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Substance Name: Ifosfamide [USAN:USP:INN:BAN:JAN]
RN: 3778-73-2
UNII: UM20QQM95Y
InChIKey: HOMGKSMUEGBAAB-UHFFFAOYSA-N

Note

  • Positional isomer of CYCLOPHOSPHAMIDE which is active as an alkylating agent and an immunosuppressive agent.

Molecular Formula

  • C7-H15-Cl2-N2-O2-P

Molecular Weight

  • 261.0875
 

Classification Codes

Classification Codes

  • Alkylating Agents
  • Antineoplastic
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Ifosfamide
  • Ifosfamide [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Ifosfamide

Synonyms

  • 2,3-(N,N(sup 1)-Bis(2-chloroethyl)diamido)-1,3,2-oxazaphosphoridinoxyd
  • 3-(2-Chloroethyl)-2-((2-chloroethyl)amino)perhydro-2H-1,3,2-oxazaphosphorine oxide
  • 3-(2-Chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
  • A 4942
  • ASTA Z 4942
  • BRN 0611835
  • CCRIS 352
  • Cyfos
  • EINECS 223-237-3
  • Holoxan
  • Holoxan 1000
  • HSDB 7023
  • I-Phosphamide
  • Ifex
  • Ifosfamid
  • Ifosfamida
  • Ifosfamida [INN-Spanish]
  • Ifosfamide
  • Ifosfamidum
  • Ifosfamidum [INN-Latin]
  • Ifsofamide
  • Iphosphamid
  • Iphosphamide
  • Isoendoxan
  • Isofosfamide
  • Isophosphamide
  • Mitoxana
  • MJF 9325
  • MJF-9325
  • N,3-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide
  • N,N-Bis(beta-chloroethyl)-amino-N',O-propylene-phosphoric acid ester diamide
  • N-(2-Chloraethyl)-N'-(2-chloraethyl)-N',O-propylen-phosphorsaureester-diamid
  • N-(2-Chloraethyl)-N'-(2-chloraethyl)-N',O-propylen-phosphorsaureester-diamid [German]
  • N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylenephosphoric acid diamide
  • N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide
  • Naxamide
  • NCI-C01638
  • NSC 109724
  • NSC-109724
  • UNII-UM20QQM95Y
  • Z 4942
  • Z-4942
  • Z4942

Systematic Names

  • 1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-, 2-oxide
  • 2H-1,3,2-Oxazaphosphorin-2-amine, N,3-bis(2-chloroethyl)tetrahydro-, 2-oxide
  • 2H-1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-, 2-oxide (8CI)
  • Ifosfamide
  • Isophosphamide

Superlist Names

  • Ifosfamide
  • Isophosphamide

Registry Numbers

CAS Registry Number

  • 3778-73-2

FDA UNII

  • UM20QQM95Y

Other Registry Numbers

  • 36341-88-5
  • 84711-20-6

System Generated Number

  • 0003778732

Structure Descriptors

InChI

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

InChIKey

HOMGKSMUEGBAAB-UHFFFAOYSA-N

Smiles

C1CN(P(=O)(OC1)NCCCl)CCCl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intraperitoneal 100mg/kg (100mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
cat LDLo intraperitoneal 100mg/kg (100mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
dog LDLo intraperitoneal 50mg/kg (50mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
dog LDLo intravenous 66mg/kg (66mg/kg) BLOOD: HEMORRHAGE

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA		 National Technical Information Service. Vol. PB220-927,
guinea pig LDLo intraperitoneal 400mg/kg (400mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: ATAXIA

BEHAVIORAL: MUSCLE WEAKNESS		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
human TDLo intravenous 130mg/kg/13D- (130mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: HEMATURIA		 Cancer Research. Vol. 32, Pg. 921, 1972.
human TDLo intravenous 1915mg/kg/2W- (1915mg/kg) KIDNEY, URETER, AND BLADDER: "INFLAMMATION, NECROSIS, OR SCARRING OF BLADDER"

KIDNEY, URETER, AND BLADDER: HEMATURIA		 Lancet. Vol. 2, Pg. 657, 1980.
human TDLo intravenous 2298mg/kg/3D- (2298mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA

BLOOD: LEUKOPENIA		 European Journal of Cancer. Vol. 12, Pg. 195, 1976.
human TDLo intravenous 2873mg/kg/5D- (2873mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

KIDNEY, URETER, AND BLADDER: HEMATURIA		 Cancer Research. Vol. 36, Pg. 2945, 1976.
human TDLo oral 100mg/kg (100mg/kg) BLOOD: THROMBOCYTOPENIA

BLOOD: LEUKOPENIA		 Cancer Chemotherapy Reports, Part 3. Vol. 3, Pg. 33, 1972.
human TDLo oral 150mg/kg (150mg/kg) KIDNEY, URETER, AND BLADDER: PROTEINURIS

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

GASTROINTESTINAL: NAUSEA OR VOMITING		 Cancer Research. Vol. 32, Pg. 921, 1972.
mouse LD50 intraperitoneal 397mg/kg (397mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 1149, 1974.
mouse LD50 intraperitoneal 415mg/kg (415mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Archivum Immunologiae et Therapiae Experimentalis. Vol. 34, Pg. 293, 1986.
mouse LD50 intravenous 338mg/kg (338mg/kg) BEHAVIORAL: ATAXIA

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
mouse LD50 oral 1005mg/kg (1005mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
mouse LD50 oral 2600mg/kg (2600mg/kg)   Archivum Immunologiae et Therapiae Experimentalis. Vol. 34, Pg. 293, 1986.
mouse LD50 oral 2600mg/kg (2600mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Archivum Immunologiae et Therapiae Experimentalis. Vol. 34, Pg. 293, 1986.
mouse LD50 subcutaneous 656mg/kg (656mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rabbit LDLo intraperitoneal 200mg/kg (200mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: MUSCLE WEAKNESS		 Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat LD50 intraperitoneal 140mg/kg (140mg/kg)   United States Patent Document. Vol. #3732340,
rat LD50 intravenous 190mg/kg (190mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat LD50 intravenous 190mg/kg (190mg/kg) BLOOD: NORMOCYTIC ANEMIA Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat LD50 oral 143mg/kg (143mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat LD50 oral 143mg/kg (143mg/kg) BLOOD: NORMOCYTIC ANEMIA Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat LD50 subcutaneous 160mg/kg (160mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat LD50 subcutaneous 160mg/kg (160mg/kg) BLOOD: NORMOCYTIC ANEMIA Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat LD50 unreported 325mg/kg (325mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1369, 1975.
women TDLo intravenous 218mg/kg (218mg/kg) BRAIN AND COVERINGS: DEMYELINATION

BRAIN AND COVERINGS: CHANGES IN SURFACE EEG		 Journal of Toxicology, Clinical Toxicology. Vol. 27, Pg. 293, 1989.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 39-41 deg C   EXP
log P (octanol-water) 0.86 (none)   EXP
Water Solubility 3780 mg/L 25 EST
Vapor Pressure 2.98E-05 mm Hg 25 EST
Henry's Law Constant 1.36E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.28E-11 cm3/molecule-sec 25 EST

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