Compounds > dechloroethylifosfamide
Page last updated: 2024-12-07

dechloroethylifosfamide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

dechloroethylifosfamide: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID119105
CHEMBL ID87851
CHEBI ID80562
SCHEMBL ID15577974
MeSH IDM0114643

Synonyms (23)

Synonym
CHEMBL87851
chebi:80562 ,
2h-1,3,2-oxazaphosphorin-2-amine, 3-(2-chloroethyl)tetrahydro-, 2-oxide
dechloroethylifosfamide
2-dce-iff
2-dechloroethylifosfamide
2-amino-3-(2-chloroethyl)tetrahydro-2h-1,3,2-oxazophosphorine-2-o-xide
2-dclif
3-(2-chloroethyl)tetrahydro-2h-1,3,2-oxazaphosphorin-2-amine 2-oxide
53459-55-5
3-(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
105308-45-0
AKOS006278025
unii-iib78d4dqa
iib78d4dqa ,
SCHEMBL15577974
2-dechloroethylifosfamide, (+/-)-
(rs)-2-de(chloroethyl)ifosfamide
Q27149606
3-(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine
DTXSID90909417
EN300-6736451
2-amino-3-(2-chloroethyl)-1,3,2lambda5-oxazaphosphinan-2-one

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" This will adversely affect the health and well-being of children, especially when the developing kidney is exposed to toxic agents that may lead to acute glomerular, tubular or combined toxicity."( Cytochrome P450 3A and 2B6 in the developing kidney: implications for ifosfamide nephrotoxicity.
Aleksa, K; Gelboin, H; Ito, S; Koren, G; Krausz, K; Matsell, D, 2005)		0.33
" The authors' multidimensional analysis model revealed that besides the total ifosfamide dose and co-administration of other toxic drugs, polymorphic locus of GSTP1 gene may be one of the factors determining a higher toxicity of the cytostatic agent."( Role of GSTM1, GSTP1, and GSTT1 gene polymorphism in ifosfamide metabolism affecting neurotoxicity and nephrotoxicity in children.
Misiura, K; Zielińska, E; Zubowska, M, 2005)		0.33

Pharmacokinetics

ExcerptReferenceRelevance
" As compared with the values obtained on day 1, on day 5 the terminal half-life and AUC values determined for IF were reduced by 30% (6."( Comparative pharmacokinetics of ifosfamide, 4-hydroxyifosfamide, chloroacetaldehyde, and 2- and 3-dechloroethylifosfamide in patients on fractionated intravenous ifosfamide therapy.
Kurowski, V; Wagner, T, 1993)		0.5
" This study reports the results of a pharmacokinetic study of the parent drug and the two dechloroethylated metabolites in 22 patients on a 10-day continuous infusion of ifosfamide."( Pharmacokinetics of ifosfamide, 2- and 3-dechloroethylifosfamide in plasma and urine of cancer patients treated with a 10-day continuous infusion of ifosfamide.
Beijnen, JH; Bult, A; Kaijser, GP; Keizer, HJ; Underberg, WJ, )		0.4
" These results indicate that there is no identifiable pharmacokinetic basis for insistence on either bolus or infusional methods of IFOS administration."( The pharmacokinetics and metabolism of ifosfamide during bolus and infusional administration: a randomized cross-over study.
Brennan, C; Hartley, JM; Nicholson, PW; Singer, JM; Souhami, RL, 1998)		0.3
" The population pharmacokinetic model was built in a sequential manner, starting with a covariate-free model and progressing to a covariate model with the aid of generalised additive modelling."( Population pharmacokinetics and exploratory pharmacodynamics of ifosfamide and metabolites after a 72-h continuous infusion in patients with soft tissue sarcoma.
Beijnen, JH; Keizer, HJ; Kerbusch, T; Mathĵt, RA; Ouwerkerk, J; Rodenhuis, S; Schellens, JH, 2001)		0.31
" Autoinduction, dependent on ifosfamide levels, was characterised by an induction half-life of 11."( Population pharmacokinetics and exploratory pharmacodynamics of ifosfamide and metabolites after a 72-h continuous infusion in patients with soft tissue sarcoma.
Beijnen, JH; Keizer, HJ; Kerbusch, T; Mathĵt, RA; Ouwerkerk, J; Rodenhuis, S; Schellens, JH, 2001)		0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
organonitrogen heterocyclic compoundAny organonitrogen compound containing a cyclic component with nitrogen and at least one other element as ring member atoms.
organophosphorus compoundAn organophosphorus compound is formally a compound containing at least one carbon-phosphorus bond, but the term is often extended to include esters and thioesters.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
Ifosfamide Action Pathway821
Ifosfamide Metabolism Pathway821

Bioassays (21)

Assay IDTitleYearJournalArticle
AID7614Portion of holoxan excreted in the form of the metabolite from 1200 mL of urine on day 3 was determined in embryonal rhabdomyosarcoma patients treated with ifosfamide1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7775Percent ratio of the enantiomeric form (+)R extracted from the urine of embryonal rhabdomyosarcoma patients was determined1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7772Portion of holoxan excreted in the form of the metabolite from 1700 mL of urine on day 5 was determined in embryonal rhabdomyosarcoma patients treated with ifosfamide1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7973Quantity of the metabolite found in the urine of the embryonal rhabdomyosarcoma patients treated with ifosfamide from 2310 mL of urine tested on day 41983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID184802acute toxicity against rat after iv administration1999Journal of medicinal chemistry, Jul-15, Volume: 42, Issue:14
Chemical stability and fate of the cytostatic drug ifosfamide and its N-dechloroethylated metabolites in acidic aqueous solutions.
AID7967Quantity of the metabolite found in the urine of the embryonal rhabdomyosarcoma patients treated with ifosfamide from 1200 mL of urine tested on day 71983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7970Quantity of the metabolite found in the urine of the embryonal rhabdomyosarcoma patients treated with ifosfamide from 1500 mL of urine tested on day 91983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7821Quantity of the metabolite found in the urine of the embryonal rhabdomyosarcoma patients treated with ifosfamide from 1200 mL of urine tested on day 31983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7969Quantity of the metabolite found in the urine of the embryonal rhabdomyosarcoma patients treated with ifosfamide from 1300 mL of urine tested on day 81983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7972Quantity of the metabolite found in the urine of the embryonal rhabdomyosarcoma patients treated with ifosfamide from 1700 mL of urine tested on day 51983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7774Percent ratio of the enantiomeric form (+)R extracted from the urine of alveolar rhabdomyosarcoma patients was determined1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7770Portion of holoxan excreted in the form of the metabolite from 1500 mL of urine on day 9 was determined in embryonal rhabdomyosarcoma patients treated with ifosfamide1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7616Portion of holoxan excreted in the form of the metabolite from 1300 mL of urine on day 6 was determined in embryonal rhabdomyosarcoma patients treated with ifosfamide1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7617Portion of holoxan excreted in the form of the metabolite from 1300 mL of urine on day 8 was determined in embryonal rhabdomyosarcoma patients treated with ifosfamide1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7968Quantity of the metabolite found in the urine of the embryonal rhabdomyosarcoma patients treated with ifosfamide from 1300 mL of urine tested on day 61983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7771Portion of holoxan excreted in the form of the metabolite from 1600 mL of urine on day 10 was determined in embryonal rhabdomyosarcoma patients treated with ifosfamide1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7615Portion of holoxan excreted in the form of the metabolite from 1200 mL of urine on day 7 was determined in embryonal rhabdomyosarcoma patients treated with ifosfamide1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7971Quantity of the metabolite found in the urine of the embryonal rhabdomyosarcoma patients treated with ifosfamide from 1600 mL of urine tested on day 101983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7773Portion of holoxan excreted in the form of the metabolite from 2310 mL of urine on day 4 was determined in embryonal rhabdomyosarcoma patients treated with ifosfamide1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7777Percent ratio of the enantiomeric form (-)S extracted from the urine of embryonal rhabdomyosarcoma patients was determined1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
AID7776Percent ratio of the enantiomeric form (-)S extracted from the urine of alveolar rhabdomyosarcoma patients was determined1983Journal of medicinal chemistry, May, Volume: 26, Issue:5
Stereospecific synthesis of chiral metabolites of ifosfamide and their determination in the urine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.56)18.7374
1990's9 (50.00)18.2507
2000's7 (38.89)29.6817
2010's1 (5.56)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.14

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.14 (24.57)
Research Supply Index3.18 (2.92)
Research Growth Index5.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.14)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (15.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (85.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chloroacetaldehyde
[no description available]		7.4120organochlorine compound
acetaldehyde
Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.		7.4120aldehydecarcinogenic agent;
EC 3.5.1.4 (amidase) inhibitor;
electron acceptor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
mutagen;
oxidising agent;
Saccharomyces cerevisiae metabolite;
teratogenic agent
ifosfamide
[no description available]		6.55183ifosfamidesalkylating agent;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
xenobiotic
deuterium
Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.		7.4220dihydrogen
phosphoramidic acid
phosphoramidic acid: urease inhibitor; RN given refers to parent cpd; structure; do not confuse with phosphoramidites, which are organophosphorus compounds		210phosphoric acid derivative
2,2'-dithiodiethanesulfonic acid
[no description available]		3.3811
isophosphamide mustard
isophosphamide mustard: antitumor metabolite of ifosfamide; palifosfamide-tris is a salt with tris; structure in first source		4.2841phosphorodiamide
dechloroethylcyclophosphamide
dechloroethylcyclophosphamide: structure given in first source; RN given refers to parent cpd		11.38153phosphorodiamide
carboxyifosfamide
carboxyifosfamide: structure given in first source		4.0531phosphorodiamide
4-hydroxyifosfamide
[no description available]		4.8442ifosfamides
mesna
Mesna: A sulfhydryl compound used to prevent urothelial toxicity by inactivating metabolites from ANTINEOPLASTIC AGENTS, such as IFOSFAMIDE or CYCLOPHOSPHAMIDE.		8.3811organosulfonic acid
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		0210
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		02.0210
Encephalopathy, Toxic
[description not available]		02.0210
Benign Neoplasms, Brain
[description not available]		02.0210
Leucocythaemia
[description not available]		02.0210
Brain Neoplasms
Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.		02.0210
Kidney Diseases
Pathological processes of the KIDNEY or its component tissues.		02.0210
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		02.0210
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.4220
Cancer of Cervix
[description not available]		01.9810
Uterine Cervical Neoplasms
Tumors or cancer of the UTERINE CERVIX.		01.9810
Carcinoma, Bronchial
[description not available]		03.7821
Cancer of Lung
[description not available]		03.7821
Carcinoma, Bronchogenic
Malignant neoplasm arising from the epithelium of the BRONCHI. It represents a large group of epithelial lung malignancies which can be divided into two clinical groups: SMALL CELL LUNG CANCER and NON-SMALL-CELL LUNG CARCINOMA.		03.7821
Lung Neoplasms
Tumors or cancer of the LUNG.		03.7821
Carcinoma, Oat Cell
[description not available]		03.3811
Carcinoma, Non-Small Cell Lung
[description not available]		03.3811
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		03.3811
Carcinoma, Small Cell
An anaplastic, highly malignant, and usually bronchogenic carcinoma composed of small ovoid cells with scanty neoplasm. It is characterized by a dominant, deeply basophilic nucleus, and absent or indistinct nucleoli. (From Stedman, 25th ed; Holland et al., Cancer Medicine, 3d ed, p1286-7)		03.3811
Carcinoma, Anaplastic
[description not available]		01.9910
Cancer of Rectum
[description not available]		01.9910
Carcinoma
A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.		01.9910
Rectal Neoplasms
Tumors or cancer of the RECTUM.		01.9910
Sarcoma, Epithelioid
[description not available]		04.3522
Ewing Sarcoma
[description not available]		03.3811
Sarcoma
A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.		04.3522
Sarcoma, Ewing
A malignant tumor of the bone which always arises in the medullary tissue, occurring more often in cylindrical bones. The tumor occurs usually before the age of 20, about twice as frequently in males as in females.		03.3811
Cancer of Colon
[description not available]		01.9810
Colonic Neoplasms
Tumors or cancer of the COLON.		01.9810