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Tesamorelin

HCID 178785310
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Grundinformationen

CAS
804475-66-9
Standard-SMILES
[H]/N=C(\N)NCCC[C@H](NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CCCN/C(N)=N/[H])NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCN/C(N)=N/[H])NC(=O)[C@H](CO)NC(=O)[C@H](CCSC)NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCN/C(N)=N/[H])NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCN/C(N)=N/[H])NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)C/C=C/CC)[C@@H](C)CC)[C@@H](C)O)C(C)C)[C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCN/C(N)=N/[H])C(=O)N[C@@H](CC(C)C)C(N)=O
Weitere Aktionen
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InChIKey
QBEPNUQJQWDYKU-BMGKTWPMSA-N
Summenformel
C221H366N72O67S
Durchschnittliche Molmasse
5.136 g/mol

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
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
Englischer Name
Egrifta
Summenformel
C221H366N72O67S
Molmasse
5135.77794

Namen und Synonyme

Tesamorelin218949-48-5TH9507MQG94M5EEODTXSID00583207TH 9507tesamorelinatesamorelinetesamorelinumTH-9507CHEBI:63626GHRH(1-44)
Weitere Namen anzeigen
TesamerelinHigh Pure Peptides Th9507 Tesamorelin Powder 2mg/Vial
RefChem:57140N-((3E)-1-oxo-3-hexenyl)Somatoliberin (human pancreatic islet)DTXCID30533972H01AC06Egrifta804475-66-9UNII-MQG94M5EEOTesamorelin [USAN:INN]

Datenbank-Bezeichner

CAS
804475-66-9
ChEMBL
CHEMBL1237026

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-23,3
Polarare Oberfläche (TPSA)
2.360 Ų
H-Brücken-Donoren
83
H-Brücken-Akzeptoren
76
Frei drehbare Bindungen
187
Schwere Atome
361
Formalladung
0
Komplexität
12.800

Experimentelle und physikochemische Eigenschaften

BiologicsBiologic product () -> Rx; Disc -> FDA Purple Book

Physikochemische Eigenschaften

InChIKey
QBEPNUQJQWDYKU-BMGKTWPMSA-N

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

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 Eintrag

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 Einträge

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.

MeSH Pharmacological ClassificationSignal molecules that are involved in the control of cell growth and differentiation.
Absorption, Distribution and Excretion · 2 Einträge

The absolute bioavailability was determined to be less than 4% in healthy adult subjects following a 2 mg subcutaneous dose.

9.4±3.1 L/kg in healthy subjects. 10.5±6.1 L/kg in HIV-infected patients.

Anwendungen · 2 Einträge

BeschreibungTesamorelin acetate is an analog of growth hormone-releasing hormone (GHRH) that was approved in the United States in 2010 for treatment of lipodystrophy in HIV patients. Tesomorelin is an analog of GHRH. GHRH stimulates the synthesis and release of GH. In the pituitary, GH is secreted in a pulsatile manner. GH control is regulated by somatostatin and the negative feedback regulator, IGF-1. Direct administration of GH to patients with lipodystrophy decreases VAT but has associated side effects such as fluid retention and joint swelling. Because of the side effects associated with direct GH administration, GHRH represents a attractive mechanism for increasing GH levels. Tesomorelin is an analog of GHRH in which the N-terminal amino acid, Tyr, is amidated with a trans-3-hexenoyl group. Capping of the N-terminus protects GHRH from cleavage by DPP-4. Tesomorelin demonstrates enhanced stability compared with GHRH in animal models.

VerwendenEgrifta (Tesamorelin) is used to reduce excess abdominal fat in HIV-infected lipodystrophy patients. Some HIV medicines cause this side effect (increased fat in the upper back and abdomen and decreased fat in the arms and legs.) Tesamorelin works by making the body produce more growth hormone. This medicine should not be used for weight loss.

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