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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
Structure of 10-HYDROXYCAMPTOTHECIN

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

HIDE SMILES / InChI

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

Description
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
106.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A mutation in subunit B of the DNA polymerase alpha-primase complex from Novikoff hepatoma cells concomitant with a conformational change and abnormal catalytic properties of the DNA polymerase alpha-primase complex.
2001 Aug
Antiangiogenic potential of 10-hydroxycamptothecin.
2001 Aug 24
Metabolism and biliary excretion of the novel anticancer agent 10-hydroxycamptothecin in the isolated perfused rat liver.
2001 Dec
Synthesis and biological evaluation of novel A-ring modified hexacyclic camptothecin analogues.
2001 May 10
Effects of 10-hydroxycamptothecin, delivered from locally injectable poly(lactide-co-glycolide) microspheres, in a murine human oral squamous cell carcinoma regression model.
2001 May-Jun
Relationship between lactone ring forms of HCPT and their antitumor activities.
2001 Sep
[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
[Effect of the change of caspase-3 activity on the neoadjuvant chemotherapy-induced apoptosis of large-intestinal carcinoma cells].
2003 Apr
[The evaluation of LFH or LFPH in the treatment of advanced cancer of gastric cardia and colorectal cancer].
2003 May
Antisense therapy targeting MDM2 oncogene in prostate cancer: Effects on proliferation, apoptosis, multiple gene expression, and chemotherapy.
2003 Sep 30
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
Camptothecin and 10-hydroxycamptothecin from Camptotheca acuminata hairy roots.
2004 Jan
Enhanced 7-ethyl-10-hydroxycamptothecin (SN-38) lethality by methylselenocysteine is associated with Chk2 phosphorylation at threonine-68 and down-regulation of Cdc6 expression.
2004 Jul
[Anti-tumor effects of 10-hydroxycamptothecinc-treated DC-Hepa1-6 fusion vaccines].
2004 Jun
Effect of pressure on the proton transfer rate from a photoacid to a solvent. 4. Photoacids in methanol.
2005 Jun 2
Synthesis and antitumor activity of A-ring modified hexacyclic analogues of camptothecin.
2005 Mar
[Pharmacokinetic study of intraperitoneal chemotherapy with HCPT].
2005 Oct
Dendritic supramolecular assemblies for drug delivery.
2005 Sep 14
Hydroxycamptothecin-induced apoptosis in hepatoma SMMC-7721 cells and the role of mitochondrial pathway.
2006 Aug
Novel colon-specific microspheres with highly dispersed hydroxycamptothecin cores: their preparation, release behavior, and therapeutic efficiency against colonic cancer.
2006 Dec
Bcl-2 siRNA induced apoptosis and increased sensitivity to 5-fluorouracil and HCPT in HepG2 cells.
2006 Jan
Development and validation of a sensitive reversed-phase HPLC method to determine intracellular accumulation of hydroxycamptothecin.
2006 Jun 7
[Experimental study of hydroxycamptothecine and theprubicine in the treatment of adenoid cystic carcinoma lung metastases].
2006 May
Gamma-pyranone derivatives and other constituents from Erigeron annuus.
2006 May
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 Sep
Antitumor effects of hydroxycamptothecin-loaded poly[ethylene glycol]-poly [gamma-benzyl-L-glutamate] micelles against oral squamous cell carcinoma.
2007
Polymeric micelle systems of hydroxycamptothecin based on amphiphilic N-alkyl-N-trimethyl chitosan derivatives.
2007 Apr 1
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
Determination of hydroxycamptothecin affinities to albumin and membranes by steady-state fluorescence anisotropy measurements.
2007 Jul
Effect of pH and human serum albumin on the cytotoxicity of a glucuronide prodrug of 9-aminocamptothecin.
2007 Jun
Synthesis of alginic acid-poly[2-(diethylamino)ethyl methacrylate] monodispersed nanoparticles by a polymer-monomer pair reaction system.
2007 Mar
[Hydroxycamptothecin promotes the apoptosis of prostate cancer cell line PC-3].
2007 Oct
Changes in the protein spectrum of mitochondria isolated from hydroxycamptothecin-treated hepatoma cells.
2007 Oct
[Preparation of PEG-modified nanostructured lipid carriers loaded with hydroxycamptothecin and tissue distribution in mice].
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
by admin
on Thu Jul 06 02:28:28 UTC 2023
Edited
by admin
on Thu Jul 06 02:28:28 UTC 2023
Record UNII
9Z01632KRV
Record Status Validated (UNII)
Record Version
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Name Type Language
10-HYDROXYCAMPTOTHECIN
Common Name English
(S)-10-HYDROXYCAMPTOTHECIN
Common Name English
10-HCPT
Common Name English
(+)-10-HYDROXYCAMPTOTHECIN
Common Name English
10-Hydroxycamptothecin [WHO-DD]
Common Name English
1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE, 4-ETHYL-4,9-DIHYDROXY-, (4S)-
Systematic Name English
HYDROXYCAMPTOTHECIN
Common Name English
NSC-107124
Code English
IRINOTECAN RELATED COMPOUND A [USP-RS]
Common Name English
IRINOTECAN RELATED COMPOUND A
USP-RS  
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID00941444
Created by admin on Thu Jul 06 02:28:28 UTC 2023 , Edited by admin on Thu Jul 06 02:28:28 UTC 2023
PRIMARY
SMS_ID
100000087613
Created by admin on Thu Jul 06 02:28:28 UTC 2023 , Edited by admin on Thu Jul 06 02:28:28 UTC 2023
PRIMARY
CAS
19685-09-7
Created by admin on Thu Jul 06 02:28:28 UTC 2023 , Edited by admin on Thu Jul 06 02:28:28 UTC 2023
PRIMARY
FDA UNII
9Z01632KRV
Created by admin on Thu Jul 06 02:28:28 UTC 2023 , Edited by admin on Thu Jul 06 02:28:28 UTC 2023
PRIMARY
RS_ITEM_NUM
1347610
Created by admin on Thu Jul 06 02:28:28 UTC 2023 , Edited by admin on Thu Jul 06 02:28:28 UTC 2023
PRIMARY
EVMPD
SUB23339
Created by admin on Thu Jul 06 02:28:28 UTC 2023 , Edited by admin on Thu Jul 06 02:28:28 UTC 2023
PRIMARY
PUBCHEM
97226
Created by admin on Thu Jul 06 02:28:28 UTC 2023 , Edited by admin on Thu Jul 06 02:28:28 UTC 2023
PRIMARY
NSC
107124
Created by admin on Thu Jul 06 02:28:28 UTC 2023 , Edited by admin on Thu Jul 06 02:28:28 UTC 2023
PRIMARY
DRUG BANK
DB12385
Created by admin on Thu Jul 06 02:28:28 UTC 2023 , Edited by admin on Thu Jul 06 02:28:28 UTC 2023
PRIMARY
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TRANSPORTER -> SUBSTRATE
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP