ChemFOnt: Showing chemical card for Cyclophosphamide (CFc000009026)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:02 UTC

Chemfont ID

CFc000009026

Molecule Identification

Common Name

Cyclophosphamide

Definition

Precursor of an alkylating nitrogen mustard antineoplastic and immunosuppressive agent that must be activated in the liver to form the active aldophosphamide. It has been used in the treatment of lymphoma and leukemia. Its side effect, alopecia, has been used for defleecing sheep. Cyclophosphamide may also cause sterility, birth defects, mutations, and cancer. [PubChem]

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Cyclophosphamide	ChEBI
(RS)-Cyclophosphamide	ChEBI
2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide	ChEBI
Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester	ChEBI
Cyclophosphamide anhydrous	ChEBI
N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide	ChEBI
Cytoxan	Kegg
Cyclophosphamide monohydrate	HMDB
Cytophosphan	HMDB
Sendoxan	HMDB
Anhydrous, cyclophosphamide	HMDB
Cyclophosphamide, (S)-isomer	HMDB
Cyclophosphane	HMDB
Cytophosphane	HMDB
Endoxan	HMDB
Neosar	HMDB
Cyclophosphamide, (R)-isomer	HMDB
Monohydrate, cyclophosphamide	HMDB
Procytox	HMDB
(+,-)-2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide monohydrate	HMDB

Chemical Formula

C₇H₁₅Cl₂N₂O₂P

Average Molecular Weight

261.086

Monoisotopic Molecular Weight

260.02481966

IUPAC Name

2-[bis(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one

Traditional Name

2-[bis(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one

CAS Registry Number

6055-19-2

SMILES

ClCCN(CCCl)P1(=O)NCCCO1

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Nitrogen mustard compounds

Direct Parent

Nitrogen mustard compounds

Alternative Parents

Substituents

Nitrogen mustard
Phosphoric monoester diamide
Organic phosphoric acid derivative
Oxazaphosphinane
Organic phosphoric acid amide
Oxacycle
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organochloride
Organopnictogen compound
Organohalogen compound
Organic oxygen compound
Alkyl chloride
Alkyl halide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:4027 )
nitrogen mustard (CHEBI:4027 )
phosphorodiamide (CHEBI:4027 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014672)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cyclophosphamide Action Pathway (PathBank: SMP0000447)

Metabolic pathway

Cyclophosphamide Metabolism Pathway (PathBank: SMP0000604)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	15.1 g/L	ALOGPS
logP	0.76	ALOGPS
logP	0.097	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	13.43	ChemAxon
pKa (Strongest Basic)	0.084	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.48 m³·mol⁻¹	ChemAxon
Polarizability	23.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon