1-(2-chloroethyl)-3-(2-(dimethylaminosulfonyl)ethyl)-1-nitrosourea profile

ID Source	ID
PubMed CID	55456
CHEMBL ID	2104789
SCHEMBL ID	27914
MeSH ID	M0150238

Synonym
urea, 1-(2-chloroethyl)-3-[2-(dimethylaminosulfonyl)ethyl] 1-nitroso
nsc-608678
nsc608678
tauromustine
tauricyt
tcnu
ls-2667 ,
tauromustine [inn]
2-((((2-chloroethyl)nitrosoamino)carbonyl)amino)-n,n-dimethylethanesulfonamide
ethanesulfonamide, 2-((((2-chloroethyl)nitrosoamino)carbonyl)amino)-n,n-dimethyl-
ccris 6346
tauromustina [inn-spanish]
1-(2-chloroethyl)-3-(2-(dimethylaminosulfonyl)ethyl)-1-nitrosourea
1-(2-chloroethyl)-3-(2-(dimethylsulfamoyl)ethyl)-1-nitrosourea
tauromustinum [inn-latin]
1-(2-chloroethyl)-3-[2-(dimethylsulfamoyl)ethyl]-1-nitrosourea
85977-49-7
unii-511f69k76y
tauromustinum
tauromustina
511f69k76y ,
CHEMBL2104789
tauromustine [who-dd]
tauromustine [mart.]
SCHEMBL27914
DTXSID20235317
2-(3-(2-chloroethyl)-3-nitrosoureido)-n,n-dimethylethane-1-sulfonamide
Q27260849

Excerpt	Reference	Relevance
" In comparison with control cells that were transfected with the parent vector, the ATase-expressing clones were considerably more resistant to the toxic effects of the methylating agents N-methyl-N-nitrosourea and methylmethanesulphonate or the chloroethylating agents Mz or taurine chloroethylnitrosourea, but unchanged in their susceptibility to the bis-chloroethylating agent nitrogen mustard."	( Transfection of murine multi-potent haemopoietic stem cells with an E. coli DNA alkyltransferase gene confers resistance to the toxic effects of alkylating agents. Dexter, TM; Jelinek, J; Kleibl, K; Margison, GP, 1988)	0.27

Excerpt	Reference	Relevance
"The pharmacokinetic properties of tauromustine (TCNU) were studied in 31 cancer patients who participated in phase I trials."	( Pharmacokinetics of tauromustine in cancer patients. Phase I studies. Ellman, M; Gunnarsson, PO; Hansen, HH; Macpherson, JS; Polacek, J; Smyth, JF; Vibe-Petersen, J; Warrington, PS, 1989)	0.28
"The pharmacokinetic profiles of 5-fluorouracil (5-FU) and tauromustine (TCNU) were investigated in NMRI mice following their administration either alone or as part of simultaneous or sequential combinations."	( 5-Fluorouracil causes alterations in the pharmacokinetic profile of tauromustine in NMRI mice. Bibby, MC; Hill, SR, 1994)	0.29

Excerpt	Reference	Relevance
" The results show that the route of administration influences plasma concentrations, bioavailability and tissue and tumour concentrations."	( Effects of routes of administration of TCNU on its plasma, tissue and tumour concentrations. Bibby, MC; Bloomer, JC; Double, JA; Loadman, PM, 1988)	0.27

Excerpt	Relevance	Reference
" TCNU was given orally at a dosage of 130 mg/m2 every fifth week."	( Phase II study of tauromustine in disseminated malignant melanoma. Bergh, J; Blomquist, E; Gjedde, SB; Lindegaard-Madsen, E; Mouridsen, HT; Nolte, H, 1989)	0.28
" The absolute levels of TCNU obtained with a dose of 100 mg TCNU/kg bodyweight were at most time points, three to four times those obtained with dosage of 25 mg TCNU/kg."	( Experimental cerebral and plasma pharmacokinetic studies of TCNU: implications for brain tumour chemotherapy. Macpherson, JS; Miller, JD; Smyth, J; Whittle, IR, 1987)	0.27

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	26 (47.27)	18.7374
1990's	29 (52.73)	18.2507
2000's	0 (0.00)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	7 (11.11%)	5.53%
Reviews	1 (1.59%)	6.00%
Case Studies	1 (1.59%)	4.05%
Observational	0 (0.00%)	0.25%
Other	54 (85.71%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
melatonin [no description available]	1.97	1	0	acetamides; tryptamines	anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger
taurine [no description available]	9.5	55	7	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	2	1	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
amifostine anhydrous Amifostine: A phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia.. amifostine : An organic thiophosphate that is the S-phospho derivative of 2-[(3-aminopropyl)amino]ethanethiol. A prodrug for the free thiol, WR-1065, which is used as a cytoprotectant in cancer chemotherapy and radiotherapy.	1.97	1	0	diamine; organic thiophosphate	antioxidant; prodrug; radiation protective agent
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.	2.89	4	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
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.	5.31	7	2	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
hydralazine Hydralazine: A direct-acting vasodilator that is used as an antihypertensive agent.. hydralazine : The 1-hydrazino derivative of phthalazine; a direct-acting vasodilator that is used as an antihypertensive agent.	2.38	2	0	azaarene; hydrazines; ortho-fused heteroarene; phthalazines	antihypertensive agent; vasodilator agent
lomustine [no description available]	2.67	3	0	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
mechlorethamine nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.	1.97	1	0	nitrogen mustard; organochlorine compound	alkylating agent
methyl methanesulfonate [no description available]	1.97	1	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
pamidronate [no description available]	1.97	1	0	phosphonoacetic acid
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2.39	2	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
procarbazine Procarbazine: An antineoplastic agent used primarily in combination with mechlorethamine, vincristine, and prednisone (the MOPP protocol) in the treatment of Hodgkin's disease.. procarbazine : A benzamide obtained by formal condensation of the carboxy group of 4-[(2-methylhydrazino)methyl]benzoic acid with the amino group of isopropylamine. An antineoplastic chemotherapy drug used for treatment of Hodgkin's lymphoma. Metabolism yields azo-procarbazine and hydrogen peroxide, which results in the breaking of DNA strands.	1.97	1	0	benzamides; hydrazines	antineoplastic agent
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).	1.97	1	0	aziridines
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	1.97	1	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
pregnenolone [no description available]	2	1	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
nornitrogen mustard nornitrogen mustard: structure; RN given refers to parent cpd	1.97	1	0	nitrogen mustard
methylnitrosourea Methylnitrosourea: A nitrosourea compound with alkylating, carcinogenic, and mutagenic properties.. N-methyl-N-nitrosourea : A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by methyl and nitroso groups.	1.97	1	0	N-nitrosoureas	alkylating agent; carcinogenic agent; mutagen; teratogenic agent
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	1.97	1	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
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).	1.97	1	0	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
vindesine Vindesine: Vinblastine derivative with antineoplastic activity against CANCER. Major side effects are myelosuppression and neurotoxicity. Vindesine is used extensively in chemotherapy protocols (ANTINEOPLASTIC COMBINED CHEMOTHERAPY PROTOCOLS).	2.38	2	0	methyl ester; organic heteropentacyclic compound; organic heterotetracyclic compound; primary carboxamide; tertiary alcohol; tertiary amino compound; vinca alkaloid	antineoplastic agent
mitozolomide mitozolomide: RN & structure given in first source	3.76	2	1
clomesone clomesone: structure & RN given in first source	1.98	1	0
estramustine Estramustine: A nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties.. estramustine : A carbamate ester obtained by the formal condensation of the hydroxy group of 17beta-estradiol with the carboxy group of bis(2-chloroethyl)carbamic acid.	1.97	1	0	17beta-hydroxy steroid; carbamate ester; organochlorine compound	alkylating agent; antineoplastic agent; radiation protective agent
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.	1.98	1	0	L-phenylalanine derivative; nitrogen mustard; non-proteinogenic L-alpha-amino acid; organochlorine compound	alkylating agent; antineoplastic agent; carcinogenic agent; drug allergen; immunosuppressive agent
tamoxifen [no description available]	1.97	1	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
detorubicin [no description available]	1.97	1	0
ecomustine ecomustine: structure given in first source	1.97	1	0
levoleucovorin Levoleucovorin: A folate analog consisting of the pharmacologically active isomer of LEUCOVORIN.. (6S)-5-formyltetrahydrofolic acid : The pharmacologically active (6S)-stereoisomer of 5-formyltetrahydrofolic acid.	4.06	3	1	5-formyltetrahydrofolic acid	antineoplastic agent; metabolite
dacarbazine (E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.	1.97	1	0	dacarbazine

Condition	Relationship Strength	Studies	Trials
Adenocarcinoma, Basal Cell [description not available]	3.76	11	0
Cancer of Colon [description not available]	3.48	8	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	3.76	11	0
Colonic Neoplasms Tumors or cancer of the COLON.	3.48	8	0
Cancer of Liver [description not available]	1.98	1	0
Cancer of Lung [description not available]	5.06	10	1
Colorectal Cancer [description not available]	5.18	6	2
Liver Neoplasms Tumors or cancer of the LIVER.	1.98	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	5.06	10	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	5.18	6	2
Malignant Melanoma [description not available]	5.38	5	3
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)	5.38	5	3
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)	1.98	1	0
Leukocytopenia [description not available]	4.33	2	2
Thrombopenia [description not available]	4.33	2	2
Leukopenia A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).	4.33	2	2
Thrombocytopenia A subnormal level of BLOOD PLATELETS.	4.33	2	2
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	1.98	1	0
Abnormalities, Autosome [description not available]	2.39	2	0
Anaplastic Astrocytoma [description not available]	3.77	2	1
Benign Neoplasms, Brain [description not available]	4.05	3	1
Glial Cell Tumors [description not available]	3.76	2	1
Astrocytoma Neoplasms of the brain and spinal cord derived from glial cells which vary from histologically benign forms to highly anaplastic and malignant tumors. Fibrillary astrocytomas are the most common type and may be classified in order of increasing malignancy (grades I through IV). In the first two decades of life, astrocytomas tend to originate in the cerebellar hemispheres; in adults, they most frequently arise in the cerebrum and frequently undergo malignant transformation. (From Devita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2013-7; Holland et al., Cancer Medicine, 3d ed, p1082)	3.77	2	1
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.	4.05	3	1
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	3.76	2	1
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	3.76	2	1
Astrocytoma, Grade IV [description not available]	1.97	1	0
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.	1.97	1	0
Carcinoma, Non-Small Cell Lung [description not available]	3.36	1	1
Metastase [description not available]	3.76	2	1
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.	3.36	1	1
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	3.76	2	1
Carcinoma, Oat Cell [description not available]	2.37	2	0
Carcinoma, Epidermoid [description not available]	1.97	1	0
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)	1.97	1	0
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)	2.37	2	0
B16 Melanoma [description not available]	1.97	1	0
Adenocarcinoma Of Kidney [description not available]	1.97	1	0
Cancer of Kidney [description not available]	1.97	1	0
Carcinoma, Renal Cell A heterogeneous group of sporadic or hereditary carcinoma derived from cells of the KIDNEYS. There are several subtypes including the clear cells, the papillary, the chromophobe, the collecting duct, the spindle cells (sarcomatoid), or mixed cell-type carcinoma.	1.97	1	0
Kidney Neoplasms Tumors or cancers of the KIDNEY.	1.97	1	0
Cancer of Prostate [description not available]	1.97	1	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	1.97	1	0
Benign Neoplasms [description not available]	3.8	4	0
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.	3.8	4	0
Experimental Mammary Neoplasms [description not available]	1.97	1	0
Breast Cancer [description not available]	2.37	2	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.37	2	0
Milk-Alkali Syndrome [description not available]	1.97	1	0
Hypercalcemia Abnormally high level of calcium in the blood.	1.97	1	0
Neoplasms, Bronchial [description not available]	1.97	1	0
Bronchial Neoplasms Tumors or cancer of the BRONCHI.	1.97	1	0
Blood Diseases [description not available]	2.37	2	0
Hematologic Diseases Disorders of the blood and blood forming tissues.	2.37	2	0
Emesis [description not available]	1.97	1	0
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	1.97	1	0
Menopause The last menstrual period. Permanent cessation of menses (MENSTRUATION) is usually defined after 6 to 12 months of AMENORRHEA in a woman over 45 years of age. In the United States, menopause generally occurs in women between 48 and 55 years of age.	1.97	1	0

1-(2-chloroethyl)-3-(2-(dimethylaminosulfonyl)ethyl)-1-nitrosourea

Cross-References

Synonyms (28)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Research

Studies (55)

Market Indicators

Research Demand Index: 10.21

Study Types

1-(2-chloroethyl)-3-(2-(dimethylaminosulfonyl)ethyl)-1-nitrosourea

Cross-References

Synonyms (28)

Research Excerpts

Toxicity

Pharmacokinetics

Bioavailability

Dosage Studied

Research

Studies (55)

Market Indicators

Research Demand Index: 10.21

Study Types

Related Drugs (30)

Related Conditions (57)