MedKoo Cat#: 555800 | Name: NB-598 free base
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Description:

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

NB-598 is a potent competitive inhibitor of squalene epoxidase (SE). NB-598 suppresses triglyceride biosynthesis through the farnesol pathway. NB-598 suppresses the secretion of cholesterol and triacylglycerol and simultaneously reduces apolipoprotein B in HepG2 cells. NB-598 reduced basolaterally secreted radioactivity in cholesterol, cholesterol ester, PL and TG. Furthermore, NB-598 suppressed the basolateral secretion of apolipoprotein (apo) B. When microsomes prepared from control Caco-2 cells were incubated with 10 microM NB-598, acyl CoA:cholesterol acyltransferase (ACAT) activity was inhibited slightly.

Chemical Structure

NB-598 free base
NB-598 free base
CAS#131060-14-5 (free base)

Theoretical Analysis

MedKoo Cat#: 555800

Name: NB-598 free base

CAS#: 131060-14-5 (free base)

Chemical Formula: C27H31NOS2

Exact Mass: 449.1847

Molecular Weight: 449.67

Elemental Analysis: C, 72.12; H, 6.95; N, 3.11; O, 3.56; S, 14.26

Price and Availability

Size Price Availability Quantity
50mg USD 750.00 2 Weeks
100mg USD 1,350.00 2 Weeks
200mg USD 2,150.00 2 Weeks
500mg USD 3,450.00 2 Weeks
1g USD 4,850.00 2 Weeks
2g USD 6,950.00 2 Weeks
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Synonym
NB-598 free base; NB-598; NB 598; NB598;
IUPAC/Chemical Name
(E)-N-ethyl-6,6-dimethyl-N-[[3-[(4-thiophen-3-ylthiophen-2-yl)methoxy]phenyl]methyl]hept-2-en-4-yn-1-amine
InChi Key
KIRGLCXNEVICOG-SOFGYWHQSA-N
InChi Code
InChI=1S/C27H31NOS2/c1-5-28(14-8-6-7-13-27(2,3)4)18-22-10-9-11-25(16-22)29-19-26-17-24(21-31-26)23-12-15-30-20-23/h6,8-12,15-17,20-21H,5,14,18-19H2,1-4H3/b8-6+
SMILES Code
CC(C)(C)C#C/C=C/CN(CC)CC1=CC=CC(OCC2=CC(C3=CSC=C3)=CS2)=C1
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
More Info
Product Data
Biological target:
NB-598 is a potent and competitive inhibitor of squalene epoxidase (SE).
In vitro activity:
NB598 significantly inhibited both basal and glucose-stimulated insulin secretion from mouse pancreatic islets. CaV channels were markedly inhibited by NB598. Rapid photolytic release of intracellular caged Ca2+ and simultaneous measurements of the changes in membrane capacitance revealed that NB598 also inhibited exocytosis independently from CaV channels. Reference: Endocrinology. 2008 Oct;149(10):5136-45. https://pubmed.ncbi.nlm.nih.gov/18599549/
In vivo activity:
A single oral administration of NB-598 inhibited cholesterol synthesis from [14C]acetate in rats. Moreover, multiple oral administration of NB-598 to dogs decreased serum total and low density lipoprotein cholesterol levels and increased serum squalene levels. Reference: J Biol Chem. 1990 Oct 25;265(30):18075-8. https://pubmed.ncbi.nlm.nih.gov/2211682/
Solvent mg/mL mM
Solubility
DMSO 90.0 200.15
Ethanol 10.0 22.24
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 449.67 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. Xia F, Xie L, Mihic A, Gao X, Chen Y, Gaisano HY, Tsushima RG. Inhibition of cholesterol biosynthesis impairs insulin secretion and voltage-gated calcium channel function in pancreatic beta-cells. Endocrinology. 2008 Oct;149(10):5136-45. doi: 10.1210/en.2008-0161. Epub 2008 Jul 3. PMID: 18599549. 2. Horie M, Iwasawa Y, Satoh T, Shimizu A, Nagata Y, Kamei T. Effects of NB-598, a potent squalene epoxidase inhibitor, on the apical membrane uptake of cholesterol and basolateral membrane secretion of lipids in Caco-2 cells. Biochem Pharmacol. 1993 Jul 20;46(2):297-305. doi: 10.1016/0006-2952(93)90418-v. PMID: 8347152. 3. Zhang Z, Wu W, Jiao H, Chen Y, Ji X, Cao J, Yin F, Yin W. Squalene epoxidase promotes hepatocellular carcinoma development by activating STRAP transcription and TGF-β/SMAD signalling. Br J Pharmacol. 2022 Dec 29. doi: 10.1111/bph.16024. Epub ahead of print. PMID: 36581319. 4. Horie M, Tsuchiya Y, Hayashi M, Iida Y, Iwasawa Y, Nagata Y, Sawasaki Y, Fukuzumi H, Kitani K, Kamei T. NB-598: a potent competitive inhibitor of squalene epoxidase. J Biol Chem. 1990 Oct 25;265(30):18075-8. PMID: 2211682.
In vitro protocol:
1. Xia F, Xie L, Mihic A, Gao X, Chen Y, Gaisano HY, Tsushima RG. Inhibition of cholesterol biosynthesis impairs insulin secretion and voltage-gated calcium channel function in pancreatic beta-cells. Endocrinology. 2008 Oct;149(10):5136-45. doi: 10.1210/en.2008-0161. Epub 2008 Jul 3. PMID: 18599549. 2. Horie M, Iwasawa Y, Satoh T, Shimizu A, Nagata Y, Kamei T. Effects of NB-598, a potent squalene epoxidase inhibitor, on the apical membrane uptake of cholesterol and basolateral membrane secretion of lipids in Caco-2 cells. Biochem Pharmacol. 1993 Jul 20;46(2):297-305. doi: 10.1016/0006-2952(93)90418-v. PMID: 8347152.
In vivo protocol:
1. Zhang Z, Wu W, Jiao H, Chen Y, Ji X, Cao J, Yin F, Yin W. Squalene epoxidase promotes hepatocellular carcinoma development by activating STRAP transcription and TGF-β/SMAD signalling. Br J Pharmacol. 2022 Dec 29. doi: 10.1111/bph.16024. Epub ahead of print. PMID: 36581319. 2. Horie M, Tsuchiya Y, Hayashi M, Iida Y, Iwasawa Y, Nagata Y, Sawasaki Y, Fukuzumi H, Kitani K, Kamei T. NB-598: a potent competitive inhibitor of squalene epoxidase. J Biol Chem. 1990 Oct 25;265(30):18075-8. PMID: 2211682.
1: Horie M, Iwasawa Y, Satoh T, Shimizu A, Nagata Y, Kamei T. Effects of NB-598, a potent squalene epoxidase inhibitor, on the apical membrane uptake of cholesterol and basolateral membrane secretion of lipids in Caco-2 cells. Biochem Pharmacol. 1993 Jul 20;46(2):297-305. doi: 10.1016/0006-2952(93)90418-v. PMID: 8347152. 2: Horie M, Hayashi M, Satoh T, Hotta H, Nagata Y, Ishida F, Kamei T. An inhibitor of squalene epoxidase, NB-598, suppresses the secretion of cholesterol and triacylglycerol and simultaneously reduces apolipoprotein B in HepG2 cells. Biochim Biophys Acta. 1993 May 20;1168(1):45-51. PMID: 8504141. 3: Nagata Y, Horie M, Hidaka Y, Yonemoto M, Hayashi M, Watanabe H, Ishida F, Kamei T. Effect of an inhibitor of squalene epoxidase, NB-598, on lipid metabolism in Hep G2 cells. Chem Pharm Bull (Tokyo). 1992 Feb;40(2):436-40. doi: 10.1248/cpb.40.436. PMID: 1606641. 4: Hidaka Y, Hotta H, Nagata Y, Iwasawa Y, Horie M, Kamei T. Effect of a novel squalene epoxidase inhibitor, NB-598, on the regulation of cholesterol metabolism in Hep G2 cells. J Biol Chem. 1991 Jul 15;266(20):13171-7. PMID: 1649182. 5: Horie M, Sawasaki Y, Fukuzumi H, Watanabe K, Iizuka Y, Tsuchiya Y, Kamei T. Hypolipidemic effects of NB-598 in dogs. Atherosclerosis. 1991 Jun;88(2-3):183-92. doi: 10.1016/0021-9150(91)90080-m. PMID: 1892485. 6: Horie M, Tsuchiya Y, Hayashi M, Iida Y, Iwasawa Y, Nagata Y, Sawasaki Y, Fukuzumi H, Kitani K, Kamei T. NB-598: a potent competitive inhibitor of squalene epoxidase. J Biol Chem. 1990 Oct 25;265(30):18075-8. PMID: 2211682.