Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H16N2O5 |
| Molecular Weight | 364.3514 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@@]1(O)C(=O)OCC2=C1C=C3N(CC4=C3N=C5C=CC(O)=CC5=C4)C2=O
InChI
InChIKey=HAWSQZCWOQZXHI-FQEVSTJZSA-N
InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1
| Molecular Formula | C20H16N2O5 |
| Molecular Weight | 364.3514 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16596197
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16596197
10-Hydroxycamptothecin (10-HCPT), an indole alkaloid isolated from a Chinese tree, Camptotheca acuminate, inhibits the activity of topoisomerase I and has a broad spectrum of anticancer activity in vitro and in vivo. However, its use has been limited due to its water-insolubility and toxicity with i.v. administration. Prolonged elimination of 10-HCPT in vivo may have a significant impact on its therapeutic effects. 10-HCPT is metabolized to its carboxylate form and glucuronides.It was investigated that relatively low dose of 10-HCPT is able to inhibit the growth of colon cancer, facilitating the development of a new protocol of human trials with this anticancer drug.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hydroxycamptothecin-loaded nanoparticles enhance target drug delivery and anticancer effect. | 2008-05-04 |
|
| Synthesis and cytotoxic activity of new 9-substituted camptothecins. | 2008-05-01 |
|
| Prospecting for Camptothecines from Nothapodytes nimmoniana in the Western Ghats, South India: identification of high-yielding sources of camptothecin and new families of camptothecines. | 2008-04 |
|
| Development of efficient RNA interference system using EGF-displaying phagemid particles. | 2008-04 |
|
| Benzyl ether-linked glucuronide derivative of 10-hydroxycamptothecin designed for selective camptothecin-based anticancer therapy. | 2008-03-27 |
|
| [Preparation of PEG-modified nanostructured lipid carriers loaded with hydroxycamptothecin and tissue distribution in mice]. | 2008-01 |
|
| Intraperitoneal chemotherapy with hydroxycamptothecin reduces peritoneal carcinomatosis: results of an experimental study. | 2008-01 |
|
| Additive immunosuppressive effect of hydroxycamptothecin and cyclosporine on rejection of heart transplantation in rats. | 2007-12 |
|
| Arguside A: a new cytotoxic triterpene glycoside from the sea cucumber Bohadschia argus Jaeger. | 2007-12 |
|
| [Hydroxycamptothecin promotes the apoptosis of prostate cancer cell line PC-3]. | 2007-10 |
|
| Changes in the protein spectrum of mitochondria isolated from hydroxycamptothecin-treated hepatoma cells. | 2007-10 |
|
| Preparation, characterization and biodistribution of the lactone form of 10-hydroxycamptothecin (HCPT)-loaded bovine serum albumin (BSA) nanoparticles. | 2007-08-01 |
|
| [Effects of hydroxycamptothecin and teniposide on proliferation and apoptosis of gastric cancer cell line BGC-823]. | 2007-08 |
|
| Determination of hydroxycamptothecin affinities to albumin and membranes by steady-state fluorescence anisotropy measurements. | 2007-07 |
|
| Hydroxycamptothecin deactivation rates and binding to model membranes and HSA determined by fluorescence spectra analysis. | 2007-07 |
|
| [10-hydroxy-camptothecin plus fluorouracil/leucovorin for the treatment of patients with advanced colorectal cancer]. | 2007-06-05 |
|
| 10-Hydroxycamptothecin loaded nanoparticles: preparation and antitumor activity in mice. | 2007-06-04 |
|
| Effect of pH and human serum albumin on the cytotoxicity of a glucuronide prodrug of 9-aminocamptothecin. | 2007-06 |
|
| siRNA-mediated Bcl-2 and Bcl-xl gene silencing sensitizes human hepatoblastoma cells to chemotherapeutic drugs. | 2007-04-19 |
|
| Polymeric micelle systems of hydroxycamptothecin based on amphiphilic N-alkyl-N-trimethyl chitosan derivatives. | 2007-04-01 |
|
| [Lethal effect of adenovirus-mediated HSV-TK gene in combination with hydroxycamptothecin on human bladder cancer in vitro]. | 2007-04 |
|
| Crystal structure of the Geobacillus stearothermophilus carboxylesterase Est55 and its activation of prodrug CPT-11. | 2007-03-16 |
|
| Synthesis of alginic acid-poly[2-(diethylamino)ethyl methacrylate] monodispersed nanoparticles by a polymer-monomer pair reaction system. | 2007-03 |
|
| The thermodynamic dissociation constants of the anticancer drugs camptothecine, 7-ethyl-10-hydroxycamptothecine, 10-hydroxycamptothecine and 7-ethylcamptothecine by the least-squares nonlinear regression of multiwavelength spectrophotometric pH-titration data. | 2007-02-19 |
|
| Characteristics of the microbial community in rhizosphere of Camptotheca acuminata cultured with exotic invasive plant Eupatorium adenophorum. | 2007-02 |
|
| Thermal behavior and thermal decarboxylation of 10-hydroxycamptothecin in the solid state. | 2007-01-17 |
|
| Extraction and composition of three naturally occurring anti-cancer alkaloids in Camptotheca acuminata seed and leaf extracts. | 2007-01 |
|
| Antitumor effects of hydroxycamptothecin-loaded poly[ethylene glycol]-poly [gamma-benzyl-L-glutamate] micelles against oral squamous cell carcinoma. | 2007 |
|
| Enhanced nuclear delivery and cytotoxic activity of hydroxycamptothecin using o/w emulsions. | 2007 |
|
| [Erythromycin inhibits the proliferation of HERG K+ channel highly expressing cancer cells and shows synergy with anticancer drugs]. | 2006-12-19 |
|
| Novel colon-specific microspheres with highly dispersed hydroxycamptothecin cores: their preparation, release behavior, and therapeutic efficiency against colonic cancer. | 2006-12 |
|
| Oxaliplatin plus hydroxycamptothecine versus oxaliplatin plus 5-fluorouracil and leucovorin in treatment of advanced colorectal cancer. | 2006-11-05 |
|
| Chitosan surface-modified hydroxycamptothecin loaded nanoparticles with enhanced transport across Caco-2 cell monolayer. | 2006-10-20 |
|
| Bcl-XL small interfering RNA enhances sensitivity of Hepg2 hepatocellular carcinoma cells to 5-fluorouracil and hydroxycamptothecin. | 2006-10 |
|
| Stealth PEG-PHDCA niosomes: effects of chain length of PEG and particle size on niosomes surface properties, in vitro drug release, phagocytic uptake, in vivo pharmacokinetics and antitumor activity. | 2006-09 |
|
| [Short-term effects of chemotherapy combined with hydroxycamptothecine and oxaliplatin in treatment of recurrent and metastatic colorectal cancer]. | 2006-08 |
|
| [Effect of several anti-tumor drugs on apoptosis induction in Jurkat cell line]. | 2006-08 |
|
| Hydroxycamptothecin-induced apoptosis in hepatoma SMMC-7721 cells and the role of mitochondrial pathway. | 2006-08 |
|
| Development and validation of a sensitive reversed-phase HPLC method to determine intracellular accumulation of hydroxycamptothecin. | 2006-06-07 |
|
| [In vitro chemo-sensitivity MTT assay guided intraperitoneal chemotherapy for malignant ascites]. | 2006-06 |
|
| [Experimental study of hydroxycamptothecine and theprubicine in the treatment of adenoid cystic carcinoma lung metastases]. | 2006-05 |
|
| Gamma-pyranone derivatives and other constituents from Erigeron annuus. | 2006-05 |
|
| [Establishment of a multidrug-resistant cell line BEL-7402/5-FU of human hepatocellular carcinoma and its biological characteristics]. | 2006-05 |
|
| Anticancer effects of low-dose 10-hydroxycamptothecin in human colon cancer. | 2006-05 |
|
| [Effect of hydroxycamptothecin on apoptosis-inducing factor (AIF) expression and on AIF translocation in human hepatocellular cancer cell SMMC-7721]. | 2006-04 |
|
| [Preparation of 10-hydroxycamptothecin semisolid lipid nanoparticles and investigation of its stability]. | 2006-01 |
|
| Bcl-2 siRNA induced apoptosis and increased sensitivity to 5-fluorouracil and HCPT in HepG2 cells. | 2006-01 |
|
| Stealth PEG-PHDCA niosomes: effects of chain length of PEG on niosomes in vitro complement consumption and phagocytic uptake. | 2005-11 |
|
| [Synthesis and spectral characterization of 10-hydroxycamptothecin]. | 2005-11 |
|
| Effect of pressure on the proton transfer rate from a photoacid to a solvent. 4. Photoacids in methanol. | 2005-06-02 |
Patents
Sample Use Guides
mice: 10-Hydroxycamptothecin (10-HCPT) was administered via p.o. once per two or four days at doses of 1, 2.5, 5, 7.5 mg/kg (volume of injection: 0.1 ml/20 g of body weight), respectively. The control group received propylene glycol vehicle once per two days.
Route of Administration:
Oral
The effect of 10-HYDROXYCAMPTOTHECIN (10-HCPT) on the proliferation activity of RAW264.7 cells was detected using Cell Counting Kit-8 (CCK-8). CCK-8 detection showed that 10-HCPT with a certain concentration (1 ng/ml to 5 ng/ml) had no effect on cell proliferation (P>0.05); 10-HCPT could inhibit the generation of osteoclasts. With the increase of the concentration of 10-HCPT, the number of osteoclasts generated from cells cultured with 10-HCPT [1 ng/ml (86±11.14), 2 ng/ml (66.67±7.51), 5ng/ml (27.67±6.51)] was much lower than that of the control group (145±8.19), and the difference was statistically significant (all P=0, P less than 0.05).
| Substance Class |
Chemical
Created
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admin
on
Edited
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on
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| Record UNII |
9Z01632KRV
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| Record Status |
Validated (UNII)
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| Record Version |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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TRANSPORTER -> SUBSTRATE |
Down-regulation of ABCB5?resulted in a gain of drug sensitivity to camptothecin 10-OH, 5-fluorouracil, and mitoxantrone.
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| Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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