Onalespib

HCID 11955716

Teilstruktursuche Ähnliche Strukturen suchen

Grundinformationen

CAS: 912999-49-6
Standard-SMILES: CC(C)c1cc(C(=O)N2Cc3ccc(CN4CCN(C)CC4)cc3C2)c(O)cc1O
InChIKey: IFRGXKKQHBVPCQ-UHFFFAOYSA-N
Summenformel: C24H31N3O3
Durchschnittliche Molmasse: 409,5 g/mol
Monoisotopische Masse: 409,23654185

Überblick

Onalespib is a member of the class of isoindoles that is isoindole in which the amino group has been acylated by a 2,4-dihydroxy-5-isopropylbenzoyl group and in which position 5 of the isoidole moiety has been substituted by a (4-methylpiperazin-1-yl)methyl group. A second-generation Hsp90 inhibitor. It has a role as an antineoplastic agent and a Hsp90 inhibitor. It is a tertiary carboxamide, a member of benzamides, a member of isoindoles, a member of resorcinols and a N-alkylpiperazine.

Namen und Bezeichner

Bevorzugter Name: Onalespib
IUPAC: (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone
Englischer Name: Onalespib
Summenformel: C24H31N3O3
Molmasse: 409.52

Namen und Synonyme

Onalespib912999-49-6AT13387AT-13387AT 13387onalespibumQ7Y33N57ZZATI13387XATI-13387X(2,4-Dihydroxy-5-isopropylphenyl)-(5-(4-methylpiperazin-1-ylmethyl)-1,3-dihydroisoindol-2-yl)methanoneCHEBI:140592DTXSID80238485

Weitere Namen anzeigen

CS-1866ATI-13387AT13387, >=98%Onalespib LactateAT13387(Onalespib)ATI-13387

Methanone, (1,3-dihydro-5-((4-methyl-1-piperazinyl)methyl)-2H-isoindol-2-yl)(2,4-dihydroxy-5-(1-methylethyl)phenyl)-4-{5-[(4-methylpiperazin-1-yl)methyl]-2,3-dihydro-1H-isoindole-2-carbonyl}-6-(propan-2-yl)benzene-1,3-diol4-(5-((4-methylpiperazin-1-yl)methyl)-2,3-dihydro-1H-isoindole-2-carbonyl)-6-(propan-2-yl)benzene-1,3-diolRefChem:856776DTXCID00160976Onalespib (AT13387)(2,4-Dihydroxy-5-isopropylphenyl)(5-((4-methylpiperazin-1-yl)methyl)isoindolin-2-yl)methanone912999-49-6 (free base)

Datenbank-Bezeichner

CAS: 912999-49-6
PubChem CID: 11955716
DTXSID: DTXSID80238485
ChEMBL: CHEMBL1214827
ChEBI: CHEBI:140592
UNII: Q7Y33N57ZZ
Nikkaji: J3.146.978C

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,1
Polarare Oberfläche (TPSA): 67,3 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 4
Schwere Atome: 30
Formalladung: 0
Komplexität: 592

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

LogP2.87

Physikochemische Eigenschaften

Siedepunkt: 605.7 · 605.7±55.0 °C(Predicted)
Dichte: 1.237 · 1.237
storage temp.: -20 °C · Store at -20°C
Löslichkeit: 2 O; · insoluble in H2O; ≥13.25 mg/mL in DMSO; ≥47.7 mg/mL in EtOH with ultrasonic
Aggregatzustand: solid
pka: 8.5 · 8.50±0.48(Predicted)
Farbe: White to off-white
InChI: InChI=1S/C24H31N3O3/c1-16(2)20-11-21(23(29)12-22(20)28)24(30)27-14-18-5-4-17(10-19(18)15-27)13-26-8-6-25(3)7-9-26/h4-5,10-12,16,28-29H,6-9,13-15H2,1-3H3
InChIKey: IFRGXKKQHBVPCQ-UHFFFAOYSA-N
SMILES: C(N1CC2=C(C1)C=CC(CN1CCN(C)CC1)=C2)(C1=CC(C(C)C)=C(O)C=C1O)=O

Sicherheit und Regulatorisches

Sicherheitsdaten

Alarmwort: Warnung
Gefahrenhinweise: Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Anwendungen · 1 Eintrag

BeschreibungOnalespib, also known as AT13387, is a selective inhibitor of Hsp90 (IC50 = 18 nM). It induces the degradation of specific Hsp90 client proteins, including mutant EGFR, for up to seven days in tumor cell lines in vitro and up to three days in vivo. Onalespib is retained in tumor xenografts and is efficacious in a range of xenograft models. It differs from other HSP90 inhibitors in its longer duration of target inhibition and its favorable toxicity profile in phase I studies in patients with refractory solid tumors.