250694-19-0

Basic information

• Product Name: 3(R)-(Dodecylsulfonamido)-4-(trimethylammonium)butyrate
• Synonyms: ST-1420
• CAS NO: 250694-19-0
• Molecular Formula: C₁₉H₄₀N₂O₄S
• Molecular Weight: 392.60565
• Mol File: 250694-19-0.mol

Chemical Properties

• CAS DataBase Reference: 3(R)-(Dodecylsulfonamido)-4-(trimethylammonium)butyrate(CAS DataBase Reference)
• NIST Chemistry Reference: 3(R)-(Dodecylsulfonamido)-4-(trimethylammonium)butyrate(250694-19-0)
• EPA Substance Registry System: 3(R)-(Dodecylsulfonamido)-4-(trimethylammonium)butyrate(250694-19-0)

Safety Data

• Hazardous Substances Data: 250694-19-0(Hazardous Substances Data)

Relevant articles and documents

Discovery of a long-chain carbamoyl aminocarnitine derivative, a reversible carnitine palmitoyltransferase inhibitor with antiketotic and antidiabetic activity

The synthesis and pharmacological activity of reversible CPT I inhibitors as potential antiketotic and antidiabetic drugs are reported. Such inhibitors constitute a series of enantiomerically pure aminocarnitine derivatives having the general formula (CH3)3N+CH2CH(ZR) CH2COO- (with Z = ureido, carbamate, sulfonamide, and sulfamide moieties; R = C7-C14 linear alkyl chains). A primary pharmacological screening based on the evaluation of CPT I activity in intact rat liver (L-CPT I) mitochondria revealed the best activity for the (R) forms of ureidic derivative 17 (ZR = NHCONHR, R = C14), sulfonamidic derivative 7 (ZR = NHSO2R, R = C12), and sulfamidic derivative 9 (ZR = NHSO2NHR, R = C11). The IC50 values are 1.1, 0.7, and 0.8 μM, respectively. For the carbamic derivative 11 (ZR = NHCOOR, R = C8), an IC50 of 9.5 μM was observed. In addition, an extraordinarily high selectivity toward the liver isoform with respect to the heart isoform (muscle-CPT I M-CPT I) was found for the ureidic compound 17 (IC50(M-CPT I) vs IC50(L-CPTI) = 39.4), as well as for other ureidic or carbamic compounds. Diabetic db/db mice treated orally with 17 and 7 for 45 days at a dose of 50 mg/kg twice a day showed a good reduction of serum glucose levels with respect to the untreated db/db mice (p a potential antiketotic and antidiabetic drug.

Reversible carnitine palmitoyltransferase inhibitors with broad chemical diversity as potential antidiabetic agents

A series of carnitine related compounds of general formula XCH2CHZRCH2Y were evaluated as CPT I inhibitors in intact rat liver (L-CPT I) and heart mitochondria (M-CPT I). Derivative 27 (ZR = -HNSO2R, R = C12, X