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MedKoo Cat#: 530393 | Name: PD 146176
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Description:

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

PD 146176, also known as NSC 168807, is a potent and selective inhibitor of reticulocyte 15-lipoxygenase-1.

Chemical Structure

PD 146176
PD 146176
CAS#4079-26-9

Theoretical Analysis

MedKoo Cat#: 530393

Name: PD 146176

CAS#: 4079-26-9

Chemical Formula: C15H11NS

Exact Mass: 237.0612

Molecular Weight: 237.32

Elemental Analysis: C, 75.92; H, 4.67; N, 5.90; S, 13.51

Price and Availability

Size Price Availability Quantity
10mg USD 450.00
25mg USD 700.00 2 Weeks
50mg USD 1,075.00 2 Weeks
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Related CAS #
No Data
Synonym
PD 146176; PD-146176; PD146176; NSC 168807; NSC-168807; NSC168807.
IUPAC/Chemical Name
6,11-dihydro-[1]benzothiopyrano[4,3-b]indole
InChi Key
ZGOOPZVQMLHPFM-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H11NS/c1-3-7-13-10(5-1)12-9-17-14-8-4-2-6-11(14)15(12)16-13/h1-8,16H,9H2
SMILES Code
C1(N2)=C(CSC3=CC=CC=C31)C4=C2C=CC=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
>2 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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
PD146176 (NSC168807), a 15-Lipoxygenase (15-LO) inhibitor, inhibits rabbit reticulocyte 15-LO (Ki=197 nM, IC50=0.54 μM).
In vitro activity:
Treatment of -Se BAEC with TNFalpha/cyclohexamide (CHX) exhibited elevated levels of apoptosis, which was significantly reduced by the addition of a specific 15-lipoxygenase inhibitor PD146176. Furthermore, the addition of 15-HPETE to PD146176-treated BAEC, partially restored TNF/CHX-induced apoptosis. Reference: Prostaglandins Other Lipid Mediat. 2005 May;76(1-4):19-34. https://pubmed.ncbi.nlm.nih.gov/15967159/
In vivo activity:
To provide further evidence for a role of 15-LO, the effects of PD 146176 on the development of atherosclerosis in cholesterol-fed rabbits were assessed. PD 146176 inhibited rabbit reticulocyte 15-LO through a mixed noncompetitive mode with a Ki of 197 nM. Furthermore, LDL isolated from PD 146176-treated animals was as susceptible as that from controls to oxidation ex vivo by either copper or ABAP. 5. PD 146176 was very effective in suppressing atherogenesis, especially in the aortic arch where lesion coverage diminished from 15 +/- 4 to 0% (P < 0.02); esterified cholesterol content was reduced from 2.1 +/- 0.7 to 0 micrograms mg-1 (P < 0.02) in this region. Reference: Br J Pharmacol. 1997 Apr;120(7):1199-206. https://pubmed.ncbi.nlm.nih.gov/9105693/
Solvent mg/mL mM
Solubility
DMF 10.0 42.14
DMF:PBS (pH 7.2) (1:5) 0.2 0.63
DMSO 26.4 111.39
Ethanol 11.3 47.57
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 237.32 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. Du Y, Taylor CG, Aukema HM, Zahradka P. PD146176 affects human EA.hy926 endothelial cell function by differentially modulating oxylipin production of LOX, COX and CYP epoxygenase. Biochim Biophys Acta Mol Cell Biol Lipids. 2022 Jul;1867(7):159156. doi: 10.1016/j.bbalip.2022.159156. Epub 2022 Mar 30. PMID: 35367352. 2. Sordillo LM, Weaver JA, Cao YZ, Corl C, Sylte MJ, Mullarky IK. Enhanced 15-HPETE production during oxidant stress induces apoptosis of endothelial cells. Prostaglandins Other Lipid Mediat. 2005 May;76(1-4):19-34. doi: 10.1016/j.prostaglandins.2004.10.007. PMID: 15967159. 3. Bocan TM, Rosebury WS, Mueller SB, Kuchera S, Welch K, Daugherty A, Cornicelli JA. A specific 15-lipoxygenase inhibitor limits the progression and monocyte-macrophage enrichment of hypercholesterolemia-induced atherosclerosis in the rabbit. Atherosclerosis. 1998 Feb;136(2):203-16. doi: 10.1016/s0021-9150(97)00204-9. Erratum in: Atherosclerosis 1998 Jul;139(1):201. PMID: 9543090. 4. Sendobry SM, Cornicelli JA, Welch K, Bocan T, Tait B, Trivedi BK, Colbry N, Dyer RD, Feinmark SJ, Daugherty A. Attenuation of diet-induced atherosclerosis in rabbits with a highly selective 15-lipoxygenase inhibitor lacking significant antioxidant properties. Br J Pharmacol. 1997 Apr;120(7):1199-206. doi: 10.1038/sj.bjp.0701007. PMID: 9105693; PMCID: PMC1564586.
In vitro protocol:
1. Du Y, Taylor CG, Aukema HM, Zahradka P. PD146176 affects human EA.hy926 endothelial cell function by differentially modulating oxylipin production of LOX, COX and CYP epoxygenase. Biochim Biophys Acta Mol Cell Biol Lipids. 2022 Jul;1867(7):159156. doi: 10.1016/j.bbalip.2022.159156. Epub 2022 Mar 30. PMID: 35367352. 2. Sordillo LM, Weaver JA, Cao YZ, Corl C, Sylte MJ, Mullarky IK. Enhanced 15-HPETE production during oxidant stress induces apoptosis of endothelial cells. Prostaglandins Other Lipid Mediat. 2005 May;76(1-4):19-34. doi: 10.1016/j.prostaglandins.2004.10.007. PMID: 15967159.
In vivo protocol:
1. Bocan TM, Rosebury WS, Mueller SB, Kuchera S, Welch K, Daugherty A, Cornicelli JA. A specific 15-lipoxygenase inhibitor limits the progression and monocyte-macrophage enrichment of hypercholesterolemia-induced atherosclerosis in the rabbit. Atherosclerosis. 1998 Feb;136(2):203-16. doi: 10.1016/s0021-9150(97)00204-9. Erratum in: Atherosclerosis 1998 Jul;139(1):201. PMID: 9543090. 2. Sendobry SM, Cornicelli JA, Welch K, Bocan T, Tait B, Trivedi BK, Colbry N, Dyer RD, Feinmark SJ, Daugherty A. Attenuation of diet-induced atherosclerosis in rabbits with a highly selective 15-lipoxygenase inhibitor lacking significant antioxidant properties. Br J Pharmacol. 1997 Apr;120(7):1199-206. doi: 10.1038/sj.bjp.0701007. PMID: 9105693; PMCID: PMC1564586.
1: Da-Costa-Rocha I, Prieto JM. In Vitro Effects of Selective COX and LOX Inhibitors and Their Combinations with Antineoplastic Drugs in the Mouse Melanoma Cell Line B16F10. Int J Mol Sci. 2021 Jun 17;22(12):6498. doi: 10.3390/ijms22126498. PMID: 34204367; PMCID: PMC8234702. 2: Yan B, Wang Y, Li Y, Wang C, Zhang L. Inhibition of arachidonate 15-lipoxygenase reduces the epithelial-mesenchymal transition in eosinophilic chronic rhinosinusitis with nasal polyps. Int Forum Allergy Rhinol. 2019 Mar;9(3):270-280. doi: 10.1002/alr.22243. Epub 2018 Nov 19. PMID: 30452122. 3: Walters JLH, De Iuliis GN, Dun MD, Aitken RJ, McLaughlin EA, Nixon B, Bromfield EG. Pharmacological inhibition of arachidonate 15-lipoxygenase protects human spermatozoa against oxidative stress. Biol Reprod. 2018 Jun 1;98(6):784-794. doi: 10.1093/biolre/ioy058. PMID: 29546268. 4: Di Meco A, Li JG, Blass BE, Abou-Gharbia M, Lauretti E, Praticò D. 12/15-Lipoxygenase Inhibition Reverses Cognitive Impairment, Brain Amyloidosis, and Tau Pathology by Stimulating Autophagy in Aged Triple Transgenic Mice. Biol Psychiatry. 2017 Jan 15;81(2):92-100. doi: 10.1016/j.biopsych.2016.05.023. Epub 2016 Jun 4. Erratum in: Biol Psychiatry. 2024 Jun 1;95(11):1055. doi: 10.1016/j.biopsych.2024.04.002. PMID: 27499089. 5: Chu J, Li JG, Giannopoulos PF, Blass BE, Childers W, Abou-Gharbia M, Praticò D. Pharmacologic blockade of 12/15-lipoxygenase ameliorates memory deficits, Aβ and tau neuropathology in the triple-transgenic mice. Mol Psychiatry. 2015 Nov;20(11):1329-38. doi: 10.1038/mp.2014.170. Epub 2015 Jan 6. PMID: 25560760. 6: Chen Y, Peng C, Abraham SA, Shan Y, Guo Z, Desouza N, Cheloni G, Li D, Holyoake TL, Li S. Arachidonate 15-lipoxygenase is required for chronic myeloid leukemia stem cell survival. J Clin Invest. 2014 Sep;124(9):3847-62. doi: 10.1172/JCI66129. Epub 2014 Aug 8. PMID: 25105362; PMCID: PMC4151200. 7: Bhattacharya A, Hamilton R, Jernigan A, Zhang Y, Sabia M, Rahman MM, Li Y, Wei R, Chaudhuri A, Van Remmen H. Genetic ablation of 12/15-lipoxygenase but not 5-lipoxygenase protects against denervation-induced muscle atrophy. Free Radic Biol Med. 2014 Feb;67:30-40. doi: 10.1016/j.freeradbiomed.2013.10.002. Epub 2013 Oct 8. PMID: 24121057. 8: Alsalem M, Wong A, Millns P, Arya PH, Chan MS, Bennett A, Barrett DA, Chapman V, Kendall DA. The contribution of the endogenous TRPV1 ligands 9-HODE and 13-HODE to nociceptive processing and their role in peripheral inflammatory pain mechanisms. Br J Pharmacol. 2013 Apr;168(8):1961-74. doi: 10.1111/bph.12092. PMID: 23278358; PMCID: PMC3623065. 9: Wu MY, Lin TH, Chiu YC, Liou HC, Yang RS, Fu WM. Involvement of 15-lipoxygenase in the inflammatory arthritis. J Cell Biochem. 2012 Jul;113(7):2279-89. doi: 10.1002/jcb.24098. PMID: 22573549. 10: Walters JN, Bickford JS, Beachy DE, Newsom KJ, Herlihy JD, Peck MV, Qiu X, Nick HS. cPLA(2)α gene activation by IL-1β is dependent on an upstream kinase pathway, enzymatic activation and downstream 15-lipoxygenase activity: a positive feedback loop. Cell Signal. 2011 Dec;23(12):1944-51. doi: 10.1016/j.cellsig.2011.07.002. Epub 2011 Jul 12. PMID: 21771656; PMCID: PMC3407964. 11: Baragatti B, Coceani F. Arachidonic acid epoxygenase and 12(S)-lipoxygenase: evidence of their concerted involvement in ductus arteriosus constriction to oxygen. Can J Physiol Pharmacol. 2011 May;89(5):329-34. doi: 10.1139/y11-025. Epub 2011 May 27. PMID: 21619415. 12: Peskar BM, Ehrlich K, Schuligoi R, Peskar BA. Role of lipoxygenases and lipoxin A(4)/annexin-1 receptor in gastric protection induced by 20% ethanol or sodium salicylate in rats. Pharmacology. 2009;84(5):310-3. doi: 10.1159/000248165. Epub 2009 Oct 16. PMID: 19844131. 13: Peskar BM, Ehrlich K, Schuligoi R, Peskar BA. Role of lipoxygenases and the lipoxin A(4)/annexin 1 receptor in ischemia-reperfusion-induced gastric mucosal damage in rats. Pharmacology. 2009;84(5):294-9. doi: 10.1159/000244017. Epub 2009 Oct 8. PMID: 19816089. 14: Nair DG, Funk CD. A cell-based assay for screening lipoxygenase inhibitors. Prostaglandins Other Lipid Mediat. 2009 Dec;90(3-4):98-104. doi: 10.1016/j.prostaglandins.2009.09.006. Epub 2009 Oct 3. PMID: 19804839. 15: Jeon SG, Moon HG, Kim YS, Choi JP, Shin TS, Hong SW, Tae YM, Kim SH, Zhu Z, Gho YS, Kim YK. 15-lipoxygenase metabolites play an important role in the development of a T-helper type 1 allergic inflammation induced by double- stranded RNA. Clin Exp Allergy. 2009 Jun;39(6):908-17. doi: 10.1111/j.1365-2222.2009.03211.x. Epub 2009 Feb 25. PMID: 19260872. 16: Seiler A, Schneider M, Förster H, Roth S, Wirth EK, Culmsee C, Plesnila N, Kremmer E, Rådmark O, Wurst W, Bornkamm GW, Schweizer U, Conrad M. Glutathione peroxidase 4 senses and translates oxidative stress into 12/15-lipoxygenase dependent- and AIF-mediated cell death. Cell Metab. 2008 Sep;8(3):237-48. doi: 10.1016/j.cmet.2008.07.005. PMID: 18762024. 17: Succol F, Praticò D. A role for 12/15 lipoxygenase in the amyloid beta precursor protein metabolism. J Neurochem. 2007 Oct;103(1):380-7. doi: 10.1111/j.1471-4159.2007.04742.x. PMID: 17877641. 18: Mangino MJ, Brounts L, Harms B, Heise C. Lipoxin biosynthesis in inflammatory bowel disease. Prostaglandins Other Lipid Mediat. 2006 Mar;79(1-2):84-92. doi: 10.1016/j.prostaglandins.2005.10.004. Epub 2005 Dec 27. PMID: 16516812. 19: Klein RF, Allard J, Avnur Z, Nikolcheva T, Rotstein D, Carlos AS, Shea M, Waters RV, Belknap JK, Peltz G, Orwoll ES. Regulation of bone mass in mice by the lipoxygenase gene Alox15. Science. 2004 Jan 9;303(5655):229-32. doi: 10.1126/science.1090985. PMID: 14716014. 20: Bocan TM, Rosebury WS, Mueller SB, Kuchera S, Welch K, Daugherty A, Cornicelli JA. A specific 15-lipoxygenase inhibitor limits the progression and monocyte-macrophage enrichment of hypercholesterolemia-induced atherosclerosis in the rabbit. Atherosclerosis. 1998 Feb;136(2):203-16. doi: 10.1016/s0021-9150(97)00204-9. Erratum in: Atherosclerosis 1998 Jul;139(1):201. PMID: 9543090.