(4S)-4α-エチル-4,9-ジヒドロキシ-1H-ピラノ[3',4':6,7]インドリジノ[1,2-b]キノリン-3,14(4H,12H)-ジオン

Hydroxycamptothecin

HCID 97226CAS 19685-09-7

部分構造検索類似構造を探す

基本情報

標準SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3cc(O)ccc3nc2-1
InChIKey: HAWSQZCWOQZXHI-FQEVSTJZSA-N
分子式: C20H16N2O5
平均分子量: 364.4 g/mol
単同位体質量: 364.10592161

概要

10-Hydroxycamptothecin is a pyranoindolizinoquinoline.

名称と識別子

優先名称: 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
現地名: (4S)-4α-エチル-4,9-ジヒドロキシ-1H-ピラノ[3',4':6,7]インドリジノ[1,2-b]キノリン-3,14(4H,12H)-ジオン
英語名: 10-Hydroxycamptothecin
分子式: C20H16N2O5
分子量: 364.35

名称と別名

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

名称をさらに表示

(4S)-4α-エチル-4,9-ジヒドロキシ-3,4,12,14-テトラヒドロ-1H-ピラノ[3',4':6,7]インドリジノ[1,2-b]キノリン-3,14-ジオン(4S)-4α-エチル-4,12-ジヒドロ-4,9-ジヒドロキシ-1H-ピラノ[3',4':6,7]インドリジノ[1,2-b]キノリン-3,14-ジオン(4S)-9-ヒドロキシ-4-ヒドロキシ-4-エチル-1H-ピラノ[3',4':6,7]インドリジノ[1,2-b]キノリン-3,14(4H,12H)-ジオン4α-エチル-4β,9-ジヒドロキシ-1H-ピラノ[3',4':6,7]インドリジノ[1,2-b]キノリン-3,14(4H,12H)-ジオン(4S)-4,9-ジヒドロキシ-4-エチル-1H-ピラノ[3',4':6,7]インドリジノ[1,2-b]キノリン-3,14(4H,12H)-ジオン(20S)-10-ヒドロキシカンプトテシン(4S)-4α-エチル-4,9-ジヒドロキシ-1H-ピラノ[3',4':6,7]インドリジノ[1,2-b]キノリン-3,14(4H,12H)-ジオン(4S)-4α-エチル-4β,9-ジヒドロキシ-1H-ピラノ[3',4':6,7]インドリジノ[1,2-b]キノリン-3,14(4H,12H)-ジオン(4S)-4-エチル-4,9-ジヒドロキシ-1H-ピラノ[3',4':6,7]インドリジノ[1,2-b]キノリン-3,14(4H,12H)-ジオンヒドロキシカンプトテシン, 10-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

データベース識別子

CAS: 19685-09-7、64439-81-2
PubChem CID: 97226
DTXSID: DTXSID00941444
ChEMBL: CHEMBL273862
ChEBI: CHEBI:81395
UNII: 9Z01632KRV
EC Number: 613-598-9、805-668-4
Nikkaji: J258.662B、J3.021.724A

物性

構造計算による物性

XLogP: 0.6
極性表面積: 100 Å²
水素結合供与体数: 2
水素結合受容体数: 6
回転可能結合数: 1
重原子数: 27
形式電荷: 0
複雑度: 774

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

Collision Cross Section · 2 件

187 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

201.21 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 265 · 265-270°C
沸点: 820.7 · 820.7±65.0 °C(Predicted)
比重(密度): 1.6 · 1.60
貯蔵温度: -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
溶解性: 23.8 mg/mL · ≥23.8 mg/mL in DMSO with gentle warming; insoluble in EtOH; insoluble in H2O
酸解離定数(Pka): 8.93 · 8.93±0.40(Predicted)
外見: powder to crystal
色: White to Yellow to Orange
InChI: InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1
InChIKey: HAWSQZCWOQZXHI-FQEVSTJZSA-N
SMILES: N1C2C(=CC(O)=CC=2)C=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O
CAS データベース: 19685 · 19685-09-7(CAS DataBase Reference)

化学的性質

化学的特性Yellow Solid

安全と法規制

GHS分類

GHS Classification · 6 件

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]

危険有害性情報

Hazard Classes and Categories · 2 件

Skin Irrit. 2 (97.4%)

Acute Tox. 3 (80%)

安全データ

hs_code: 29349990
safety_code: 24/25

化学と産業

薬理情報

MeSH Pharmacological ClassificationAgents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

応用分野 · 2 件

説明DNA 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.

使用A Camptothecin derivative; a topoisomerase inhibitor for cancer therapy