Identification

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Name
Camptothecin
Accession Number
DB04690
Type
Small Molecule
Groups
Experimental
Description

Camptothecin is an alkaloid isolated from the stem wood of the Chinese tree, Camptotheca acuminata. This compound selectively inhibits the nuclear enzyme DNA topoisomerase, type I. Several semisynthetic analogs of camptothecin have demonstrated antitumor activity.

Structure
Thumb
Synonyms
  • (+)-camptothecin
  • (+)-camptothecine
  • (S)-(+)-camptothecin
  • 20(S)-camptothecine
  • 21,22-Secocamptothecin-21-oic acid lactone
  • Camptothecine
  • D-camptothecin
Categories
UNII
XT3Z54Z28A
CAS number
7689-03-4
Weight
Average: 348.352
Monoisotopic: 348.11100701
Chemical Formula
C20H16N2O4
InChI Key
VSJKWCGYPAHWDS-FQEVSTJZSA-N
InChI
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
IUPAC Name
(19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
SMILES
CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=CC4=CC=CC=C4N=C13)C2=O

Pharmacology

Indication

Investigated for the treatment of cancer.

Pharmacodynamics

Camptothecin demonstrated strong anticancer activity in preliminary clinical trials but also low solubility and adverse drug reaction. Camptothecin is believed to be a potent topoisomerase inhibitor that interferes with the essential function of topoisomerase in DNA replication.

Mechanism of action

Camptothecin binds to the topoisomerase I and DNA complex resulting in a ternary complex, stabilizing it and preventing DNA re-ligation and therefore causes DNA damage which results in apoptosis.

TargetActionsOrganism
UDNA topoisomerase 1Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Acute oral toxicity (LD50) in mouse: 50.1 mg/kg

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbemaciclibThe serum concentration of Camptothecin can be increased when it is combined with Abemaciclib.
AcebutololThe serum concentration of Camptothecin can be increased when it is combined with Acebutolol.
AcetaminophenThe serum concentration of Camptothecin can be increased when it is combined with Acetaminophen.
Acetylsalicylic acidThe serum concentration of Camptothecin can be increased when it is combined with Acetylsalicylic acid.
AfatinibThe serum concentration of Camptothecin can be increased when it is combined with Afatinib.
AlbendazoleThe serum concentration of Camptothecin can be increased when it is combined with Albendazole.
AldosteroneThe serum concentration of Camptothecin can be increased when it is combined with Aldosterone.
AlectinibThe serum concentration of Camptothecin can be increased when it is combined with Alectinib.
AlfentanilThe serum concentration of Camptothecin can be increased when it is combined with Alfentanil.
AlitretinoinThe serum concentration of Camptothecin can be increased when it is combined with Alitretinoin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not Available

References

Synthesis Reference

Tadashi Miyasaka, Seigo Sawada, Kenichiro Nokata, Masahiko Mutai, "Photochemical process for preparing camptothecin derivatives." U.S. Patent US4545880, issued March, 1976.

US4545880
General References
  1. Wall ME, Wani MC: Camptothecin and taxol: from discovery to clinic. J Ethnopharmacol. 1996 Apr;51(1-3):239-53; discussion 253-4. [PubMed:9213622]
  2. Kepler JA, Wani MC, McNaull JN, Wall ME, Levine SG: Plant antitumor agents. IV. An approach toward the synthesis of camptothecin. J Org Chem. 1969 Dec;34(12):3853-8. [PubMed:5357525]
External Links
KEGG Compound
C01897
PubChem Compound
24360
PubChem Substance
46507644
ChemSpider
22775
BindingDB
50008923
ChEBI
27656
ChEMBL
CHEMBL65
PharmGKB
PA153590860
HET
EHD
Wikipedia
Camptothecin
PDB Entries
1t8i
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentAdenocarcinoma of the Pancreas / Recurrent Pancreatic Carcinoma / Stage III Pancreatic Cancer / Stage IV Pancreatic Cancer / Unresectable Pancreatic Carcinoma1
0TerminatedTreatmentGlioblastomas / Gliosarcoma / Neoplasms, Brain1
1Active Not RecruitingTreatmentAdult Hodgkin Lymphoma / Adult Non-Hodgkin's Lymphoma / Advanced Malignant Solid Neoplasm / Carcinoma, Breast / Carcinoma, Pancreatic / Colon Carcinoma / Deleterious BRCA1 Gene Mutation / Estrogen Receptor Negative / HER2/Neu Negative / Lung, Carcinoma / Lymphoma, Hodgkins / Metastatic Colon Cancer / Metastatic Malignant Neoplasm / Metastatic Malignant Solid Neoplasm / Metastatic Solid Neoplasm / Neoplasms, Advanced Solid / Non-Hodgkin's Lymphoma (NHL) / Ovarian Carcinoma / Progesterone Receptor Negative / Solid Neoplasms / Stage III Breast Cancer / Stage III Breast Cancer AJCC V7 / Stage III Colon Cancer / Stage III Colon Cancer AJCC v7 / Stage III Lung Cancer / Stage III Lung Cancer AJCC v7 / Stage III Ovarian Cancer / Stage III Ovarian Cancer AJCC v6 and v7 / Stage III Pancreatic Cancer / Stage III Pancreatic Cancer AJCC v6 and v7 / Stage IIIA Breast Cancer / Stage IIIA Breast Cancer AJCC v7 / Stage IIIA Colon Cancer / Stage IIIA Colon Cancer AJCC v7 / Stage IIIA Ovarian Cancer / Stage IIIA Ovarian Cancer AJCC v6 and v7 / Stage IIIB Breast Cancer / Stage IIIB Breast Cancer AJCC v7 / Stage IIIB Colon Cancer / Stage IIIB Colon Cancer AJCC v7 / Stage IIIB Ovarian Cancer / Stage IIIB Ovarian Cancer AJCC v6 and v7 / Stage IIIC Breast Cancer / Stage IIIC Breast Cancer AJCC v7 / Stage IIIC Colon Cancer / Stage IIIC Colon Cancer AJCC v7 / Stage IIIC Ovarian Cancer / Stage IIIC Ovarian Cancer AJCC v6 and v7 / Stage IV Breast Cancer / Stage IV Breast Cancer AJCC v6 and v7 / Stage IV Colon Cancer AJCC v7 / Stage IV Lung Cancer / Stage IV Lung Cancer AJCC v7 / Stage IV Ovarian Cancer / Stage IV Ovarian Cancer AJCC v6 and v7 / Stage IV Pancreatic Cancer / Stage IV Pancreatic Cancer AJCC v6 and v7 / Stage IVA Colon Cancer / Stage IVA Colon Cancer AJCC v7 / Stage IVA Pancreatic Cancer / Stage IVB Colon Cancer / Stage IVB Colon Cancer AJCC v7 / Stage IVB Pancreatic Cancer / Triple-Negative Breast Carcinoma / Unresectable Malignant Neoplasm / Unresectable Solid Neoplasm1
1Active Not RecruitingTreatmentAdult Solid Neoplasm1
1Active Not RecruitingTreatmentAdvanced Cancers / BRAF NP_004324.2:p.V600X / KRAS wt Allele / Metastatic Malignant Solid Neoplasm / Stage IV Colorectal Cancer AJCC v7 / Stage IVA Colorectal Cancer AJCC v7 / Stage IVB Colorectal Cancer AJCC v7 / Unresectable Solid Neoplasm1
1Active Not RecruitingTreatmentPrimary Brain Tumors / Tumors, Solid1
1CompletedTreatmentAdvanced Gastrointestinal Tumors1
1CompletedTreatmentAdvanced Solid Tumors1
1CompletedTreatmentAdvanced Solid Tumors / Hepatocellular,Carcinoma1
1CompletedTreatmentMetastatic Colon Cancer / Recurrent Colon Cancer / Recurrent Rectal Cancer / Stage IV Rectal Cancer1
1CompletedTreatmentRecurrent Colon Carcinoma / Recurrent Rectal Carcinoma / Stage IVA Colon Cancer / Stage IVA Rectal Cancer / Stage IVB Colon Cancer / Stage IVB Rectal Cancer1
1CompletedTreatmentTumors, Solid1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific2
1RecruitingTreatmentAdult Anaplastic Astrocytoma / Adult Anaplastic Oligoastrocytoma / Adult Anaplastic Oligodendroglioma / Adult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Gliomas / Progressive Disease / Recurrent Adult Brain Tumor / Recurrent Anaplastic Astrocytoma / Recurrent Anaplastic Oligoastrocytoma / Recurrent Anaplastic Oligodendroglioma / Recurrent Glioblastoma / Recurrent Gliosarcoma / Recurrent Malignant Gliomas / Recurrent WHO Grade III Glioma / UGT1A1*28 Allele Negative1
1RecruitingTreatmentAdult Solid Neoplasm / Advanced Malignant Solid Neoplasm / Metastatic Malignant Neoplasm / Metastatic Malignant Solid Neoplasm / Metastatic Solid Neoplasm / Neoplasms, Advanced Solid / Refractory Malignant Neoplasm / Unresectable Malignant Neoplasm / Unresectable Solid Neoplasm1
1RecruitingTreatmentAdvanced Cancers / Advanced Malignant Neoplasm / Recurrent Malignant Neoplasm / Refractory Malignant Neoplasm1
1RecruitingTreatmentChildhood Solid Neoplasm / Recurrent Central Nervous System Neoplasm / Recurrent Malignant Solid Neoplasm / Recurrent Solid Neoplasm / Refractory Central Nervous System Neoplasm / Refractory Malignant Solid Neoplasm1
1RecruitingTreatmentColorectal Cancers / Malignant Neoplasms of Digestive Organs / Stage IV Colorectal Cancer AJCC v8 / Stage IVA Colorectal Cancer AJCC v8 / Stage IVB Colorectal Cancer AJCC v8 / Stage IVC Colorectal Cancer AJCC v81
1RecruitingTreatmentRecurrent Central Nervous System Neoplasm / Recurrent Lymphoma / Recurrent Malignant Solid Neoplasm / Refractory Central Nervous System Neoplasm / Refractory Lymphomas / Refractory Malignant Solid Neoplasm1
1WithdrawnTreatmentStage IVA Colorectal Cancer / Stage IVB Colorectal Cancer1
1, 2Active Not RecruitingTreatmentPancreatic Adenocarcinoma Metastatic / Recurrent Pancreatic Carcinoma / Stage III Pancreatic Cancer / Stage IV Pancreatic Cancer1
1, 2CompletedTreatmentMalignancies / Tumors, Solid1
1, 2RecruitingTreatmentBorderline Resectable Pancreatic Adenocarcinoma / Resectable Pancreatic Ductal Adenocarcinoma1
1, 2RecruitingTreatmentCentral Nervous System Embryonal Tumor With Rhabdoid Features / Central Nervous System Embryonal Tumor, Not Otherwise Specified / Central Nervous System Ganglioneuroblastoma / Childhood Central Nervous System Neoplasm / Childhood Solid Neoplasm / Embryonal Tumor With Multilayered Rosettes, C19MC-Altered / Pinealoblastoma / Primary Central Nervous System Neoplasm / Recurrent Childhood Central Nervous System Embryonal Neoplasm / Recurrent Childhood Medulloblastoma / Recurrent Childhood Supratentorial Embryonal Tumor, Not Otherwise Specified / Recurrent Childhood Supratentorial Primitive Neuroectodermal Tumor / Recurrent Malignant Solid Neoplasm / Recurrent Medulloblastoma / Recurrent Neuroblastoma / Recurrent Rhabdomyosarcoma / Recurrent Solid Neoplasm / Refractory Malignant Solid Neoplasm / Refractory Medulloblastoma / Refractory Neuroblastoma / Refractory Rhabdomyosarcoma1
1, 2TerminatedTreatmentStage IV Colorectal Cancer1
1, 2WithdrawnTreatmentAdenocarcinoma of the Pancreas / Colon Adenocarcinoma / Pancreatic Adenocarcinoma Metastatic / Pancreatic Ductal Adenocarcinoma / Rectal Adenocarcinoma / Stage III Pancreatic Cancer / Stage IIIA Colon Cancer / Stage IIIA Rectal Cancer / Stage IIIB Colon Cancer / Stage IIIB Rectal Cancer / Stage IIIC Colon Cancer / Stage IIIC Rectal Cancer / Stage IV Pancreatic Cancer / Stage IVA Colon Cancer / Stage IVA Rectal Cancer / Stage IVB Colon Cancer / Stage IVB Rectal Cancer1
2Active Not RecruitingTreatmentColon Adenocarcinoma / ERBB2 Gene Amplification / Rectal Adenocarcinoma / Recurrent Colon Carcinoma / Recurrent Rectal Carcinoma / Stage III Colon Cancer AJCC v7 / Stage III Rectal Cancer AJCC v7 / Stage IIIA Colon Cancer AJCC v7 / Stage IIIA Rectal Cancer AJCC v7 / Stage IIIB Colon Cancer AJCC v7 / Stage IIIB Rectal Cancer AJCC v7 / Stage IIIC Colon Cancer AJCC v7 / Stage IIIC Rectal Cancer AJCC v7 / Stage IV Colon Cancer AJCC v7 / Stage IV Rectal Cancer AJCC v7 / Stage IVA Colon Cancer AJCC v7 / Stage IVA Rectal Cancer AJCC v7 / Stage IVB Colon Cancer AJCC v7 / Stage IVB Rectal Cancer AJCC v71
2Active Not RecruitingTreatmentColorectal Cancers1
2Active Not RecruitingTreatmentPancreatic Adenocarcinoma Metastatic / Recurrent Pancreatic Carcinoma / Stage IV Pancreatic Cancer / Stage IV Pancreatic Cancer AJCC v6 and v71
2Active Not RecruitingTreatmentRecurrent Childhood Medulloblastoma / Recurrent Childhood Pineoblastoma / Recurrent Childhood Supratentorial Embryonal Tumor, Not Otherwise Specified / Recurrent Childhood Supratentorial Primitive Neuroectodermal Tumor1
2CompletedSupportive CareColorectal Cancers / Nausea and vomiting1
2CompletedTreatmentAdenocarcinoma of the Esophagus / Adenocarcinomas of the Gastroesophageal Junction / Advanced Gastric Cancer / Diffuse Adenocarcinoma of the Stomach / Intestinal Adenocarcinoma of the Stomach / Mixed Adenocarcinoma of the Stomach / Recurrent Esophageal Cancer / Recurrent Gastric Cancer / Squamous Cell Carcinoma of the Esophagus / Stage IIIB Esophageal Cancer / Stage IIIB Gastric Cancer / Stage IIIC Esophageal Cancer / Stage IIIC Gastric Cancer / Stage IV Esophageal Cancer1
2CompletedTreatmentAdult Glioblastoma / Adult Gliosarcoma / Recurrent Adult Brain Neoplasm / Recurrent Adult Brain Tumor1
2CompletedTreatmentAdult Rhabdomyosarcoma / Childhood Alveolar Rhabdomyosarcoma / Childhood Embryonal Rhabdomyosarcoma / Metastatic Childhood Soft Tissue Sarcoma / Stage IV Adult Soft Tissue Sarcoma / Untreated Childhood Rhabdomyosarcoma1
2CompletedTreatmentChildhood Cerebral Anaplastic Astrocytoma / Childhood Oligodendroglioma / Childhood Spinal Cord Neoplasm / Recurrent Childhood Brain Stem Glioma / Recurrent Childhood Ependymoma / Recurrent Childhood Medulloblastoma1
2CompletedTreatmentColorectal Cancers1
2CompletedTreatmentEsophageal Cancers / Malignant Neoplasm of Stomach1
2CompletedTreatmentExtensive Stage Small Cell Lung Cancer1
2CompletedTreatmentGanglioneuroblastoma / Recurrent Neuroblastoma1
2CompletedTreatmentLung Cancers2
2Not Yet RecruitingTreatmentAdenocarcinoma of the Pancreas / Malignant Neoplasm of Pancreas1
2RecruitingTreatmentAdenocarcinoma of the Pancreas / Resectable Pancreatic Cancers / Resectable Pancreatic Carcinoma1
2RecruitingTreatmentAdenocarcinoma of the Pancreas / Stage IIA Pancreatic Cancer / Stage IIB Pancreatic Cancer / Stage III Pancreatic Cancer1
2RecruitingTreatmentAdvanced Bile Duct Carcinoma / Advanced Gallbladder Carcinoma / Refractory Bile Duct Carcinoma / Refractory Gallbladder Carcinoma / Stage III Distal Bile Duct Cancer AJCC v8 / Stage III Gallbladder Cancer AJCC v8 / Stage III Intrahepatic Bile Duct Cancer AJCC v8 / Stage IIIA Distal Bile Duct Cancer AJCC v8 / Stage IIIA Gallbladder Cancer AJCC v8 / Stage IIIA Intrahepatic Bile Duct Cancer AJCC v8 / Stage IIIB Distal Bile Duct Cancer AJCC v8 / Stage IIIB Gallbladder Cancer AJCC v8 / Stage IIIB Intrahepatic Bile Duct Cancer AJCC v8 / Stage IV Distal Bile Duct Cancer AJCC v8 / Stage IV Gallbladder Cancer AJCC v8 / Stage IV Intrahepatic Bile Duct Cancer AJCC v8 / Stage IVA Gallbladder Cancer AJCC v8 / Stage IVB Gallbladder Cancer AJCC v81
2TerminatedTreatmentExtensive Stage Small Cell Lung Cancer / Refractory Small cell lung cancer1
2TerminatedTreatmentLung Neoplasms, Non-Small Cell Lung Cancer1
2TerminatedTreatmentRecurrent Colorectal Carcinoma / Stage IVA Colorectal Cancer / Stage IVB Colorectal Cancer1
2TerminatedTreatmentRecurrent Non-Small Cell Lung Carcinoma / Stage IIIA Non-Small Cell Lung Cancer / Stage IIIb Non-small Cell Lung Cancer / Stage IV Non-Small Cell Lung Cancer1
2WithdrawnTreatmentBiliary Tract Cancer1
3Active Not RecruitingTreatmentAlpha Fetoprotein Increased / PRETEXT Stage 1 Hepatoblastoma / PRETEXT Stage 2 Hepatoblastoma / PRETEXT Stage 3 Hepatoblastoma / PRETEXT Stage 4 Hepatoblastoma1
3CompletedTreatmentMucinous Adenocarcinoma of the Rectum / Rectal Mucinous Adenocarcinoma / Rectal Signet Ring Cell Adenocarcinoma / Recurrent Rectal Cancer / Recurrent Rectal Carcinoma / Signet Ring Adenocarcinoma of the Rectum / Stage IIA Rectal Cancer / Stage IIA Rectal Cancer AJCC v7 / Stage IIB Rectal Cancer / Stage IIB Rectal Cancer AJCC v7 / Stage IIC Rectal Cancer / Stage IIC Rectal Cancer AJCC v7 / Stage IIIA Rectal Cancer / Stage IIIA Rectal Cancer AJCC v7 / Stage IIIB Rectal Cancer / Stage IIIB Rectal Cancer AJCC v7 / Stage IIIC Rectal Cancer / Stage IIIC Rectal Cancer AJCC v7 / Stage IVA Rectal Cancer / Stage IVA Rectal Cancer AJCC v7 / Stage IVB Rectal Cancer / Stage IVB Rectal Cancer AJCC v71
3CompletedTreatmentSarcomas1
3RecruitingTreatmentBotryoid-Type Embryonal Rhabdomyosarcoma / Rhabdomyosarcoma, Alveolar / Rhabdomyosarcoma, Embryonal / Rhabdomyosarcomas / Sclerosing Rhabdomyosarcoma / Spindle Cell Rhabdomyosarcoma / Untreated Childhood Rhabdomyosarcoma1
3RecruitingTreatmentEwing Family of Tumors / Ewing's Sarcoma (ES) / Ewing's Tumor Metastatic / Ewing's Tumor Recurrent / Metastatic Ewing's Sarcoma / Neoplasms / Neoplasms by Histologic Type / Neoplasms, Bone Tissue / Neoplasms, Connective and Soft Tissue / Neoplasms, Connective Tissue / Rare Diseases / Sarcomas1
Not AvailableRecruitingNot AvailableBiliary Tract Cancer / Colo-rectal Cancer / Esophageal Cancers / Gall Bladder Cancer / Liver Cancer / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach1
Not AvailableWithdrawnTreatmentCentral Nervous System Metastases / Male Breast Cancer / Recurrent Breast Cancer / Stage IV Breast Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)275-277 °CVolkmann
logP1.74HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.511 mg/mLALOGPS
logP1.91ALOGPS
logP1.22ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)3.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area79.73 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.49 m3·mol-1ChemAxon
Polarizability36.4 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.841
Blood Brain Barrier-0.6345
Caco-2 permeable-0.5555
P-glycoprotein substrateSubstrate0.6039
P-glycoprotein inhibitor INon-inhibitor0.7852
P-glycoprotein inhibitor IINon-inhibitor0.9762
Renal organic cation transporterNon-inhibitor0.8376
CYP450 2C9 substrateNon-substrate0.8311
CYP450 2D6 substrateNon-substrate0.8454
CYP450 3A4 substrateSubstrate0.546
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5591
Ames testNon AMES toxic0.5393
CarcinogenicityNon-carcinogens0.8187
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.3261 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9939
hERG inhibition (predictor II)Non-inhibitor0.902
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0009000000-d761f92f05da35fcdccc
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0009000000-f0c6f4a14bb1034d2b44
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0009000000-21af02e2bc86f07c0100
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0149000000-a4935b6e6f5d88de2237

Taxonomy

Description
This compound belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Camptothecins
Sub Class
Not Available
Direct Parent
Camptothecins
Alternative Parents
Quinolines and derivatives / Pyranopyridines / Pyridinones / Benzenoids / Tertiary alcohols / Heteroaromatic compounds / Carboxylic acid esters / Lactams / Lactones / Azacyclic compounds
show 7 more
Substituents
Camptothecin / Pyranopyridine / Quinoline / Pyridinone / Pyridine / Benzenoid / Heteroaromatic compound / Tertiary alcohol / Carboxylic acid ester / Lactam
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinoline alkaloid, pyranoindolizinoquinoline (CHEBI:27656) / Alkaloids, Quinoline alkaloids (C01897)

Targets

Details
1. DNA topoisomerase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Poly(a) rna binding
Specific Function
Releases the supercoiling and torsional tension of DNA introduced during the DNA replication and transcription by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a singl...
Gene Name
TOP1
Uniprot ID
P11387
Uniprot Name
DNA topoisomerase 1
Molecular Weight
90725.19 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Teicher BA: Next generation topoisomerase I inhibitors: Rationale and biomarker strategies. Biochem Pharmacol. 2008 Mar 15;75(6):1262-71. Epub 2007 Oct 22. [PubMed:18061144]
  3. van der Merwe M, Bjornsti MA: Mutation of Gly721 alters DNA topoisomerase I active site architecture and sensitivity to camptothecin. J Biol Chem. 2008 Feb 8;283(6):3305-15. Epub 2007 Dec 4. [PubMed:18056711]
  4. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Schmid B, Chung DE, Warnecke A, Fichtner I, Kratz F: Albumin-binding prodrugs of camptothecin and doxorubicin with an Ala-Leu-Ala-Leu-linker that are cleaved by cathepsin B: synthesis and antitumor efficacy. Bioconjug Chem. 2007 May-Jun;18(3):702-16. Epub 2007 Mar 23. [PubMed:17378599]
  2. Wang ZM, Ho JX, Ruble JR, Rose J, Ruker F, Ellenburg M, Murphy R, Click J, Soistman E, Wilkerson L, Carter DC: Structural studies of several clinically important oncology drugs in complex with human serum albumin. Biochim Biophys Acta. 2013 Dec;1830(12):5356-74. doi: 10.1016/j.bbagen.2013.06.032. Epub 2013 Jul 6. [PubMed:23838380]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Li D, Jang SH, Kim J, Wientjes MG, Au JL: Enhanced drug-induced apoptosis associated with P-glycoprotein overexpression is specific to antimicrotubule agents. Pharm Res. 2003 Jan;20(1):45-50. [PubMed:12608535]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Ma Y, Wink M: The beta-carboline alkaloid harmine inhibits BCRP and can reverse resistance to the anticancer drugs mitoxantrone and camptothecin in breast cancer cells. Phytother Res. 2010 Jan;24(1):146-9. doi: 10.1002/ptr.2860. [PubMed:19548284]

Drug created on September 11, 2007 11:49 / Updated on November 02, 2019 01:45