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(+)-Camptothecin

CAS No.
7689-03-4
Chemical Name:
(+)-Camptothecin
Synonyms
CAMPTOTHECIN;CaMpathecin;CAMPTOTHECINE;(20S)-CAMPTOTHECIN;1,6-DIHYDROXY-7-GLUCURONOSYLFLAVONE;5,6-DIHYDROXY-7-GLUCURONOSYLFLAVONE;CAMPTOTHECIN, CAMPTOTHECA ACUMINATA;¹CS-1388;nsc94600
CBNumber:
CB2381608
Molecular Formula:
C20H16N2O4
Molecular Weight:
348.35
MDL Number:
MFCD00081076
MOL File:
7689-03-4.mol
MSDS File:
SDS
Modify Date:2022-08-15 17:36:43

(+)-Camptothecin Properties

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
form solid
pka pKa 10.83 (Uncertain)
color yellow
Water Solubility insoluble
Merck 14,1735
BRN 631069
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKey VSJKWCGYPAHWDS-FQEVSTJZSA-N
CAS DataBase Reference 7689-03-4(CAS DataBase Reference)
FDA UNII XT3Z54Z28A
NCI Dictionary of Cancer Terms camptothecin

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06,GHS08
Signal word  Danger
Hazard statements  H301-H340
Precautionary statements  P202-P264-P270-P280-P301+P310-P405
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

(+)-Camptothecin price More Price(62)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C9911 (S)-(+)-Camptothecin ≥90% (HPLC), powder 7689-03-4 100mg $116 2022-05-15 Buy
Sigma-Aldrich C9911 (S)-(+)-Camptothecin ≥90% (HPLC), powder 7689-03-4 250mg $254 2022-05-15 Buy
Sigma-Aldrich C9911 (S)-(+)-Camptothecin ≥90% (HPLC), powder 7689-03-4 1g $716 2022-05-15 Buy
Sigma-Aldrich 208925 Camptothecin, Camptotheca acuminata - CAS 2114454 - Calbiochem A cell-permeable DNA topoisomerase I inhibitor. 7689-03-4 50MG $89.3 2022-05-15 Buy
TCI Chemical C1495 (S)-(+)-Camptothecin >97.0%(HPLC) 7689-03-4 1g $352 2022-04-27 Buy
Product number Packaging Price Buy
C9911 100mg $116 Buy
C9911 250mg $254 Buy
C9911 1g $716 Buy
208925 50MG $89.3 Buy
C1495 1g $352 Buy

(+)-Camptothecin Chemical Properties,Uses,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

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

Uses

antineoplastic

Uses

Antitumor agent;Topoisomerase I inhibitor

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

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.

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).

Biological Activity

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

Biochem/physiol Actions

(S)-(+)-Camptothecin binds irreversibly 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. The enzyme complex is ubiquinated and destroyed by the 26S proteasome, thus depleting cellular topoisomerase I. Blocks the cell cycle in S-phase at low does and induces apoptosis in a large number of normal and tumor cell lines by cell cycle-dependent and cell cycle-independent processes.

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).

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.

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.

References

1) Hsiang et al. (1985) Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I.; J. Biol. Chem., 260 14873 2) Li et al. (2006) Review camptothecin: current perspectives; Curr. Med. Chem., 13 2021

(+)-Camptothecin Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 594)Suppliers
Supplier Tel Email Country ProdList Advantage
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 47501 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806 sales@capotchem.com China 29803 60
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 22021 55
Hangzhou FandaChem Co.,Ltd.
+8615858145714 fandachem@gmail.com China 9404 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3623 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29960 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254 linda@hubeijusheng.com CHINA 28229 58
Accela ChemBio Inc.
(+1)-858-699-3322 info@accelachem.com United States 19969 58
Hebei Guanlang Biotechnology Co., Ltd.
+86-19930503282 +86-19930503282 alice@crovellbio.com China 6095 58
NanJing Spring & Autumn Biological Engineering CO., LTD.
+8613815430202 sale02@cqherb.com CHINA 376 58

View Lastest Price from (+)-Camptothecin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2022-09-08 (+)-Camptothecin
7689-03-4
US $0.00 / KG 1KG ≥98% HPLC 1000KG Changsha Staherb Natural Ingredients Co., Ltd.
2022-05-17 (+)-Camptothecin
7689-03-4
US $1.10 / g 1g 99.9% Min 100 Tons Dideu Industries Group Limited
2022-02-25 Camptothecin
7689-03-4
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • (+)-Camptothecin
    7689-03-4
  • US $0.00 / KG
  • ≥98% HPLC
  • Changsha Staherb Natural Ingredients Co., Ltd.
  • Camptothecin
    7689-03-4
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
CaMpetothecin (4S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione CaMptothecin(NATURAL) 4-ETHYL-4-HYDROXY-1H-PYRANO[3',4':6,7]INDOLIZINO[1,2-B]QUINOLINE-3,14(4H,12H)DIONE 5,6-DIHYDROXY-4-OXO-2-PHENYL-4H-1-BENZOPYRAN-7-YL BETA-D-GLUCOPYRANOSIDURONIC ACID (+)-CAMPTOTHECIN (s)-droxy 1h-pyrano(3’,4’:6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione,4-ethyl-4-hy (+)-Camptothecin 4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Campthecin Topotecan Related CoMpound C 20(s)-camptothecine 21,22-secocamptothecin-21-oicacidlactone 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline- 3,14(4H,12H)-dione,4-ethyl-4-hydroxy-, (S)- (20RS)-Camptothecin (RS)-Camptothecin rac-4α*-Hydroxy-4-ethyl-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione d-Camptothecin (+)-Camptothecin,98% 5,6-DIHYDROXY-4-OXO-2-PHENYL-4H-1-BENZOPYRAN-7-YL BETA-D-GLUCOPYRANOSIDURONIC ACI Camptothecin,from Camptotheca acuminata (S)-4-Ethyl-4-hydroxyl-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3, 14(4H,12H)-dione nsc100880 nsc94600 (S)-4-ETHYL-4-HYDROXY-1,12-DIHYDRO-4H-2-OXA-6,12A-DIAZA-DIBENZO[B,H]FLUORENE-3,13-DIONE (S)-4-ETHYL-4-HYDROXY-1H-PYRANO-[3',4':6,7]INDOLIZINO[1,2-B]QUINOLINE-3,14(4H,12H)-DIONE (S)-(+)-CAMPTOTHECIN 4-Ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza -dibenzo[b,h]fluorene-3,13-dione Camptothecin,95% Camptohecin (S)-(+)-CAMPTOTHECINE CAMPTOTHECINE 95-98% CAMPTOTHECIN(P) Baicalin std. ¹ 19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0² Camptothecin 7689-03-4 Irinotecan EP Impurity D CS-1388 (+)-Camptothecin ( CPT ) CAMPTOTHECIN (IRINOTECAN EP IMPURITY D) IRINOTECAN EP IMPURITY D (CAMPTOTHECIN) (S)-4-ethyl-4-hydroxy-1H-pyrano camptothecincamptothecine Irinotecan Impurity 14 (+)-Camptothecin,>97% 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)- (+)-Camptothecin USP/EP/BP (+)-Camptothecine (S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione (Irinotecan Impurity) Camptothecin (Campathecin) (S)-(+)-Camptothecin, ≥98%(HPLC) CamptothecinQ: What is Camptothecin Q: What is the CAS Number of Camptothecin Q: What is the storage condition of Camptothecin (+)-Camptothecin TIANFUCHEM-- 7689-03-4--High purity (+)-Camptothecin in stock (+)-Camptothecin, 98%, Topotecan Related Compound C ((S)-4-Ethyl-4-hydroxy-1H-pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline- (1672280)