Hydroxycamptothecin
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Grundinformationen
- CAS
19685-09-7- Standard-SMILES
CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3cc(O)ccc3nc2-1- InChIKey
HAWSQZCWOQZXHI-FQEVSTJZSA-N- Summenformel
- C20H16N2O5
- Durchschnittliche Molmasse
- 364,4 g/mol
- Monoisotopische Masse
- 364,10592161
Überblick
10-Hydroxycamptothecin is a pyranoindolizinoquinoline.
Namen und Bezeichner
- Bevorzugter Name
- Hydroxycamptothecin
- IUPAC
- (19S)-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
- Englischer Name
- 10-Hydroxycamptothecin
- Summenformel
- C20H16N2O5
- Molmasse
- 364.35
Namen und Synonyme
10-Hydroxycamptothecin19685-09-7(S)-10-HydroxycamptothecinHydroxycamptothecin10-hydroxycamptothecine10-HCPTNSC-1071249Z01632KRV(19S)-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione(19S)-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo(11.8.0.02,11.04,9.015,20)henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dioneRefChem:77529613-598-9
Weitere Namen anzeigen
SN38HCPT10-hydroxycamptothecin,HCPTAmpuleNSC 107124HYDROCAMPTOTHECINEhydroxy-camptotheci
(S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione(4S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione10-Hydroxy camptothecinHydroxycamptothecineCamptothecin, hydroxy-Camptothecine, 10-hydroxy-10-Hydroxy-CamptothecinMFCD02093100
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 0,6
- Polarare Oberfläche (TPSA)
- 100 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 27
- Formalladung
- 0
- Komplexität
- 774
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Collision Cross Section
187 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
201.21 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 265 · 265-270°C
- Siedepunkt
- 820.7 · 820.7±65.0 °C(Predicted)
- Dichte
- 1.6 · 1.60
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- Löslichkeit
- 23.8 mg/mL · ≥23.8 mg/mL in DMSO with gentle warming; insoluble in EtOH; insoluble in H2O
- pka
- 8.93 · 8.93±0.40(Predicted)
- Aggregatzustand
- powder to crystal
- Farbe
- White to Yellow to Orange
- InChI
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
Warning
H315 (97.4%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H301+H311+H331 (20%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
Gefahrenhinweise
Hazard Classes and Categories
Skin Irrit. 2 (97.4%)
Acute Tox. 3 (80%)
Sicherheitsdaten
- hs_code
- 29349990
- safety_code
- 24/25
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological ClassificationAgents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
Anwendungen
BeschreibungDNA topoisomerases relax supercoiled DNA during replication, transcription, recombination, repair, and chromosome condensation. The relaxation of DNA supercoiling by topoisomerase I at single-strand breaks represents a target for anticancer agents to intercalate between DNA base pairs, leading to the activation of apoptotic and cell cycle arrest pathways. (S)-10-hydroxy-Camptothecin is an inhibitor of topoisomerase I originally isolated from the Chinese tree C. acuminata. It is a member of the camptothecin family that demonstrates less toxicity than its parent compound. (S)-10-hydroxy-Camptothecin has strong anti-tumor activity against a wide range of experimental tumors including L1210 leukemia cells (IC50 = 1.15 μM). In vitro treatment of human HepG2 cells with 5-20 μM (S)-10-hydroxy-camptothecin results in cell cycle arrest at the G2/M phase.
VerwendenA Camptothecin derivative; a topoisomerase inhibitor for cancer therapy
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