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 |
|---|---|---|
| Relationship between lactone ring forms of HCPT and their antitumor activities. | 2001 Sep |
|
| [Anticancer effect of hydroxycampothecin on oral squamous carcinoma cell line]. | 2002 Apr |
|
| [Cell cycle block and apoptosis in rabbit lens epithelial cells induced by hydroxycamptothecine]. | 2002 Mar |
|
| Homocamptothecin-daunorubicin association overcomes multidrug-resistance in breast cancer MCF7 cells. | 2002 May |
|
| [Inhibition of hydroxycamptothecin on laryngeal squamous carcinoma cell line]. | 2003 Apr |
|
| [Experimental studies on treatment of nasopharyngeal carcinoma with combination regimen of hydroxycamptothecin and etoposide]. | 2003 Apr |
|
| Antisense protein kinase A RIalpha acts synergistically with hydroxycamptothecin to inhibit growth and induce apoptosis in human cancer cells: molecular basis for combinatorial therapy. | 2003 Mar |
|
| [The evaluation of LFH or LFPH in the treatment of advanced cancer of gastric cardia and colorectal cancer]. | 2003 May |
|
| Characterization of inhibitors of specific carboxylesterases: development of carboxylesterase inhibitors for translational application. | 2004 Aug |
|
| Synthesis and biological evaluation of bis and monocarbonate prodrugs of 10-hydroxycamptothecins. | 2004 Aug 1 |
|
| Topoisomerase I and II inhibitors control caspase-2 pre-messenger RNA splicing in human cells. | 2004 Jan |
|
| Camptothecin and 10-hydroxycamptothecin from Camptotheca acuminata hairy roots. | 2004 Jan |
|
| [Anti-tumor effects of 10-hydroxycamptothecinc-treated DC-Hepa1-6 fusion vaccines]. | 2004 Jun |
|
| [Antitumor effects of chemotherapeutic drugs on fresh human gastric cancer cells and their relationships to expressions of P-glycoprotein and glutathione S transferase-pi]. | 2005 Apr |
|
| Effect of pressure on the proton transfer rate from a photoacid to a solvent. 4. Photoacids in methanol. | 2005 Jun 2 |
|
| [Synthesis and spectral characterization of 10-hydroxycamptothecin]. | 2005 Nov |
|
| [Effect of hydroxycamptothecin on apoptosis-inducing factor (AIF) expression and on AIF translocation in human hepatocellular cancer cell SMMC-7721]. | 2006 Apr |
|
| Novel colon-specific microspheres with highly dispersed hydroxycamptothecin cores: their preparation, release behavior, and therapeutic efficiency against colonic cancer. | 2006 Dec |
|
| [Erythromycin inhibits the proliferation of HERG K+ channel highly expressing cancer cells and shows synergy with anticancer drugs]. | 2006 Dec 19 |
|
| [Experimental study of hydroxycamptothecine and theprubicine in the treatment of adenoid cystic carcinoma lung metastases]. | 2006 May |
|
| Polymeric micelle systems of hydroxycamptothecin based on amphiphilic N-alkyl-N-trimethyl chitosan derivatives. | 2007 Apr 1 |
|
| [Effects of hydroxycamptothecin and teniposide on proliferation and apoptosis of gastric cancer cell line BGC-823]. | 2007 Aug |
|
| Additive immunosuppressive effect of hydroxycamptothecin and cyclosporine on rejection of heart transplantation in rats. | 2007 Dec |
|
| 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 Feb 19 |
|
| Thermal behavior and thermal decarboxylation of 10-hydroxycamptothecin in the solid state. | 2007 Jan 17 |
|
| 10-Hydroxycamptothecin loaded nanoparticles: preparation and antitumor activity in mice. | 2007 Jun 4 |
|
| Crystal structure of the Geobacillus stearothermophilus carboxylesterase Est55 and its activation of prodrug CPT-11. | 2007 Mar 16 |
|
| Changes in the protein spectrum of mitochondria isolated from hydroxycamptothecin-treated hepatoma cells. | 2007 Oct |
|
| Development of efficient RNA interference system using EGF-displaying phagemid particles. | 2008 Apr |
|
| [Preparation of PEG-modified nanostructured lipid carriers loaded with hydroxycamptothecin and tissue distribution in mice]. | 2008 Jan |
|
| Intraperitoneal chemotherapy with hydroxycamptothecin reduces peritoneal carcinomatosis: results of an experimental study. | 2008 Jan |
|
| Synthesis and cytotoxic activity of new 9-substituted camptothecins. | 2008 May 1 |
|
| Hydroxycamptothecin-loaded nanoparticles enhance target drug delivery and anticancer effect. | 2008 May 4 |
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
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Edited
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| Record UNII |
9Z01632KRV
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| Record Status |
Validated (UNII)
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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TRANSPORTER -> SUBSTRATE |
Down-regulation of ABCB5αresulted 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)
USP
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