cyclophosphamide   Click here for help

GtoPdb Ligand ID: 7154

Synonyms: cytophosphane | Cytoxan® | Endoxan®
Approved drug
cyclophosphamide is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Cyclophosphamide is an alkylating agent of the nitrogen mustard type. It is converted in vivo to the active metabolite 4-hydroxy cyclophosphamide by liver cytochrome P450 (CYP) enzymes. It is used mainly as a cancer chemotherapeutic. It can be used to treat autoimmune conditions, but as it has severe and life-threatening side-effects, other less toxic medications may be the preferred option following an acuteautoimmune crisis.
Cyclophosphamide is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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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 CDK toolkit. 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
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.

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Canonical SMILES ClCCN(P1(=O)NCCCO1)CCCl
Isomeric SMILES ClCCN(P1(=O)NCCCO1)CCCl
InChI InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
InChI Key CMSMOCZEIVJLDB-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Used as an antineoplastic agent to treat various malignancies. This drug is also used to treat certain cases of pediatric nephrotic syndrome (kidney disease) and as an immunosuppressant to control rejection following organ or bone marrow transplantation..
Mechanism Of Action and Pharmacodynamic Effects Click here for help
As a DNA alkylating (cross-linking) agent, cyclophosphamide treatment irreversibly interferes with DNA replication, RNA transcription and general disruption of nucleic acid function. This action causes cell death. Due to the complex and varied nature of nucleic acids we do not include DNA or RNA as targets on this database.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com