7-Ethyl-10-hydroxycamptothecin
- Product Name
- 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
- Formula Weight
- 392.4
- MOL File
- 86639-52-3.mol
7-Ethyl-10-hydroxycamptothecin Property
- 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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H302Harmful if swallowed
H372Causes damage to organs through prolonged or repeated exposure
- Precautionary statements
-
P202Do not handle until all safety precautions have been read and understood.
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P308+P313IF exposed or concerned: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- H0165
- Product name
- 7-Ethyl-10-hydroxycamptothecin
- Purity
- ≥98% (HPLC), powder
- Packaging
- 10mg
- Price
- $195
- Updated
- 2024/03/01
- Product number
- PHR2718
- Product name
- Irinotecan Related Compound B
- Purity
- Pharmaceutical Secondary Standard; Certified Reference Material, certified reference material, pharmaceutical secondary standard, pkg of 20?mg
- Packaging
- 20MG
- Price
- $668
- Updated
- 2024/03/01
- Product number
- 1347631
- Product name
- Irinotecan Related Compound B
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 10mg
- Price
- $1380
- Updated
- 2024/03/01
- Product number
- E0748
- Product name
- 7-Ethyl-10-hydroxycamptothecin
- Purity
- >98.0%(HPLC)
- Packaging
- 1g
- Price
- $313
- Updated
- 2024/03/01
- Product number
- E0748
- Product name
- 7-Ethyl-10-hydroxycamptothecin
- Purity
- >98.0%(HPLC)
- Packaging
- 100mg
- Price
- $53
- Updated
- 2024/03/01
7-Ethyl-10-hydroxycamptothecin Chemical Properties,Usage,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
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View Lastest Price from 7-Ethyl-10-hydroxycamptothecin manufacturers
- Product
- 7-Ethyl-10-Hydroxycamptothecin 86639-52-3
- Price
- US $10.70/kg
- Min. Order
- 10kg
- Purity
- 99%
- Supply Ability
- 10000kg
- Release date
- 2024-08-01
- Product
- 7-Ethyl-10-hydroxycamptothecin 86639-52-3
- Price
- US $10.00-7.00/g
- Min. Order
- 1g
- Purity
- 99.9%
- Supply Ability
- 50KG
- Release date
- 2024-06-07
- Product
- 7-Ethyl-10-hydroxycamptothecin 86639-52-3
- Price
- US $8.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2024-03-29