3',5'-dichloromethotrexate profile

3',5'-dichloromethotrexate: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	10713
CHEMBL ID	3137680
SCHEMBL ID	10653854
MeSH ID	M0045912

Synonym
unii-29ns58s465
4-26-00-03834 (beilstein handbook reference)
29ns58s465 ,
3',5'-dichloromethotrexate
nci-c04875
3988 b 129-4
methotrexate, dichloro-
3988-b-129-4
528-74-5
nsc29630
3',5'-dichloroamethopterin
3',5'-dichloro-4-amino-4-deoxy-n(sup10)-methylpteroglutamic acid
nsc-29630
nsc 29630
dichloromethotrexate
dichloroamethopterin
3,5-dichloromethotrexate
l-glutamic acid, n-[[(2,4-diamino-6-pteridinyl)methyl][methyl]amino]-3,5-dichlorobenzoyl]-
(2s)-2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid
amethopterin, 3',5'-dichloro-
brn 0073523
glutamic acid, n-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, l-
ccris 4602
3',5'-dichloro-4-amino-4-deoxy-n(sup 10)-methylpteroglutamic acid
l-glutamic acid, n-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-
glutamic acid, n-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-
n-(3,5-dichloro-4-((2,4-diamino-6-pteridinyl)methyl)methyl)methylaminobenzoylglutamic acid
n-(3,5-dichloro-4-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl)glutamic acid
n-(3,5-dichloro-4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)- l-glutamic acid
(2s)-2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
2-[[3,5-dichloro-4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid
CHEMBL3137680
SCHEMBL10653854
MCEHFIXEKNKSRW-LBPRGKRZSA-N
glutamic acid, n-[3,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-, l-
n-(3,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl](methyl)amino]benzoyl)glutamic acid #
l-glutamic acid, n-[3,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-
DTXSID3024996
3',5'-dichloromethotrexate; methotrexate, dichloro-; nsc 145883; nsc 29630
(3,5-dichloro-4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzoyl)-l-glutamic acid
AKOS040746763

Excerpt	Relevance	Reference
" The toxicity of DCM was dose-dependent; the maximum tolerated dosage excalation plan was 400 mg/m2 x 2 weeks, 800 mg/m2 x 2 weeks, and then 1,200 mg/m2 weekly."	( Evaluation of weekly escalating doses of dichloromethotrexate in patients with hepatocellular carcinoma and other solid tumors. Donehower, RC; Eddy, JL; Ihde, DC; Myers, CE; Tester, WJ, 1982)	0.26

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	37 (97.37)	18.7374
1990's	1 (2.63)	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	2 (4.76%)	5.53%
Reviews	2 (4.76%)	6.00%
Case Studies	1 (2.38%)	4.05%
Observational	0 (0.00%)	0.25%
Other	37 (88.10%)	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
formic acid formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.	1.93	1	0	monocarboxylic acid	antibacterial agent; astringent; metabolite; protic solvent; solvent
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	1.97	1	0	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
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.	1.96	1	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.	5.14	3	1	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
methyl methanesulfonate [no description available]	1.95	1	0	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
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).	3.06	1	0	aziridines
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.	4.16	5	0	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; radiosensitizing agent
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	1.97	1	0	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
cytarabine [no description available]	1.96	1	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
dichlorodiphenyldichloroethane Dichlorodiphenyldichloroethane: An organochlorine insecticide that is slightly irritating to the skin. (From Merck Index, 11th ed, p482)	3.06	1	0	chlorophenylethane; monochlorobenzenes; organochlorine insecticide	xenobiotic metabolite
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	1.96	1	0	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	1.95	1	0	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
guanazole Guanazole: A cytostatic triazole derivative which is not to be confused with guanazolo, the generic name for 8-azaguanine.. guanazole : An aromatic amine that is 1,2,4-triazole substituted at positions 3 and 5 by amino groups.	3.06	1	0	aromatic amine; triazoles	antineoplastic agent; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor
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.	1.96	1	0	organofluorine compound; pyrimidine 5'-deoxyribonucleoside	antimetabolite; antineoplastic agent; prodrug
razoxane Razoxane: An antimitotic agent with immunosuppressive properties.	1.95	1	0	N-alkylpiperazine
methotrexate [no description available]	13.48	38	2	dicarboxylic 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
aminopterin Aminopterin: A folic acid derivative used as a rodenticide that has been shown to be teratogenic.	1.96	1	0	dicarboxylic acid	EC 1.5.1.3 (dihydrofolate reductase) inhibitor; mutagen
mercaptopurine Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.	1.96	1	0	aryl thiol; purines; thiocarbonyl compound	anticoronaviral agent; antimetabolite; antineoplastic agent
bilirubin [no description available]	1.97	1	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
7-hydroxymethotrexate [no description available]	1.95	1	0	folic acids
flavin mononucleotide Flavin Mononucleotide: A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues.	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.	1.96	1	0	5-formyltetrahydrofolic acid	antineoplastic agent; metabolite
5-methyltetrahydrofolate 5-methyltetrahydrofolate : A group of heterocyclic compounds based on the 5-methyl-5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid or L-glutamate units.	1.97	1	0

Condition	Relationship Strength	Studies	Trials
Experimental Leukemia [description not available]	2.85	4	0
Leucocythaemia [description not available]	2.34	2	0
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)	2.34	2	0
Benign Neoplasms [description not available]	2.87	4	0
Experimental Neoplasms [description not available]	2.63	3	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.	2.87	4	0
Hepatocellular Carcinoma [description not available]	3.97	5	0
Cancer of Liver [description not available]	4.12	6	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	3.97	5	0
Liver Neoplasms Tumors or cancer of the LIVER.	4.12	6	0
Carcinoma, Anaplastic [description not available]	2.65	3	0
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	2.65	3	0
Incontinentia Pigmenti Achromians [description not available]	1.95	1	0
Benign Neoplasms, Brain [description not available]	1.96	1	0
Astrocytoma, Grade IV [description not available]	1.96	1	0
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.	1.96	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.	1.96	1	0
Cancer of Colon [description not available]	3.98	5	0
Cancer of Rectum [description not available]	3.57	3	0
Colonic Neoplasms Tumors or cancer of the COLON.	3.98	5	0
Rectal Neoplasms Tumors or cancer of the RECTUM.	3.57	3	0
Carcinoma, Epidermoid [description not available]	4.04	3	1
Cancer of Head [description not available]	2.37	2	0
Local Neoplasm Recurrence [description not available]	1.96	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)	4.04	3	1
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	2.37	2	0
Cancer of Cervix [description not available]	2.66	3	0
Uterine Cervical Neoplasms Tumors or cancer of the UTERINE CERVIX.	2.66	3	0
Leukemia L 1210 [description not available]	2.36	2	0
Leukemia, Lymphocytic [description not available]	1.96	1	0
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	1.96	1	0
Reticulum Cell-Like Sarcoma, Yoshida [description not available]	1.95	1	0
Carcinoma, Non-Small Cell Lung [description not available]	3.36	1	1
Cancer of Lung [description not available]	3.36	1	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
Lung Neoplasms Tumors or cancer of the LUNG.	3.36	1	1
Distorted Hearing [description not available]	1.97	1	0
Vestibular Diseases Pathological processes of the VESTIBULAR LABYRINTH which contains part of the balancing apparatus. Patients with vestibular diseases show instability and are at risk of frequent falls.	1.97	1	0
Cochlear Diseases Pathological processes of the snail-like structure (COCHLEA) of the inner ear (LABYRINTH) which can involve its nervous tissue, blood vessels, or fluid (ENDOLYMPH).	1.97	1	0
Acute Liver Injury, Drug-Induced [description not available]	2.37	2	0
Hepatitis INFLAMMATION of the LIVER.	1.97	1	0
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.	2.37	2	0
Adenocarcinoma, Basal Cell [description not available]	1.96	1	0
Gastroduodenal Ulcer [description not available]	1.96	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	1.96	1	0
Peptic Ulcer Ulcer that occurs in the regions of the GASTROINTESTINAL TRACT which come into contact with GASTRIC JUICE containing PEPSIN and GASTRIC ACID. It occurs when there are defects in the MUCOSA barrier. The common forms of peptic ulcers are associated with HELICOBACTER PYLORI and the consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).	1.96	1	0
Bladder Cancer [description not available]	1.97	1	0
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	1.97	1	0
Cancer of Esophagus [description not available]	3.35	1	1
Blood Diseases [description not available]	3.35	1	1
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	3.35	1	1
Hematologic Diseases Disorders of the blood and blood forming tissues.	3.35	1	1

Assay ID	Title	Year	Journal	Article
AID1079944	Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079947	Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079941	Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079936	Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079945	Animal toxicity known. [column 'TOXIC' in source]
AID1079935	Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079931	Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079949	Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079938	Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079943	Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079940	Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079937	Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079939	Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079934	Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079933	Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079948	Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079946	Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079942	Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079932	Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

3',5'-dichloromethotrexate

Description

Cross-References

Synonyms (41)

Research Excerpts

Dosage Studied

Bioassays (19)

Research

Studies (38)

Market Indicators

Research Demand Index: 10.45

Study Types

3',5'-dichloromethotrexate

Description

Cross-References

Synonyms (41)

Research Excerpts

Dosage Studied

Bioassays (19)

Research

Studies (38)

Market Indicators

Research Demand Index: 10.45

Study Types

Related Drugs (23)

Related Conditions (52)