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

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
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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)
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Safety

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
45
RIDADR 
2811
WGK Germany 
3
RTECS 
UQ0491000
HazardClass 
6.1
PackingGroup 
Ⅲ
HS Code 
29399990
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H0165
Product name
7-Ethyl-10-hydroxycamptothecin
Purity
≥98% (HPLC), powder
Packaging
10mg
Price
$195
Updated
2024/03/01
Sigma-Aldrich
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
Sigma-Aldrich
Product number
1347631
Product name
Irinotecan Related Compound B
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
10mg
Price
$1380
Updated
2024/03/01
TCI Chemical
Product number
E0748
Product name
7-Ethyl-10-hydroxycamptothecin
Purity
>98.0%(HPLC)
Packaging
1g
Price
$313
Updated
2024/03/01
TCI Chemical
Product number
E0748
Product name
7-Ethyl-10-hydroxycamptothecin
Purity
>98.0%(HPLC)
Packaging
100mg
Price
$53
Updated
2024/03/01
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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

Preparation Products

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

Hebei Chuanghai Biotechnology Co,.LTD
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
Hebei Ganmiao New material Technology Co., LTD
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
Henan Fengda Chemical Co., Ltd
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

86639-52-3, 7-Ethyl-10-hydroxycamptothecinRelated Search:

Ethyl acetate Ethyl formate Ethyl acrylate Ethylparaben 10-HYDROXYCAMPTOTHECIN 4-Ethyl-4,10-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Ethyl vanillin 1-Hydroxyethylidene-1,1-diphosphonic acid (+)-Camptothecin Ethylbenzene Ethanol Ethyl propionate 10-Hydroxycamptothecin sodium:(2S)-2-[12-ethyl-8-(hydroxymethyl)-9-oxo-2-(4-piperidin-1-ylpiperidine-1-carbonyl)oxy-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate Irinotecan 7,11-Diethyl-10-hydroxycaMptothecin Irinotecan Impurity 6 12-Hydroxy Irinotecan

  • 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
  • (S)-4,11-diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
  • Irinotecan Related CoMpound B
  • 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
  • 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
  • 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-HYDROXYCAMPTOTHECINE
  • 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
  • SN38
  • 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
  • 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&gt
  • 7-Ethyl-10-hydroxycamptothecin USP/EP/BP
  • SN-38 （Synonyms: NK012）
  • Irinotecan EP Impurity E/ Irinotecan Related Compound B (7-Ethyl-10-Hydroxy Camptothecin/ 11-Ethyl-9-Hydroxy Camptothecin)
  • 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