Page last updated: 2024-12-07

dechloroethylcyclophosphamide

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

Description

dechloroethylcyclophosphamide: structure given in first source; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID114861
CHEMBL ID87658
CHEBI ID80558
SCHEMBL ID18634264
MeSH IDM0177512

Synonyms (27)

Synonym
CHEMBL87658
chebi:80558 ,
dechloroethylcyclophosphamide
n-dechloroethylcyclophosphamide
asta 4968
monochloroethylcyclophosphamide
2h-1,3,2-oxazaphosphorin-2-amine, n-(2-chloroethyl)tetrahydro-, 2-oxide
n-(2-chloroethyl)tetrahydro-2h-1,3,2-oxazaphosphorin-2-amine 2-oxide
36761-83-8
3-dechloroethylifosfamide
FT-0665552
n-(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
AKOS006276510
c6q3uc3wp5 ,
unii-c6q3uc3wp5
2-(2-chloroethylamino)tetrahydro-2h-1,3,2-oxazaphosphorine 2-oxide
n-dechloroethyl cyclophosphamide
asta-4968
3-dechloroethylifosfamide, (+/-)-
SCHEMBL18634264
n-(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine
2-((2-chloroethyl)amino)-1,3,2-oxazaphosphinane 2-oxide
Q27149602
2-[(2-chloroethyl)amino]-tetrahydro-2h-1,3,2-oxazaphosphorine 2-oxide
n-(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine
DTXSID30909416
2-[(2-chloroethyl)amino]-1,3,2|e?-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
)
0.29
" 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,
)
0.13
" 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 in vivo modulation of these alternative, competing pathways of P-450 metabolism was investigated in pharmacokinetic studies carried out in the rat model."( In vivo modulation of alternative pathways of P-450-catalyzed cyclophosphamide metabolism: impact on pharmacokinetics and antitumor activity.
Brain, EG; Drewes, P; Gustafsson, K; Hecht, JE; Waxman, DJ; Yu, LJ, 1999
)
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
"Three plasma samples and a 24-hour urine collection for day 1 of the first three cycles of chemotherapy were analysed in 30 patients, and the pharmacokinetic parameters of the respective drugs were estimated by population pharmacokinetic methods (nonlinear mixed-effects model [NONMEM] software)."( Population pharmacokinetics of the BEACOPP polychemotherapy regimen in Hodgkin's lymphoma and its effect on myelotoxicity.
Busse, D; Diehl, V; Engert, A; Fuhr, U; Hempel, G; Jaehde, U; Jetter, A; Josting, A; Kasel, D; Klimm, B; Merkel, U; Reif, S; Rietbrock, S; Schwab, M; Wilde, S, 2007
)
0.34
"The pharmacokinetic parameters and respective covariates were similar to the published data."( Population pharmacokinetics of the BEACOPP polychemotherapy regimen in Hodgkin's lymphoma and its effect on myelotoxicity.
Busse, D; Diehl, V; Engert, A; Fuhr, U; Hempel, G; Jaehde, U; Jetter, A; Josting, A; Kasel, D; Klimm, B; Merkel, U; Reif, S; Rietbrock, S; Schwab, M; Wilde, S, 2007
)
0.34
" A population pharmacokinetic model for cyclophosphamide was developed using non-linear mixed effects modelling and metabolite AUC values were compared between days and courses."( Pharmacokinetics of cyclophosphamide and its metabolites in paediatric patients receiving high-dose myeloablative therapy.
Boddy, AV; Chinnaswamy, G; Cole, M; Errington, J; Foot, A; Veal, GJ, 2011
)
0.37

Dosage Studied

ExcerptRelevanceReference
"The results show that the individual pharmacokinetics of BEACOPP drugs are an important link between dosage and toxicity."( Population pharmacokinetics of the BEACOPP polychemotherapy regimen in Hodgkin's lymphoma and its effect on myelotoxicity.
Busse, D; Diehl, V; Engert, A; Fuhr, U; Hempel, G; Jaehde, U; Jetter, A; Josting, A; Kasel, D; Klimm, B; Merkel, U; Reif, S; Rietbrock, S; Schwab, M; Wilde, S, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phosphorodiamide
[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 (4)

PathwayProteinsCompounds
Cyclophosphamide Action Pathway922
Ifosfamide Action Pathway821
Cyclophosphamide Metabolism Pathway922
Ifosfamide Metabolism Pathway821

Bioassays (23)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
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.
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.
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.
AID152510In vivo antitumor activity against murine P388 leukemia; No activity1999Journal 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.
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.
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.
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.
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.
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.
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.
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.
AID97384In vitro antitumor activity against murine leukemic L1210 cells; No activity1999Journal 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.
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.
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.
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.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (4.35)18.7374
1990's13 (56.52)18.2507
2000's6 (26.09)29.6817
2010's3 (13.04)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: 12.20

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 Index12.20 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index5.60 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (16.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (84.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]