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Substance Name: Camptothecin
RN: 7689-03-4
UNII: XT3Z54Z28A
InChIKey: VSJKWCGYPAHWDS-FQEVSTJZSA-N

Note

  • 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.

Molecular Formula

  • C20-H16-N2-O4

Molecular Weight

  • 348.3564
 

Classification Codes

  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Topoisomerase I Inhibitors
  • Topoisomerase Inhibitors
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Names and Synonyms

Name of Substance

  • Camptothecin

MeSH Heading

  • Camptothecin

Synonyms

  • 20(S)-Camptothecine
  • 21,22-Secocamptothecin-21-oic acid lactone
  • AI3-62475
  • BRN 0631069
  • Camptothecin
  • Camptothecine
  • CCRIS 8162
  • NSC 100880
  • NSC 94600
  • UNII-XT3Z54Z28A

Systematic Names

  • 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
  • Camptothecine (8CI)

Registry Numbers

CAS Registry Number

  • 7689-03-4

FDA UNII

  • XT3Z54Z28A

System Generated Number

  • 0007689034

Structure Descriptors

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

InChIKey

VSJKWCGYPAHWDS-FQEVSTJZSA-N

Smiles

CC[C@@]1(c2cc-3n(c(=O)c2COC1=O)Cc4c3nc5ccccc5c4)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 64mg/kg (64mg/kg)   Cancer Research. Vol. 39, Pg. 2204, 1979.
mouse LD50 intravenous 38mg/kg (38mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 oral 50100ug/kg (50.1mg/kg)   Gan to Kagaku Ryoho. Cancer and Chemotherapy. Vol. 14, Pg. 850, 1987.
rat LD50 intravenous 234mg/kg (234mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 14, Pg. 487, 1972.
rat LD50 oral 153mg/kg (153mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 14, Pg. 487, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 1.74 (none)   EXP
Water Solubility 207 mg/L 25 EST
Vapor Pressure 3.76E-15 mm Hg 25 EST
Henry's Law Constant 2.79E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.72E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.