LP-935509
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MedKoo CAT#: 564790

CAS#: 1454555-29-3

Description: LP-935509 is a potent inhibitor of the Adapter protein-2 Associated Kinase 1 (AAK1). LP-935509, caused a reduced pain response in phase II formalin and reversed fully established pain behavior following the SNL procedure. LP-935509 also reduced evoked pain responses in the rat chronic constriction injury (CCI) model and the rat streptozotocin model of diabetic peripheral neuropathy.

Chemical Structure

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LP-935509
CAS# 1454555-29-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 564790
Name: LP-935509
CAS#: 1454555-29-3
Chemical Formula: C20H24N6O3
Exact Mass: 396.19
Molecular Weight: 396.451
Elemental Analysis: C, 60.59; H, 6.10; N, 21.20; O, 12.11

Price and Availability

Size Price Availability Quantity
50mg USD 550 2 Weeks
100mg USD 950 2 Weeks
200mg USD 1450 2 Weeks
500mg USD 2950 2 Weeks
1g USD 4250 2 Weeks
2g USD 6850 2 Weeks
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Related CAS #: 1454555-29-3,

Synonym: LP935509; LP 935509; LP-935509

IUPAC/Chemical Name: 4-[3-(2-Methoxy-pyridin-3-yl)-pyrazolo[1,5-a]pyrimidin-5-yl]-piperazine-1-carboxylic acid isopropyl ester

InChi Key: GOOYSJIWTIHOGW-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H24N6O3/c1-14(2)29-20(27)25-11-9-24(10-12-25)17-6-8-26-18(23-17)16(13-22-26)15-5-4-7-21-19(15)28-3/h4-8,13-14H,9-12H2,1-3H3

SMILES Code: O=C(N1CCN(C2=NC3=C(C4=CC=CN=C4OC)C=NN3C=C2)CC1)OC(C)C

Appearance: 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

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

Product Data:
Product Data
Instruction:
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Biological target: LP-935509 is an orally active, potent, selective, ATP-competitive and brain-penetrant inhibitor of adaptor protein-2 associated kinase 1 (AAK1) with an IC50 of 3.3 nM and a Ki of 0.9 nM, respectively. LP-935509 is also a potent inhibitor of BIKE (IC50=14 nM) and a modest inhibitor of GAK (IC50=320 nM).
In vitro activity: To test the activity of LP-935509 in an intact cellular system, the compound was incubated with HEK293 cells overexpressing human AAK1 and the human μ2 protein. These studies showed that LP-935509 inhibited μ2 phosphorylation with an IC50 value of 2.8 ± 0.4 nM (n = 26) (Supplemental Fig. 1B; Table 1). Reference: J Pharmacol Exp Ther. 2016 Sep;358(3):371-86. https://pubmed.ncbi.nlm.nih.gov/27411717/
In vivo activity: The effect of LP-935509 on antinociception was further explored in rats because this species is commonly used to evaluate novel antinociceptive agents. In CCI animals, oral LP-935509 caused a dose-dependent reversal of thermal hyperalgesia (Fig. 6A), cold allodynia (Fig. 6B), mechanical allodynia (Fig. 6C), and mechanical hyperalgesia (Fig. 6D). In particular, LP-935509 completely reversed thermal hyperalgesia and mechanical allodynia at 10 and 30 mg/kg, with most assays showing significant antinociceptive activity at lower doses (ranging from 0.3 mg/kg to 3 mg/kg). Reference: J Pharmacol Exp Ther. 2016 Sep;358(3):371-86. https://pubmed.ncbi.nlm.nih.gov/27411717/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 126.12

Preparing Stock Solutions

The following data is based on the product molecular weight 396.451000000000000000000000000000 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. Kostich W, Hamman BD, Li YW, Naidu S, Dandapani K, Feng J, Easton A, Bourin C, Baker K, Allen J, Savelieva K, Louis JV, Dokania M, Elavazhagan S, Vattikundala P, Sharma V, Das ML, Shankar G, Kumar A, Holenarsipur VK, Gulianello M, Molski T, Brown JM, Lewis M, Huang Y, Lu Y, Pieschl R, O'Malley K, Lippy J, Nouraldeen A, Lanthorn TH, Ye G, Wilson A, Balakrishnan A, Denton R, Grace JE, Lentz KA, Santone KS, Bi Y, Main A, Swaffield J, Carson K, Mandlekar S, Vikramadithyan RK, Nara SJ, Dzierba C, Bronson J, Macor JE, Zaczek R, Westphal R, Kiss L, Bristow L, Conway CM, Zambrowicz B, Albright CF. Inhibition of AAK1 Kinase as a Novel Therapeutic Approach to Treat Neuropathic Pain. J Pharmacol Exp Ther. 2016 Sep;358(3):371-86. doi: 10.1124/jpet.116.235333. Epub 2016 Jul 13. PMID: 27411717; PMCID: PMC4998676.
In vitro protocol: 1. Kostich W, Hamman BD, Li YW, Naidu S, Dandapani K, Feng J, Easton A, Bourin C, Baker K, Allen J, Savelieva K, Louis JV, Dokania M, Elavazhagan S, Vattikundala P, Sharma V, Das ML, Shankar G, Kumar A, Holenarsipur VK, Gulianello M, Molski T, Brown JM, Lewis M, Huang Y, Lu Y, Pieschl R, O'Malley K, Lippy J, Nouraldeen A, Lanthorn TH, Ye G, Wilson A, Balakrishnan A, Denton R, Grace JE, Lentz KA, Santone KS, Bi Y, Main A, Swaffield J, Carson K, Mandlekar S, Vikramadithyan RK, Nara SJ, Dzierba C, Bronson J, Macor JE, Zaczek R, Westphal R, Kiss L, Bristow L, Conway CM, Zambrowicz B, Albright CF. Inhibition of AAK1 Kinase as a Novel Therapeutic Approach to Treat Neuropathic Pain. J Pharmacol Exp Ther. 2016 Sep;358(3):371-86. doi: 10.1124/jpet.116.235333. Epub 2016 Jul 13. PMID: 27411717; PMCID: PMC4998676.
In vivo protocol: 1. Kostich W, Hamman BD, Li YW, Naidu S, Dandapani K, Feng J, Easton A, Bourin C, Baker K, Allen J, Savelieva K, Louis JV, Dokania M, Elavazhagan S, Vattikundala P, Sharma V, Das ML, Shankar G, Kumar A, Holenarsipur VK, Gulianello M, Molski T, Brown JM, Lewis M, Huang Y, Lu Y, Pieschl R, O'Malley K, Lippy J, Nouraldeen A, Lanthorn TH, Ye G, Wilson A, Balakrishnan A, Denton R, Grace JE, Lentz KA, Santone KS, Bi Y, Main A, Swaffield J, Carson K, Mandlekar S, Vikramadithyan RK, Nara SJ, Dzierba C, Bronson J, Macor JE, Zaczek R, Westphal R, Kiss L, Bristow L, Conway CM, Zambrowicz B, Albright CF. Inhibition of AAK1 Kinase as a Novel Therapeutic Approach to Treat Neuropathic Pain. J Pharmacol Exp Ther. 2016 Sep;358(3):371-86. doi: 10.1124/jpet.116.235333. Epub 2016 Jul 13. PMID: 27411717; PMCID: PMC4998676.

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1: Louis JV, Lu Y, Pieschl R, Tian Y, Hong Y, Dandapani K, Naidu S, Vikramadithyan RK, Dzierba C, Sarvasiddhi SK, Nara SJ, Bronson J, Macor JE, Albright C, Kostich W, Li YW. [(3)H]BMT-046091 a potent and selective radioligand to determine AAK1 distribution and target engagement. Neuropharmacology. 2017 May 15;118:167-174. doi: 10.1016/j.neuropharm.2017.03.015. Epub 2017 Mar 15. PubMed PMID: 28315351. 2: Kostich W, Hamman BD, Li YW, Naidu S, Dandapani K, Feng J, Easton A, Bourin C, Baker K, Allen J, Savelieva K, Louis JV, Dokania M, Elavazhagan S, Vattikundala P, Sharma V, Das ML, Shankar G, Kumar A, Holenarsipur VK, Gulianello M, Molski T, Brown JM, Lewis M, Huang Y, Lu Y, Pieschl R, O'Malley K, Lippy J, Nouraldeen A, Lanthorn TH, Ye G, Wilson A, Balakrishnan A, Denton R, Grace JE, Lentz KA, Santone KS, Bi Y, Main A, Swaffield J, Carson K, Mandlekar S, Vikramadithyan RK, Nara SJ, Dzierba C, Bronson J, Macor JE, Zaczek R, Westphal R, Kiss L, Bristow L, Conway CM, Zambrowicz B, Albright CF. Inhibition of AAK1 Kinase as a Novel Therapeutic Approach to Treat Neuropathic Pain. J Pharmacol Exp Ther. 2016 Sep;358(3):371-86. doi: 10.1124/jpet.116.235333. Epub 2016 Jul 13. PubMed PMID: 27411717; PubMed Central PMCID: PMC4998676.