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Camptothecin
Natural API
Camptothecin.jpg
Camptothecin fruit.jpg

Camptothecin

Camptothecin (CAS: 7689-03-4) is a pentacyclic indole alkaloid isolated from Camptotheca acuminata (Nyssaceae family). As a specific inhibitor of topoisomerase I (Topo I), its unique antitumor mechanism has pioneered new directions in cancer drug development. Derivatives such as irinotecan and topotecan have become first-line clinical chemotherapeutic agents. In 2020, WHO listed it as an "Essential Medicine" and a representative anticancer natural product.

Product Name: Camptothecin

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

CAS No.​: 7689-03-4

Molecular Formula: C₂₀H₁₆N₂O₄

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    Camptothecin

    Basic information

    Product Name: Camptothecin

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

    CAS No.​: 7689-03-4

    Molecular Formula: C₂₀H₁₆N₂O₄

    Physicochemical Properties:

    Parameter

    Value/Description

    ​Appearance​

    Pale yellow needles (anhydrous)

    ​Melting Point​

    264-267°C (decomposition)

    ​Solubility​

    Very low in water (0.001 mg/mL), soluble in DMSO/alkaline aqueous solutions

    ​logP​

    1.8 (moderate lipophilicity)

    ​Optical Rotation​

    [α]²⁵D = +42° (c=0.5, chloroform)

     Quality Standard: CP2020,JP,Customer Made

    Specification

    Test Items

    Standard

    Camptothecin (CAS: 7689-03-4)

    98% by HPLC

    Loss on drying

    ≤1.0%

    Residue on ignition

    ≤0.3%

    Key Features

    index_10-7

    Natural Source

    0.01-0.05% in Camptotheca bark, higher in seeds (0.1-0.3%).
    index_10-7

    Mechanism

    Stabilizes Topo I-DNA cleavable complexes, inducing DNA breaks.
    index_10-7

    Clinical Impact

    First clinically used Topo I inhibitor; annual sales of derivatives exceed $1 billion.

    Pharmacological Mechanisms

    1.Molecular Mechanism

    Molecular Mechanism2

    2.Pharmacokinetics

    Absorption

    Oral bioavailability <5% (poor solubility + first-pass effect).

    Distribution

    Tissue concentrations > plasma (liver/spleen/tumor ratio 10:1).

    Metabolism

    Hepatic CYP3A4 oxidation (forms 10-hydroxycamptothecin).

    Excretion

    Primarily biliary (85% clearance in 72h).

    Clinical Applications​

    Indications & Protocols​

    ​Cancer Type​

    ​Derivative Drug​

    ​Efficacy Data​

    ​Colorectal Cancer​

    Irinotecan + FOLFIRI

    OS extended by 4.5 months*

    ​Small Cell Lung Cancer​

    Topotecan monotherapy

    ORR 35%

    ​Ovarian Cancer​

    Belotecan liposome

    PFS 9.2 months

    *Phase III trial (n=1200)

    Special Populations​

    l Hepatic Impairment: Child-Pugh C contraindicated for irinotecan.

    l Elderly: Reduce topotecan dose by 25% (↑myelosuppression risk).

    Dosage and Administration

    Formulations​

    Injection: Camptothecin sodium salt (pH 9.0 solution, 2 mg/mL).

    ​Nanoformulations: PLGA-encapsulated (preclinical).

    Topical: 0.1% ointment (experimental).Dosing Guidelines

    Dosing Guidelines​

    Use​

    ​Dose​

    ​Notes​

    Clinical Trials

    1.5 mg/m² IV qd×5

    Monitor hematuria

    Combination Therapy

    Follow derivative guidelines

    Premedicate for nausea

    Topical Use

    0.1% bid

    Limited to cutaneous T-cell lymphoma

    Safety Evaluation

    Adverse Reactions​

    System​

    ​Incidence​

    ​Manifestations​

    Myelosuppression

    80%

    Grade III/IV neutropenia

    Gastrointestinal

    70%

    Delayed diarrhea (treat with cholinesterase inhibitors)

    Urinary

    15%

    Hemorrhagic cystitis (alkalinize urine)

    Contraindications & Interactions​

    Absolute CI:
    Pregnancy (teratogenic in animals).
    UGT1A1 * 28 homozygotes (↑5× irinotecan toxicity risk).

    Cautions:CYP3A4 inhibitors (e.g., ketoconazole): AUC may↑50%.

    Research Progress Green max

    Novel Formulations​

    SN38 Liposomes: Direct delivery of active metabolite (Phase II).

    pH-Responsive Polymers: Tumor microenvironment-targeted release (pH <6.8).

    New Indications​

    Triple-Negative Breast Cancer: Combos with PARP inhibitors (preclinical synergy).

    Glioblastoma: BBB-penetrating nanoparticles (↑60% survival in animals)

    Camptothecin fruit

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