Exatecan - DrugBank

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

Identification

Name

Exatecan

Accession Number

DB12185

Type

Small Molecule

Groups

Investigational

Description

Exatecan has been used in trials studying the treatment of Sarcoma, Leukemia, Lymphoma, Lung Cancer, and Liver Cancer, among others.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Not Available

External IDs

DX-8951 / DX-8951f

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Exatecan Mesylate	D2VJ1CC26Q	197720-53-9	FXQZOHBMBQTBMJ-MWPGLPCQSA-N	Details

Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

Categories

UNII

OC71PP0F89

CAS number

171335-80-1

Weight

Average: 435.455
Monoisotopic: 435.159434363

Chemical Formula

C₂₄H₂₂FN₃O₄

InChI Key

ZVYVPGLRVWUPMP-FYSMJZIKSA-N

InChI

InChI=1S/C24H22FN3O4/c1-3-24(31)14-6-18-21-12(8-28(18)22(29)13(14)9-32-23(24)30)19-16(26)5-4-11-10(2)15(25)7-17(27-21)20(11)19/h6-7,16,31H,3-5,8-9,26H2,1-2H3/t16-,24-/m0/s1

IUPAC Name

(10S,23S)-23-amino-10-ethyl-18-fluoro-10-hydroxy-19-methyl-8-oxa-4,15-diazahexacyclo[14.7.1.0^{2,14}.0^{4,13}.0^{6,11}.0^{20,24}]tetracosa-1(24),2(14),6(11),12,15,17,19-heptaene-5,9-dione

SMILES

CC[[email protected]@]1(O)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=C(F)C(C)=C4CC[[email protected]](N)C3=C14)C2=O

Pharmacology

Indication

Not Available

Structured Indications

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

Drug	Interaction	Drug group
Acetyldigitoxin	Acetyldigitoxin may decrease the cardiotoxic activities of Exatecan.	Approved
Bevacizumab	Bevacizumab may increase the cardiotoxic activities of Exatecan.	Approved, Investigational
Cabazitaxel	The risk or severity of adverse effects can be increased when Cabazitaxel is combined with Exatecan.	Approved
Cyclophosphamide	Cyclophosphamide may increase the cardiotoxic activities of Exatecan.	Approved, Investigational
Deslanoside	Deslanoside may decrease the cardiotoxic activities of Exatecan.	Approved
Digitoxin	Digitoxin may decrease the cardiotoxic activities of Exatecan.	Approved
Digoxin	Digoxin may decrease the cardiotoxic activities of Exatecan.	Approved
Docetaxel	The risk or severity of adverse effects can be increased when Docetaxel is combined with Exatecan.	Approved, Investigational
Oleandrin	Anvirzel may decrease the cardiotoxic activities of Exatecan.	Experimental
Ouabain	Ouabain may decrease the cardiotoxic activities of Exatecan.	Approved
Paclitaxel	The risk or severity of adverse effects can be increased when Paclitaxel is combined with Exatecan.	Approved, Vet Approved
Trastuzumab	Trastuzumab may increase the cardiotoxic activities of Exatecan.	Approved, Investigational

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

Not Available

External Links

Resource	Link
ChemSpider	133194
ChEBI	135709
ChEMBL	CHEMBL1614650

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Brain and Central Nervous System Tumors / Malignant Lymphomas / Unspecified Childhood Solid Tumor, Protocol Specific	1
1	Completed	Treatment	Leukemias / Myelodysplastic Syndromes	1
1	Completed	Treatment	Unspecified Adult Solid Tumor, Protocol Specific	1
2	Completed	Treatment	Cancer, Breast	1
2	Completed	Treatment	Cancer, Ovarian / Fallopian Tube Cancer / Primary Peritoneal Cavity Cancer	1
2	Completed	Treatment	Cervical Cancers	1
2	Completed	Treatment	Esophageal Cancers / Malignant Neoplasm of Stomach	1
2	Completed	Treatment	Extrahepatic Bile Duct Cancer / Gallbladder Cancer / Liver Cancer	1
2	Completed	Treatment	Liver Cancer	1
2	Completed	Treatment	Lung Cancers	1
2	Completed	Treatment	Malignant Neoplasm of Pancreas	1
2	Completed	Treatment	Prostate Cancer	1
2	Completed	Treatment	Sarcomas	3
3	Completed	Treatment	Malignant Neoplasm of Pancreas	1

Properties

State

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.221 mg/mL	ALOGPS
logP	1.67	ALOGPS
logP	1.55	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	115.8 m³·mol^-1	ChemAxon
Polarizability	45.45 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not 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