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Substance Name: Cyclophosphamide [USP:INN]
RN: 50-18-0
UNII: 6UXW23996M
InChIKey: CMSMOCZEIVJLDB-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

Molecular Weight

  • 261.0875
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Alkylating Agents
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Experimental Pesticide
  • Human Data
  • Immunologic Factors
  • Immunosuppressive Agents
  • Mutagens
  • Mutation Data
  • Myeloablative Agonists
  • Noxae
  • Reproductive Effect
  • Tumor Data
  • Unspecified / Unclassified Pesticide

Superlist Classification Codes

  • Known to be a Carcinogen
  • Overall Carcinogenic Evaluation: Group 1
  • Reportable Quantity (RQ) = 10 lb

Names and Synonyms

Results Name

  • Cyclophosphamide [USP:INN]

Name of Substance

  • Cyclophosphamide
  • Cyclophosphamide (anhydrous)
  • Cyclophosphamide [USP:INN]

MeSH Heading

  • Cyclophosphamide

Synonyms

  • (+-)-Cyclophosphamide
  • (RS)-Cyclophosphamide
  • 1-Bis(2-chloroethyl)amino-1-oxo-2-aza-5-oxaphosphoridin
  • 2-(Bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorine 2-oxide
  • 2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazophosphorine 2-oxide
  • 4-27-00-09750 (Beilstein Handbook Reference)
  • 4-Hydroxy-cyclophosphan-mamophosphatide
  • AI3-26198
  • ASTA B518
  • B 518
  • Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester
  • BRN 0011744
  • CB 4564
  • CCRIS 188
  • Ciclofosfamida
  • Ciclofosfamida [INN-Spanish]
  • Ciclophosphamide
  • Ciclophosphamide [INN]
  • Clafen
  • Claphene
  • Cyclophosphamid
  • Cyclophosphamide
  • Cyclophosphamidum
  • Cyclophosphamidum [INN-Latin]
  • Cyclophosphan
  • Cyclophosphane
  • Cyclophosphanum
  • Cyclophosphoramide
  • Cyclostin
  • Cyklofosfamid
  • Cyklofosfamid [Czech]
  • Cytophosphan
  • Cytophosphane
  • Cytoxan
  • D,L-Cyclophosphamide
  • EINECS 200-015-4
  • Endoxan
  • Endoxan R
  • Endoxan-asta
  • Endoxana
  • Endoxanal
  • Genoxal
  • HSDB 3047
  • Lyophilized cytoxan
  • N,N-Bis(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide
  • N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide
  • N,N-Bis(beta-chloroethyl)-N',O-propylenephosphoric acid ester diamide
  • N,N-Bis(beta-chloroethyl)-N',O-trimethylenephosphoric acid ester diamide
  • N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid
  • N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid [German]
  • N,N-Di(2-chloroethyl)-N,O-propylene-phosphoric acid ester diamide
  • NCI-C04900
  • Neosar
  • NSC 26271
  • NSC-26271
  • Occupation, cyclophosphamide exposure
  • Phosphorodiamidic acid, N,N-bis(2-chloroethyl)-N'-(3-hydroxypropyl)-, intramol. ester
  • Procytox
  • RCRA waste number U058
  • Sendoxan
  • SK 20501
  • UNII-6UXW23996M
  • Zyklophosphamid
  • Zyklophosphamid [German]

Systematic Names

  • 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide
  • 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide (9CI)
  • 2H-1,3,2-Oxazaphosphorine, 2-(bis(2-chloroethyl)amino)tetrahydro-, 2-oxide
  • Cyclophosphamide

Superlist Names

  • 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide
  • Cyclophosphamide (anhydrous form)
  • Cyclophosphamide (anhydrous)
  • RCRA waste no. U058

Registry Numbers

CAS Registry Number

  • 50-18-0

FDA UNII

  • 6UXW23996M

Other Registry Numbers

  • 60007-95-6
  • 75526-90-8

Related Registry Number

  • 6055-19-2 (monohydrate)

System Generated Number

  • 0000050180

Structure Descriptors

InChI

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

InChIKey

CMSMOCZEIVJLDB-UHFFFAOYSA-N

Smiles

N([P@@]1(NCCCO1)=O)(CCCl)CCCl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intraperitoneal 50mg/kg (50mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
child TDLo oral 2500ug/kg (2.5mg/kg)   American Journal of Diseases of Children. Vol. 140, Pg. 1094, 1986.
child TDLo oral 2500ug/kg (2.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD American Journal of Diseases of Children. Vol. 140, Pg. 1094, 1986.
dog LDLo intraperitoneal 50mg/kg (50mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
dog LDLo intravenous 11mg/kg (11mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 191, 1965.
domestic animals - goat/sheep LD50 intravenous 45100ug/kg (45.1mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES

CARDIAC: OTHER CHANGES

LIVER: OTHER CHANGES
Dongbei Nongxueyuan Xuebao. Journal of Northeast Agricultural College. Vol. 34, Pg. 56, 1980.
guinea pig LDLo intraperitoneal 200mg/kg (200mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: ATAXIA
Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
hamster LD10 parenteral 110mg/kg (110mg/kg)   Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980.
hamster LD50 intraperitoneal 429mg/kg (429mg/kg)   Cancer Letters Vol. 2, Pg. 267, 1977.
hamster LD50 oral 763mg/kg (763mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Experientia. Vol. 37, Pg. 401, 1981.
human TDLo oral 20mg/kg (20mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES

GASTROINTESTINAL: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Arthritis and Rheumatism. Vol. 12, Pg. 663, 1969.
man LDLo multiple routes 45mg/kg/26W-I (45mg/kg) BLOOD: OTHER CHANGES American Journal of the Medical Sciences. Vol. 254, Pg. 48, 1967.
man TDLo oral 56mg/kg/26D-I (56mg/kg) BLOOD: AGRANULOCYTOSIS American Journal of Medicine. Vol. 81, Pg. 1059, 1986.
man TDLo oral 56mg/kg/4W-I (56mg/kg) LIVER: OTHER CHANGES Southern Medical Journal. Vol. 78, Pg. 222, 1985.
man TDLo oral 579mg/kg/2Y-I (579mg/kg) LIVER: OTHER CHANGES

LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
American Journal of Gastroenterology. Vol. 95, Pg. 845, 2000.
monkey LDLo intravenous 45mg/kg (45mg/kg)   Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 191, 1965.
monkey LDLo intravenous 45mg/kg (45mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 191, 1965.
mouse LD50 intraperitoneal 110mg/kg (110mg/kg)   Farmakologiya i Toksikologiya Vol. 41, Pg. 90, 1978.
mouse LD50 intraperitoneal 420mg/kg (420mg/kg)   Archivum Immunologiae et Therapiae Experimentalis. Vol. 34, Pg. 263, 1986.
mouse LD50 intraperitoneal 420mg/kg (420mg/kg) BEHAVIORAL: ATAXIA Archivum Immunologiae et Therapiae Experimentalis. Vol. 34, Pg. 263, 1986.
mouse LD50 intravenous 140mg/kg (140mg/kg)   "Radiation-Induced Cancer, Proceedings of a Symposium, Athens, 1969," Lanham, MD, Bernan-UNIPUB, 1969Vol. -, Pg. 97, 1969.
mouse LD50 oral 137mg/kg (137mg/kg)   Russian Pharmacology and Toxicology Vol. 36, Pg. 240, 1973.
mouse LD50 parenteral 315mg/kg (315mg/kg)   Transplantation. Vol. 13, Pg. 316, 1972.
mouse LD50 subcutaneous 200mg/kg (200mg/kg)   Advances in the Study of Birth Defects. Vol. 2, Pg. 95, 1979.
mouse LD50 unreported 480mg/kg (480mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 157S, 1968.
mouse LDLo intratracheal 200mg/kg (200mg/kg)   Toxicology Letters. Vol. 30, Pg. 63, 1986.
rabbit LDLo intraperitoneal 200mg/kg (200mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rabbit LDLo intravenous 300mg/kg (300mg/kg)   Journal of Toxicological Sciences. Vol. 34, Pg. 308, 1999.
rat LD50 intracrebral > 400ug/kg (0.4mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 18, Pg. 760, 1966.
rat LD50 intraperitoneal 40mg/kg (40mg/kg)   Clinical Proceedings of the Children's Hospital of the District of Columbia. Vol. 18, Pg. 307, 1962.
rat LD50 intravenous 148mg/kg (148mg/kg) BLOOD: NORMOCYTIC ANEMIA Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat LD50 oral 100mg/kg (100mg/kg)   Drugs in Japan Vol. -, Pg. 516, 1995.
rat LD50 subcutaneous 144mg/kg (144mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat LD50 subcutaneous 144mg/kg (144mg/kg) BLOOD: NORMOCYTIC ANEMIA Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat LD50 unreported 190mg/kg (190mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 157S, 1968.
women LDLo oral 16mg/kg/4D-I (16mg/kg) BLOOD: OTHER CHANGES American Journal of the Medical Sciences. Vol. 254, Pg. 48, 1967.
women TDLo intravenous 13500ug/kg (13.5mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE Annals of Internal Medicine. Vol. 116, Pg. 92, 1992.
women TDLo intravenous 60mg/kg/9W-I (60mg/kg)   Archives of Internal Medicine. Vol. 145, Pg. 548, 1985.
women TDLo oral 45mg/kg (45mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES Arthritis and Rheumatism. Vol. 15, Pg. 530, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 51.5 deg C   EXP
log P (octanol-water) 0.63 (none)   EXP
Water Solubility 4.00E+04 mg/L 20 EXP
Vapor Pressure 4.45E-05 mm Hg 25 EST
Henry's Law Constant 1.40E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.03E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.