기본 정보
- CAS
86639-52-3- 표준 SMILES
CCc1c2c(nc3ccc(O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC- InChIKey
FJHBVJOVLFPMQE-QFIPXVFZSA-N- 분자식
- C22H20N2O5
- 평균 분자량
- 392.4 g/mol
- 단동위원소 질량
- 392.13722174
개요
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.
이름 및 식별자
- 우선 이름
- 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
- 영어명
- 7-Ethyl-10-hydroxycamptothecin
- 분자식
- C22H20N2O5
- 분자량
- 392.4
이름 및 동의어
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-
이름 더 보기
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)-
데이터베이스 식별자
- CAS
86639-52-3- PubChem CID
- 104842
- DTXSID
DTXSID4040399- ChEMBL
CHEMBL837- ChEBI
CHEBI:8988- UNII
- 0H43101T0J
- EC Number
- 643-093-9
- Nikkaji
- J353.490A
물성
구조 계산 물성
- XLogP
- 1.4
- 극성 표면적
- 100 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 29
- 형식 전하
- 0
- 복잡도
- 820
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Listed in ZINC15
물리화학적 성질
- 녹는점
- 217 °C · 217 °C
- 끓는 점
- 810.3 · 810.3±65.0 °C(Predicted)
- 밀도
- 1.51 · 1.51±0.1 g/cm3(Predicted)
- 굴절률
- 21.5 ° · 21.5 ° (C=0.2, THF)
- 저장 조건
- 2 · 2-8°C
- 용해도
- 1 mg/mL · DMSO: 용해성1mg/mL
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 9.13 · 9.13±0.40(Predicted)
- 색상
- 회백색
- 안정성
- 2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO의 솔루션은 최대 1개월 동안 -20°에서 보관할 수 있습니다.
- 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
화학적 성질
Light-Yellow Solid
안전 및 규제
GHS 분류
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.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 3 (75%)
안전 데이터
- wgk
- 3
- rtecs
- UQ0491000
- ridadr
- 2811
- HS 번호
- 29399990
- risk_code
- 25
- hazard_code
- T
- safety_code
- 45
- 포장분류
- Ⅲ
- 위험 등급
- 6.1
- Hazard Classifications
- Acute Tox. 4 OralRepr. 1BSTOT RE 1
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
화학 및 산업
약리 정보
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
응용 분야
용도7-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.
제조 방법
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].
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하류 제품
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추가 설명
정의ChEBI: 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.
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