Camptothecin
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 406279

CAS#: 7689-03-4

Description: 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. It was isolated from the bark and stem of Camptotheca acuminata (Camptotheca, Happy tree), a tree native to China used as a cancer treatment in Traditional Chinese Medicine. CPT showed remarkable anticancer activity in preliminary clinical trials but also low solubility and (high) adverse drug reaction. Because of these disadvantages synthetic and medicinal chemists have developed numerous syntheses of Camptothecin and various derivatives to increase the benefits of the chemical, with good results. Two CPT analogues have been approved and are used in cancer chemotherapy today, topotecan and irinotecan.


Price and Availability

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Price

1g
USD 120
10g
USD 650
100g
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Size
Price

2g
USD 190
20g
USD 950
200g
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Size
Price

5g
USD 350
50g
USD 1650

Camptothecin purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406279
Name: Camptothecin
CAS#: 7689-03-4
Chemical Formula: C20H16N2O4
Exact Mass: 348.11101
Molecular Weight: 348.35
Elemental Analysis: C, 68.96; H, 4.63; N, 8.04; O, 18.37


Synonym: Camptothecine; (S)-(+)-Camptothecin; d-Camptothecin; 20(S)-Camptothecine; (+)-Camptothecin; Camptothecin; CPT.

IUPAC/Chemical Name: (S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

InChi Key: VSJKWCGYPAHWDS-FQEVSTJZSA-N

InChi Code: InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1

SMILES Code: O=C1[C@](O)(CC)C2=C(CO1)C(N3CC4=CC5=CC=CC=C5N=C4C3=C2)=O


Technical Data

Appearance:
Light yellow solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Bala V, Rao S, Boyd BJ, Prestidge CA. Prodrug and nanomedicine approaches for the delivery of the camptothecin analogue SN38. J Control Release. 2013 Nov 28;172(1):48-61. doi: 10.1016/j.jconrel.2013.07.022. Epub 2013 Aug 6. Review. PubMed PMID: 23928356.

2: Huang Q, Wang L, Lu W. Evolution in medicinal chemistry of E-ring-modified Camptothecin analogs as anticancer agents. Eur J Med Chem. 2013 May;63:746-57. doi: 10.1016/j.ejmech.2013.01.058. Epub 2013 Mar 21. Review. PubMed PMID: 23578545.

3: Beretta GL, Gatti L, Perego P, Zaffaroni N. Camptothecin resistance in cancer: insights into the molecular mechanisms of a DNA-damaging drug. Curr Med Chem. 2013;20(12):1541-65. Review. PubMed PMID: 23432590.

4: Tomicic MT, Kaina B. Topoisomerase degradation, DSB repair, p53 and IAPs in cancer cell resistance to camptothecin-like topoisomerase I inhibitors. Biochim Biophys Acta. 2013 Jan;1835(1):11-27. doi: 10.1016/j.bbcan.2012.09.002. Epub 2012 Sep 21. Review. PubMed PMID: 23006513.

5: Beretta GL, Zuco V, De Cesare M, Perego P, Zaffaroni N. Namitecan: a hydrophilic camptothecin with a promising preclinical profile. Curr Med Chem. 2012;19(21):3488-501. Review. PubMed PMID: 22680917.

6: Mollica A, Stefanucci A, Feliciani F, Cacciatore I, Cornacchia C, Pinnen F. Delivery methods of camptothecin and its hydrosoluble analogue irinotecan for treatment of colorectal cancer. Curr Drug Deliv. 2012 Mar;9(2):122-31. Review. PubMed PMID: 22283650.

7: Beretta GL, Zuco V, Perego P, Zaffaroni N. Targeting DNA topoisomerase I with non-camptothecin poisons. Curr Med Chem. 2012;19(8):1238-57. Review. PubMed PMID: 22204335.

8: Sheng C, Miao Z, Zhang W. New strategies in the discovery of novel non-camptothecin topoisomerase I inhibitors. Curr Med Chem. 2011;18(28):4389-409. Review. PubMed PMID: 21861816.

9: Beretta GL, Cossa G, Gatti L, Zunino F, Perego P. Tyrosyl-DNA phosphodiesterase 1 targeting for modulation of camptothecin-based treatment. Curr Med Chem. 2010;17(15):1500-8. Review. PubMed PMID: 20166932.

10: Sirikantaramas S, Yamazaki M, Saito K. A survival strategy: the coevolution of the camptothecin biosynthetic pathway and self-resistance mechanism. Phytochemistry. 2009 Oct-Nov;70(15-16):1894-8. doi: 10.1016/j.phytochem.2009.07.034. Epub 2009 Aug 24. Review. PubMed PMID: 19709698.