Details
Stereochemistry | UNKNOWN |
Molecular Formula | C7H15Cl2N2O3P |
Molecular Weight | 277.085 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1CCOP(=O)(NCCCl)N1CCCl
InChI
InChIKey=JHUJMHKRHQPBRG-UHFFFAOYSA-N
InChI=1S/C7H15Cl2N2O3P/c8-2-4-10-15(13)11(5-3-9)7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13)
Molecular Formula | C7H15Cl2N2O3P |
Molecular Weight | 277.085 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Ifosfamide (IF) is a widely used antitumor prodrug. It is in the oxazaphosphorine class of alkylating agents, and it is effective against solid tumors. Ifosfamide mechanism of crosslinking DNA plays a major role in preventing cancer cells from proliferating. Ifosfamide is approved by FDA for the treatment of germ cell testicular cancer.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3253870/
Curator's Comment: Ifosfamide crosses the blood-brain barrier and may cause encephalopathy.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | IFEX Approved UseIfosfamide injection, used in combination with certain other approved antineoplastic agents, is indicated for third line chemotherapy of germ cell testicular cancer. It should be used in combination with a prophylactic agent for hemorrhagic cystitis, such as mesna. Launch Date1988 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
346 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9528844 |
3 g/m² single, intravenous dose: 3 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
200 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1795004 |
1.5 g/m² single, oral dose: 1.5 g/m² route of administration: Oral experiment type: SINGLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
203 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1795004 |
1.5 g/m² single, intravenous dose: 1.5 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2197 mM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9528844 |
3 g/m² single, intravenous dose: 3 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1360 μM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1795004 |
1.5 g/m² single, oral dose: 1.5 g/m² route of administration: Oral experiment type: SINGLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1520 μM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1795004 |
1.5 g/m² single, intravenous dose: 1.5 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
7.54 mM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8339288 |
3 g/m² 1 times / day multiple, intravenous dose: 3 g/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.33 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9528844 |
3 g/m² single, intravenous dose: 3 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1795004 |
1.5 g/m² single, oral dose: 1.5 g/m² route of administration: Oral experiment type: SINGLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1795004 |
1.5 g/m² single, intravenous dose: 1.5 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.12 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8339288 |
3 g/m² 1 times / day multiple, intravenous dose: 3 g/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
IFOSFAMIDE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
100% |
unknown |
IFOSFAMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
18 g/m2 1 times / day multiple, intravenous MTD Dose: 18 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 g/m2, 1 times / day Sources: |
unhealthy, 45 |
DLT: Neutropenia, Infection... Dose limiting toxicities: Neutropenia (grade 4, 83.3%) Sources: Infection (severe, 33.3%) Thrombocytopenia (grade 4, 66.7%) |
2.25 g/m2 1 times / day multiple, intravenous MTD Dose: 2.25 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 2.25 g/m2, 1 times / day Sources: |
unhealthy, 45 |
DLT: Neutropenia, Febrile neutropenia... Dose limiting toxicities: Neutropenia (grade 4, 66.7%) Sources: Febrile neutropenia (grade 5, 33.3%) Thrombocytopenia (grade 4, 66.7%) Anemia (grade 4, 66.7%) |
1.2 g/m2 1 times / day multiple, intravenous Recommended Dose: 1.2 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 1.2 g/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Nephrotoxicity, Renal failure... AEs leading to discontinuation/dose reduction: Nephrotoxicity (severe) Sources: Renal failure (severe) Cystitis hemorrhagic (severe) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Thrombocytopenia | grade 4, 66.7% DLT |
18 g/m2 1 times / day multiple, intravenous MTD Dose: 18 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 g/m2, 1 times / day Sources: |
unhealthy, 45 |
Neutropenia | grade 4, 83.3% DLT |
18 g/m2 1 times / day multiple, intravenous MTD Dose: 18 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 g/m2, 1 times / day Sources: |
unhealthy, 45 |
Infection | severe, 33.3% DLT |
18 g/m2 1 times / day multiple, intravenous MTD Dose: 18 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 18 g/m2, 1 times / day Sources: |
unhealthy, 45 |
Anemia | grade 4, 66.7% DLT |
2.25 g/m2 1 times / day multiple, intravenous MTD Dose: 2.25 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 2.25 g/m2, 1 times / day Sources: |
unhealthy, 45 |
Neutropenia | grade 4, 66.7% DLT |
2.25 g/m2 1 times / day multiple, intravenous MTD Dose: 2.25 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 2.25 g/m2, 1 times / day Sources: |
unhealthy, 45 |
Thrombocytopenia | grade 4, 66.7% DLT |
2.25 g/m2 1 times / day multiple, intravenous MTD Dose: 2.25 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 2.25 g/m2, 1 times / day Sources: |
unhealthy, 45 |
Febrile neutropenia | grade 5, 33.3% DLT, Disc. AE |
2.25 g/m2 1 times / day multiple, intravenous MTD Dose: 2.25 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 2.25 g/m2, 1 times / day Sources: |
unhealthy, 45 |
Cystitis hemorrhagic | severe Disc. AE |
1.2 g/m2 1 times / day multiple, intravenous Recommended Dose: 1.2 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 1.2 g/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Nephrotoxicity | severe Disc. AE |
1.2 g/m2 1 times / day multiple, intravenous Recommended Dose: 1.2 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 1.2 g/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Renal failure | severe Disc. AE |
1.2 g/m2 1 times / day multiple, intravenous Recommended Dose: 1.2 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 1.2 g/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/9157990/ |
yes | |||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
poor | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
Page: 28.0 |
yes | no (co-administration study) Comment: Coadministration of ifosfamide with ketoconazole or rifampin did not produce changes inthe pharmacokinetics of the parent or metabolites that may result in an increased benefit of ifosfamidetherapy. (https://pubmed.ncbi.nlm.nih.gov/11503007/) Page: 28.0 |
||
Page: 28.0 |
yes | no (co-administration study) Comment: Coadministration of ifosfamide with ketoconazole or rifampin did not produce changes inthe pharmacokinetics of the parent or metabolites that may result in an increased benefit of ifosfamidetherapy. (https://pubmed.ncbi.nlm.nih.gov/11503007/) Page: 28.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Intratumoral injection of encapsulated cells producing an oxazaphosphorine activating cytochrome P450 for targeted chemotherapy. | 1998 |
|
Prospective evaluation of high-dose ifosfamide-related nephrotoxicity in young adult patients with recurrent osteosarcoma previously treated with cisplatin, methotrexate and standard-dose ifosfamide. | 1999 Jan |
|
Injection of encapsulated cells producing an ifosfamide-activating cytochrome P450 for targeted chemotherapy to pancreatic tumors. | 1999 Jun 30 |
|
Development of ifosfamide-induced nephrotoxicity: prospective follow-up in 75 patients. | 1999 Mar |
|
Risk factors for long-term outcome of ifosfamide-induced nephrotoxicity in children. | 1999 May |
|
Methylene blue in the treatment and prevention of ifosfamide-induced encephalopathy: report of 12 cases and a review of the literature. | 2000 Jan |
|
Subacute central nervous system degeneration in a child: an unusual manifestation of ifosfamide intoxication. | 2000 Jul |
|
Distinctive potentiating effects of cisplatin and/or ifosfamide combined with etoposide in human small cell lung carcinoma xenografts. | 2000 May |
|
Two episodes of ifosfamide-related neurotoxicity in the same patient following different schedules and doses of the drug. A case report. | 2000 Nov-Dec |
|
A phase II study of weekly alternating chemotherapy in extensive-stage small cell lung cancer. | 2001 |
|
Comparison of double and triple high-dose chemotherapy with autologous blood stem cell transplantation in patients with metastatic breast cancer. | 2001 |
|
[Post-operative neoadjuvant chemotherapy before radiotherapy as compared to immediate radiotherapy followed by maintenance chemotherapy in the treatment of medulloblastoma in childhood: results of German prospective randomised trial HIT'91]. | 2001 Apr |
|
[Pigmented villonodular synovitis: apropos of 3 cases]. | 2001 Apr |
|
The current status of docetaxel for advanced non-small cell lung cancer. | 2001 Feb |
|
Sustained response of sarcomatoid renal-cell carcinoma to MAID chemotherapy: case report and review of the literature. | 2001 Feb |
|
Selective use of whole-lung irradiation for patients with Ewing sarcoma family tumors and pulmonary metastases at the time of diagnosis. | 2001 Feb |
|
[Is it useful to perform a (67)gallium scintigraphy in the follow-up of patients with gastric lymphoma?]. | 2001 Feb |
|
Adult Gaucher disease in association with primary malignant bone tumors. | 2001 Feb 1 |
|
[Prostatic angiosarcoma: report of a new case]. | 2001 Jan |
|
Anticancer drug-induced kidney disorders. | 2001 Jan |
|
Should we always choose a nonparametric test when comparing two apparently nonnormal distributions? | 2001 Jan |
|
Docetaxel and ifosfamide as second line treatment for patients with advanced or metastatic urothelial cancer after failure of platinum chemotherapy: a phase 2 study. | 2001 Jan |
|
Carboplatin/ifosfamide window therapy for osteosarcoma: results of the St Jude Children's Research Hospital OS-91 trial. | 2001 Jan 1 |
|
A randomized trial of amifostine as a cytoprotective agent in patients receiving chemotherapy for small cell lung cancer. | 2001 Jan 5 |
|
A phase II study of dose-intense ifosfamide plus epirubicin with hematopoietic growth factors for the treatment of patients with advanced soft tissue sarcomas; a novel sequential schedule. | 2001 Mar |
|
Gemcitabine for the treatment of non-small-cell lung cancer. | 2001 Mar |
|
Intrasellar rhabdomyosarcoma: case report. | 2001 Mar |
|
Topoisomerase IIalpha and other drug resistance markers in advanced non-small cell lung cancer. | 2001 May |
|
A novel alkylating agent, glufosfamide, enhances the activity of gemcitabine in vitro and in vivo. | 2007 Aug |
Sample Use Guides
30-min infusion at a dose of 1.2 grams per m2 per day for 5 consecutive days
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1968886/
Human testicular germ cell tumour lines H 12.1 and 2102 EP were treated with ifosfamide at 50 mg kg-1 day-1.
Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 23:05:48 GMT 2025
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Record UNII |
ARX5AJ985I
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Record Status |
Validated (UNII)
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Record Version |
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PRODRUG -> METABOLITE ACTIVE |
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METABOLITE -> PARENT |
URINE
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |