EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

(S)-(+)-camptothecin
1H-pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-

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CAS Number: 7689-03-4Picture of molecule3D/inchi
FDA UNII: XT3Z54Z28A
Nikkaji Web:J2.266G
Beilstein Number:0631069
MDL:MFCD00081076
XlogP3-AA:1.00 (est)
Molecular Weight:348.35832000
Formula:C20 H16 N2 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:pale yellow crystalline powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 757.00 °C. @ 760.00 mm Hg (est)
Flash Point: 773.00 °F. TCC ( 411.60 °C. ) (est)
logP (o/w): 1.740
Soluble in:
 water, 207 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Camptothecin 98%
BOC Sciences
For experimental / research use only.
Camptothecine
Odor: characteristic
Use: Camptothecin (CPT) is a cytotoxic quinoline alkaloid which inhibits the DNA enzyme topoisomerase I (topo I). It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of natural products for anticancer drugs.
Changsha Organic Herb
Camptothecine Camptothecin
Glentham Life Sciences
(S)-(+)-Camptothecin
Santa Cruz Biotechnology
For experimental / research use only.
(S)-(+)-Camptothecin ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
(S)-(+)-Camptothecin ≥90% (HPLC), powder
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 64 mg/kg
Cancer Research. Vol. 39, Pg. 2204, 1979.

intravenous-mouse LD50 38 mg/kg
National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986

oral-mouse LD50 50100 ug/kg
Gan to Kagaku Ryoho. Cancer and Chemotherapy. Vol. 14, Pg. 850, 1987.

intravenous-rat LD50 234 mg/kg
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 14, Pg. 487, 1972.

oral-rat LD50 153 mg/kg
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 14, Pg. 487, 1972.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (S)-(+)-camptothecin usage levels up to:
 not for fragrance use.
 
Recommendation for (S)-(+)-camptothecin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :24360
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0007689034
RTECS:UQ0492000 for cas# 7689-03-4
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):24360
Pubchem (sid):134988863
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C01897
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2939.90.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 camptotheca acuminata bark
Search Trop Picture
 
Synonyms:
(+)-camptothecin
(S)-camptothecin
20(S)-camptothecin
21,22-secocamptothecin-21-oic acid lactone
(+)-camptothecine
(S)-camptothecine
20(S)-camptothecine
 camptothecine (S,+)
 camptothecinum
(4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)-
1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
1H-pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
 

Articles:

PubMed:Preparation of camptothecin-loaded targeting nanoparticles and their antitumor effects on hepatocellular carcinoma cell line H22.
PubMed:Functional and molecular defects of hiPSC-derived neurons from patients with ATM deficiency.
PubMed:SN38 polymeric nanoparticles: in vitro cytotoxicity and in vivo antitumor efficacy in xenograft balb/c model with breast cancer versus irinotecan.
PubMed:Salivary α-amylase, serum albumin, and myoglobin protect against DNA-damaging activities of ingested dietary agents in vitro.
PubMed:A Simple HPLC Method with Fluorescence Detection for Simultaneous Determination of 10-methoxycamptothecin and its Metabolite 10-hydroxycamptothecin in Rat Liver Tissue.
PubMed:Chemotherapy usage patterns in a US-wide cohort of patients with metastatic colorectal cancer.
PubMed:The role of intestinal microbiota in development of irinotecan toxicity and in toxicity reduction through dietary fibres in rats.
PubMed:Novel anti-glioblastoma agents and therapeutic combinations identified from a collection of FDA approved drugs.
PubMed:Free radical scavenging, antiproliferative activities and profiling of variations in the level of phytochemicals in different parts of broccoli (Brassica oleracea italica).
PubMed:Comparison of KRAS genotype: therascreen assay vs. LNA-mediated qPCR clamping assay.
PubMed:Design, modeling, synthesis and biological activity evaluation of camptothecin-linked platinum anticancer agents.
PubMed:Graphene oxide as a nanocarrier for loading and delivery of medicinal drugs and as a biosensor for detection of serum albumin.
PubMed:Aflibercept.
PubMed:TNFα and Fas/FasL pathways are involved in 9-Methoxycamptothecin-induced apoptosis in cancer cells with oxidative stress and G2/M cell cycle arrest.
PubMed:Anthocyanins suppress the cleavable complex formation by irinotecan and diminish its DNA-strand-breaking activity in the colon of Wistar rats.
PubMed:Food and Drug Administration approval of cetuximab and a new KRAS genetic test for metastatic colorectal cancer: major advance but just the tip of the biomarker iceberg.
PubMed:Colon cancer cell chemosensitisation by fish oil emulsion involves apoptotic mitochondria pathway.
PubMed:Irinotecan (CPT-11) chemotherapy alters intestinal microbiota in tumour bearing rats.
PubMed:Potential repurposing of known drugs as potent bacterial β-glucuronidase inhibitors.
PubMed:Milk fermented by Propionibacterium freudenreichii induces apoptosis of HGT-1 human gastric cancer cells.
PubMed:Modulation of irinotecan-induced genomic DNA damage by theanine.
PubMed:When do you need a validated assay?
PubMed:Early dissemination of bevacizumab for advanced colorectal cancer: a prospective cohort study.
PubMed:In vitro cytotoxic effect of ethanol extract prepared from sporophyll of Undaria pinnatifida on human colorectal cancer cells.
PubMed:Anthocyanin-rich blackberry extract suppresses the DNA-damaging properties of topoisomerase I and II poisons in colon carcinoma cells.
PubMed:Obacunone and obacunone glucoside inhibit human colon cancer (SW480) cells by the induction of apoptosis.
PubMed:Prospective phase II study of FOLFIRI for mCRC in Japan, including the analysis of UGT1A1 28/6 polymorphisms.
PubMed:Anthocyanin-rich extracts suppress the DNA-damaging effects of topoisomerase poisons in human colon cancer cells.
PubMed:Plant-derived bioactive compounds produced by endophytic fungi.
PubMed:Bevacizumab and glioblastomas, a single-centre experience: how disease history and characteristics may affect clinical outcome.
PubMed:Bevacizumab plus irinotecan-based regimens in the treatment of metastatic colorectal cancer.
PubMed:Effects of camptothecin, etoposide and Ca2+ on caspase-3 activity and myofibrillar disruption of chicken during postmortem ageing.
PubMed:Repair of DNA damage induced by the mycotoxin alternariol involves tyrosyl-DNA phosphodiesterase 1.
PubMed:Leveraging learning from a phase III colorectal cancer clinical trial: outcomes, methodology, meta-analysis and pharmacogenetics.
PubMed:Polysaccharopeptides derived from Coriolus versicolor potentiate the S-phase specific cytotoxicity of Camptothecin (CPT) on human leukemia HL-60 cells.
PubMed:Ongoing challenges in drug interaction safety: from exposure to pharmacogenomics.
PubMed:Pregnane X Receptor (PXR) expression in colorectal cancer cells restricts irinotecan chemosensitivity through enhanced SN-38 glucuronidation.
PubMed:The evolving role of monoclonal antibodies in colorectal cancer: early presumptions and impact on clinical trial development.
PubMed:[A case of advanced gastric cancer that a medical therapy effect was provided grade 3 by a histopathological diagnosis after long-term chemotherapy].
PubMed:[Intestinal absorption and secretion mechanism of carboxylate drugs].
PubMed:Attenuation of cytogenetic effects by erythropoietin in human lymphocytes in vitro and P388 ascites tumor cells in vivo treated with irinotecan (CPT-11).
PubMed:Cytoprotective activity of amifostine on cultured human lymphocytes exposed to irinotecan.
PubMed:FDA review of a panitumumab (Vectibix) clinical trial for first-line treatment of metastatic colorectal cancer.
PubMed:Single and combined supplementation of glutamine and n-3 polyunsaturated fatty acids on host tolerance and tumour response to 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxy-camptothecin (CPT-11)/5-fluorouracil chemotherapy in rats bearing Ward colon tumour.
PubMed:Cytoreductive surgery plus hyperthermic intraperitoneal chemotherapy improves survival in selected patients with peritoneal carcinomatosis from abdominal and pelvic malignancies: results of 21 cases.
PubMed:Effects of nutritional support in patients with colorectal cancer during chemotherapy.
PubMed:[The study of dynamic acccumulation of camptothecin in Camptotheca acuminata fruit by TLCS].
PubMed:[Prevention of irinotecan hydrochloride-induced diarrhea by oral administration of Lactobacillus casei strain Shirota in rats].
PubMed:Food-drug interaction of (-)-epigallocatechin-3-gallate on the pharmacokinetics of irinotecan and the metabolite SN-38.
PubMed:Pharmacogenetic testing for uridine diphosphate glucuronosyltransferase 1A1 polymorphisms: are we there yet?
PubMed:U.S. Food and Drug Administration approval: panitumumab for epidermal growth factor receptor-expressing metastatic colorectal carcinoma with progression following fluoropyrimidine-, oxaliplatin-, and irinotecan-containing chemotherapy regimens.
PubMed:Synergy between cetuximab and chemotherapy in tumors of the gastrointestinal tract.
PubMed:Proteome response in HT-29 human colorectal cancer cells to two apoptosis-inducing compounds with different mode of action.
PubMed:Nutritional modulation of antitumor efficacy and diarrhea toxicity related to irinotecan chemotherapy in rats bearing the ward colon tumor.
PubMed:Photochemical properties of camptothecin in the presence of copper(II) ions: the role of radicals as prospective species in photodynamic therapy.
PubMed:UGT1A1*28 genotype and irinotecan-induced neutropenia: dose matters.
PubMed:[Bevacizumab (Avastin)].
PubMed:Insights, challenges, and future directions in irinogenetics.
PubMed:[A case report of small cell carcinoma of the esophagus successfully treated by irinotecan and cisplatin].
PubMed:The role of SN-38 exposure, UGT1A1*28 polymorphism, and baseline bilirubin level in predicting severe irinotecan toxicity.
PubMed:Topotecan in combination with cisplatin for the treatment of stage IVB, recurrent, or persistent cervical cancer.
PubMed:Adding pharmacogenetics information to drug labels: lessons learned.
PubMed:Reproductive toxicity evaluation of a new camptothecin anticancer agent, CKD-602, in pregnant/lactating female rats and their offspring.
PubMed:TPMT, UGT1A1 and DPYD: genotyping to ensure safer cancer therapy?
PubMed:Evaluation of the toxic potentials of a new camptothecin anticancer agent CKD-602 on fertility and early embryonic development in rats.
PubMed:Clinical and pharmacokinetic study evaluating the effect of food on the disposition of 9-nitrocamptothecin and its 9-aminocamptothecin metabolite in patients with solid tumors.
PubMed:Anthocyanidins modulate the activity of human DNA topoisomerases I and II and affect cellular DNA integrity.
PubMed:Critical evaluation of current treatments in metastatic colorectal cancer.
PubMed:Embryotoxic effects of CKD-602, a new camptothecin anticancer agent, in rats.
PubMed:4-Week repeated intravenous dose toxicity study of a new camptothecin anticancer agent CKD-602 in dogs.
PubMed:Effect of yerba mate (Ilex paraguariensis) tea on topoisomerase inhibition and oral carcinoma cell proliferation.
PubMed:Phase I pharmacokinetic, food effect, and pharmacogenetic study of oral irinotecan given as semisolid matrix capsules in patients with solid tumors.
PubMed:Future directions of liposome- and immunoliposome-based cancer therapeutics.
PubMed:Antifungal activity of camptothecin, trifolin, and hyperoside isolated from Camptotheca acuminata.
PubMed:Bevacizumab for advanced colorectal cancer.
PubMed:Subacute toxicity evaluation of a new camptothecin anticancer agent CKD-602 administered by intravenous injection to rats.
PubMed:A novel mouse model of rectal cancer established by orthotopic implantation of colon cancer cells.
PubMed:Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.
PubMed:FDA drug approval summaries: oxaliplatin.
PubMed:Ascorbic acid suppresses drug-induced apoptosis in human colon cancer cells by scavenging mitochondrial superoxide anions.
PubMed:Glucuronidation as a mechanism of intrinsic drug resistance in human colon cancer: reversal of resistance by food additives.
PubMed:Nitric oxide levels in human preneoplastic colonocytes determine their susceptibility toward antineoplastic agents.
PubMed:Nitric oxide suppresses apoptosis in human colon cancer cells by scavenging mitochondrial superoxide anions.
PubMed:Antiproliferative activity of apples is not due to phenolic-induced hydrogen peroxide formation.
PubMed:Erbitux trial flawed from the beginning, committee finds.
PubMed:Lessons learned from the Saltz and Mayo Clinic regimens.
PubMed:Postmarketing re-evaluation of irinotecan plus 5-fluorouracil/leucovorin for first-line treatment of metastatic colorectal cancer.
PubMed:Irinotecan/5-fluorouracil/leucovorin in advanced colorectal cancer: Oncologic Drugs Advisory committee summary.
PubMed:Review of the role of CPT-11 in the treatment of colorectal cancer.
PubMed:In vitro pharmacodynamics of CKD-602 in HT-29 cells.
PubMed:9-nitrocamptothecin liposome aerosol: lack of subacute toxicity in dogs.
PubMed:Release of annexin V-binding membrane microparticles from cultured human umbilical vein endothelial cells after treatment with camptothecin.
PubMed:Cellular prion protein is expressed on endothelial cells and is released during apoptosis on membrane microparticles found in human plasma.
PubMed:Clinical phase II study and pharmacological evaluation of rubitecan in non-pretreated patients with metastatic colorectal cancer-significant effect of food intake on the bioavailability of the oral camptothecin analogue.
PubMed:Promising drug is victim of bad business.
PubMed:ImClone BLA is declined.
PubMed:[A case of esophageal small-cell carcinoma responding to chemotherapy with CTP-11].
PubMed:Oxaliplatin: a new agent for colorectal cancer.
PubMed:Dietary flavone is a potent apoptosis inducer in human colon carcinoma cells.
PubMed:From the Food and Drug Administration.
PubMed:FDA approves irinotecan as first-line therapy for colorectal cancer.
PubMed:Irinotecan (CPT-11) induced colitis: report of a case and review of Food and Drug Administration MEDWATCH reporting.
PubMed:New agents in gastrointestinal malignancies: Part 1: Irinotecan in clinical practice.
PubMed:Irinotecan hydrochloride: drug profile and nursing implications of a topoisomerase I inhibitor in patients with advanced colorectal cancer.
PubMed:Cell cycle-dependent chronotoxicity of irinotecan hydrochloride in mice.
PubMed:9-Nitrocamptothecin inhibits tumor recrosis factor-mediated activation of human immunodeficiency virus type 1 and enhances apoptosis in a latently infected T cell clone.
PubMed:Topotecan in the treatment of gynecologic cancer.
PubMed:Annexin-V and TUNEL use in monitoring the progression of apoptosis in plants.
PubMed:The current status of irinotecan (CPT-11) in the United States.
PubMed:Basic research plays a key role in new patient treatments.
PubMed:Topotecan: after FDA and ASCO, what's next?
PubMed:FDA approve bark-derived drug.
PubMed:Camptothecin, a selective plant growth regulator.
 
Notes:
an alkaloid isolated from the stem wood of the chinese tree, camptotheca acuminata. this compound selectively inhibits the nuclear enzyme dna topoisomerases, type i. several semisynthetic analogs of camptothecin have demonstrated antitumor activity.
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