Compounds > 4-hydroxycyclophosphamide
Page last updated: 2024-11-07

4-hydroxycyclophosphamide

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

Description

4-hydroxycyclophosphamide: primary activation metabolite of cyclophosphamide; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-hydroxycyclophosphamide : A phosphorodiamide that consists of 2-amino-1,3,2-oxazaphosphinan-4-ol 2-oxide having two 2-chloroethyl groups attached to the exocyclic nitrogen. [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]

Cross-References

ID SourceID
PubMed CID99735
CHEMBL ID731
CHEBI ID1864
SCHEMBL ID406857
MeSH IDM0059325

Synonyms (34)

Synonym
2h-1,2-oxazaphosphorin-4-ol, 2-[bis(2-chloroethyl)amino]tetrahydro-, 2-oxide
nsc-196562
nsc196562
brn 0526395
nsc 196562
2h-1,3,2-oxazaphosphorin-4-ol, tetrahydro-2-(bis(2-chloroethyl)amino)-, 2-oxide
2h-1,3,2-oxazaphosphorin-4-ol, 2-(bis(2-chloroethyl)amino)tetrahydro-, 2-oxide
tetrahydro-2-(bis(2-chloroethyl)amino)-2h-1,3,2-oxazaphosphorin-4-ol 2-oxide
ccris 5125
2-(bis(2-chloroethyl)amino)tetrahydro-2h-1,3,2-oxazaphosphorin-4-ol 2-oxide
40277-05-2
C07643
4-hydroxycyclophosphamide
CHEMBL731
chebi:1864 ,
61903-30-8
FT-0669503
unii-1xbf4e50hs
1xbf4e50hs ,
2-[bis(2-chloroethyl)amino]-1,3,2-oxazaphosphinan-4-ol 2-oxide
SCHEMBL406857
RANONBLIHMVXAJ-UHFFFAOYSA-N
(r,s)-4-hydroxy cyclophosphamide
2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2lambda5-oxazaphosphinan-4-ol
FT-0701358
(r,s)-4-hydroxy cyclophosphamide preparation kit
BCP27753
Q15711643
2-(bis(2-chloroethyl)amino)-4-hydroxy-1,3,2-oxazaphosphinane 2-oxide
A937181
2-[bis(2-chloroethyl)amino]-4-hydroxy-1,3,2lambda~5~-oxazaphosphinan-2-one
DTXSID90960669
PD159485
2-(bis(2-chloroethyl)amino)-4-hydroxy-1,3,2-oxazaphosphinane2-oxide

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The LD50 (30 day) for cyclophosphamide without halothane was 251 mg/kg; with 2 h subsequent exposure to halothane it was 152 mg/kg; and with 20 h subsequent exposure to halothane it was 158 mg/kg."( Increased toxicity of the antitumor drug cyclophosphamide in mice in the presence of the volatile anesthetic agent halothane.
Kooistra, KL; Powis, G; Rosenow, S; Van Dyke, RA, 1986)		0.27
" Cyclophosphamide was not directly toxic to SEC, but in coculture of SEC and hepatocytes, cyclophosphamide was significantly more toxic to SEC."( Cellular target of cyclophosphamide toxicity in the murine liver: role of glutathione and site of metabolic activation.
DeLeve, LD, 1996)		0.29
"One hundred and eighty nine Chinese SLE patients treated with CPA induction therapy (200 mg, every other day) were recruited and adverse reactions were recorded."( Genetic markers in CYP2C19 and CYP2B6 for prediction of cyclophosphamide's 4-hydroxylation, efficacy and side effects in Chinese patients with systemic lupus erythematosus.
Chen, L; Chen, Z; Guan, S; Huang, M; Li, J; Liang, L; Shu, W; Wang, X; Yang, X; Zhang, Y, 2016)		0.43
"Our findings have indicated that genetic markers of drug metabolizing enzymes could predict the 4-hydroxylation, adverse reactions and clinical efficacy of CPA."( Genetic markers in CYP2C19 and CYP2B6 for prediction of cyclophosphamide's 4-hydroxylation, efficacy and side effects in Chinese patients with systemic lupus erythematosus.
Chen, L; Chen, Z; Guan, S; Huang, M; Li, J; Liang, L; Shu, W; Wang, X; Yang, X; Zhang, Y, 2016)		0.43
"The dose-limiting toxic effect of cyclophosphamide (CY) is cardiotoxicity."( Role of metabolites of cyclophosphamide in cardiotoxicity.
Kawano, Y; Kurauchi, K; Miyahara, E; Nishikawa, T; Okamoto, Y, 2017)		0.46
" It is shown that not acrolein, but OHCP itself is the true toxic metabolite of cyclophosphamide."( Causes and possibilities to circumvent cyclophosphamide toxicity.
Voelcker, G, 2020)		0.56
"Cyclophosphamide is a widely used anticancer and immunosuppressive prodrug that unfortunately causes severe adverse effects, including cardiotoxicity."( Cardiotoxicity of cyclophosphamide's metabolites: an in vitro metabolomics approach in AC16 human cardiomyocytes.
Araújo, AM; Bastos, ML; Carvalho, F; Costa, VM; Dionísio, F; Duarte-Araújo, M; Guedes de Pinho, P, 2022)		0.72

Pharmacokinetics

To build a population pharmacokinetic (PK) model of cyclophosphamide (CY) and its metabolite, 4-hydroxycycloph phosphamide (HCY) in patients undergoing allogeneic haematopoietic stem cell transplantation (HSCT) To identify covariates, including genetic polymorphisms, which affect CY and HCY PK parameters.

ExcerptReferenceRelevance
" There was a non-significant trend to a shorter half-life of CP compared to reported values."( Pharmacokinetics and metabolism of cyclophosphamide administered after total body irradiation of bone marrow transplant recipients.
Ehninger, G; Kolb, H; Schuler, U; Wagner, T; Waidelich, P, 1991)		0.28
" treatment in two patients, and the pharmacokinetic parameter, area under the plasma disappearance curve, was determined for each metabolite in each patient for both routes of drug administration."( Plasma pharmacokinetics of cyclophosphamide and its cytotoxic metabolites after intravenous versus oral administration in a randomized, crossover trial.
Alberts, DS; Horne, K; Peng, YM; Phillips, JG; Roe, DJ; Struck, RF, 1987)		0.27
" In order to examine whether these different pharmacokinetic behaviors might account at least in part for the known differences of antitumor activity and toxicity of CP between humans and laboratory animals, the authors studied the influence of pharmacokinetics of activated CP on therapeutic efficacy and toxicity after injection of 4-(S-ethanol)-sulfido-cyclophosphamide (P1), a pro drug of activated CP, into nude mice bearing heterotransplanted human bladder sarcoma."( Pharmacokinetics of "activated" cyclophosphamide and therapeutic efficacies.
Hohorst, HJ; Voelcker, G; Wagner, T; Wientzek, C, 1984)		0.27
" Pharmacokinetic measurements in mice demonstrated that this behaviour is due to the elimination of "activated" cyclophosphamide by Michaelis-Menten kinetics (Km = 146 nmol X ml-1, Vmax = 18 nmol X ml-1 X min-1) and to the fact that increasing blood concentration of "activated" cyclophosphamide is accompanied by its increased distribution towards the peripheral compartment as may be seen from the volumes of distribution of the peripheral and central compartments."( [Pharmacokinetics of cyclophosphamide and cyclophosphamide metabolites in the mouse and their influence on the therapeutic effect of "activated" cyclophosphamide (4-hydroxycyclophosphamide) (author's transl)].
Haeglsperger, R; Voelcker, G, 1982)		0.46
" and a pharmacokinetic and enzyme turn-over model applied to data using NONMEM."( A mechanism-based pharmacokinetic-enzyme model for cyclophosphamide autoinduction in breast cancer patients.
Abdel-Rehim, M; Bielenstein, M; Björkstrand, B; Hassan, M; Johansson, M; Karlsson, MO; Ljungman, P; Nilsson, C; Olsson, H; Svensson, US, 1999)		0.3
" The results are consistent with those obtained for cancer patients, in spite of a wide interpatient variability of concentrations and pharmacokinetic parameters."( Pharmacokinetics of cyclophosphamide (CP) and 4-OH-CP/aldophosphamide in systemic vasculitis.
Belfayol-Pisanté, L; Fauvelle, F; Guillevin, L; Tod, M, )		0.13
" The aim of this study was to develop a population pharmacokinetic model describing the complex pharmacokinetics of CP, 4OHCP, 2DCECP, and PM when CP is administered in a high-dose combination with thiotepa and carboplatin."( Population pharmacokinetics of cyclophosphamide and its metabolites 4-hydroxycyclophosphamide, 2-dechloroethylcyclophosphamide, and phosphoramide mustard in a high-dose combination with Thiotepa and Carboplatin.
Beijnen, JH; de Jonge, ME; Huitema, AD; Rodenhuis, S; van Dam, SM, 2005)		0.56
"Dose-related toxicity of cyclophosphamide may be reduced and therapeutic efficacy may be improved by pharmacokinetic sampling and dose adjustment to achieve a target area under the curve (AUC) for two of its metabolites, hydroxycyclophosphamide (HCY) and carboxyethylphosphoramide mustard (CEPM)."( Real-time dose adjustment of cyclophosphamide in a preparative regimen for hematopoietic cell transplant: a Bayesian pharmacokinetic approach.
McCune, JS; McDonald, GB; Phillips, B; Ren, AG; Salinger, DH; Shen, DD; Slattery, JT; Vicini, P, 2006)		0.33
" Bayesian estimation of individual pharmacokinetic parameters was accomplished from limited (i."( Real-time dose adjustment of cyclophosphamide in a preparative regimen for hematopoietic cell transplant: a Bayesian pharmacokinetic approach.
McCune, JS; McDonald, GB; Phillips, B; Ren, AG; Salinger, DH; Shen, DD; Slattery, JT; Vicini, P, 2006)		0.33
"We developed dose adjustment software that potentially can be used to adjust cyclophosphamide dosing in a clinical setting, thus expanding the opportunity for pharmacokinetic individualization of cyclophosphamide."( Real-time dose adjustment of cyclophosphamide in a preparative regimen for hematopoietic cell transplant: a Bayesian pharmacokinetic approach.
McCune, JS; McDonald, GB; Phillips, B; Ren, AG; Salinger, DH; Shen, DD; Slattery, JT; Vicini, P, 2006)		0.33
" The plasma concentrations of cyclophosphamide and 4-hydroxycyclophosphamide were determined by high-performance liquid chromatography, and pharmacokinetic parameters were calculated."( Genetic polymorphisms of CYP2B6 affect the pharmacokinetics/pharmacodynamics of cyclophosphamide in Japanese cancer patients.
Ebi, H; Fujiki, Y; Itoh, K; Kanada, Y; Komagata, S; Minami, H; Mukai, H; Nakajima, M; Yokoi, T, 2007)		0.59
"05) higher clearance and shorter half-life of cyclophosphamide than heterozygotes and homozygotes of CYP2B6*1."( Genetic polymorphisms of CYP2B6 affect the pharmacokinetics/pharmacodynamics of cyclophosphamide in Japanese cancer patients.
Ebi, H; Fujiki, Y; Itoh, K; Kanada, Y; Komagata, S; Minami, H; Mukai, H; Nakajima, M; Yokoi, T, 2007)		0.34
" The relationship between allelic variants and the elimination pharmacokinetic parameters noninducible cyclophosphamide clearance (CL(nonind)), inducible cyclophosphamide clearance (CL(ind)) and elimination rate constant of 4-hydroxycyclophosphamide (k(4OHCP)) were evaluated using nonlinear mixed effects modelling."( Influence of polymorphisms of drug metabolizing enzymes (CYP2B6, CYP2C9, CYP2C19, CYP3A4, CYP3A5, GSTA1, GSTP1, ALDH1A1 and ALDH3A1) on the pharmacokinetics of cyclophosphamide and 4-hydroxycyclophosphamide.
Beijnen, JH; Doodeman, VD; Ekhart, C; Huitema, AD; Rodenhuis, S; Smits, PH, 2008)		0.72
" In this pediatric population, the authors' objectives were (1) to quantify and explain the pharmacokinetic variability of cyclophosphamide and 2 of its metabolites, hydroxycyclophosphamide (HCY) and carboxyethylphosphoramide mustard (CEPM), and (2) to apply a population pharmacokinetic model to describe the disposition of cyclophosphamide and these metabolites."( Population pharmacokinetics of cyclophosphamide and metabolites in children with neuroblastoma: a report from the Children's Oncology Group.
Blough, DK; McCune, JS; Oglesby, C; Park, JR; Salinger, DH; Vicini, P, 2009)		0.35
"Glomerulonephritis patients (n = 23) participated in a pharmacokinetic evaluation."( Cyclophosphamide and 4-hydroxycyclophosphamide pharmacokinetics in patients with glomerulonephritis secondary to lupus and small vessel vasculitis.
Blaisdell, J; Bridges, AS; Brouwer, KL; Dooley, MA; Falk, RJ; Frye, RF; Goldstein, JA; Hogan, SL; Hu, Y; Joy, MS; La, M; Wang, J, 2012)		0.7
" A statistically significant relationship was found between increased serum albumin and increased half-life (0."( Cyclophosphamide and 4-hydroxycyclophosphamide pharmacokinetics in patients with glomerulonephritis secondary to lupus and small vessel vasculitis.
Blaisdell, J; Bridges, AS; Brouwer, KL; Dooley, MA; Falk, RJ; Frye, RF; Goldstein, JA; Hogan, SL; Hu, Y; Joy, MS; La, M; Wang, J, 2012)		0.7
"To build a population pharmacokinetic (PK) model of cyclophosphamide (CY) and its metabolite, 4-hydroxycyclophosphamide (HCY), in patients undergoing allogeneic haematopoietic stem cell transplantation (HSCT) and to identify covariates, including genetic polymorphisms, which affect CY and HCY PK parameters."( Population pharmacokinetics analysis of cyclophosphamide with genetic effects in patients undergoing hematopoietic stem cell transplantation.
Choi, B; Han, N; Kim, IW; Kim, MG; Oh, JM; Park, S; Yun, HY, 2013)		0.61
" This study describes the development and validation of an analytical method of HCY enantiomers in human plasma by high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) that can be applied to pharmacokinetic studies, filling this gap in the literature."( Enantioselective analysis of 4-hydroxycyclophosphamide in human plasma with application to a clinical pharmacokinetic study.
Cass, QB; de Castro, FA; Lanchote, VL; Marques, MP; Rocha, OP; Scatena, Gdos S; Simões, BP, 2016)		0.73
"To develop a simultaneous population pharmacokinetic model of cyclophosphamide (CY) and 4-hydroxycyclophosphamide (4-OH) in patients with glomerulonephritis."( Population pharmacokinetics of cyclophosphamide and 4-hydroxycyclophosphamide metabolite in patients with autoimmune glomerulonephritis.
Charkoftaki, G; Cooper, JC; Dokoumetzidis, A; Iliopoulou, VN; Joy, MS, 2021)		1.09
"In total, 23 patients participated in a pharmacokinetic evaluation using dense plasma sampling."( Population pharmacokinetics of cyclophosphamide and 4-hydroxycyclophosphamide metabolite in patients with autoimmune glomerulonephritis.
Charkoftaki, G; Cooper, JC; Dokoumetzidis, A; Iliopoulou, VN; Joy, MS, 2021)		0.87
" The following estimates were found for the main CY pharmacokinetic parameters: total clearance, 13."( Population pharmacokinetics of cyclophosphamide and 4-hydroxycyclophosphamide metabolite in patients with autoimmune glomerulonephritis.
Charkoftaki, G; Cooper, JC; Dokoumetzidis, A; Iliopoulou, VN; Joy, MS, 2021)		0.87
"A population pharmacokinetic model was developed for CY and 4-OH in patients with autoimmune glomerulonephritis."( Population pharmacokinetics of cyclophosphamide and 4-hydroxycyclophosphamide metabolite in patients with autoimmune glomerulonephritis.
Charkoftaki, G; Cooper, JC; Dokoumetzidis, A; Iliopoulou, VN; Joy, MS, 2021)		0.87

Compound-Compound Interactions

ExcerptReferenceRelevance
" We studied the antileukemic effect of (1) Single-cycle complement-mediated lysis by two different monoclonal antibodies (MoAbs) (M195 [CD33] and F23 [CD13] 40 micrograms/mL), reactive with distinct antigens found on early myeloid cells and monocytes, used alone and in combinations; (2) 4-Hydroperoxycyclophosphamide (4-HC) (80 mumol/L or 100 mumol/L) alone; or (3) combined with VP-16 (5 micrograms/mL) and (4) a cocktail of 1 through 3 as above (combined immunochemotherapy)."( Autologous bone marrow transplantation in acute myelogenous leukemia: in vitro treatment with myeloid-specific monoclonal antibodies and drugs in combination.
Clarkson, BD; Gasparetto, C; Gulati, SC; Lemoli, RM; Moore, MA; Scheinberg, DA, 1991)		0.28
" The aim of this study was to develop a population pharmacokinetic model describing the complex pharmacokinetics of CP, 4OHCP, 2DCECP, and PM when CP is administered in a high-dose combination with thiotepa and carboplatin."( Population pharmacokinetics of cyclophosphamide and its metabolites 4-hydroxycyclophosphamide, 2-dechloroethylcyclophosphamide, and phosphoramide mustard in a high-dose combination with Thiotepa and Carboplatin.
Beijnen, JH; de Jonge, ME; Huitema, AD; Rodenhuis, S; van Dam, SM, 2005)		0.56

Bioavailability

ExcerptReferenceRelevance
" So after single intraperitoneal (IP) injection of 300 mg/kg P1 which caused a bioavailability of 36 mumol/ml-1/minute a 67% inhibition of tumor growth was achieved, whereas a tumor growth reduction of 83% was obtained after injection of the same dose in 6 fractions resulting in constant blood levels with a bioavailability of only 17 mumol/ml-1/minute."( Pharmacokinetics of "activated" cyclophosphamide and therapeutic efficacies.
Hohorst, HJ; Voelcker, G; Wagner, T; Wientzek, C, 1984)		0.27

Dosage Studied

ExcerptRelevanceReference
" Single-agent and combined dose-response patterns consisting of decreasing viability with increasing drug concentration were observed consistently."( Characterization of in vitro chemosensitivity of perioperative human ovarian malignancies by adenosine triphosphate chemosensitivity assay.
Averette, HE; Gerhardt, RT; Guerra, L; Perras, JP; Petru, E; Ramos, R; Sevin, BU, 1991)		0.28
"13 following systemic dosing of CP and IF, respectively."( Cerebrospinal fluid penetration of active metabolites of cyclophosphamide and ifosfamide in rhesus monkeys.
Arndt, CA; Balis, FM; Colvin, OM; McCully, CL; Poplack, DG, 1988)		0.27
"Individualization of dosing of the FEC regimen using therapeutic drug monitoring and attempts to find concentration-response relationships may be successful, but requires that the exposure of all three drugs is considered simultaneously."( Lack of relationship between systemic exposure for the component drug of the fluorouracil, epirubicin, and 4-hydroxycyclophosphamide regimen in breast cancer patients.
Bergh, J; Fjällskog, ML; Freijs, A; Karlsson, MO; Larsson, R; Nygren, P; Sandström, M, 1996)		0.51
"The aim of this study was to determine how the in vitro dose-response effects of chemotherapeutic agents should be analyzed and reported."( Sigmoid model versus median-effect analysis for obtaining dose-response curves for in vitro chemosensitivity testing.
Petru, E; Pöch, G; Vychodil-Kahr, S, 1999)		0.3
" Dose-response curves (DRCs) were calculated by non-linear (sigmoid model: SigmaPlot) and linear curve fitting (median-effect analysis: CalcuSyn)."( Sigmoid model versus median-effect analysis for obtaining dose-response curves for in vitro chemosensitivity testing.
Petru, E; Pöch, G; Vychodil-Kahr, S, 1999)		0.3
"We developed dose adjustment software that potentially can be used to adjust cyclophosphamide dosing in a clinical setting, thus expanding the opportunity for pharmacokinetic individualization of cyclophosphamide."( Real-time dose adjustment of cyclophosphamide in a preparative regimen for hematopoietic cell transplant: a Bayesian pharmacokinetic approach.
McCune, JS; McDonald, GB; Phillips, B; Ren, AG; Salinger, DH; Shen, DD; Slattery, JT; Vicini, P, 2006)		0.33
"Cyclophosphamide-based regimens are front-line treatment for numerous pediatric malignancies; however, current dosing methods result in considerable interpatient variability in tumor response and toxicity."( Population pharmacokinetics of cyclophosphamide and metabolites in children with neuroblastoma: a report from the Children's Oncology Group.
Blough, DK; McCune, JS; Oglesby, C; Park, JR; Salinger, DH; Vicini, P, 2009)		0.35
" Simulations using various dose regimens allow for informed dosing before the initiation of therapy."( Population pharmacokinetics of cyclophosphamide and 4-hydroxycyclophosphamide metabolite in patients with autoimmune glomerulonephritis.
Charkoftaki, G; Cooper, JC; Dokoumetzidis, A; Iliopoulou, VN; Joy, MS, 2021)		0.87
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
alkylating agentHighly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role 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]

Drug Classes (3)

ClassDescription
nitrogen mustardCompounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
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 (8)

PathwayProteinsCompounds
Metabolism14961108
Biological oxidations150276
Phase I - Functionalization of compounds69175
Cytochrome P450 - arranged by substrate type30110
Xenobiotics450
Cyclophosphamide Action Pathway922
Cyclophosphamide Metabolism Pathway922
Cyclophosphamide Pathway, Pharmacokinetics73

Bioassays (4)

Assay IDTitleYearJournalArticle
AID213601In vitro cytotoxicity against V-79 chinese hamster lung fibroblasts (3 hr drug exposure time) by clonogenic assay2004Journal of medicinal chemistry, Jul-15, Volume: 47, Issue:15
Sulfonyl-containing aldophosphamide analogues as novel anticancer prodrugs targeted against cyclophosphamide-resistant tumor cell lines.
AID7786Half life period in human plasma using phosphate buffer (0.1 M)2004Journal of medicinal chemistry, Jul-15, Volume: 47, Issue:15
Sulfonyl-containing aldophosphamide analogues as novel anticancer prodrugs targeted against cyclophosphamide-resistant tumor cell lines.
AID96366In vitro cytotoxicity tested as inhibitory concentration against carcinoma KB cell line2001Bioorganic & medicinal chemistry letters, May-21, Volume: 11, Issue:10
Anodic oxidation of ifosfamide and cyclophosphamide: a biomimetic metabolism model of the oxazaphosphorinane anticancer drugs.
AID19116Half life period in phosphate buffer (0.1 M)2004Journal of medicinal chemistry, Jul-15, Volume: 47, Issue:15
Sulfonyl-containing aldophosphamide analogues as novel anticancer prodrugs targeted against cyclophosphamide-resistant tumor cell lines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (129)

TimeframeStudies, This Drug (%)All Drugs %
pre-199037 (28.68)18.7374
1990's37 (28.68)18.2507
2000's34 (26.36)29.6817
2010's15 (11.63)24.3611
2020's6 (4.65)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.14

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.14 (24.57)
Research Supply Index5.02 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index27.81 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.14)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials17 (12.78%)5.53%
Reviews1 (0.75%)6.00%
Case Studies1 (0.75%)4.05%
Observational0 (0.00%)0.25%
Other114 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
chloroacetaldehyde
[no description available]		2.0110organochlorine 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.		2.0110aldehydecarcinogenic 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
chlorine
chloride : A halide anion formed when chlorine picks up an electron to form an an anion.		1.9510halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite
mercaptoethanol
Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.		1.9610alkanethiol;
primary alcohol		geroprotector
azathioprine
Azathioprine: An immunosuppressive agent used in combination with cyclophosphamide and hydroxychloroquine in the treatment of rheumatoid arthritis. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance has been listed as a known carcinogen. (Merck Index, 11th ed). azathioprine : A thiopurine that is 6-mercaptopurine in which the mercapto hydrogen is replaced by a 1-methyl-4-nitroimidazol-5-yl group. It is a prodrug for mercaptopurine and is used as an immunosuppressant, prescribed for the treatment of inflammatory conditions and after organ transplantation and also for treatment of Crohn's didease and MS.		1.9610aryl sulfide;
C-nitro compound;
imidazoles;
thiopurine		antimetabolite;
antineoplastic agent;
carcinogenic agent;
DNA synthesis inhibitor;
hepatotoxic agent;
immunosuppressive agent;
prodrug
busulfan
[no description available]		4.6232methanesulfonate esteralkylating agent;
antineoplastic agent;
carcinogenic agent;
insect sterilant;
teratogenic agent
verapamil
Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.		2.2110aromatic ether;
nitrile;
polyether;
tertiary amino compound
carmustine
Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.		7.420N-nitrosoureas;
organochlorine compound		alkylating agent;
antineoplastic agent
ciprofloxacin
Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.		2.0110aminoquinoline;
cyclopropanes;
fluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone;
zwitterion		antibacterial drug;
antiinfective agent;
antimicrobial agent;
DNA synthesis inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
environmental contaminant;
topoisomerase IV inhibitor;
xenobiotic
etanidazole
Etanidazole: A nitroimidazole that sensitizes hypoxic tumor cells that are normally resistant to radiation therapy.. etanidazole : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2-nitro-1H-imidazol-1-yl)acetic acid with the amino group of ethanolamine. Used as a radiosensitising agent for hypoxic tumour cells.		3.3711C-nitro compound;
imidazoles;
monocarboxylic acid amide		alkylating agent;
antineoplastic agent;
prodrug;
radiosensitizing agent
ethacrynic acid
Ethacrynic Acid: A compound that inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.. etacrynic acid : An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.		1.9910aromatic ether;
aromatic ketone;
dichlorobenzene;
monocarboxylic acid		EC 2.5.1.18 (glutathione transferase) inhibitor;
ion transport inhibitor;
loop diuretic
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		11.0361nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
halothane
[no description available]		1.9610haloalkane;
organobromine compound;
organochlorine compound;
organofluorine compound		inhalation anaesthetic
ifosfamide
[no description available]		2.8940ifosfamidesalkylating agent;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
xenobiotic
mechlorethamine
nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.		2.6630nitrogen mustard;
organochlorine compound		alkylating agent
methoxyamine
methoxyamine: analytical reagent for aldehydes and ketones; strong irritant, can probably produce methemoglobinemia; RN given refers to parent cpd; structure		1.9610organooxygen compound
orphenadrine
Orphenadrine: A muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm.. orphenadrine : A tertiary amino compound which is the phenyl-o-tolylmethyl ether of 2-(dimethylamino)ethanol.		1.9910ether;
tertiary amino compound		antidyskinesia agent;
antiparkinson drug;
H1-receptor antagonist;
muscarinic antagonist;
muscle relaxant;
NMDA receptor antagonist;
parasympatholytic
thalidomide
Thalidomide: A piperidinyl isoindole originally introduced as a non-barbiturate hypnotic, but withdrawn from the market due to teratogenic effects. It has been reintroduced and used for a number of immunological and inflammatory disorders. Thalidomide displays immunosuppressive and anti-angiogenic activity. It inhibits release of TUMOR NECROSIS FACTOR-ALPHA from monocytes, and modulates other cytokine action.. thalidomide : A racemate comprising equimolar amounts of R- and S-thalidomide.. 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione : A dicarboximide that is isoindole-1,3(2H)-dione in which the hydrogen attached to the nitrogen is substituted by a 2,6-dioxopiperidin-3-yl group.		4.4430phthalimides;
piperidones
thiotepa
Thiotepa: A very toxic alkylating antineoplastic agent also used as an insect sterilant. It causes skin, gastrointestinal, CNS, and bone marrow damage. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), thiotepa may reasonably be anticipated to be a carcinogen (Merck Index, 11th ed).		11.1262aziridines
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		2.6730mitomycinalkylating agent;
antineoplastic agent
floxuridine
Floxuridine: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.. floxuridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.		2.0210nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
serine
Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.		1.9910L-alpha-amino acid;
proteinogenic amino acid;
serine family amino acid;
serine zwitterion;
serine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
cyanides
Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.		1.9610pseudohalide anionEC 1.9.3.1 (cytochrome c oxidase) inhibitor
bromodeoxyuridine
Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.		2.0410pyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
methionine
Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.		1.9910aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical
acetonitrile
acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.		2.0610aliphatic nitrile;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
NMR chemical shift reference compound;
polar aprotic solvent
acrolein
[no description available]		3.85120enalherbicide;
human xenobiotic metabolite;
toxin
ethyl acetate
ethyl acetate : The acetate ester formed between acetic acid and ethanol.		2.0610acetate ester;
ethyl ester;
volatile organic compound		EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor;
metabolite;
polar aprotic solvent;
Saccharomyces cerevisiae metabolite
indazoles
Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.		2.4620indazole
thiazoles
[no description available]		1.99101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
pyrazines
Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.		4.4430diazine;
pyrazines		Daphnia magna metabolite
cyanamide
Cyanamide: A cyanide compound which has been used as a fertilizer, defoliant and in many manufacturing processes. It often occurs as the calcium salt, sometimes also referred to as cyanamide. The citrated calcium salt is used in the treatment of alcoholism.. cyanamide : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an amino group.		6.9610nitrile;
one-carbon compound		EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor
thiazolidines
Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.		1.9910thiazolidine
triethylenephosphoramide
Triethylenephosphoramide: An insect chemosterilant and an antineoplastic agent.		3.8121phosphoramide
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.4620acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
deoxycytidine
[no description available]		2.0210pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
4-(4-nitrobenzyl)pyridine
[no description available]		3.3711
2-chloroethyl isocyanate
[no description available]		210
methionine sulfoximine
methionine sulfoximine : A non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine .		1.9710methionine derivative;
non-proteinogenic alpha-amino acid;
sulfoximide
doxifluridine
doxifluridine : A pyrimidine 5'-deoxyribonucleoside that is 5-fluorouridine in which the hydroxy group at the 5' position is replaced by a hydrogen. It is an oral prodrug of the antineoplastic agent 5-fluorouracil. Designed to circumvent the rapid degradation of 5-fluorouracil by dihydropyrimidine dehydrogenase in the gut wall, it is converted into 5-fluorouracil in the presence of pyrimidine nucleoside phosphorylase.		2.0210organofluorine compound;
pyrimidine 5'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
prodrug
cladribine
[no description available]		210organochlorine compound;
purine 2'-deoxyribonucleoside		antineoplastic agent;
immunosuppressive agent
buthionine sulfoximine
Buthionine Sulfoximine: A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7). 2-amino-4-(S-butylsulfonimidoyl)butanoic acid : A non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group carries an oxo, imino and butyl groups.. S-butyl-DL-homocysteine (S,R)-sulfoximine : A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.		1.9710diastereoisomeric mixture;
homocysteines;
non-proteinogenic alpha-amino acid;
sulfoximide		EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor;
ferroptosis inducer
deuterium
Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.		1.9610dihydrogen
misonidazole
Misonidazole: A nitroimidazole that sensitizes normally radio-resistant hypoxic cells to radiation. It may also be directly cytotoxic to hypoxic cells and has been proposed as an antineoplastic.		1.9710
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		2.0610benzenes;
phenyl acetates
carboxyphosphamide
carboxyphosphamide: metabolite of cyclophosphamide; RN given refers to cpd without isomeric designation; structure		6.9610nitrogen mustard
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		4.0931taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
etoposide
[no description available]		4.0531beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
perfosfamide
4-hydroperoxycyclophosphamide : A phosphorodiamide that is the active metabolite of the nitrogen mustard cyclophosphamide. It has potent antineoplastic and immunosuppressive properties.		2.0210nitrogen mustard;
organochlorine compound;
peroxol;
phosphorodiamide		alkylating agent;
antineoplastic agent;
drug allergen;
immunosuppressive agent;
metabolite
epirubicin
Epirubicin: An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.		8.6230aminoglycoside;
anthracycline antibiotic;
anthracycline;
deoxy hexoside;
monosaccharide derivative;
p-quinones;
primary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone		antimicrobial agent;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
topotecan
Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.		2.0210pyranoindolizinoquinolineantineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor
gemcitabine
gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.		2.0210organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
environmental contaminant;
immunosuppressive agent;
photosensitizing agent;
prodrug;
radiosensitizing agent;
xenobiotic
2,2'-dithiodiethanesulfonic acid
[no description available]		1.9610
goralatide
goralatide: from fetal calf bone marrow; exerts a high inhibitory activity on the proliferation of hematopoietic pluripotent stem cells. goralatide : A tetrapeptide that is Ser-Asp-Lys-Pro in which the N-terminal amino group carries an acetyl group. It is selective inhibitor of primitive haematopoietic cell proliferation and exhibits anti-inflammatory, anti-fibrotic, and pro-angiogenic properties.		3.0810oligopeptide;
tetrapeptide		anti-inflammatory agent;
pro-angiogenic agent
methylthioethanol
2-methylthioethanol : A primary alcohol that is the S-methyl derivative of mercaptoethanol. It is found as a volatile component in Cucumis melo Var. cantalupensis.		2.0210aliphatic sulfide;
primary alcohol		plant metabolite;
xenobiotic metabolite
phosphoramide mustard
[no description available]		6.37153nitrogen mustard;
phosphorodiamide
isophosphamide mustard
isophosphamide mustard: antitumor metabolite of ifosfamide; palifosfamide-tris is a salt with tris; structure in first source		2.0210phosphorodiamide
mafosfamide
mafosfamide: RN given refers to cis-(+-)-isomer		2.420
cyanates
Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).		210
aldophosphamide
aldophosphamide: metabolite of cyclophosphamide		5.24121nitrogen mustard
florox reagent
Florox Reagent: reagent for analysis of ketosteroids; structure		1.9810
methotrexate
[no description available]		210dicarboxylic acid;
monocarboxylic acid amide;
pteridines		abortifacient;
antimetabolite;
antineoplastic agent;
antirheumatic drug;
dermatologic drug;
DNA synthesis inhibitor;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
immunosuppressive agent
4-hydroperoxydechlorocyclophosphamide
4-hydroperoxydechlorocyclophosphamide: preactivated analog of cyclophosphamide that undergoes an elimination reaction to yield acrolein & dechlorophosphoramide mustard; structure given in first source		1.9710
docetaxel anhydrous
Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.		2.0210secondary alpha-hydroxy ketone;
tetracyclic diterpenoid		antimalarial;
antineoplastic agent;
photosensitizing agent
troleandomycin
Troleandomycin: A macrolide antibiotic that is similar to ERYTHROMYCIN.. troleandomycin : A semi-synthetic macrolide antibiotic obtained by acetylation of the three free hydroxy groups of oleandomycin. Troleandomycin is only found in individuals that have taken the drug.		1.9910acetate ester;
epoxide;
macrolide antibiotic;
monosaccharide derivative;
polyketide;
semisynthetic derivative		EC 1.14.13.97 (taurochenodeoxycholate 6alpha-hydroxylase) inhibitor;
xenobiotic
lenalidomide
[no description available]		4.4430aromatic amine;
dicarboximide;
isoindoles;
piperidones		angiogenesis inhibitor;
antineoplastic agent;
immunomodulator
4-hydroxyifosfamide
[no description available]		2.940ifosfamides
bortezomib
[no description available]		4.4430amino acid amide;
L-phenylalanine derivative;
pyrazines		antineoplastic agent;
antiprotozoal drug;
protease inhibitor;
proteasome inhibitor
carboplatin
[no description available]		9.8842
melphalan
Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.		2.6830L-phenylalanine derivative;
nitrogen mustard;
non-proteinogenic L-alpha-amino acid;
organochlorine compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent
bilirubin
[no description available]		3.8121biladienes;
dicarboxylic acid		antioxidant;
human metabolite;
mouse metabolite
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		1.9610cysteiniumfundamental metabolite
axitinib
[no description available]		2.4620aryl sulfide;
benzamides;
indazoles;
pyridines		antineoplastic agent;
tyrosine kinase inhibitor;
vascular endothelial growth factor receptor antagonist
perfosfamide
[no description available]		2.3820
pirarubicin
[no description available]		1.9810anthracycline
nad
NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.		1.9510organophosphate oxoanioncofactor;
human metabolite;
hydrogen acceptor;
Saccharomyces cerevisiae metabolite
hoe 33342
bisbenzimide ethoxide trihydrochloride: benzimidazole fluorescent dye		2.0510
mesna
Mesna: A sulfhydryl compound used to prevent urothelial toxicity by inactivating metabolites from ANTINEOPLASTIC AGENTS, such as IFOSFAMIDE or CYCLOPHOSPHAMIDE.		1.9610organosulfonic acid
chiniofon
Hydroxyquinolines: The 8-hydroxy derivatives inhibit various enzymes and their halogenated derivatives, though neurotoxic, are used as topical anti-infective agents, among other uses.		1.9810
asta z 7557
Asta Z 7557: metabolite of cyclophosphamide		7.3720
novobiocin
Novobiocin: An antibiotic compound derived from Streptomyces niveus. It has a chemical structure similar to coumarin. Novobiocin binds to DNA gyrase, and blocks adenosine triphosphatase (ATPase) activity. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p189). novobiocin : A coumarin-derived antibiotic obtained from Streptomyces niveus.		210carbamate ester;
ether;
hexoside;
hydroxycoumarin;
monocarboxylic acid amide;
monosaccharide derivative;
phenols		antibacterial agent;
antimicrobial agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
Escherichia coli metabolite;
hepatoprotective agent
roquinimex
roquinimex: structure in first source		1.9810aromatic amide
dacarbazine
(E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.		2.9710dacarbazine
aprepitant
Aprepitant: A morpholine neurokinin-1 (NK1) receptor antagonist that is used in the management of nausea and vomiting caused by DRUG THERAPY, and for the prevention of POSTOPERATIVE NAUSEA AND VOMITING.. aprepitant : A morpholine-based antiemetic, which is or the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/neurokinin 1 (NK1) receptors.		2.0510(trifluoromethyl)benzenes;
cyclic acetal;
morpholines;
triazoles		antidepressant;
antiemetic;
neurokinin-1 receptor antagonist;
peripheral nervous system drug;
substance P receptor antagonist
phosphorus radioisotopes
Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Autoimmune Disease
[description not available]		02.3110
Bright Disease
A historical classification which is no longer used. It described acute glomerulonephritis, acute nephritic syndrome, or acute nephritis. Named for Richard Bright.		03.9321
Autoimmune Diseases
Disorders that are characterized by the production of antibodies that react with host tissues or immune effector cells that are autoreactive to endogenous peptides.		02.3110
Glomerulonephritis
Inflammation of the renal glomeruli (KIDNEY GLOMERULUS) that can be classified by the type of glomerular injuries including antibody deposition, complement activation, cellular proliferation, and glomerulosclerosis. These structural and functional abnormalities usually lead to HEMATURIA; PROTEINURIA; HYPERTENSION; and RENAL INSUFFICIENCY.		03.9321
Cardiac Toxicity
[description not available]		02.6320
Cardiotoxicity
Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.		02.6320
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		02.730
Breast Cancer
[description not available]		07.21186
Diffuse Mixed Small and Large Cell Lymphoma
[description not available]		02.3110
Breast Neoplasms
Tumors or cancer of the human BREAST.		07.21186
Lymphoma, Non-Hodgkin
Any of a group of malignant tumors of lymphoid tissue that differ from HODGKIN DISEASE, being more heterogeneous with respect to malignant cell lineage, clinical course, prognosis, and therapy. The only common feature among these tumors is the absence of giant REED-STERNBERG CELLS, a characteristic of Hodgkin's disease.		02.3110
Alopecia Cicatrisata
[description not available]		02.4620
Alopecia
Absence of hair from areas where it is normally present.		02.4620
Glomerulonephritis, Lupus
[description not available]		02.1110
Lupus Nephritis
Glomerulonephritis associated with autoimmune disease SYSTEMIC LUPUS ERYTHEMATOSUS. Lupus nephritis is histologically classified into 6 classes: class I - normal glomeruli, class II - pure mesangial alterations, class III - focal segmental glomerulonephritis, class IV - diffuse glomerulonephritis, class V - diffuse membranous glomerulonephritis, and class VI - advanced sclerosing glomerulonephritis (The World Health Organization classification 1982).		02.1110
Libman-Sacks Disease
[description not available]		05.6432
Lupus Erythematosus, Systemic
A chronic, relapsing, inflammatory, and often febrile multisystemic disorder of connective tissue, characterized principally by involvement of the skin, joints, kidneys, and serosal membranes. It is of unknown etiology, but is thought to represent a failure of the regulatory mechanisms of the autoimmune system. The disease is marked by a wide range of system dysfunctions, an elevated erythrocyte sedimentation rate, and the formation of LE cells in the blood or bone marrow.		05.6432
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		02.4120
Cancer of Prostate
[description not available]		02.0510
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.0510
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		03.3120
Glioblastoma with Sarcomatous Component
[description not available]		02.0610
Angiogenesis, Pathologic
[description not available]		02.0610
Gliosarcoma
Rare mixed tumors of the brain and rarely the spinal cord which contain malignant neuroectodermal (glial) and mesenchymal components, including spindle-shaped fibrosarcoma cells. These tumors are highly aggressive and present primarily in adults as rapidly expanding mass lesions. They may arise in tissue that has been previously irradiated. (From Br J Neurosurg 1995 Apr;9(2):171-8)		02.0610
Angiitis
[description not available]		03.4611
Vasculitis
Inflammation of any one of the blood vessels, including the ARTERIES; VEINS; and rest of the vasculature system in the body.		08.4611
Benign Neoplasms
[description not available]		05.451
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		05.451
Cancer of Ovary
[description not available]		05.3372
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		05.3372
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.0210
Metastase
[description not available]		02.0210
Cancer, Second Primary
[description not available]		02.0210
Multiple Primary Neoplasms
[description not available]		02.0210
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.0210
Carcinoma, Epidermoid
[description not available]		02.0210
Cancer of Cervix
[description not available]		02.0210
Carcinoma, Squamous Cell
A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)		02.0210
Uterine Cervical Neoplasms
Tumors or cancer of the UTERINE CERVIX.		02.0210
Hematologic Malignancies
[description not available]		03.4111
Hematologic Neoplasms
Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.		03.4111
Cancer, Embryonal
[description not available]		03.8221
Neoplasms, Germ Cell and Embryonal
Neoplasms composed of primordial GERM CELLS of embryonic GONADS or of elements of the germ layers of the EMBRYO, MAMMALIAN. The concept does not refer to neoplasms located in the gonads or present in an embryo or FETUS.		03.8221
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)		02.0310
Germinoblastoma
[description not available]		02.420
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		02.420
Kahler Disease
[description not available]		07.8101
Multiple Myeloma
A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.		07.8101
Leukemia L 1210
[description not available]		02.940
Bladder Cancer
[description not available]		01.9610
Urinary Bladder Neoplasms
Tumors or cancer of the URINARY BLADDER.		01.9610
EHS Tumor
[description not available]		01.9610
Experimental Mammary Neoplasms
[description not available]		02.3620
Di Guglielmo Disease
[description not available]		01.9810
Leukemia, Erythroblastic, Acute
A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.		01.9810
Leucocythaemia
[description not available]		05.7542
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)		05.7542
Hepatic Veno Occlusive Disease
[description not available]		01.9910
Hepatic Veno-Occlusive Disease
Liver disease that is caused by injuries to the ENDOTHELIAL CELLS of the vessels and subendothelial EDEMA, but not by THROMBOSIS. Extracellular matrix, rich in FIBRONECTINS, is usually deposited around the HEPATIC VEINS leading to venous outflow occlusion and sinusoidal obstruction.		01.9910
Cancer of Liver
[description not available]		01.9910
Liver Neoplasms
Tumors or cancer of the LIVER.		01.9910
Chronic Illness
[description not available]		01.9910
Benign Cerebellar Neoplasms
[description not available]		01.9910
Arachnoidal Cerebellar Sarcoma, Circumscribed
[description not available]		01.9910
Local Neoplasm Recurrence
[description not available]		02.3920
Chronic Disease
Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).		01.9910
Medulloblastoma
A malignant neoplasm that may be classified either as a glioma or as a primitive neuroectodermal tumor of childhood (see NEUROECTODERMAL TUMOR, PRIMITIVE). The tumor occurs most frequently in the first decade of life with the most typical location being the cerebellar vermis. Histologic features include a high degree of cellularity, frequent mitotic figures, and a tendency for the cells to organize into sheets or form rosettes. Medulloblastoma have a high propensity to spread throughout the craniospinal intradural axis. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2060-1)		01.9910
Mast-Cell Sarcoma
A unifocal malignant tumor that consists of atypical pathological MAST CELLS without systemic involvement. It causes local destructive growth in organs other than in skin or bone marrow.		01.9910
B-Cell Chronic Lymphocytic Leukemia
[description not available]		0210
Leukemia, Lymphocytic, Chronic, B-Cell
A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.		0210
Experimental Neoplasms
[description not available]		0210
Astrocytoma, Grade IV
[description not available]		0210
Herpes Simplex Virus Infection
[description not available]		0210
Glioblastoma
A malignant form of astrocytoma histologically characterized by pleomorphism of cells, nuclear atypia, microhemorrhage, and necrosis. They may arise in any region of the central nervous system, with a predilection for the cerebral hemispheres, basal ganglia, and commissural pathways. Clinical presentation most frequently occurs in the fifth or sixth decade of life with focal neurologic signs or seizures.		0210
Herpes Simplex
A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)		0210
Disease Exacerbation
[description not available]		0210
Reticulum Cell-Like Sarcoma, Yoshida
[description not available]		01.9510
Bone Marrow Diseases
Diseases involving the BONE MARROW.		02.8910
Malignant Melanoma
[description not available]		02.8910
Experimental Radiation Injuries
[description not available]		02.8910
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		02.8910
Recrudescence
[description not available]		01.9810
Adenocarcinoma, Basal Cell
[description not available]		01.9810
Cancer of the Uterus
[description not available]		01.9810
Cancer of Endometrium
[description not available]		01.9810
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		01.9810
Uterine Neoplasms
Tumors or cancer of the UTERUS.		01.9810
Endometrial Neoplasms
Tumors or cancer of ENDOMETRIUM, the mucous lining of the UTERUS. These neoplasms can be benign or malignant. Their classification and grading are based on the various cell types and the percent of undifferentiated cells.		01.9810
Acute Myelogenous Leukemia
[description not available]		03.3611
Leukemia, Myeloid, Acute
Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.		03.3611
Granulocytic Leukemia, Chronic
[description not available]		01.9710
Leukemia, Myelogenous, Chronic, BCR-ABL Positive
Clonal hematopoetic disorder caused by an acquired genetic defect in PLURIPOTENT STEM CELLS. It starts in MYELOID CELLS of the bone marrow, invades the blood and then other organs. The condition progresses from a stable, more indolent, chronic phase (LEUKEMIA, MYELOID, CHRONIC PHASE) lasting up to 7 years, to an advanced phase composed of an accelerated phase (LEUKEMIA, MYELOID, ACCELERATED PHASE) and BLAST CRISIS.		01.9710
Acute Disease
Disease having a short and relatively severe course.		03.3511
Acute Liver Injury, Drug-Induced
[description not available]		01.9610
Bladder Diseases
[description not available]		01.9610
Benign Neoplasms, Brain
[description not available]		01.9610
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.		01.9610
Kidney Diseases
Pathological processes of the KIDNEY or its component tissues.		01.9610
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		01.9610