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Substance Name: Cyclophosphamide [USP:INN:BAN:JAN]
RN: 6055-19-2
UNII: 8N3DW7272P
InChIKey: PWOQRKCAHTVFLB-UHFFFAOYSA-N

Note

  • 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.

Molecular Formula

  • C7-H15-Cl2-N2-O2-P.H2-O

Molecular Weight

  • 279.1023
 

Classification Codes

  • Alkylating Agents
  • Antineoplastic
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Antirheumatic Agents
  • Immunologic Factors
  • Immunosuppressant
  • Immunosuppressive Agents
  • Mutagens
  • Mutation Data
  • Myeloablative Agonists
  • Noxae
  • Reproductive Effect
  • Tumor Data

Names and Synonyms

Name of Substance

  • Cyclophosphamide
  • Cyclophosphamide [USP:INN:BAN:JAN]

MeSH Heading

  • Cyclophosphamide

Synonyms

  • (+-)-2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide monohydrate
  • (Bis(chloro-2-ethyl)amino)-2-tetrahydro-3,4,5,6-oxazaphosphorine-1,3,2-oxide-2 monohydrate
  • 1-Bis(2-chloroethyl)amino-1-oxo-2-aza-5-oxaphosphoridine monohydrate
  • 2-(Bis(2-chloroethyl)amino)-1-oxa-3-aza-2-phosphocyclohexane 2-oxide monohydrate
  • 2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide monohydrate
  • 2-(Di(2-chloroethyl)amino)-1-oxa-3-aza-2-phosphacyclohexane-2-oxide monohydrate
  • 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide, monohydrate, (+-)
  • Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester monohydrate
  • CCRIS 7469
  • Ciclophosphamide hydrat
  • Cyclic N',O-propylene ester of N,N-bis(2-chloroethyl)phosphorodiamidic acid monohydrate
  • Cyclophosphamide
  • Cyclophosphamide hydrate
  • Cyclophosphamide monohydrate
  • Cytoxan
  • Cytoxan (Lyophilized)
  • Cytoxan hydrate
  • Endoxan monohydrate
  • N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxaphosphorin-2-amine, 2-oxide monohydrate
  • N,N-Bis(beta-chloroethyl)-N',O-propylenephosphoric acid ester amide monohydrate
  • N,N-Bis(beta-chloroethyl)-N',O-trimethylenephosphoric acid ester diamide monohydrate
  • N,N-Bis(beta-cloraethyl) N'-O-propylenphosphorildiamid monohydratum
  • N,N-Bis(beta-cloraethyl) N'-O-propylenphosphorildiamid monohydratum [Romanian]
  • N,N-Di(2-chloroethyl)amino-N,O-propylene phosphoric acid ester diamide monohydrate
  • Neosar
  • NSC 26271
  • UNII-8N3DW7272P

Systematic Names

  • 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide, monohydrate
  • 2H-1,3,2-Oxazaphosphorine, tetrahydro-2-(bis(2-chloroethyl)amino)-, 2-oxide, monohydrate
  • Cyclophosphamide hydrate

Superlist Names

  • Cyclophosphamide
  • Cyclophosphamide (hydrated)

Registry Numbers

CAS Registry Number

  • 6055-19-2

FDA UNII

  • 8N3DW7272P

Related Registry Number

  • 50-18-0 (Parent)

System Generated Number

  • 0006055192

Molecular Formulas

Molecular Formula

  • C7-H15-Cl2-N2-O2-P.H2-O

Molecular Formula Fragments

  • C7-H15-Cl2-N2-O2-P
  • COMPONENT
  • H2-O

Structure Descriptors

InChI

InChI=1S/C7H15Cl2N2O2P.H2O/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14;/h1-7H2,(H,10,12);1H2

InChIKey

PWOQRKCAHTVFLB-UHFFFAOYSA-N

Smiles

O.ClCCN(CCCl)P1(=O)NCCCO1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 40mg/kg (40mg/kg)   Deutsche Medizinische Wochenschrift. Vol. 83, Pg. 453, 1958.
dog LD50 oral 44mg/kg (44mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING
Toxicology and Applied Pharmacology. Vol. 4, Pg. 324, 1962.
guinea pig LD50 intravenous 400mg/kg (400mg/kg)   Deutsche Medizinische Wochenschrift. Vol. 83, Pg. 453, 1958.
mouse LD50 intravenous 275mg/kg (275mg/kg)   Toxicology and Applied Pharmacology. Vol. 4, Pg. 324, 1962.
mouse LD50 oral 350mg/kg (350mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

BEHAVIORAL: ATAXIA

BLOOD: HEMORRHAGE
Toxicology and Applied Pharmacology. Vol. 4, Pg. 324, 1962.
rabbit LD50 intravenous 130mg/kg (130mg/kg)   Deutsche Medizinische Wochenschrift. Vol. 83, Pg. 453, 1958.
rat LD50 intraperitoneal 121mg/kg (121mg/kg)   Farmacia Vol. 18, Pg. 409, 1970.
rat LD50 oral 94mg/kg (94mg/kg) BLOOD: HEMORRHAGE

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

BEHAVIORAL: ATAXIA
Toxicology and Applied Pharmacology. Vol. 4, Pg. 324, 1962.