MedKoo Biosciences

PF-8380
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 503216

CAS#: 1144035-53-9

Description: PF-8380 is a potent autotaxin inhibitor with an IC(50) of 2.8 nM in isolated enzyme assay and 101 nM in human whole blood. PF-8380 has adequate oral bioavailability and exposures required for in vivo testing of autotaxin inhibition. Autotaxin's role in producing LPA in plasma and at the site of inflammation was tested in a rat air pouch model. The specific inhibitor PF-8380 , dosed orally at 30 mg/kg, provided >95% reduction in both plasma and air pouch LPA within 3 h, indicating autotaxin is a major source of LPA during inflammation. At 30 mg/kg PF-8380 reduced inflammatory hyperalgesia with the same efficacy as 30 mg/kg naproxen.

Chemical Structure

PF-8380

CAS# 1144035-53-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 503216
Name: PF-8380
CAS#: 1144035-53-9
Chemical Formula: C22H21Cl2N3O5
Exact Mass: 477.09
Molecular Weight: 478.326
Elemental Analysis: C, 55.24; H, 4.43; Cl, 14.82; N, 8.78; O, 16.72

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 450
200mg	USD 750
500mg	USD 1450
1g	USD 2250
2g	USD 3950
5g	USD 5950
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: PF8380; PF-8380; PF 8380.

IUPAC/Chemical Name: 3,5-dichlorobenzyl 4-(3-oxo-3-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)propyl)piperazine-1-carboxylate

InChi Key: JMSUDQYHPSNBSN-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H21Cl2N3O5/c23-16-9-14(10-17(24)12-16)13-31-22(30)27-7-5-26(6-8-27)4-3-19(28)15-1-2-18-20(11-15)32-21(29)25-18/h1-2,9-12H,3-8,13H2,(H,25,29)

SMILES Code: O=C(N1CCN(CCC(C2=CC=C3NC(OC3=C2)=O)=O)CC1)OCC4=CC(Cl)=CC(Cl)=C4

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: >5 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:

View handling instruction

Biological target:	PF-8380 is a potent autotaxin inhibitor with an IC50 of 2.8 nM in isolated enzyme assay and 101 nM in human whole blood.
In vitro activity:	TBD
In vivo activity:	Autotaxin's role in producing LPA in plasma and at the site of inflammation was tested in a rat air pouch model. The specific inhibitor PF-8380, dosed orally at 30 mg/kg, provided >95% reduction in both plasma and air pouch LPA within 3 h, indicating autotaxin is a major source of LPA during inflammation. At 30 mg/kg PF-8380 reduced inflammatory hyperalgesia with the same efficacy as 30 mg/kg naproxen. Inhibition of plasma autotaxin activity correlated with inhibition of autotaxin at the site of inflammation and in ex vivo whole blood. Furthermore, a close pharmacokinetic/pharmacodynamic relationship was observed, which suggests that LPA is rapidly formed and degraded in vivo. Reference: J Pharmacol Exp Ther. 2010 Jul;334(1):310-7. https://pubmed.ncbi.nlm.nih.gov/20392816/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	5.0	10.45
	DMF:PBS (pH 7.2) (1:6)	0.1	0.29
	DMSO	35.2	73.64

Preparing Stock Solutions

The following data is based on the product molecular weight 478.326000000000000000000000000000 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.

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. Roy S, Chakrabarti M, Dasgupta H, Mahale A, Tripathi S, Sharma V, Banerjee M, Kulkarni OP. Inhibition of Autotaxin Ameliorates LPA-Mediated Neuroinflammation and Alleviates Neurological Dysfunction in Acute Hepatic Encephalopathy. ACS Chem Neurosci. 2022 Oct 5;13(19):2829-2841. doi: 10.1021/acschemneuro.2c00046. Epub 2022 Sep 16. PMID: 36112416. 2. Gierse J, Thorarensen A, Beltey K, Bradshaw-Pierce E, Cortes-Burgos L, Hall T, Johnston A, Murphy M, Nemirovskiy O, Ogawa S, Pegg L, Pelc M, Prinsen M, Schnute M, Wendling J, Wene S, Weinberg R, Wittwer A, Zweifel B, Masferrer J. A novel autotaxin inhibitor reduces lysophosphatidic acid levels in plasma and the site of inflammation. J Pharmacol Exp Ther. 2010 Jul;334(1):310-7. doi: 10.1124/jpet.110.165845. Epub 2010 Apr 14. PMID: 20392816.
In vitro protocol:	TBD
In vivo protocol:	1. Roy S, Chakrabarti M, Dasgupta H, Mahale A, Tripathi S, Sharma V, Banerjee M, Kulkarni OP. Inhibition of Autotaxin Ameliorates LPA-Mediated Neuroinflammation and Alleviates Neurological Dysfunction in Acute Hepatic Encephalopathy. ACS Chem Neurosci. 2022 Oct 5;13(19):2829-2841. doi: 10.1021/acschemneuro.2c00046. Epub 2022 Sep 16. PMID: 36112416. 2. Gierse J, Thorarensen A, Beltey K, Bradshaw-Pierce E, Cortes-Burgos L, Hall T, Johnston A, Murphy M, Nemirovskiy O, Ogawa S, Pegg L, Pelc M, Prinsen M, Schnute M, Wendling J, Wene S, Weinberg R, Wittwer A, Zweifel B, Masferrer J. A novel autotaxin inhibitor reduces lysophosphatidic acid levels in plasma and the site of inflammation. J Pharmacol Exp Ther. 2010 Jul;334(1):310-7. doi: 10.1124/jpet.110.165845. Epub 2010 Apr 14. PMID: 20392816.

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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1: Szepanowski F, Derksen A, Steiner I, Meyer Zu Hörste G, Daldrup T, Hartung HP, Kieseier BC. Fingolimod promotes peripheral nerve regeneration via modulation of lysophospholipid signaling. J Neuroinflammation. 2016 Jun 10;13(1):143. doi: 10.1186/s12974-016-0612-9. PubMed PMID: 27283020; PubMed Central PMCID: PMC4901498. 2: Velasco M, O'Sullivan C, Sheridan GK. Lysophosphatidic acid receptors (LPARs): Potential targets for the treatment of neuropathic pain. Neuropharmacology. 2016 Apr 5. pii: S0028-3908(16)30129-0. doi: 10.1016/j.neuropharm.2016.04.002. [Epub ahead of print] Review. PubMed PMID: 27059127. 3: Katsifa A, Kaffe E, Nikolaidou-Katsaridou N, Economides AN, Newbigging S, McKerlie C, Aidinis V. The Bulk of Autotaxin Activity Is Dispensable for Adult Mouse Life. PLoS One. 2015 Nov 16;10(11):e0143083. doi: 10.1371/journal.pone.0143083. eCollection 2015. PubMed PMID: 26569406; PubMed Central PMCID: PMC4646642. 4: Navab M, Chattopadhyay A, Hough G, Meriwether D, Fogelman SI, Wagner AC, Grijalva V, Su F, Anantharamaiah GM, Hwang LH, Faull KF, Reddy ST, Fogelman AM. Source and role of intestinally derived lysophosphatidic acid in dyslipidemia and atherosclerosis. J Lipid Res. 2015 Apr;56(4):871-87. doi: 10.1194/jlr.M056614. Epub 2015 Feb 2. PubMed PMID: 25646365; PubMed Central PMCID: PMC4373744. 5: Bhave SR, Dadey DY, Karvas RM, Ferraro DJ, Kotipatruni RP, Jaboin JJ, Hallahan AN, Dewees TA, Linkous AG, Hallahan DE, Thotala D. Autotaxin Inhibition with PF-8380 Enhances the Radiosensitivity of Human and Murine Glioblastoma Cell Lines. Front Oncol. 2013 Sep 17;3:236. doi: 10.3389/fonc.2013.00236. eCollection 2013. PubMed PMID: 24062988; PubMed Central PMCID: PMC3775313. 6: Salous AK, Panchatcharam M, Sunkara M, Mueller P, Dong A, Wang Y, Graf GA, Smyth SS, Morris AJ. Mechanism of rapid elimination of lysophosphatidic acid and related lipids from the circulation of mice. J Lipid Res. 2013 Oct;54(10):2775-84. doi: 10.1194/jlr.M039685. Epub 2013 Aug 15. PubMed PMID: 23948545; PubMed Central PMCID: PMC3770090. 7: St-Cœur PD, Ferguson D, Morin P Jr, Touaibia M. PF-8380 and closely related analogs: synthesis and structure-activity relationship towards autotaxin inhibition and glioma cell viability. Arch Pharm (Weinheim). 2013 Feb;346(2):91-7. doi: 10.1002/ardp.201200395. Epub 2013 Jan 8. PubMed PMID: 23300119. 8: Gierse J, Thorarensen A, Beltey K, Bradshaw-Pierce E, Cortes-Burgos L, Hall T, Johnston A, Murphy M, Nemirovskiy O, Ogawa S, Pegg L, Pelc M, Prinsen M, Schnute M, Wendling J, Wene S, Weinberg R, Wittwer A, Zweifel B, Masferrer J. A novel autotaxin inhibitor reduces lysophosphatidic acid levels in plasma and the site of inflammation. J Pharmacol Exp Ther. 2010 Jul;334(1):310-7. doi: 10.1124/jpet.110.165845. Epub 2010 Apr 14. PubMed PMID: 20392816.

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