| Identification | Back Directory | [Name]
3-(tetradecylcarbamoylamino)-4-trimethylammonio-butanoate | [CAS]
250694-07-6 | [Synonyms]
ST1326
CS-1483
TEGLICAR
KB-80830
SPB-80348
CHEBI:41251
CHEMBL1231506
UNII-8V3VQ6HMII
Teglicar(ST-1326
4-trimethylammonio-TDCAB
3-(tetradecylcarbamoylamino)-4-trimethylammonio-butanoate
ST1326)：3-(tetradecylcarbamoylamino)-4-trimethylammonio-butanoate
TEGLICAR; 250694-07-6; UNII-8V3VQ6HMII; 4-TRIMETHYLAMMONIO-TDCAB; CHEMBL1231506; CHEBI:41251; SPB-80348; KB-80830 | [Molecular Formula]
C22H45N3O3 | [MDL Number]
MFCD05260853 | [MOL File]
250694-07-6.mol | [Molecular Weight]
399.62 |
| Chemical Properties | Back Directory | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO | [form ]
Solid | [color ]
White to off-white | [InChI]
1S/C22H45N3O3/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-23-22(28)24-20(18-21(26)27)19-25(2,3)4/h20H,5-19H2,1-4H3,(H2-,23,24,26,27,28) | [InChIKey]
BMZYTDRMCBZVNH-UHFFFAOYSA-N | [SMILES]
[O-]C(C[C@@H](NC(NCCCCCCCCCCCCCC)=O)C[N+](C)(C)C)=O |
| Hazard Information | Back Directory | [Uses]
Teglicar is a selective and reversible orally active liver isoform of carnitine palmitoyl-transferase 1 (L-CPT1) inhibitor with an IC50 value of 0.68 μM and a Ki value of 0.36 μM. Teglicar has a potential antihyperglycemic propert. Teglicar can be used for the research of diabetes and neurodegenerative disease including Huntington's disease (HD)[1][2]. | [General Description]
ST1326 contains an aliphatic carbon chain and is structurally similar to palmitoylcarnitine. | [Biochem/physiol Actions]
ST1326 is a reversible inhibitor of carnitine palmitoyltransferases. It shows anti tumor action in leukemia cell lines. | [in vivo]
Teglicar (oral, 80 mg/kg, once a day, for 30 days or infusion, 5.3 mg/kg/h, for 3 h) reduces the endogenous glucose production (262%) without affecting peripheral glucose utilization in SD rats[1].
Teglicar (gavage, 50 mg/kg, single or long-term 100 mg/kg/day for 30 days) not affects heart 2-[3H]deoxyglucose uptake in C57BL6/J mice[1].
Teglicar (gavage, 50 mg/kg, twice a day, for 45 days) reduces postabsorptive glycemia (238%), water consumption (231%), and fructosamine (230%) in db/db mice[1].
Teglicar (30 mg/kg, twice a day, for 26 days) normalized glycemia (219%) and insulinemia (253%) and increases HTGC but not affects liver and peripheral insulin sensitivity in high-fat diet C57BL/6J mice[1].
Teglicar (oral, 50 μM, was added to the surface of fly food, 1, 8, 12, and 15 days) ameliorates the neurodegenerative phenotype in a drosophila Huntington's Disease Model by acting on the expression of carnitine-related genes[2]. | Animal Model: | SD rats[1] | | Dosage: | 80 mg/kg, 5.3 mg/kg | | Administration: | oral, 80 mg/kg, once a day, for 30 days or infusion, 5.3 mg/kg/h, for 3 h | | Result: | Reduced basal insulin levels, showed a higher triglyceride and low glycogen content in the liver, without any change in liver weight.
Showed a rapid drop in glycemia, suppressed EGP (EGP2) diminished by 62% and not affected peripheral glucose utilization (GU).
|
| Animal Model: | C57BL6/J mice[1] | | Dosage: | 50 mg/kg, 100 mg/kg | | Administration: | gavage, 50 mg/kg, single or long-term 100 mg/kg/day for 30 days. | | Result: | Did not modify etomoxir-induced M-CPT1 inhibition and failed to determine significant changes in 2-DG heart uptake, heart weights, and triglyceride content. |
| Animal Model: | db/db mice[1] | | Dosage: | 50 mg/kg | | Administration: | gavage, 50 mg/kg, twice a day, for 45 days | | Result: | Induced a significant reduction of postabsorptive serum glucose, reduced serum fructosamine and average daily water consumption, increased Serum FFAs, but did not change insulin levels, triglycerides, alanine aminotransferase, also induced a significant reduction of glucose AUC during ITT.
Did not induce any variation in the content of PPAR-α and its target gene product MCAD and peroxisomal b-oxidation in liver and heart of db/db mice.
|
| Animal Model: | High-fat diet C57BL/6J mice[1] | | Dosage: | 30 mg/kg | | Administration: | 30 mg/kg, twice a day, for 26 days | | Result: | Did not affect food intake, did not change body weight and serum FFAs and triglycerides and did not affect glucose intolerant. |
| [References]
[1] Roberto Conti, et al. Selective reversible inhibition of liver carnitine palmitoyl-transferase 1 by teglicar reduces gluconeogenesis and improves glucose homeostasis. Diabetes. 2011 Feb;60(2):644-51. DOI:10.2337/db10-0346
[2] Carla Bertapelle, et al. The Reversible Carnitine Palmitoyltransferase 1 Inhibitor (Teglicar) Ameliorates the Neurodegenerative Phenotype in a Drosophila Huntington's Disease Model by Acting on the Expression of Carnitine-Related Genes. Molecules DOI:10.3390/molecules27103125 |
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