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(+)-Camptothecin

Product Name
(+)-Camptothecin
CAS No.
7689-03-4
Chemical Name
(+)-Camptothecin
Synonyms
¹CS-1388;nsc94600;(s)-droxy;nsc100880;Campthecin;CaMpathecin;Camptohecin;CAMPTOTHECIN;CAMPTOTHECINE
CBNumber
CB2381608
Molecular Formula
C20H16N2O4
Formula Weight
348.35
MOL File
7689-03-4.mol
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(+)-Camptothecin Property

Melting point:
260 °C (dec.)(lit.)
alpha 
D25 +31.3° (in chloroform-methanol, 8:2)
Boiling point:
482.73°C (rough estimate)
Density 
1.3112 (rough estimate)
refractive index 
1.5700 (estimate)
storage temp. 
2-8°C
solubility 
chloroform/methanol (4:1): 4 mg/mL
pka
pKa 10.83 (Uncertain)
form 
solid
color 
yellow
Water Solubility 
insoluble
Merck 
14,1735
BRN 
631069
InChIKey
VSJKWCGYPAHWDS-FQEVSTJZSA-N
CAS DataBase Reference
7689-03-4(CAS DataBase Reference)
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Safety

Hazard Codes 
T,Xi,Xn
Risk Statements 
36/37/38-25-20/21/22
Safety Statements 
45-36/37/39-26-36
RIDADR 
UN 1544 6.1/PG 3
WGK Germany 
3
RTECS 
UQ0492000
Hazard Note 
Irritant
HazardClass 
6.1
PackingGroup 
HS Code 
29399990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P321Specific treatment (see … on this label).

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C9911
Product name
(S)-(+)-Camptothecin
Purity
≥90% (HPLC), powder
Packaging
100 mg
Price
$109
Updated
2021/12/16
Sigma-Aldrich
Product number
C9911
Product name
(S)-(+)-Camptothecin
Purity
≥90% (HPLC), powder
Packaging
250 mg
Price
$239
Updated
2021/12/16
Sigma-Aldrich
Product number
C9911
Product name
(S)-(+)-Camptothecin
Purity
≥90% (HPLC), powder
Packaging
1 g
Price
$676
Updated
2021/12/16
TCI Chemical
Product number
C1495
Product name
(S)-(+)-Camptothecin
Purity
>97.0%(HPLC)
Packaging
1g
Price
$362
Updated
2021/12/16
TCI Chemical
Product number
C1495
Product name
(S)-(+)-Camptothecin
Purity
>97.0%(HPLC)
Packaging
100mg
Price
$61
Updated
2021/12/16
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(+)-Camptothecin Chemical Properties,Usage,Production

Description

Camptothecin is an alkaloid derived from Xi Shu (Camptotheca acuminata), which belongs to Nyssaceae. The traditional Chinese medicine Camptotheca acuminata (Xi Shu) has been collected in the Compilation of Chinese Herbal Medicine, Chinese Materia Medica, and Great Dictionary of Chinese Medicine. Camptotheca acuminata (Xi Shu) is widely distributed in the basin of Yangtze river and the southwestern provinces. The main medicinal parts of Camptotheca acuminata (Xi Shu) are root bark and fruit, which get rid of heat and toxic materials and eliminate the disease.

Description

DNA topoisomerases relax DNA torsional strain created during replication, transcription, recombination, repair, and chromosome condensation. The relaxation of DNA supercoiling by topoisomerase I at single-strand breaks enables anticancer agents to reversibly trap the complex by intercalating between DNA base pairs at the cleavage site, thus inhibiting religa Camptothecin is a cytotoxic, quinoline alkaloid, discovered as the active principle of extracts from the Chinese tree C. acuminate, that inhibits the DNA enzyme topoisomerase I (Top1). It binds the Top1-DNA cleavage complex, inducing DNA-strand breaks. Camptothecin has strong anti-tumor activity against a wide range of experimental tumors and inhibits both DNA and RNA synthesis in mammalian cells. It displays cytotoxity in HT-29 cells with an IC50 value of 10 nM and induces DNA damage at concentrations as low as 51 nM in whole cells and 12 nM in isolated nuclei in in vitro assays.

Chemical Properties

light yellow crystal powde

Physical properties

Appearance: pale yellow needlelike crystal. Solubility: slightly soluble in ethanol and chloroform; poorly soluble in water; camptothecin fails to generate stable salt with acid, whereas it can produce sodium salt which is soluble in water by reacting with heated sodium hydroxide solution. Melting point: 264–267?°C. Camptothecin derivatives

History

In 1966, Wall M E et? al. from the United States isolated an alkaloid from Camptotheca acuminata and defined its chemical structure. The in?vitro anticancer tests revealed the anticancer activity of the tryptophan-terpene alkaloid, which is known as camptothecin and received widely concern. In 1975, Corey et?al. first opened the door for the chiral synthesis of camptothecin, but the reaction step was long and the yield rate was very low. It was not until 1997 that Ciufolini et?al. developed a new method for the synthesis of camptothecin by five steps, with a total yield rate up to 51%. The great breakthrough in the chemical synthesis of camptothecin has made its extensive application become a reality.
Hydroxycamptothecin, as a camptothecin derivative with a hydroxyl group on the tenth carbon atom, is widely used for the treatment of various cancers. In 1969, researchers from Shanghai Institute of Materia Medica found that hydroxycamptothecin possessed potent anticancer activity and low toxicity. And this finding promoted the production and clinical application of hydroxycamptothecin, but its usage was interrupted for technology and quality. In the 1980s, hydroxycamptothecin was reproduced for clinical application with an improvement in producing technology, and hydroxycamptothecin got its approval number in 1986 for clinical usage in China. In the 1990s, the US Food and Drug Administration approved the clinical application of topotecan and irinotecan, which played a significant role in the prevention and treatment of cancers.

Uses

Antitumor alkaloid. Binds irreversible to the DNA-topoisomerase I complex, inhibiting the reassociation of DNA after cleavage by topoisomerase I and traps the enzyme in a covalent linkage with DNA. A cytotoxic antitumor agent

Uses

antineoplastic

Uses

Antitumor agent;Topoisomerase I inhibitor

Uses

10-hydroxycamptothecine precursor, topoisomerase inhibitor, binds irreversibly to DNA-topoisomerase I complex

Definition

ChEBI: A pyranoindolizinoquinoline that is pyrano[3',4':6,7]indolizino[1,2-b]quinoline which is substituted by oxo groups at positions 3 and 14, and by an ethyl group and a hydroxy group at position 4 (the S enantiomer).

Indications

It is mainly used in digestive tract tumors and has a good effect on gastric cancer, rectal cancer, and colon cancer. Besides, it can improve the surgical resection of advanced gastric cancer and also has some therapeutic effect on bladder cancer and lung adenocarcinoma. Moreover, camptothecin can be used for treatment of psoriasis, warts, acute and chronic leukemia, and hepatosplenomegaly caused by schistosomiasis.

Biological Activity

Cytotoxic plant alkaloid with antitumor properties; prototypic DNA topoisomerase I inhibitor.

Pharmacology

The pharmacology of camptothecin was mainly manifested as antitumor activity. Camptothecin specifically targeted topoisomerase I and exerted anticancer activity by inhibiting the synthesis of DNA.?Camptothecin mainly influenced the S phase of cell cycle and was considered as a specific inhibitor agent of cell cycle. The results of animal experiments showed that camptothecin had some inhibitory effects on leukemia, Yoshida sarcoma, and Ehrlich ascites carcinoma.
Previous clinical trials showed that camptothecin and its analogs have therapeutic effects on bladder cancer, brain cancer, breast cancer, cervical cancer, colon cancer, neural stromal tumor, lymphoreticulosis, lung cancer, leukemia, lymphoma, melanoma, ovarian cancer, pancreatic cancer, pediatric cancer, prostate cancer, and liver cancer.
Injection of camptothecin (2.5?mg/ml, 5–10?mg/day) with a treatment course of 140?mg achieved effective rate of 44.8% and 38.3% for gastric cancer and colon cancer, respectively. Hydroxycamptothecin can be used for the prevention and treatment of gastric, liver, head, and neck cancer and leukemia, and the effective rate is 44%. In addition, the dimethyl sulfoxide solution of camptothecin was also successfully used for treatment of psoriasis.

Anticancer Research

Camptothecin (CPT) is a monoterpene indole alkaloid which is isolatedfrom the Chinese plant, Camptotheca acuminata (Nyssaceae) (Wall et al. 1966).CPT is used in cancer treatment since it is a potent inhibitor of DNA topoisomeraseI, which leads to DNA damage and the apoptosis in cancer cells. Studies have shownthat CPT itself is not suitable for clinical application since it has low water solubilityand certain side effects; therefore, water-soluble CPT derivatives such as topotecan and irinotecan were synthesized and have been successfully used for thetreatment of ovarian, lung, and colorectal cancers, and CPT has been approved by theFood and Drug Administration (FDA) of the USA. Currently, topotecan and irinotecanare all synthesized from natural camptothecin which is mainly extracted fromCamptotheca acuminata (Beegum et al. 2007). Subsequently, CPT was also recognizedand extracted from other plant species such as Ervatamia heyneana (Gunasekeraet al. 1979), Melliodendron megacarpum (Arisawa et al. 1981), Nothapodytes foetida(Govindachari and Viswanathan 1972), and Ophiorrhiza species (Beegum et al.2007). However, the extraction of CPT from plants is limited because of low yields(about 1 mg/g dry weight) and scanty natural resources (Lopez-Meyer et al. 1994),and scientists have used biotechnological ways especially cell culture methods forthe production of CPT and its derivatives (Kai et al. 2015).

Anticancer Research

CPT is extracted from Camptotheca acuminata, also called Chinese ornamentaltree. Irinotecan and topotecan are semisynthetic derivatives of camptothecin, whichcan be used for the therapy of colorectal and ovarian and small cell lung carcinoma,respectively (Shoeb 2006). Camptothecin is a potent antitumor agent that targetstopoisomerase I (Desai et al. 2008). The synthetic derivatives of camptothecin[20-(S)-9-nitrocamptothecin and 20-(S)-camptothecin] have the antitumor effects inbreast, prostate, and melanoma cancers. CPT-11 is a new derivative that showsantitumor effects against metastatic colorectal cancer (Hosseini and Ghorbani2015). It selectively inhibits topoisomerase I which is involved in cleavage andreassembly of DNA (Balunas and Kinghorn 2005). Camptothecin inhibits thesynthesis of nucleic acid in L-120 cells and HeLa cells (Desai et al. 2008).

Anticancer Research

It has low watersolubility and sideeffects. Thus, usedfor clinical purposes.The chemicalmodification of itsderivatives (e.g.,topotecan andirinotecan) iscurrently used inchemotherapy.

Clinical Use

Because of the toxicity and side effects of camptothecin, the currently used agents in clinical applications are camptothecin derivatives like topotecan, irinotecan, and hydroxycamptothecin. Topotecan, a water-soluble camptothecin derivative developed by SmithKline Beecham, was approved by FDA in 1996 for the treatment of ovarian cancer. As another water-soluble camptothecin derivative approved by FDA in 1996, irinotecan was mainly used in the treatment of advanced colorectal cancer. In addition, it was also shown to have obvious inhibitory effect on small cell lung cancer and leukemia. Hydroxycamptothecin possesses a broad-spectrum antitumor activity and was clinically used for intravesical therapy of bladder cancer. In addition, it has remarkable curative effect on colon cancer, breast cancer, gastric cancer, and leukemia.

(+)-Camptothecin Preparation Products And Raw materials

Raw materials

Preparation Products

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(+)-Camptothecin Suppliers

Tianyuan Natural Product Co.,Ltd.
Tel
028-85012281
Fax
86-28-85121102
Email
xianlihong8888@163.com
Country
China
ProdList
49
Advantage
62
Taizhou Hoyoo Chemical Co.,Ltd
Tel
0576-88666163-
Fax
0576-88666163
Email
hoyoochem@yahoo.com
Country
China
ProdList
177
Advantage
58
Chembest Research Laboratories Limited
Tel
021-20908456-
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
5947
Advantage
61
Wuhan DKY Technology Co.,Ltd.
Tel
27-81302488- ;27-81302488-
Fax
027-81302088
Email
info@dkybpc.com;2851686510@qq.com
Country
China
ProdList
2025
Advantage
58
Guangzhou Tomums Life Science Co., Ltd.
Tel
020-31155029-
Fax
020-31155029
Email
sales@tomums.cn
Country
China
ProdList
4704
Advantage
58
Nanjing Bencao Yikang Biotechnology Co., Ltd
Tel
025-69790911-
Email
522593521@qq.com
Country
China
ProdList
946
Advantage
58
SiChuang NanBu Honesty Technology Co., Ltd.
Tel
0838-5675166
Fax
0838-5675535
Email
nbcxkj@126.com
Country
China
ProdList
669
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Sichuan Ruibo Technology Co., Ltd
Tel
+86-817-5586080
Fax
+86-817-5527378
Email
sales@scrbkj.com
Country
China
ProdList
42
Advantage
69
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
+86-021-61259100
Fax
86-21-61259102
Email
int02@meryer.com
Country
China
ProdList
40264
Advantage
62
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View Lastest Price from (+)-Camptothecin manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Camptothecin 7689-03-4
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-09-25
NanJing Spring & Autumn Biological Engineering CO., LTD.
Product
Camptothecin 7689-03-4 7689-03-4
Price
US $12.50/mg
Min. Order
20mg
Purity
≥98%
Supply Ability
1000.00 kgs
Release date
2019-07-16
NanJing Spring & Autumn Biological Engineering CO., LTD.
Product
Camptothecin 7689-03-4 7689-03-4
Price
US $58.12/g
Min. Order
10mg
Purity
≥98%
Supply Ability
100.00 kgs
Release date
2019-06-25

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