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ChemicalBook >> CAS DataBase List >>7-Ethyl-10-hydroxycamptothecin

7-Ethyl-10-hydroxycamptothecin

CAS No.
86639-52-3
Chemical Name:
7-Ethyl-10-hydroxycamptothecin
Synonyms
SN38;7-ETHYL-10-HYDROXYCAMPTOTHECINE;Irinotecan Related CoMpound B;(S)-4,11-diethyl-4,9-dihydroxy-1,12-dihydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione;(S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;Irinotecan EP Impurity E/ Irinotecan Related Compound B (7-Ethyl-10-Hydroxy Camptothecin/ 11-Ethyl-9-Hydroxy Camptothecin);EHCPT;NK 012;SN-38:SN38;2H5]-SN-38
CBNumber:
CB5320664
Molecular Formula:
C22H20N2O5
Molecular Weight:
392.4
MDL Number:
MFCD06762720
MOL File:
86639-52-3.mol
MSDS File:
SDS
Last updated:2024-11-19 23:02:33

7-Ethyl-10-hydroxycamptothecin Properties

Melting point 217 °C
Boiling point 810.3±65.0 °C(Predicted)
Density 1.51±0.1 g/cm3(Predicted)
refractive index 21.5 ° (C=0.2, THF)
storage temp. 2-8°C
solubility DMSO: soluble1mg/mL
form powder
pka 9.13±0.40(Predicted)
color Off-white
Stability Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
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 DataBase Reference 86639-52-3(CAS DataBase Reference)
FDA UNII 0H43101T0J

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H360D-H372
Precautionary statements  P202-P260-P264-P270-P301+P312-P308+P313
Hazard Codes  T
Risk Statements  25
Safety Statements  45
RIDADR  2811
WGK Germany  3
RTECS  UQ0491000
HazardClass  6.1
PackingGroup  Ⅲ
HS Code  29399990
NFPA 704
0
2 0

7-Ethyl-10-hydroxycamptothecin price More Price(62)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich H0165 7-Ethyl-10-hydroxycamptothecin ≥98% (HPLC), powder 86639-52-3 10mg $195 2024-03-01 Buy
Sigma-Aldrich PHR2718 Irinotecan Related Compound B Pharmaceutical Secondary Standard; Certified Reference Material, certified reference material, pharmaceutical secondary standard, pkg of 20?mg 86639-52-3 20MG $668 2024-03-01 Buy
Sigma-Aldrich 1347631 Irinotecan Related Compound B United States Pharmacopeia (USP) Reference Standard 86639-52-3 10mg $1380 2024-03-01 Buy
TCI Chemical E0748 7-Ethyl-10-hydroxycamptothecin >98.0%(HPLC) 86639-52-3 1g $313 2024-03-01 Buy
TCI Chemical E0748 7-Ethyl-10-hydroxycamptothecin >98.0%(HPLC) 86639-52-3 100mg $53 2024-03-01 Buy
Product number Packaging Price Buy
H0165 10mg $195 Buy
PHR2718 20MG $668 Buy
1347631 10mg $1380 Buy
E0748 1g $313 Buy
E0748 100mg $53 Buy

7-Ethyl-10-hydroxycamptothecin Chemical Properties,Uses,Production

Description

SN-38 (86639-52-3), also known as 7-Ethyl-10-hydroxycamptothecin, is the active metabolite of CPT-11 that inhibits DNA topoisomerase I (IC50 values are 0.74 and 1.9 μM in P388 and Ehrlich cells respectively). Inhibits DNA and RNA synthesis (IC50 values are 0.077 and 1.3 μM respectively) but does not affect protein synthesis. SN-38 displays potent antitumor activity against a range of human tumor cell lines (IC50 values are 3.3, 13, 19 and 22 nM for HCT-116, BEL-7402, HL60 and HeLa cells respectively).

Chemical Properties

Light-Yellow Solid

Uses

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.

Definition

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.

Biological Activity

Active metabolite of CPT-11 that inhibits DNA topoisomerase I (IC 50 values are 0.74 and 1.9 μ M in P388 and Ehrlich cells respectively). Inhibits DNA and RNA synthesis (IC 50 values are 0.077 and 1.3 μ M respectively) but does not affect protein synthesis. Displays potent antitumor activity against a range of human tumor cell lines (IC 50 values are 3.3, 13, 19 and 22 nM for HCT-116, BEL-7402, HL60 and HELA cells respectively).

Cytotoxicity

7-Ethyl-10-hydroxycamptothecin 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.

storage

Store at +4°C

structure and hydrogen bonding

7-Ethyl-10-hydroxycamptothecin belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).

References

1) Koizumi et al. (2006), Novel SN-38-incorporating polymeric micelles, NKK012, eradicate vascular endothelial growth factor-secreting bulky tumors; Cancer Res., 66 10048 2) Gao et al. (2005), Synthesis and antitumor activity of the hexacyclic camptothecin derivatives; Bioorg. Med. Chem. Lett., 15 3233 3) Kawato et al. (1991), Intracellular roles of SN-38, a metabolite of the camptothecin derivative CPT-11, in the antitumor effect of CPT-11; Cancer Res., 51 4187

7-Ethyl-10-hydroxycamptothecin Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 650)Suppliers
Supplier Tel Email Country ProdList Advantage
Xilinglab Co., Ltd.
+8618381337976 bd@xilinglab.com China 86 58
Unibest Industrial Co.,Ltd.
+86-8657427855777 +86-18758850676 info@unibestcn.com China 227 58
Hebei Chuanghai Biotechnology Co,.LTD 		+86-13131129325 sales1@chuanghaibio.com China 5889 58
Henan Fengda Chemical Co., Ltd 		+86-371-86557731 +86-13613820652 info@fdachem.com China 20284 58
Hebei Ganmiao New material Technology Co., LTD 		+86-17332992504 +86-17332992504 sales8@hbganmiao.com China 300 58
Capot Chemical Co.,Ltd. 		+86-（0）57185586718 +86-13336195806 sales@capot.com China 29791 60
Shanghai Daken Advanced Materials Co.,Ltd 		+86-371-66670886 info@dakenam.com China 18751 58
Beijing Cooperate Pharmaceutical Co.,Ltd 		010-60279497 sales01@cooperate-pharm.com CHINA 1803 55
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21634 55
Nanjing ChemLin Chemical Industry Co., Ltd. 		025-83697070 product@chemlin.com.cn CHINA 3009 60

View Lastest Price from 7-Ethyl-10-hydroxycamptothecin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
7-Ethyl-10-hydroxycamptothecin pictures 2024-12-20 7-Ethyl-10-hydroxycamptothecin
86639-52-3
 US $0.00 / g 100g ≥98%HPLC No limitation Changsha Staherb Natural Ingredients Co., Ltd.
SN-38 pictures 2024-11-19 SN-38
86639-52-3
 US $39.00-77.00 / mg 99.97% 10g TargetMol Chemicals Inc.
7-Ethyl-10-Hydroxycamptothecin pictures 2024-10-11 7-Ethyl-10-Hydroxycamptothecin
86639-52-3
 US $10.70 / kg 10kg 99% 10000kg Hebei Chuanghai Biotechnology Co,.LTD
  • SN-38 pictures
  • SN-38
    86639-52-3
  • US $39.00-77.00 / mg
  • 99.97%
  • TargetMol Chemicals Inc.

7-Ethyl-10-hydroxycamptothecin Spectrum

7-10-hydroxycamptothecin (4S)-4,9-Dihydroxy-4,11-diethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione (4S)-4,9-Dihydroxy-4α,11-diethyl-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione EHCPT 7-Ethyl-10-hydroxy-CPT (Camptothecine), SN-38 10-Hydroxycamptothecin acetate salt ,99% Irinotecan Related Compound B (10 mg) ((S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione) SN 38(7-Ethyl-10-hydroxycaMptothecin) CaMptothecin, 7-ethyl-10-hydroxy (SN-38) 7-Ethyl-10-hydroxy-20(S)-caMptothecin (4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione 7-ETHYL-10-HYDRO(20)S-CAMPTOTHECIN 7-Ethyl-10-Hydroxy Campothecin 7-Ethyl-10-hydroxycamptothecin (TECANS) 7-ethyl-10-hydrol-Camptothecin 7-ETHYL-10-HYDROXYCAMPTTHECIN(SN38) 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-, (4S)- 7-Ethyl-10-hydroxycamptothecin 4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione (S)-7-Ethyl-10-hydroxycamptothecin 7-Ethyl-10-hydroxycamptothecin, >=99% Crude Glycyrrhetinic Acid SN-38:SN38 NK 012 7-etyl-10-hydroxycaMptothecin 7,11-Diethyl-10- hydroxy-caMptothecin Ethyl-10-hydroxycaMptoth 11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione CaMptothecin 7-Ethyl-10-Hydroxy IMpurity 7-ETHYL-10-HYDROXY-CPT CAMPTOTHECIN, 7-ETHYL-10-HYDROXY 4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione 10-dihydroxy- 4’:6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione,4,7-diethyl-1h-pyrano(3 7-ethyl-10-hydroxy-captotheci 7-Ethyl-10-hydroxycamptothecin(SN-38) SN 38 Lactone Irinotecan USP RC B (4S)-4,11-Diethyl-4,9-Dihydroxy-1H-Pyrano[3,4 6,7]Indolizino[1,2-B]Quinoline-3,14(4H,12H)-Dione Irinotecan Impurity 15 7-Ethyl-10-hydroxycamptothecin 86639-52-3 Irinotecan EP Impurity E SN-38(NK-012) (S)-7-ETHYL-10-HYDROXY CAMPTOTHECIN (IRINOTECAN EP IMPURITY E) IRINOTECAN EP IMPURITY E ((S)-7-ETHYL-10-HYDROXY CAMPTOTHECIN) (S)-4,11-diethyl-4,9-dihydroxy-1H-benzo[f]pyrano[4',3':4,5]pyrido[2,1-a]isoindole-3,14(4H,12H)-dione (S)-7-Ethyl-10-hydroxy campthothecin 7-ethyl-10-hydroxycamptothecin 80-98% 7-Ethyl-10-hydroxycamptothecin> 7-Ethyl-10-hydroxycamptothecin USP/EP/BP SN-38 （Synonyms: NK012） 7-Ethyl-1-hydroxycamptothecin 7-Ethyl-10-HydroxycamptothecinQ: What is 7-Ethyl-10-Hydroxycamptothecin Q: What is the CAS Number of 7-Ethyl-10-Hydroxycamptothecin Q: What is the storage condition of 7-Ethyl-10-Hydroxycamptothecin Q: What are the applications of 7-Ethyl-10-Hydroxycamptothecin 7-Ethyl-10-hydroxy-20(S)-campthothecin Irinotecan Related Compound B ((S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3'',4'':6,7]indolizino[1,2-b] (1347631) Irinotecan EP Impurity E/ Irinotecan Related Compound B (7-Ethyl-10-Hydroxy Camptothecin/ 11-Ethyl-9-Hydroxy Camptothecin) SN38 7-ETHYL-10-HYDROXYCAMPTOTHECINE