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

Identification

Name
9-aminocamptothecin
Accession Number
DB12515
Type
Small Molecule
Groups
Investigational
Description

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

Structure
Thumb
Synonyms
  • Aminocamptothecin
External IDs
NSC-603071
Categories
UNII
5MB77ICE2Q
CAS number
91421-43-1
Weight
Average: 363.373
Monoisotopic: 363.121906039
Chemical Formula
C20H17N3O4
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of 9-aminocamptothecin can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with 9-aminocamptothecin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with 9-aminocamptothecin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with 9-aminocamptothecin.
5-androstenedioneThe metabolism of 9-aminocamptothecin can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of 9-aminocamptothecin can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 9-aminocamptothecin can be decreased when combined with 6-O-benzylguanine.
AbemaciclibThe metabolism of 9-aminocamptothecin can be decreased when combined with Abemaciclib.
AbirateroneThe metabolism of 9-aminocamptothecin can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of 9-aminocamptothecin can be decreased when combined with Acalabrutinib.
Food Interactions
Not Available

References

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

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAcute Lymphocytic Leukemia (ALL) / Leukemia, Myelocytic, Acute1
2CompletedTreatmentCancer of the Ovary1
2CompletedTreatmentEsophageal Cancers / Malignant Neoplasm of Stomach1
2CompletedTreatmentMalignant Lymphomas2
2CompletedTreatmentNeoplasms, Ovarian1

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/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

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
Aminoquinolines and derivatives / Pyranopyridines / Pyridinones / Benzenoids / Tertiary alcohols / Heteroaromatic compounds / Amino acids and derivatives / Carboxylic acid esters / Lactones / Lactams
show 8 more
Substituents
Camptothecin / Aminoquinoline / Pyranopyridine / Quinoline / Pyridinone / Pyridine / Benzenoid / Heteroaromatic compound / Tertiary alcohol / Amino acid or derivatives
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyranoindolizinoquinoline (CHEBI:80755)

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:24889073]

Drug created on October 20, 2016 16:40 / Updated on November 29, 2018 06:40