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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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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-NSmiles
C1CN(P(=O)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) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982. |
| dog | LDLo | intravenous | 66mg/kg (66mg/kg) | BLOOD: HEMORRHAGE LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA KIDNEY, URETER, AND BLADDER: OTHER CHANGES | National Technical Information Service. Vol. PB220-927, |
| guinea pig | LDLo | intraperitoneal | 400mg/kg (400mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE | Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982. |
| human | TDLo | intravenous | 130mg/kg/13D- (130mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING 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: LEUKOPENIA BLOOD: THROMBOCYTOPENIA | Cancer Chemotherapy Reports, Part 3. Vol. 3, Pg. 33, 1972. |
| human | TDLo | oral | 150mg/kg (150mg/kg) | SKIN AND APPENDAGES (SKIN): HAIR: OTHER GASTROINTESTINAL: NAUSEA OR VOMITING KIDNEY, URETER, AND BLADDER: PROTEINURIS | 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) | BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA 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) | BEHAVIORAL: ATAXIA SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982. |
| rabbit | LDLo | intraperitoneal | 200mg/kg (200mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | 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) | 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) | 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: CHANGES IN SURFACE EEG BRAIN AND COVERINGS: DEMYELINATION | 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.