7-Ethyl-10-hydroxycamptothecin
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7-Ethyl-10-hydroxycamptothecin
structure -
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CAS No:
86639-52-3
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Formula:
C22H20N2O5
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Chemical Name:
7-Ethyl-10-hydroxycamptothecin
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Synonyms:
1H-Pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione,4,11-diethyl-4,9-dihydroxy-,(4S)-;1H-Pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione,4,11-diethyl-4,9-dihydroxy-,(S)-;(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-hydroxycamptothecin;SN 38 (pharmaceutical);SN 38;10-Hydroxy-7-ethylcamptothecin;7-Ethyl-10-hydroxy-20(S)-camptothecin;SN 38 lactone;(S)-SN 38;(19S)-10,19-Diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0[2,11].0[4,9].0[15,20]]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione;113015-38-6
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CAS No:
Description
SN-38 is an active metabolite of the Topoisomerase I inhibitor Irinotecan. SN-38 inhibits DNA and RNA synthesis with IC50s of 0.077 and 1.3 μM, respectively.
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 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.|7-ethyl-10-hydroxycamptothecin (SN 38) is a liposomal formulation of the active metabolite of Irinotecan [DB00762], a chemotherapeutic pro-drug approved for the treatment of advanced colorectal cancer. 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.|A semisynthetic camptothecin derivative that inhibits DNA TOPOISOMERASE I to prevent nucleic acid synthesis during S PHASE. It is used as an antineoplastic agent for the treatment of COLORECTAL NEOPLASMS and PANCREATIC NEOPLASMS.
7-Ethyl-10-hydroxycamptothecin Basic Attributes
392.4
392.40
1592732-453-0
0H43101T0J
673596
DTXSID4040399
2942000000
Characteristics
100
1.4
light-yellow solid
1.5±0.1 g/cm3
217 °C
810.3°C at 760 mmHg
443.8±34.3 °C
1.738
DMSO: soluble 1mg/mL
−20°C
Safety Information
6.1
2811
3
25
45
UQ0491000
T
P301 + P310
H301
|Danger|H301 (78.18%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P310, P308+P313, P321, P330, P405, and P501|Aggregated GHS information provided by 56 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Investigated for use/treatment in colorectal cancer.
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%.
Compounds that inhibit the activity of DNA TOPOISOMERASE I. (See all compounds classified as Topoisomerase I Inhibitors.)
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.
7 Ethyl 10 hydroxycamptothecin
7-Ethyl-10-hydroxycamptothecin Use and Manufacturing
A metabolite of Irinotecan, a DNA topoisomerase inhibitor
Human drugs -> Rare disease (orphan)
Computed Properties
Molecular Weight:392.4
XLogP3:1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:392.13722174
Monoisotopic Mass:392.13722174
Topological Polar Surface Area:100
Heavy Atom Count:29
Complexity:820
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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