Contact us: +91 9550333722 040 - 40102781
Structured search
India
Choose your country
Different countries will display different contents
Try our best to find the right business for you.
My chemicalbook

Welcome back!

HomeProduct name list7-Ethyl-10-hydroxycamptothecin

7-Ethyl-10-hydroxycamptothecin

Synonym(s):(4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)dione;SN-38

  • CAS NO.:86639-52-3
  • Empirical Formula: C22H20N2O5
  • Molecular Weight: 392.4
  • MDL number: MFCD06762720
  • EINECS: 643-093-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-07 21:39:59
7-Ethyl-10-hydroxycamptothecin Structural

What is 7-Ethyl-10-hydroxycamptothecin?

Description

SN-38 (86639-52-3) 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

The Uses of 7-Ethyl-10-hydroxycamptothecin

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.

What are the applications of Application

SN 38 is the active metabolite of the topoisomerase-I (topo-I) inhibitor Irinotecan (CPT-11), able to inhibit DNA topoisomerase I.

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

Properties of 7-Ethyl-10-hydroxycamptothecin

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
CAS DataBase Reference 86639-52-3(CAS DataBase Reference)

Safety information for 7-Ethyl-10-hydroxycamptothecin

Signal word Danger
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
H372:Specific target organ toxicity, repeated exposure
Precautionary Statement Codes P202:Do not handle until all safety precautions have been read and understood.
P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for 7-Ethyl-10-hydroxycamptothecin

InChIKey FJHBVJOVLFPMQE-QFIPXVFZSA-N
SMILES N1C2C(=CC(O)=CC=2)C(CC)=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O

Abamectin manufacturer

JSK Chemicals

1Y
Phone:+919879767970
Whatsapp: +91 9879767970
product: 86639-52-3 99%
Inquiry

Varanous Labs Pvt Ltd

1Y
Phone:+917036248882
Whatsapp: +91 7036248882
product: 7-Ethyl-10-hydroxycamptothecin 98%
Inquiry

Avra Laboratories Pvt Ltd

1Y
Phone:+91-8008572391
Whatsapp: +91 8008572391
product: (S)-7-Ethyl-10-hydroxycamptothecin 86639-52-3 99%
Inquiry

Rivashaa Agrotech Biopharma Pvt. Ltd.

1Y
Phone:+91-7926462688
product: 86639-52-3 (S)-7-Ethyl-10-hydroxycamptothecin 98%
Inquiry

Aktinos Pharma Pvt Ltd

1Y
Phone:+914048541177
product: (S)-7-Ethyl-10-hydroxycamptothecin 98%
Inquiry

Related products of tetrahydrofuran

You may like

  • 86639-52-3 7-ETHYL-10-HYDROXYCAMPTOTHECIN 99%
    86639-52-3 7-ETHYL-10-HYDROXYCAMPTOTHECIN 99%
    86639-52-3
    View Details
  • 86639-52-3 99%
    86639-52-3 99%
    86639-52-3
    View Details
  • (S)-7-Ethyl-10-hydroxycamptothecin 98%
    (S)-7-Ethyl-10-hydroxycamptothecin 98%
    86639-52-3
    View Details
  • 7-Ethyl-10-hydroxycamptothecin CAS 86639-52-3
    7-Ethyl-10-hydroxycamptothecin CAS 86639-52-3
    86639-52-3
    View Details
  • 7-Ethyl-10-hydroxycamptothecin 98%
    7-Ethyl-10-hydroxycamptothecin 98%
    86639-52-3
    View Details
  • (S)-7-Ethyl-10-hydroxycamptothecin 86639-52-3 99%
    (S)-7-Ethyl-10-hydroxycamptothecin 86639-52-3 99%
    86639-52-3
    View Details
  • SN-38 95.00% CAS 86639-52-3
    SN-38 95.00% CAS 86639-52-3
    86639-52-3
    View Details
  • Irinotecan Related Compound B CAS 86639-52-3
    Irinotecan Related Compound B CAS 86639-52-3
    86639-52-3
    View Details
Statement: All products displayed on this website are only used for non medical purposes such as industrial applications or scientific research, and cannot be used for clinical diagnosis or treatment of humans or animals. They are not medicinal or edible.