基本情報
- CAS
86639-52-3- 標準SMILES
CCc1c2c(nc3ccc(O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC- InChIKey
FJHBVJOVLFPMQE-QFIPXVFZSA-N- 分子式
- C22H20N2O5
- 平均分子量
- 392.4 g/mol
- 単同位体質量
- 392.13722174
概要
SN-38 is a member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself. It has a role as an antineoplastic agent, a drug metabolite, an EC 5.99.1.2 (DNA topoisomerase) inhibitor and an apoptosis inducer. It is a delta-lactone, a tertiary alcohol, a member of phenols and a pyranoindolizinoquinoline.
名称と識別子
- 優先名称
- 7-Ethyl-10-Hydroxycamptothecin
- IUPAC
- (19S)-10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
- 現地名
- 7-エチル-10-ヒドロキシカンプトテシン
- 英語名
- 7-Ethyl-10-hydroxycamptothecin
- 分子式
- C22H20N2O5
- 分子量
- 392.4
名称と別名
7-Ethyl-10-hydroxycamptothecin86639-52-3SN-38SN 38 lactoneSN 3810-Hydroxy-7-ethylcamptothecinNK-0127-Ethyl-10-hydroxy-20(S)-camptothecinNK 012NK0120H43101T0JCAMPTOTHECIN, 7-ETHYL-10-HYDROXY-
名称をさらに表示
7-エチル-10-ヒドロキシカンプトテシン(4S)-4,9-ジヒドロキシ-4,11-ジエチル-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(4S)-4,11-ジエチル-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)-4,11-ジエチル-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)-4,11-ジエチル-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-4,9-ジヒドロキシ-11-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(4S)-9-ヒドロキシ-4-ヒドロキシ-4,11-ジエチル-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(5S)-3,2-(6-ヒドロキシ-4-エチルキノリン-2,3-ジイルメチレン)-5α-ヒドロキシ-5-エチル-1,6(2H,8H)-ジオキソ-7-オキサイソキノリン(4S)-4,9-ジヒドロキシ-4α,11-ジエチル-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4α,11-ジエチル-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SN38Irinotecan Related Compound B ((S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione)(4S)-9-ヒドロキシ-4-ヒドロキシ-4,11-ジエチル-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(4S)-4,11-ジエチル-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)-4,9-ジヒドロキシ-4,11-ジエチル-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,11-ジエチル-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)-4β,9-ジヒドロキシ-4,11-ジエチル-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(19S)-10,19-ジエチル-7,19-ジヒドロキシ-17-オキサ-3,13-ジアザペンタシクロ[11.8.0.02,11.04,9.015,20]ヘンイコサ-1(21),2(11),3,5,7,9,15(20)-ヘプタエン-14,18-ジオン(4S)-4β,9-ジヒドロキシ-4,11-ジエチル-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SN387-ETHYL-10-HYDROXYCAMPTOTHECINE(S)-4,11-diethyl-4,9-dihydroxy-1,12-dihydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H)-dioneIrinotecan Related CoMpound B7-10-hydroxycamptothecin(S)-7-Ethyl-10-hydroxycamptothecin(S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dioneIrinotecan EP Impurity E/ Irinotecan Related Compound B (7-Ethyl-10-Hydroxy Camptothecin/ 11-Ethyl-9-Hydroxy Camptothecin)EHCPT
CHEBI:8988DTXSID4040399(4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione(4S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione(19S)-10,19-diethyl-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(1S,2S,3R)-1-(3,4-dihydroxy-5-methoxy-phenyl)-2,3,7-trihydroxy-3-(hydroxymethyl)-6-methoxy-tetralin-2-carboxylic acid1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE, 4,11-DIETHYL-4,9-DIHYDROXY-, (4S)-H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-, (S)-
データベース識別子
- CAS
86639-52-3- PubChem CID
- 104842
- DTXSID
DTXSID4040399- ChEMBL
CHEMBL837- ChEBI
CHEBI:8988- UNII
- 0H43101T0J
- EC Number
- 643-093-9
- Nikkaji
- J353.490A
物性
構造計算による物性
- XLogP
- 1.4
- 極性表面積
- 100 Ų
- 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
- 2
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 820
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
物理化学的性質
- 融点
- 217 °C · 217 °C
- 沸点
- 810.3 · 810.3±65.0 °C(Predicted)
- 比重(密度)
- 1.51 · 1.51±0.1 g/cm3(Predicted)
- 屈折率
- 21.5 ° · 21.5 ° (C=0.2, THF)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 1 mg/mL · DMSO：可溶1mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 9.13 · 9.13±0.40(Predicted)
- 色
- オフホワイト
- 安定性
- 2 · 購入日から2年間安定です。この DMSO 溶液は、-20°C で 1 か月間保存できます。
- InChI
- InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1
- InChIKey
- FJHBVJOVLFPMQE-QFIPXVFZSA-N
- SMILES
- N1C2C(=CC(O)=CC=2)C(CC)=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O
- CAS データベース
- 86639 · 86639-52-3(CAS DataBase Reference)
化学的性質
化学的特性Light-Yellow Solid
安全と法規制
GHS分類
GHS Classification
Danger
H301 (75%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 60 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 3 (75%)
安全データ
- wgk
- 3
- rtecs
- UQ0491000
- ridadr
- 2811
- hs_code
- 29399990
- risk_code
- 25
- hazard_code
- T
- safety_code
- 45
- hazard_class
- 6.1
- packing_group
- Ⅲ
- Hazard Classifications
- Acute Tox. 4 OralRepr. 1BSTOT RE 1
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
化学と産業
薬理情報
Pharmacodynamics
SN-38 (7-ethyl-10-hydroxycamptothecin) is the active metabolite of Irinotecan (CPT-11). Irinotecan is a topoisomerase I inhibitor commercially available as Camptosar®. SN-38 has been found to be 200–2000 times more cytotoxic than CPT-11, but has not been used as an anticancer drug due to its poor solubility in pharmaceutically acceptable solvents and low affinity to lipid membranes. SN-38 also undergoes a reversible conversion to an inactive open lactone ring structure at physiological pH. LE-SN-38 is a novel lipsome based formulation containing liposomes of uniform size distribution (<200 nm). Drug entrapment efficiency of the formulation is>95%.
Mechanism of Action
The entrapment of SN-38 in lipsomes results in a more stable and more soluble form of the drug. This allows for increased affinity of SN-38 to lipid membranes and improved delivery of the drug to tumor sites. SN-38 is a highly effective cytotoxic topoisomerase I inhibitor.
MeSH Pharmacological ClassificationCompounds that inhibit the activity of DNA TOPOISOMERASE I.
Tissue LocationsKidney
Metabolite PathwaysIrinotecan Action Pathway
応用分野
使用7-ethyl-10-hydroxycamptothecin (SN 38) is a metabolite of Irinotecan, a DNA topoisomerase inhibitor. SN 38 has been used in trials studying the treatment of Cancer, Advanced Solid Tumors, Small Cell Lung Cancer, Metastatic Colorectal Cancer, and Triple Negative Breast Cancer, among others.
調製方法
製造方法7-Ethyl-10-hydroxycamptothecin (SN-38) was synthesized from 20(S)-camptothecin (1) as the starting material via a three-step route in 30–35% overall yield. first, 7-ethylation of 20(S)-camptothecin was carried out by adding hydrogen peroxide and freshly distilled propionaldehyde to an ice-cold sulfuric acid solution of the substrate in the presence of ferrous sulfate, giving 7-ethylcamptothecin (2) in 77% yield; second, N-oxidation of 2 with 30% H₂O₂ in acetic acid at 70–80 °C for 3.5 h afforded 7-ethylcamptothecin 1-oxide (3) in 78% yield; finally, photochemical 10-hydroxylation of 3 dissolved in dioxane containing an equimolar amount of sulfuric acid under irradiation with a 450 W high-pressure mercury lamp (Pyrex filter) for 30 min furnished compound 4 (SN-38) in 49% yield [5].
上流・下流製品情報
下流製品
サプライヤー100 社
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
上海宝博洛新材料科技有限公司15572878882; 15572878882 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
北京华威锐科化工有限公司0757-86329057 18934348241 · [email protected]
南部县诚信科技有限公司0838-5675166 15883665058 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [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]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
苏州泽厚生物科技有限公司0512-68716880 19984816880 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
天津万象恒远科技有限公司15722085254 · [email protected]
上海融禾医药科技发展有限公司17301719108 13341702378 · [email protected]
上海星酶生物科技有限公司18112588827
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司400-6009262 15618770481 · [email protected]
上海诺太医药科技有限公司021-50189163 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
河南多贝化工有限公司0370-2785118 17550508557 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
南京诺利斯医药科技有限公司13901585132 · [email protected]
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
上海健超生物科技有限公司150-2103-5486 18017383231 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
越林试剂021-62960152 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
成都瑞芬思德丹生物科技有限公司2355253622; 18981954830 · [email protected]
補足説明
定義ChEBI: SN-38 (7-Ethyl-10-hydroxycamptothecin) is a member of the class of pyranoindolizinoquinolines that is (4S)-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione bearing two additional ethyl substituents at positions 4 and 11 as well as two additional hydroxy substituents at positions 4 and 9. It is the active metabolite of irinotecan and is ~1000 times more active than irinotecan itself. It has a role as an apoptosis inducer, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, a drug metabolite and an antineoplastic agent. It is a pyranoindolizinoquinoline, a delta-lactone, a tertiary alcohol and a member of phenols.
関連反応
5 件
化合物ノート
読み込み中…