Vázquez-Rosa E, Shin MK, Dhar M, Chaubey K, Cintrón-Pérez CJ, Tang X, Liao X, Miller E, Koh Y, Barker S, Franke K, Crosby DR, Schroeder R, Emery J, Yin TC, Fujioka H, Reynolds JD, Harper MM, Jain MK, Pieper AA. P7C3-A20 treatment one year after TBI in mice repairs the blood-brain barrier, arrests chronic neurodegeneration, and restores cognition. Proc Natl Acad Sci U S A. 2020 Nov 3;117(44):27667-27675. doi: 10.1073/pnas.2010430117. Epub 2020 Oct 21. PMID: 33087571; PMCID: PMC7959512. 2. Hill CS, Menon DK, Coleman MP. P7C3-A20 neuroprotection is independent of Wallerian degeneration in primary neuronal culture. Neuroreport. 2018 Dec 12;29(18):1544-1549. doi: 10.1097/WNR.0000000000001146. PMID: 30334859; PMCID: PMC6250284.

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1: Walker AK, Rivera PD, Wang Q, Chuang JC, Tran S, Osborne-Lawrence S, Estill SJ, Starwalt R, Huntington P, Morlock L, Naidoo J, Williams NS, Ready JM, Eisch AJ, Pieper AA, Zigman JM. The P7C3 class of neuroprotective compounds exerts antidepressant efficacy in mice by increasing hippocampal neurogenesis. Mol Psychiatry. 2014 Apr 22. doi: 10.1038/mp.2014.34. [Epub ahead of print] PubMed PMID: 24751964.

2: Pieper AA, McKnight SL, Ready JM. P7C3 and an unbiased approach to drug discovery for neurodegenerative diseases. Chem Soc Rev. 2014 Feb 11. [Epub ahead of print] PubMed PMID: 24514864.

3: Blaya MO, Bramlett HM, Naidoo J, Pieper AA, Dietrich WD. Neuroprotective efficacy of a proneurogenic compound after traumatic brain injury. J Neurotrauma. 2014 Mar 1;31(5):476-86. doi: 10.1089/neu.2013.3135. Epub 2013 Dec 19. PubMed PMID: 24070637; PubMed Central PMCID: PMC3934600.



Additional Information

Related CAS#
CAS#1235481-90-9 (P7C3-A20 free);
CAS#1485572-67-5 (P7C3-A20 HCl salt)