StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
Huagongshe Open Project:[email protected]KI-Anbindung: llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.7.8
  1. Startseite
  2. /Verbindung

Sonidegib

HCID 24775005
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
1218778-77-8
Standard-SMILES
Cc1c(C(=O)Nc2ccc(N3C[C@@H](C)O[C@@H](C)C3)nc2)cccc1-c1ccc(OC(F)(F)F)cc1
InChIKey
VZZJRYRQSPEMTK-CALCHBBNSA-N
Summenformel
C26H26F3N3O3
Durchschnittliche Molmasse
485,5 g/mol
Monoisotopische Masse
485,19262619

Überblick

Sonidegib is a member of the classo of biphenyls that is the amide obtained by formal condensation of the carboxy group of 2-methyl-4'-(trifluoromethoxy)[1,1'-biphenyl]-3-carboxylic acid with the amino group of 6-(2,6-dimethylmorpholin-4-yl)pyridin-3-amine. Used (as its phosphate salt) for treatment of locally advanced basal cell carcinoma. It has a role as a Hedgehog signaling pathway inhibitor, an antineoplastic agent and a SMO receptor antagonist. It is a member of benzamides, a member of biphenyls, an aromatic ether, an organofluorine compound, an aminopyridine, a member of morpholines and a tertiary amino compound.

Namen und Bezeichner

Bevorzugter Name
Sonidegib
IUPAC
N-[6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-pyridinyl]-2-methyl-3-[4-(trifluoromethoxy)phenyl]benzamide
Englischer Name
NVP-LDE225
Summenformel
C26H26F3N3O3
Molmasse
485.5

Namen und Synonyme

ErismodegibSonidegib956697-53-3LDE225NVP-LDE225LDE-225LDE 225NVP-LDE 225sonidegibum0RLU3VTK5MNVP-LDE-225CHEBI:90863
Weitere Namen anzeigen
CS-65AZP-577Sonidegib HCLSONIDEGIB(LDE225)LDE225 (NVP-LDE225)LDE-225 (SONIDEGIB)
DTXSID501009335N-(6-((cis-2,6-Dimethylmorpholin-4-yl)-3-pyridyl)-2-methyl-3-(4-(trifluoromethoxy)phenyl)benzamideN-(6-((2R,6S)-2,6-Dimethylmorpholin-4-yl)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)biphenyl-3-carboxamideN-[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]-2-methyl-3-[4-(trifluoromethoxy)phenyl]benzamide(1,1'-BIPHENYL)-3-CARBOXAMIDE, N-(6-((2R,6S)-2,6-DIMETHYL-4-MORPHOLINYL)-3-PYRIDINYL)-2-METHYL-4'-(TRIFLUOROMETHOXY)-, REL-N-[6-(cis-2,6-dimethylmorpholin-4-yl)pyridin-3-yl]-2-methyl-4'-(trifluoromethoxy)[1,1'-biphenyl]-3-carboxamideN-{6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl}-2-methyl-4'-(trifluoromethoxy)-[1,1'-biphenyl]-3-carboxamideN-(6-((2R,6S)-2,6-dimethylmorpholin-4-yl)pyridin-3-yl)-2-methyl-4'-(trifluoromethoxy)-(1,1'-biphenyl)-3-carboxamide

Datenbank-Bezeichner

CAS
1218778-77-8、956697-53-3
PubChem CID
24775005
DTXSID

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,8
Polarare Oberfläche (TPSA)
63,7 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
5
Schwere Atome
35
Formalladung
0
Komplexität
691

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antineoplastic and immunomodulating agents -> Antineoplastic agents

Human Drugs · 2 Einträge

Breast Feeding; Lactation; Antineoplastic Agents; Enzyme Inhibitors; Hedgehog Pathway Inhibitors; Signal Transduction Inhibitors;

EMA approved medicines: Human medicine

Physikochemische Eigenschaften

Schmelzpunkt
154 · 154-157°C
Siedepunkt
544.5 · 544.5±50.0 °C(Predicted)
Dichte
1.255 · 1.255
storage temp.
Refrigerator
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
Aggregatzustand
White solid.
pka
9.53 · 9.53±0.70(Predicted)
Farbe
Light Purple
InChIKey
VZZJRYRQSPEMTK-CALCHBBNNA-N

Sicherheit und Regulatorisches

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

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

Most clinical trials of sonidegib included few patients and rates of liver tests abnormalities were often not reported. In isolated trials, serum ALT elevations were reported in 15% to 27% of patients and to rise above 5 times the upper limit of normal (ULN) in 1% to 6%. Rates of serum enzyme elevations were greater with higher doses, and all were apparently transient and resolved either spontaneously or with dose reductions or discontinuation. In these trials, there were no cases of clinically apparent liver injury, hepatitis with jaundice or death from liver failure. The product label for sonidegib mentions serum enzyme elevations as a possible adverse event, but does not mention liver injury with jaundice or hepatic failure. Since its approval and more widespread use, there have been no published cases of hepatotoxicity attributed to sonidegib, but it is an uncommonly used antineoplastic agent. Serum enzyme elevations were also rare with the initial hedgehog inhibitor, vismodegib, which has been implicated in causing at least one case of acute, self-limited cholestatic hepatitis (Case 1 in Vismodegib).

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

hs_code
2934999090

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein BindingSonidegib is over 97% bound to plasma proteins, and binding is independent of concentration. (2)
Pharmacodynamics · 1 Eintrag

Sonidegib has been shown to inhibit a transmembrane protein called SMO which plays a role in Hh signal transduction. This has resulted in inhibition of Hh signaling as well as antitumour activity in various animal models. In a transgenic mouse model of islet cell neoplasms, tumour volume was reduce by 95% in mice treated with sonidegib when compared with untreated mice. (2)

Mechanism of Action · 1 Eintrag

The hedgehog pathway is involved in many human cancers. Sonidegib effectively inhibits the regulator called smoothened (Smo), preventing the hedgehog pathway from functioning. As a result, tumours that depend on the hedgehog pathway are unable to grow. (1)

Biological Half-LifeHalf-life ~ 28 days (2)
Metabolism/MetabolitesSonidegib is primarily metabolized via oxidation and amide hydrolysis. (1) The enzyme responsible for the majority of metabolism is the cytochrome P450 (CYP) 3A4 enzyme. (2)
FDA Pharmacological Classification · 6 Einträge

0RLU3VTK5M

SONIDEGIB

Established Pharmacologic Class [EPC] - Hedgehog Pathway Inhibitor

Mechanisms of Action [MoA] - Smoothened Receptor Antagonists

Sonidegib is a Hedgehog Pathway Inhibitor. The mechanism of action of sonidegib is as a Smoothened Receptor Antagonist.

SONIDEGIB

Absorption, Distribution and Excretion · 3 Einträge

Sonidegib is rapidly absorbed in the fasted state with peak concentrations occurring 2-4 hours after administration. (2) However, the total absorption of Sonidegib is low (roughly 6-7%). (1)

Zugehörige Reaktionen

1
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 1022832
HRID 1022832als Produktuspto-grants-2014_05

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
DTXSID501009335
ChEMBL
CHEMBL2105737
ChEBI
CHEBI:90863
UNII
0RLU3VTK5M
EC Number
881-485-3
Nikkaji
J3.351.814E
SMILES
C1(C2=CC=C(OC(F)(F)F)C=C2)=CC=CC(C(NC2=CC=C(N3C[C@H](C)O[C@H](C)C3)N=C2)=O)=C1C |&1:24,27,r|

Around 70% of Sonidegib is eliminated in the feces, while 30% is eliminated in the urine. (2)

Estimated volume of distribution = 9166 L (2)

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

4-Trifluoromethoxyphenylboronic acid2-Chlor-5-nitropyridin3-Brom-4-methylbenzoesure5-Nitropyrimidin-2-ylamin

Anbieter100 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
济南深丽康化工科技有限公司0531-86092839 15318817273 · [email protected]
上海波以尔化工有限公司[email protected]
芷威(上海)化学科技有限公司021-20221225 13917446399 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安庆融创生物科技有限公司15001988657 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
学研惠(武汉)科技有限公司15727060112 · [email protected]
VDM Biochemicals0330-2528181 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
济南精合医药科技有限公司0531-88811783 · [email protected]
苏州岚云医药科技有限公司2332782371 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
上海遐瑞医药科技有限公司+86 21 61551611
上海昶衍化工科技有限公司021-20242659 18930833303 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
台州市科瑞生物技术有限公司0576-88813233 88205808 · [email protected]
广州市慈铭生物科技有限公司020-38082199,29065168,38082986,29878298,29866629,4000192398
上海孚一生物科技有限公司+86 (21) 61124340
上海兴鲁化工科技有限公司02120970332 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
上海缘启生物科技有限公司+86-2332782371 +86-18120098618 · [email protected]
上海楼岚生物科技有限公司021-52996696,15000506266 15000506266
执智医药科技(上海)有限公司021-57898186
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
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]
北京敬梓医药科技有限公司15011485209 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
上海德欣致远生物技术有限公司021-58088081 18317173152 · [email protected]
济南涛瑞医药科技有限公司0531-88633905 15863156350 · [email protected]
药渡经纬信息科技(北京)有限公司+86-400-851-9921 · [email protected]
上海思言生物科技有限公司021-50908862,442785678,326799392 18721037013 · [email protected]
上海必联特生物医药科技有限公司021-20786057 18918495077 · [email protected]
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
兰州安杰利生物化学科技有限公司0931-8235634 13321316780 · [email protected]
广州市齐云生物技术有限公司020-61288194 61288195 · [email protected]
上海前衍生物科技有限公司02781293128 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: A member of the classo of biphenyls that is the amide obtained by formal condensation of the carboxy group of 2-methyl-4'-(trifluoromethoxy)[1,1'-biphenyl]-3-carboxylic acid with the amino group of 6-(2,6-dimethylmorpholin-4-yl)pyridin-3-amine. Used (as it phosphate salt) for treatment of locally advanced basal cell carcinoma.