IFOSFAMIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1988)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: L01AA06
UNII: UM20QQM95Y

Structure
InChI Key HOMGKSMUEGBAAB-UHFFFAOYSA-N
Smile O=P1(NCCCl)OCCCN1CCCl
InChI
InChI=1S/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12)

Physicochemical Descriptors

Property Name Value
Molecular Formula C7H15Cl2N2O2P
Molecular Weight 261.09
AlogP 1.88
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 41.57
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 14.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 0.86 - EXP
Henry's Law Constant 1.36E-11 atm-m3/mole EST
Atmospheric OH Rate Constant 4.28E-11 cm3/molecule-sec EST
Melting Point 39-41 deg C EXP
Water Solubility 3780 mg/L EST
Vapor Pressure 2.98E-05 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor DailyMed

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Testicular Neoplasms 4 D013736 ClinicalTrials
Testicular Neoplasms 4 D013736 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Hemangiosarcoma 3 D006394 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Sarcoma, Ewing 3 D012512 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Teratoma 3 D013724 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Endometrial Neoplasms 3 D016889 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Leiomyosarcoma 3 D007890 ClinicalTrials
Liposarcoma 3 D008080 ClinicalTrials
Neurilemmoma 3 D009442 ClinicalTrials
Sarcoma, Synovial 3 D013584 ClinicalTrials
Osteosarcoma 3 D012516 ClinicalTrials
Histiocytoma 3 D051642 ClinicalTrials
Sarcoma, Alveolar Soft Part 3 D018234 ClinicalTrials
Mesenchymoma 3 D008637 ClinicalTrials
Fibrosarcoma 3 D005354 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 3 D009373 ClinicalTrials
Hemangiopericytoma 3 D006393 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Dermatofibrosarcoma 3 D018223 ClinicalTrials
Carcinoma 3 D002277 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 3 D009373 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Neuroblastoma 3 D009447 ClinicalTrials
Small Cell Lung Carcinoma 3 D055752 ClinicalTrials
Rhabdomyosarcoma 3 D012208 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Lymphoma, T-Cell, Peripheral 3 D016411 ClinicalTrials
Fallopian Tube Neoplasms 3 D005185 ClinicalTrials
Retroviridae Infections 3 D012192 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Pheochromocytoma 3 D010673 ClinicalTrials
Mediastinal Neoplasms 3 D008479 ClinicalTrials
Central Nervous System Neoplasms 3 D016543 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Fallopian Tube Neoplasms 3 D005185 ClinicalTrials
Kidney Neoplasms 3 D007680 ClinicalTrials
Lymphoma, Mantle-Cell 2 D020522 ClinicalTrials
Uterine Neoplasms 2 D014594 ClinicalTrials
Wilms Tumor 2 D009396 ClinicalTrials
Rhabdomyosarcoma, Embryonal 2 D018233 ClinicalTrials
Rhabdomyosarcoma, Alveolar 2 D018232 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Burkitt Lymphoma 2 D002051 ClinicalTrials
Urinary Bladder Neoplasms 2 D001749 ClinicalTrials
Penile Neoplasms 2 D010412 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Urethral Neoplasms 2 D014523 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 2 D017728 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Nasopharyngeal Neoplasms 2 D009303 ClinicalTrials
Neoplasm Metastasis 1 D009362 ClinicalTrials
Myeloproliferative Disorders 1 D009196 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials
Myelodysplastic Syndromes 1 D009190 ClinicalTrials

Related Entries

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Skin and subcutaneous tissue disorders Alopecia 83.0
Gastrointestinal disorders Nausea 58.0
Gastrointestinal disorders Vomiting 58.0
Renal and urinary disorders Haematuria 46.0
Metabolism and nutrition disorders Metabolic acidosis 31.0
Renal and urinary disorders Haematuria 12.0
Injury, poisoning and procedural complications Neurotoxicity 12.0
Blood and lymphatic system disorders Thrombocytopenia 10.0
Investigations Body temperature increased 8.0
Infections and infestations Infection 8.0
Injury, poisoning and procedural complications Nephropathy toxic 6.0
Renal and urinary disorders Renal failure 6.0
Renal and urinary disorders Renal impairment 6.0
Hepatobiliary disorders Hepatic function abnormal 3.0
Vascular disorders Phlebitis 2.0
General disorders and administration site conditions Asthenia 1.0
Investigations Body temperature increased 1.0
Cardiac disorders Cardiotoxicity 1.0
Blood and lymphatic system disorders Coagulopathy 1.0
Gastrointestinal disorders Constipation 1.0
Convulsion 1.0
General disorders and administration site conditions Decreased appetite 1.0
Skin and subcutaneous tissue disorders Dermatitis 1.0
Gastrointestinal disorders Diarrhoea 1.0
General disorders and administration site conditions Discomfort 1.0
Infections and infestations Encephalitis 1.0
General disorders and administration site conditions Fatigue 1.0
General disorders and administration site conditions Feeling abnormal 1.0
Immune system disorders Hypersensitivity 1.0
Vascular disorders Hypertension 1.0
Vascular disorders Hypotension 1.0
General disorders and administration site conditions Ill-defined disorder 1.0
Immune system disorders Interstitial lung disease 1.0
General disorders and administration site conditions Malaise 1.0
Nervous system disorders Neuropathy peripheral 1.0
Gastrointestinal disorders Pancreatitis 1.0
Nervous system disorders Polyneuropathy 1.0
Cardiac disorders Pulmonary oedema 1.0
Renal and urinary disorders Renal failure 1.0
Gastrointestinal disorders Salivary hypersecretion 1.0
Gastrointestinal disorders Stomatitis 1.0
Vascular disorders Thrombophlebitis 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Blood and lymphatic system disorders
14.83
General disorders and administration site conditions
14.21
Nervous system disorders
10.39
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
8.09
Injury, poisoning and procedural complications
6.68
Infections and infestations
6.6
Gastrointestinal disorders
5.49
Respiratory, thoracic and mediastinal disorders
4.53
Renal and urinary disorders
4.43
Vascular disorders
3.82
Metabolism and nutrition disorders
3.21
Psychiatric disorders
3.06
Investigations
2.04

Cross References

Resources Reference
CAS NUMBER 3778-73-2
ChEBI 5864
ChEMBL CHEMBL1024
DrugBank DB01181
DrugCentral 1421
EPA CompTox DTXSID7020760
FDA SRS UM20QQM95Y
Human Metabolome Database HMDB0015312
Guide to Pharmacology 7201
KEGG C07047
PharmGKB PA449964
PubChem 3690
SureChEMBL SCHEMBL4885
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