Camptothecin
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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.


Chemical Structure

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Camptothecin
CAS# 7689-03-4

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

Size Price Shipping out time Quantity
1g USD 120 Same day
2g USD 190 Same day
5g USD 350 Same day
10g USD 650 2 Weeks
20g USD 950 2 Weeks
50g USD 1650 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-06. Prices are subject to change without notice.

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

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

Appearance:
Light yellow solid powder

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

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).

HS Tariff Code:
2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 348.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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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.



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