NAV

9-aminocamptothecin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
9-aminocamptothecin
DrugBank Accession Number
DB12515
Background

Aminocamptothecin has been used in trials studying the treatment of Lymphoma, Gastric Cancer, Ovarian Cancer, Esophageal Cancer, and Ovarian Neoplasms, among others.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 363.373
Monoisotopic: 363.121906039
Chemical Formula
C20H17N3O4
Synonyms
  • Aminocamptothecin
External IDs
  • NSC-603071
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
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interactions in your software
AbametapirThe serum concentration of 9-aminocamptothecin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of 9-aminocamptothecin can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with 9-aminocamptothecin.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with 9-aminocamptothecin.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with 9-aminocamptothecin.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aminoquinolines and derivatives / Pyranopyridines / Pyridinones / Benzenoids / Tertiary alcohols / Heteroaromatic compounds / Amino acids and derivatives / Carboxylic acid esters / Lactones / Lactams
show 8 more
Substituents
Alcohol / Amine / Amino acid or derivatives / Aminoquinoline / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Camptothecin / Carbonyl group / Carboxylic acid derivative
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyranoindolizinoquinoline (CHEBI:80755)
Affected organisms
Not Available

Chemical Identifiers

UNII
5MB77ICE2Q
CAS number
91421-43-1
InChI Key
FUXVKZWTXQUGMW-FQEVSTJZSA-N
InChI
InChI=1S/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3/t20-/m0/s1
IUPAC Name
(19S)-8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
SMILES
CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC=C(N)C1=C3)C2=O

References

General References
Not Available
KEGG Compound
C16822
PubChem Compound
72402
PubChem Substance
347828746
ChemSpider
65333
BindingDB
50008936
ChEBI
80755
ChEMBL
CHEMBL274070
ZINC
ZINC000037866089

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedTreatmentEsophageal Cancer / Gastric Cancer1
2CompletedTreatmentLung Cancer1
2CompletedTreatmentLymphoma2
2CompletedTreatmentOvarian Cancer1
2CompletedTreatmentOvarian Cancer / Primary Peritoneal Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.633 mg/mLALOGPS
logP1.35ALOGPS
logP0.39Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.71Chemaxon
pKa (Strongest Basic)3.91Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area105.75 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity99.19 m3·mol-1Chemaxon
Polarizability37.87 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-5f0543840f84defef874
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-2e7b38615e6122de155a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-02t9-0069000000-069dedf19c1cd89ed13e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1294000000-2e3cdcf2f2c3a2169875
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0093000000-2485d88c1cd8fc20d16e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03e9-0449000000-761982b6d9eb6e8c537e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-200.3990451
predicted
DarkChem Lite v0.1.0
[M-H]-181.37733
predicted
DeepCCS 1.0 (2019)
[M+H]+199.7963451
predicted
DarkChem Lite v0.1.0
[M+H]+183.73534
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.8816451
predicted
DarkChem Lite v0.1.0
[M+Na]+190.24113
predicted
DeepCCS 1.0 (2019)

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Maier-Salamon A, Thalhammer T, Reznicek G, Bohmdorfer M, Zupko I, Hartl A, Jaeger W: Cytochrome P450 3A-mediated metabolism of the topoisomerase I inhibitor 9-aminocamptothecin: impact on cancer therapy. Int J Oncol. 2014 Aug;45(2):877-86. doi: 10.3892/ijo.2014.2473. Epub 2014 May 29. [Article]

Drug created at October 20, 2016 22:40 / Updated at June 12, 2020 16:53