4-Hydroxycyclophosphamide

HCID 99735CAS 40277-05-2

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Basic information

Standard SMILES: O=P1(N(CCCl)CCCl)NC(O)CCO1
InChIKey: RANONBLIHMVXAJ-UHFFFAOYSA-N
Molecular formula: C7H15Cl2N2O3P
Average molar mass: 277.08 g/mol
Monoisotopic mass: 276.01973433

Overview

4-hydroxycyclophosphamide is a phosphorodiamide that consists of 2-amino-1,3,2-oxazaphosphinan-4-ol 2-oxide having two 2-chloroethyl groups attached to the exocyclic nitrogen. It has a role as an alkylating agent and a metabolite. It is a phosphorodiamide, an organochlorine compound and a nitrogen mustard.

Names & identifiers

Preferred name: 4-Hydroxycyclophosphamide
IUPAC: 2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2λ5-oxazaphosphinan-4-ol
English name: 4-hydroxycyclophosphamide
Molecular formula: C7H15Cl2N2O3P
Molecular weight: 277.09

Names & synonyms

4-Hydroxycyclophosphamide40277-05-2NSC 196562NSC-1965621XBF4E50HSTetrahydro-2-(bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorin-4-ol 2-oxide2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorin-4-ol 2-oxideCHEBI:18642-[bis(2-chloroethyl)amino]-1,3,2-oxazaphosphinan-4-ol 2-oxide2-(bis(2-chloroethyl)amino)-1,3,2-oxazaphosphinan-4-ol 2-oxideRefChem:993072-[bis(2-chloroethyl)amino]-2-oxo-1,3,2lambda5-oxazaphosphinan-4-ol

Show more names

Cyclophosphamide Impurity 24-HydroxycyclophosphonamideCyclophosphamide Impurity 112H-1,3,2-Oxazaphosphorin-4-ol, 2-[bis(2-chloroethyl)amino]tetrahydro-, 2-oxide(R,S)-4-Hydroxy Cyclophosphamide [4-Hydroperoxy Cyclophosphamide (5mg) and Sodium Thiosulfate (5mg) in Water] DISCONTINUED PLEASE SEE H926301

61903-30-82-(Bis(2-chloroethyl)amino)-4-hydroxy-1,3,2-oxazaphosphinane 2-oxide(R,S)-4-Hydroxy Cyclophosphamide(R,S)-4-Hydroxy Cyclophosphamide Preparation KitCCRIS 5125UNII-1XBF4E50HSBRN 0526395DTXSID90960669

Database identifiers

CAS: 40277-05-2
PubChem CID: 99735
DTXSID: DTXSID90960669
ChEMBL: CHEMBL731
ChEBI: CHEBI:1864
UNII: 1XBF4E50HS
Nikkaji: J65.704B

Properties

Computed structural properties

XLogP: 0.2
Topological polar surface area: 61.8 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 5
Heavy atoms: 15
Formal charge: 0
Complexity: 238

Physicochemical properties

Boiling point: 387.1 · 387.1±52.0 °C(Predicted)
Density: 1.42 · 1.42±0.1 g/cm3(Predicted)
pka: 12.98 · 12.98±0.20(Predicted)
FDA UNII: 1 XBF4E50HS · 1XBF4E50HS
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338

Safety & regulation

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

Tissue LocationsKidney

Cellular LocationsExtracellular

Metabolite PathwaysCyclophosphamide Action Pathway

Suppliers17 total

济南百隆化学有限公司[email protected] · [email protected]

广州佳途科技股份有限公司81960175 18933936954 · [email protected]

广州隽唐科技有限公司020-36607679 13502246435 · [email protected]

梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]

广州九植医药科技有限公司020-89854820 · [email protected]

Additional notes

DefinitionChEBI: A phosphorodiamide that consists of 2-amino-1,3,2-oxazaphosphinan-4-ol 2-oxide having two 2-chloroethyl groups attached to the exocyclic nitrogen.