Linagliptin

한글명:Linagliptin

카스 번호668270-12-0

상품명:Linagliptin

CBNumberCB71518518

분자식C25H28N8O2

포뮬러 무게472.54

MOL 파일668270-12-0.mol

화학적 성질

녹는점	202 ºC
끓는 점	661.2±65.0 °C(Predicted)
밀도	1.39
저장 조건	Refrigerator
용해도	클로로포름(난용성), DMSO (약간 용해됨), 메탄올 (약간 용해됨)
산도 계수 (pKa)	10.01±0.20(Predicted)
물리적 상태	고체
물리적 상태	단단한 모양
색상	흰색에서 주황색으로
InChIKey	LTXREWYXXSTFRX-QGZVFWFLSA-N
SMILES	N1(CC#CC)C2=C(N(C)C(=O)N(CC3=NC(C)=C4C(=N3)C=CC=C4)C2=O)N=C1N1CCC[C@@H](N)C1

위험 및 안전 성명

HS 번호

29335990

유해 물질 데이터

668270-12-0(Hazardous Substances Data)

NFPA 704:

	0
2		0

그림문자(GHS)

Linagliptin 화학적 특성, 용도, 생산

개요
Linagliptin (trade names Tradjenta and Trajetna) is an inhibitor of dipeptidyl peptidase-4 (DPP-4) that was approved by the U.S. FDA in May 2011 for the treatment of Type 2 diabetes along with diet and exercise. Linagliptin (BI-1356) has been described as a potent highly selective, slow-off rate and long acting inhibitor of DPP-4. Linagliptin arose from optimization efforts of xanthine-based DPP-4 inhibitors with the initial lead identified from an HTS campaign. After optimizing the activity of the initial micromolar lead, two issues that needed to be addressed were activity for hERG and muscarinic receptor M1. Introduction of a butynyl group at the N7 position of the xanthine ring gave much reduced M1 affinity with no measureable hERG activity. Linagliptin inhibits DPP-4 with an IC₅₀=1 nM and is highly selective (>10,000-fold) against DPP-8 and DPP-9. Linagliptin shows no interactions with CYPs up to 50 mM. The described synthesis of linagliptin starts with 8-bromoxanthine, which is alkylated at the N-7 position to introduce the butyne group, followed by alkylation of the N-1 group to introduce the methyl-quinazoline group. Displacement of the bromide with (R)-Boc-3-amino-piperidine followed by deprotection gives linagliptin. When administered to db/db mice orally, linagliptin dose dependently reduced glucose excursion from 0.1 mg/kg (15% inhibition) to 1 mg/kg (66% inhibition).
용도
Labeled Linagliptin, intended for use as an internal standard for the quantification of Linagliptin by GC- or LC-mass spectrometry.
정의
ChEBI: A xanthine that is 7H-xanthine bearing (4-methylquinazolin-2-yl)methyl, methyl, but-2-yn-1-yl and 3-aminopiperidin-1-yl substituents at positions 1, 3, 7 and 8 respectively (the R-enantiomer). Used for treatment of type I diabetes.

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