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Teglarinad Chloride

HCID 9961434
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Grundinformationen

CAS
432037-57-5
Standard-SMILES
COCCOCCOCCOCCOC(=O)OC[n+]1ccc(NC(=NCCCCCCOc2ccc(Cl)cc2)NC#N)cc1.[Cl-]
InChIKey
DAHMXVAETAAQOZ-UHFFFAOYSA-N
Summenformel
C30H43Cl2N5O8
Durchschnittliche Molmasse
672,6 g/mol
Monoisotopische Masse
671,2488687

Überblick

GMX1777 is a water-soluble prodrug of the cyanoguanidine compound GMX1778 with potential antineoplastic activity. In vivo, apoptosis inducer GMX1777 is rapidly converted into GMX1778 through hydrolytic cleavage of a carbonate ester bond. Although the exact mechanism of action has yet to be fully elucidated, GMX1778 appears to antagonize nuclear factor-kappa B (NF-kB) transcription, resulting in the induction of tumor cell apoptosis.

Namen und Bezeichner

Bevorzugter Name
Teglarinad Chloride
IUPAC
[4-[[N'-[6-(4-chlorophenoxy)hexyl]-N-cyanocarbamimidoyl]amino]pyridin-1-ium-1-yl]methyl 2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethyl carbonate chloride
Englischer Name
1-[[[[2-[2-[2-[2-Methoxyethoxy]ethoxy]ethoxy]ethoxy]carbonyl]oxy]methyl]-4-[N'-cyano-N''-[6-[4-chlorophenoxy]hexyl]guanidino]pyridinium chloride
Summenformel
C30H43ClN5O8.Cl
Molmasse
672.61

Namen und Synonyme

Teglarinad chloride432037-57-5GMX1777EB1627D6V5QYX9MZCloruro de teglarinadChlorure de teglarinadTeglarinad chloride [USAN:INN]GMX-1777EB-1627TEGLARINAD CHLORIDE [INN]TEGLARINAD CHLORIDE [USAN]
Weitere Namen anzeigen
Gmx 1777TeglarinadGMX 1777DAHMXVAETAAQOZ-UHFFFAOYSA-NTeglarinad chloride (GMX1777)1-[[[[2-[2-[2-[2-Methoxyethoxy]ethoxy]ethoxy]ethoxy]carbonyl]oxy]methyl]-4-[N'-cyano-N''-[6-[4-chlorophenoxy]hexyl]guanidino]pyridinium chloride1-[[[[2-[2-[2-[2-Methoxyethoxy]ethoxy]ethoxy]ethoxy]carbonyl]oxy]methyl]-4-[N'-cyano-N''-[6-[4-chlorophenoxy]hexyl]guanidino]pyridinium chloride ISO 9001:2015 REACH
TEGLARINAD CHLORIDE [WHO-DD]4-((N'-(6-(4-CHLOROPHENOXY)HEXYL))-N'-CYANOCARBAMIMIDAMIDO)-1-(3-OXO-2,4,7,10,13,16-HEXAOXAHEPTADECYL)PYRIDIN-1-IUM CHLORIDEPYRIDINIUM, 4-((((6-(4-CHLOROPHENOXY)HEXYL)IMINO)(CYANOAMINO)METHYL)AMINO)-1-(3-OXO-2,4,7,10,13,16-HEXAOXAHEPTADEC-1-YL)-, CHLORIDE (1:1)Pyridinium, 4-((((6-(4-chlorophenoxy)hexyl)amino)(cyanoamino) methylene)amino)-1-(3-oxo-2,4,7,10,13,16-hexaoxaheptadec-1-yl)-, chloridePyridinium, 4-[[[[6-(4-chlorophenoxy)hexyl]amino](cyanoamino) methylene]amino]-1-(3-oxo-2,4,7,10,13,16-hexaoxaheptadec-1-yl)-, chlorideteglarinadi chloridumCHS828 ProdrugRefChem:891304

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
146 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
11
Frei drehbare Bindungen
27
Schwere Atome
45
Formalladung
0
Komplexität
802

Physikochemische Eigenschaften

Schmelzpunkt
158 · 158-159℃
Löslichkeit
200 mg/mL · DMSO: 200 mg/mL (297.35 mM)
Aggregatzustand
Solid
Farbe
White to off-white

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

GMX1777 exhibits unusually potent anti-tumor activity in preclinical animal models. The novel mechanism of action of GMX1778 supports the clinical use of GMX1777 as an anti-cancer agent. Moreover, the strong dependency of cancer cells on NAD+ to support DNA repair suggests a strong rationale for the use of GMX1777 in combination with DNA damaging agents for future trials.

Mechanism of Action · 1 Eintrag

The cytotoxicity of GMX1777, a prodrug of GMX1778, occurs exclusively through its ability to selectively inhibit nicotinamide phosphoribosyl transferase (NAMPRT). Tumor cells have elevated NAMPRT, an enzyme involved in the biosynthesis of oxidized nicotinamide adenine dinucleotide (NAD+). These cells have a high rate of NAD+ turnover due to elevated glycolysis and high ADP-ribosylation activity required for DNA repair, genome stability and telomere maintenance. These latter characteristics make cancer cells more susceptible to NAMPRT inhibition than normal cells. Although the mechanism of action of GMX1778 was initially believed to include NF-κB inhibition, a transcriptional factor that plays a role in cancer cell survival, NF-κB inhibition occurs as a consequence of ATP loss following NAMPRT inhibition and NAD+ decline.

Metabolism/MetabolitesGMX1777 is rapidly converted to GMX1778 in vivo through hydrolytic cleavage of an ester carbonate bond.

Anbieter20 Anbieter

江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
学研惠(武汉)科技有限公司15727060112 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]

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Datenbank-Bezeichner

CAS
432037-57-5
PubChem CID
9961434
ChEMBL
CHEMBL190412
UNII
D6V5QYX9MZ
上海陶术生物科技股份有限公司
+1-781-999-5354; +1-00000000000 · [email protected]
斯派螺(武汉)药物研发有限公司[email protected]
开封明仁药业有限公司0371-65741762 · [email protected]
苏州美石生物科技有限公司1173954148q · [email protected]
南通全益生物科技有限公司0513-66337626 18051384581 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
天津凯利奇生物科技有限公司15076683720 · [email protected]
Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
SHANGHAI KEAN TECHNOLOGY CO., LTD.+8613817748580 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
重庆卡兰医药有限公司[email protected]
佛山合硕医药科技有限公司15363639686 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
上海阿摩尔生物科技有限公司13370042665 18916960931 · [email protected]
淄博航宇生物科技发展有限公司+86-0533-2185556 +86-15965530500 · [email protected]