ifosfamide   Click here for help

GtoPdb Ligand ID: 7201

Synonyms: Holoxan® | Ifex® | MJF-9325 | Z-4942
Approved drug
ifosfamide is an approved drug (FDA (1988))
Compound class: Synthetic organic
Comment: Ifosfamide is a DNA alkylating drug, and has additional immunosuppressant action. Ifosfamide is biologically inactive. In vivo metabolism is necessary to generate the active substance, isophosphamide mustard (IPM; PubChem CID 100427) [1].
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 51.38
Molecular weight 260.02
XLogP 0.83
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES ClCCNP1(=O)OCCCN1CCCl
Isomeric SMILES ClCCNP1(=O)OCCCN1CCCl
InChI InChI=1S/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12)
InChI Key HOMGKSMUEGBAAB-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1988)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2λ5-oxazaphosphinan-2-one
International Nonproprietary Names Click here for help
INN number INN
2865 ifosfamide
Synonyms Click here for help
Holoxan® | Ifex® | MJF-9325 | Z-4942
Database Links Click here for help
CAS Registry No. 3778-73-2
ChEMBL Ligand CHEMBL1024
DrugBank Ligand DB01181
DrugCentral Ligand 1421
GtoPdb PubChem SID 178103776
PubChem CID 3690
Search Google for chemical match using the InChIKey HOMGKSMUEGBAAB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone HOMGKSMUEGBAAB
Search PubMed clinical trials ifosfamide
Search PubMed titles ifosfamide
Search PubMed titles/abstracts ifosfamide
UniChem Compound Search for chemical match using the InChIKey HOMGKSMUEGBAAB-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey HOMGKSMUEGBAAB-UHFFFAOYSA-N
Wikipedia Ifosfamide

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MedChemExpress
Ifosfamide (links to external site)
Cat. No. HY-17419