Tesamorelin

HCID 16137828CAS 218949-48-5

基本情報

標準SMILES: CC/C=C/CC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@H](C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(C)C)C(N)=O)[C@@H](C)CC)C(C)C)[C@@H](C)O)[C@@H](C)CC
InChIKey: QBEPNUQJQWDYKU-BMGKTWPMSA-N
分子式: C221H366N72O67S
平均分子量: 5,136 g/mol
単同位体質量: 5,132.71664025

概要

Tesamorelin is a stabilized synthetic peptide analogue of the hypothalamic peptide, Growth Hormone Releasing Hormone (GHRH) indicated for the reduction of excess abdominal fat in HIV-infected patients with lipodystrophy. Lipodystrophy is a metabolic condition characterized by insulin resistance, fat redistribution, and hyperlipidemia associated with antiretroviral therapy for HIV infection.

名称と識別子

優先名称: Tesamorelin
IUPAC: (4S)-4-[[2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-3-carboxy-2-[[(2S)-2-[[(2S)-2-[[(E)-hex-3-enoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]-3-methylpentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-5-oxopentanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoyl]amino]-3-carboxypropanoyl]amino]-3-methylpentanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-hydroxypropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]acetyl]amino]-5-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
英語名: Tesamorelin
分子式: C221H366N72O67S
分子量: 5135.86

名称と別名

Tesamorelin218949-48-5TH9507MQG94M5EEODTXSID00583207TH 9507tesamorelinatesamorelinetesamorelinumTH-9507CHEBI:63626GHRH(1-44)

名称をさらに表示

テサモレリンAdipotide/FTTPtesamorelTesamorelin 5mg/10mg/20mgTSM2D06655TirelinTimorelinTesamoreli APITesamorelin 8866

RefChem:57140N-((3E)-1-oxo-3-hexenyl)Somatoliberin (human pancreatic islet)DTXCID30533972H01AC06Egrifta804475-66-9UNII-MQG94M5EEOTesamorelin [USAN:INN]

データベース識別子

CAS: 218949-48-5
PubChem CID: 16137828
DTXSID: DTXSID00583207
ChEMBL: CHEMBL1237026

物性

構造計算による物性

XLogP: -23.3
極性表面積: 2,360 Å²
水素結合供与体数: 83
水素結合受容体数: 76
回転可能結合数: 187
重原子数: 361
形式電荷: 0
複雑度: 12,800

実験および物理化学的性質

Biologics · 3 件

Biologic product (Egrifta) -> FDA Purple Book

Biologic product (Egrifta SV) -> FDA Purple Book

Biologic product (Egrifta WR) -> FDA Purple Book

物理化学的性質

貯蔵温度: 2 · 2-8°C Refrigerator

安全と法規制

毒性情報

Hepatotoxicity · 1 件

In clinical trials in patients with HIV-associated lipodystrophy, tesamorelin therapy was not associated with de novo elevations in serum enzymes and, in some studies, was associated with decreases in preexisting ALT elevations, possibly mediated by improvements in nonalcoholic fatty liver. Instances of clinically apparent liver injury attributable to tesamorelin use have not been reported.

化学と産業

薬理情報

ATC Code · 2 件

H - Systemic hormonal preparations, excl. sex hormones and insulins

QH - Systemic hormonal preparations, excl. sex hormones and insulin

PharmacodynamicsTesamorelin stimulates growth hormone secretion, and subsequently increases IGF-1 and IGFBP-3 levels.

Mechanism of Action · 1 件

By acting on the pituitary cells in the brain, tesamorelin stimulates production and release of the endogenous hormone (hGRF). Tesamorelin therapy predisposes the patient to glucose intolerance and can also increase the risk of type 2 diabetes, so the drug is contraindicated in pregnancy.

Biological Half-Life26 and 38 minutes in healthy subjects and HIV-infected patients, respectively.

Metabolism/MetabolitesNo formal metabolism studies have been performed in humans.

FDA Pharmacological Classification · 5 件

MQG94M5EEO

TESAMORELIN

Physiologic Effects [PE] - Increased GHRH Activity

Established Pharmacologic Class [EPC] - Growth Hormone Releasing Factor Analog

Tesamorelin is a Growth Hormone Releasing Factor Analog. The physiologic effect of tesamorelin is by means of Increased GHRH Activity.

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補足説明

定義FDA Pharm Classes: Tesamorelin is a Growth Hormone Releasing Factor Analog. The physiologic effect of tesamorelin is by means of Increased GHRH Activity.