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MedKoo Cat#: 333066 | Name: Pactimibe sulfate
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Description:

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

Pactimibe, also known as CS-505, is a ACAT inhibitor. Pactimibe stabilizes atherosclerotic plaque through macrophage acyl-CoA:cholesterol acyltransferase inhibition in WHHL rabbits. Pactimibe reduces and stabilizes atherosclerotic lesions by cholesterol-lowering and direct effects in apolipoprotein E-deficient mice. Pactimibe inhibits cholesterol absorption from the intestine, reduces cholesteryl ester formation in the liver, and enhances its elimination from the body. The Triton WR-1339 experiment showed that pactimibe inhibited secretion of very low density lipoprotein cholesterol from the liver. These results suggest that pactimibe is likely to have multiple mechanisms of action responsible for its effectiveness in reducing serum cholesterol.

Chemical Structure

Pactimibe sulfate
Pactimibe sulfate
CAS#608510-47-0 (sulfate)

Theoretical Analysis

MedKoo Cat#: 333066

Name: Pactimibe sulfate

CAS#: 608510-47-0 (sulfate)

Chemical Formula: C50H82N4O10S

Exact Mass: 930.5752

Molecular Weight: 931.28

Elemental Analysis: C, 64.49; H, 8.88; N, 6.02; O, 17.18; S, 3.44

Price and Availability

Size Price Availability Quantity
5mg USD 750.00 2 Weeks
10mg USD 1,250.00 2 Weeks
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Related CAS #
608510-47-0 (sulfate) 189198-30-9 (free base)
Synonym
Pactimibe sulfate; Pactimibe; CS-505; CS505; CS 505\;
IUPAC/Chemical Name
2-(4,6-dimethyl-1-octyl-7-pivalamidoindolin-5-yl)acetic acid compound with sulfuric acid (2:1)
InChi Key
MKJQESRCXYYHFR-UHFFFAOYSA-N
InChi Code
InChI=1S/2C25H40N2O3.H2O4S/c2*1-7-8-9-10-11-12-14-27-15-13-19-17(2)20(16-21(28)29)18(3)22(23(19)27)26-24(30)25(4,5)6;1-5(2,3)4/h2*7-16H2,1-6H3,(H,26,30)(H,28,29);(H2,1,2,3,4)
SMILES Code
O=C(O)CC1=C(C)C2=C(N(CCCCCCCC)CC2)C(NC(C(C)(C)C)=O)=C1C.O=S(O)(O)=O.O=C(O)CC3=C(C)C4=C(N(CCCCCCCC)CC4)C(NC(C(C)(C)C)=O)=C3C
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 931.28 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
1: Yoshinaka Y, Shibata H, Kobayashi H, Kuriyama H, Shibuya K, Tanabe S, Watanabe T, Miyazaki A. A selective ACAT-1 inhibitor, K-604, stimulates collagen production in cultured smooth muscle cells and alters plaque phenotype in apolipoprotein E-knockout mice. Atherosclerosis. 2010 Nov;213(1):85-91. doi: 10.1016/j.atherosclerosis.2010.08.048. Epub 2010 Aug 19. PMID: 20843517. 2: Ohta M, Takahashi K, Kasai M, Shoji Y, Kunishiro K, Miike T, Kanda M, Mukai C, Shirahase H. Novel tetrahydroisoquinoline derivatives with inhibitory activities against acyl-CoA: cholesterol acyltransferase and lipid peroxidation. Chem Pharm Bull (Tokyo). 2010 Aug;58(8):1066-76. doi: 10.1248/cpb.58.1066. PMID: 20686261. 3: Takahashi K, Ohta M, Shoji Y, Kasai M, Kunishiro K, Miike T, Kanda M, Shirahase H. Novel acyl-CoA: cholesterol acyltransferase inhibitor: indoline- based sulfamide derivatives with low lipophilicity and protein binding ratio. Chem Pharm Bull (Tokyo). 2010 Aug;58(8):1057-65. doi: 10.1248/cpb.58.1057. PMID: 20686260. 4: Shoji Y, Takahashi K, Ohta M, Kasai M, Kunishiro K, Kanda M, Yogai S, Takeuchi Y, Shirahase H. Novel indoline-based acyl-CoA: cholesterol acyltransferase inhibitor: Effects of introducing a methanesulfonamide group on physicochemical properties and biological activities. Bioorg Med Chem. 2009 Aug 15;17(16):6020-31. doi: 10.1016/j.bmc.2009.06.047. Epub 2009 Jun 27. PMID: 19608421. 5: Parini P, Eriksson M, Rudel LL. Carotid atherosclerosis progression and ACAT inhibition. JAMA. 2009 Jul 15;302(3):255; author reply 256-7. doi: 10.1001/jama.2009.1000. PMID: 19602681. 6: Zhou SF, Liu JP, Lai XS. Substrate specificity, inhibitors and regulation of human cytochrome P450 2D6 and implications in drug development. Curr Med Chem. 2009;16(21):2661-805. doi: 10.2174/092986709788681985. PMID: 19601803. 7: Atherosclerosis drug fails to meet Phase III trial end point. Nat Rev Drug Discov. 2009 May;8(5):348. doi: 10.1038/nrd2879. PMID: 19404306. 8: Meuwese MC, de Groot E, Duivenvoorden R, Trip MD, Ose L, Maritz FJ, Basart DC, Kastelein JJ, Habib R, Davidson MH, Zwinderman AH, Schwocho LR, Stein EA; CAPTIVATE Investigators. ACAT inhibition and progression of carotid atherosclerosis in patients with familial hypercholesterolemia: the CAPTIVATE randomized trial. JAMA. 2009 Mar 18;301(11):1131-9. doi: 10.1001/jama.301.11.1131. PMID: 19293413. 9: Kotsuma M, Tokui T, Freudenthaler S, Nishimura K. Effect of CYP2D6 polymorphism on pharmacokinetics of a novel ACAT inhibitor, pactimibe and its unique metabolite, R-125528. Int J Clin Pharmacol Ther. 2008 Nov;46(11):545-55. doi: 10.5414/cpp46545. PMID: 19000552. 10: Takahashi K, Kasai M, Ohta M, Shoji Y, Kunishiro K, Kanda M, Kurahashi K, Shirahase H. Novel indoline-based acyl-CoA:cholesterol acyltransferase inhibitor with antiperoxidative activity: improvement of physicochemical properties and biological activities by introduction of carboxylic acid. J Med Chem. 2008 Aug 14;51(15):4823-33. doi: 10.1021/jm800248r. Epub 2008 Jul 12. PMID: 18620381. 11: Kotsuma M, Hanzawa H, Iwata Y, Takahashi K, Tokui T. Novel binding mode of the acidic CYP2D6 substrates pactimibe and its metabolite R-125528. Drug Metab Dispos. 2008 Sep;36(9):1938-43. doi: 10.1124/dmd.108.020776. Epub 2008 Jun 4. PMID: 18524873. 12: Kotsuma M, Tokui T, Freudenthaler S, Nishimura K. Effects of ketoconazole and quinidine on pharmacokinetics of pactimibe and its plasma metabolite, R-125528, in humans. Drug Metab Dispos. 2008 Aug;36(8):1505-11. doi: 10.1124/dmd.108.021394. Epub 2008 Apr 30. PMID: 18448569. 13: Kotsuma M, Tokui T, Ishizuka-Ozeki T, Honda T, Iwabuchi H, Murai T, Ikeda T, Saji H. CYP2D6-Mediated metabolism of a novel acyl coenzyme A:cholesterol acyltransferase inhibitor, pactimibe, and its unique plasma metabolite, R-125528. Drug Metab Dispos. 2008 Mar;36(3):529-34. doi: 10.1124/dmd.107.018853. Epub 2007 Dec 3. PMID: 18056254. 14: A bumpy road to breakthroughs. The news: it's hard to beat today's cardiac treatments. Heart Advis. 2006 Feb;9(2):4-5. PMID: 17763560. 15: Wiklund O. Nya medel mot ateroskleros testas. Oroande fynd med ACAT-hämmare, som tycks ha proaterogena effekter [New agents against atherosclerosis tested. Alarming findings, ACAT inhibitors seem to have proatherogenic effects]. Lakartidningen. 2006 Oct 25-31;103(43):3270. Swedish. PMID: 17117657. 16: Nicholls SJ, Sipahi I, Schoenhagen P, Wisniewski L, Churchill T, Crowe T, Goormastic M, Wolski K, Tuzcu EM, Nissen SE; ACTIVATE Investigators. Intravascular ultrasound assessment of novel antiatherosclerotic therapies: rationale and design of the Acyl-CoA:Cholesterol Acyltransferase Intravascular Atherosclerosis Treatment Evaluation (ACTIVATE) Study. Am Heart J. 2006 Jul;152(1):67-74. doi: 10.1016/j.ahj.2005.10.025. PMID: 16824833. 17: Kitayama K, Koga T, Inaba T, Fujioka T. Multiple mechanisms of hypocholesterolemic action of pactimibe, a novel acyl-coenzyme A:cholesterol acyltransferase inhibitor. Eur J Pharmacol. 2006 Aug 14;543(1-3):123-32. doi: 10.1016/j.ejphar.2006.05.036. Epub 2006 Jun 2. PMID: 16814766. 18: Rudel LL, Farese RV Jr. ACAT inhibition and the progression of coronary atherosclerosis. N Engl J Med. 2006 Jun 15;354(24):2616-7; author reply 2616-7. doi: 10.1056/NEJMc061094. PMID: 16775245. 19: Kitayama K, Tanimoto T, Koga T, Terasaka N, Fujioka T, Inaba T. Importance of acyl-coenzyme A:cholesterol acyltransferase 1/2 dual inhibition for anti- atherosclerotic potency of pactimibe. Eur J Pharmacol. 2006 Jul 1;540(1-3):121-30. doi: 10.1016/j.ejphar.2006.04.022. Epub 2006 Apr 29. PMID: 16730694. 20: Kitayama K, Koga T, Maeda N, Inaba T, Fujioka T. Pactimibe stabilizes atherosclerotic plaque through macrophage acyl-CoA:cholesterol acyltransferase inhibition in WHHL rabbits. Eur J Pharmacol. 2006 Jun 6;539(1-2):81-8. doi: 10.1016/j.ejphar.2006.03.078. Epub 2006 Apr 7. PMID: 16690054.

View History

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