Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H21Cl2N2O7P |
| Molecular Weight | 383.163 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@@H](OP(=O)(NCCCl)NCCCl)[C@H](O)[C@@H](O)[C@@H]1O
InChI
InChIKey=PSVUJBVBCOISSP-SPFKKGSWSA-N
InChI=1S/C10H21Cl2N2O7P/c11-1-3-13-22(19,14-4-2-12)21-10-9(18)8(17)7(16)6(5-15)20-10/h6-10,15-18H,1-5H2,(H2,13,14,19)/t6-,7-,8+,9-,10+/m1/s1
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.
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 |
|---|---|---|---|---|
| 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 | ||||
| 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 |
|||
| 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 |
|---|---|---|
| Nonmetastatic osteosarcoma of the extremity: results of a neoadjuvant chemotherapy protocol (IOR/OS-3) with high-dose methotrexate, intraarterial or intravenous cisplatin, doxorubicin, and salvage chemotherapy based on histologic tumor response. | 1999 Nov-Dec |
|
| Combined chemotherapy of murine mammary tumors by local activation of the prodrugs ifosfamide and 5-fluorocytosine. | 2000 Apr |
|
| Methylene blue in the treatment and prevention of ifosfamide-induced encephalopathy: report of 12 cases and a review of the literature. | 2000 Jan |
|
| Manic episode in an ifosfamide-treated patient. | 2000 Jan-Feb |
|
| Vinorelbine-based regimens as salvage treatment in patients with advanced non-small cell lung cancer: two parallel multicenter phase II trials. | 2001 |
|
| A phase II study of weekly alternating chemotherapy in extensive-stage small cell lung cancer. | 2001 |
|
| The efficacy of combination chemotherapy including intraperitoneal cisplatinum and mitoxantrone with intravenous ifosfamide in patients with FIGO stage I C ovarian carcinoma. | 2001 |
|
| Malignant mixed mullerian tumor of the ovary: report of four cases. | 2001 |
|
| Treatment of ruptured undifferentiated sarcoma of the liver in children: a report of two cases and review of the literature. | 2001 |
|
| Carnitine protects mitochondria and removes toxic acyls from xenobiotics. | 2001 |
|
| Paclitaxel by 72-hour continuous infusion followed by bolus intravenous ifosfamide or epirubicin: results of two phase I studies. | 2001 |
|
| Thymic malignancies. | 2001 |
|
| Salvage chemotherapy in relapsed germ cell tumors. | 2001 Apr |
|
| [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 |
|
| A three-drug regimen (gemcitabine, ifosfamide and cisplatin) for advanced non-small-cell lung cancer. | 2001 Apr |
|
| Modified dorsalis pedis flap for coverage of a pretibial pressure sore after hip rotationplasty. | 2001 Apr |
|
| Phase II study of paclitaxel, ifosfamide, and carboplatin in patients with recurrent or metastatic head and neck squamous cell carcinoma. | 2001 Apr 1 |
|
| The current status of docetaxel for advanced non-small cell lung cancer. | 2001 Feb |
|
| Phase II study of a high-dose ifosfamide-based chemotherapy regimen with growth factor rescue in recurrent aggressive NHL. High response rates and limited toxicity, but limited impact on long-term survival. | 2001 Feb |
|
| Sustained response of sarcomatoid renal-cell carcinoma to MAID chemotherapy: case report and review of the literature. | 2001 Feb |
|
| Chemotherapy agents in transitional cell carcinoma: the old and the new. | 2001 Feb |
|
| A comparison of methods of loco-regional chemotherapy combined with systemic chemotherapy as neo-adjuvant treatment of osteosarcoma of the extremity. | 2001 Feb |
|
| Neoadjuvant chemotherapy for high grade osteosarcoma of the extremities: long-term results for patients treated according to the Rizzoli IOR/OS-3b protocol. | 2001 Feb |
|
| Adult Gaucher disease in association with primary malignant bone tumors. | 2001 Feb 1 |
|
| A 2-step comprehensive high-dose chemoradiotherapy second-line program for relapsed and refractory Hodgkin disease: analysis by intent to treat and development of a prognostic model. | 2001 Feb 1 |
|
| How effective is dose-intensive/myeloablative therapy against Ewing's sarcoma/primitive neuroectodermal tumor metastatic to bone or bone marrow? The Memorial Sloan-Kettering experience and a literature review. | 2001 Feb 1 |
|
| [Addisonian crisis as first manifestation of adrenal gland insufficiency in patient diagnosed with lung cancer]. | 2001 Jan |
|
| A phase I clinical, pharmacological, and biological trial of interleukin 6 plus granulocyte-colony stimulating factor after ifosfamide, carboplatin, and etoposide in children with recurrent/refractory solid tumors: enhanced hematological responses but a high incidence of grade III/IV constitutional toxicities. | 2001 Jan |
|
| Should we always choose a nonparametric test when comparing two apparently nonnormal distributions? | 2001 Jan |
|
| A randomised phase II study on neo-adjuvant chemotherapy for 'high-risk' adult soft-tissue sarcoma. | 2001 Jun |
|
| Importance of surgery as salvage treatment after high dose chemotherapy failure in germ cell tumors. | 2001 Jun |
|
| A preclinical model for experimental chemotherapy of human head and neck cancer. | 2001 Jun |
|
| High-dose melphalan, etoposide, total-body irradiation, and autologous stem-cell reconstitution as consolidation therapy for high-risk Ewing's sarcoma does not improve prognosis. | 2001 Jun 1 |
|
| Immunoglobulin D myeloma presenting as an extraosseous soft tissue tumor. | 2001 Mar |
|
| [Surgical treatment of non-small cell lung cancer with mediastinal node invasion. A retrospective study]. | 2001 Mar |
|
| Necrotic, rather than apoptotic, cell death caused by cytochrome P450-activated ifosfamide. | 2001 Mar |
|
| Primary breast tumor levels of suspected molecular determinants of cellular sensitivity to cyclophosphamide, ifosfamide, and certain other anticancer agents as predictors of paired metastatic tumor levels of these determinants. Rational individualization of cancer chemotherapeutic regimens. | 2001 Mar |
|
| 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 |
|
| Ifosfamide and mitoxantrone in the treatment of recurrent and/or metastatic squamous cell carcinoma of the head and neck. | 2001 Mar |
|
| Adjuvant chemotherapy for adult soft tissue sarcomas of the extremities and girdles: results of the Italian randomized cooperative trial. | 2001 Mar 1 |
|
| Localized Ewing tumor of bone: final results of the cooperative Ewing's Sarcoma Study CESS 86. | 2001 Mar 15 |
|
| Histologic response of high-grade nonmetastatic osteosarcoma of the extremity to chemotherapy, | 2001 May |
|
| Gemcitabine and vinorelbine as second-line therapy in non-small-cell lung cancer after prior treatment with taxane+platinum-based regimens. | 2001 May |
|
| Haemoperfusion combined with haemodialysis in ifosfamide intoxication. | 2001 May |
|
| Topoisomerase IIalpha and other drug resistance markers in advanced non-small cell lung cancer. | 2001 May |
|
| Outcomes of treatment of children and adolescents with recurrent non-Hodgkin's lymphoma and Hodgkin's disease with dexamethasone, etoposide, cisplatin, cytarabine, and l-asparaginase, maintenance chemotherapy, and transplantation: Children's Cancer Group Study CCG-5912. | 2001 May 1 |
|
| Microencapsulated cell-mediated treatment of inoperable pancreatic carcinoma. | 2001 May 19 |
|
| A novel alkylating agent, glufosfamide, enhances the activity of gemcitabine in vitro and in vivo. | 2007 Aug |
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C697
Created by
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EU-Orphan Drug |
EU/3/11/851
Created by
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FDA ORPHAN DRUG |
221606
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| Code System | Code | Type | Description | ||
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m5774
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PRIMARY | Merck Index | ||
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C1612
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DB06177
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7024
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CHEMBL2107143
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1W5N8SZD9A
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SUB07941MIG
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100000084228
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DTXSID001031222
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Glufosfamide
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7590
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132682-98-5
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123628
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ACTIVE MOIETY
SUBSTANCE RECORD
