准备方法

合成路线和反应条件： 甲氨蝶呤是通过多步合成过程合成的，该过程包括4-氨基苯甲酸与2,4-二氨基-6-羟基嘧啶反应形成4-氨基-4-脱氧-N10-甲基蝶酰胺。然后将该中间体与L-谷氨酸偶联，生成甲氨蝶呤 .

工业生产方法： 甲氨蝶呤的工业生产涉及使用与实验室合成相似的反应条件进行大规模合成，但针对更高的产率和纯度进行了优化。该工艺包括严格的纯化步骤，例如结晶和色谱，以确保最终产品符合药物标准 .

化学反应分析

反应类型： 甲氨蝶呤会发生各种化学反应，包括氧化、还原和取代。

常见试剂和条件：

氧化： 甲氨蝶呤可以在酸性条件下使用过氧化氢等氧化剂进行氧化.

还原： 还原反应涉及使用硼氢化钠等还原剂.

取代： 取代反应可以在碱性条件下与胺类等亲核试剂发生.

主要产物： 这些反应形成的主要产物包括7-羟基甲氨蝶呤和其他保留一些生物活性的代谢物 .

相似化合物的比较

甲氨蝶呤在结构上与叶酸和氨甲蝶呤相似。它以其N-甲基化形式而独一无二，这增强了其作为抗代谢物的效力。类似的化合物包括：

氨甲蝶呤： 早期的抗叶酸剂，具有相似的机制，但毒性更高.

培美曲塞： 另一种用于癌症治疗的抗叶酸剂，具有更广泛的活性范围.

拉替瑞特： 一种用于治疗结直肠癌的胸苷酸合酶抑制剂.

甲氨蝶呤独特的结构和作用机制使其成为一种有价值的治疗剂，在医药和研究领域具有多种应用。

属性

IUPAC Name	(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	FBOZXECLQNJBKD-ZDUSSCGKSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Isomeric SMILES	CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C20H22N8O5	Source
Record name	METHOTREXATE
Source	CAMEO Chemicals
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Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Related CAS	15475-56-6 (hydrochloride salt), 7413-34-5 (di-hydrochloride salt)	Source
Record name	Methotrexate [USAN:USP:INN:BAN:JAN]
Source	ChemIDplus
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DSSTOX Substance ID	DTXSID4020822	Source
Record name	Methotrexate
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Molecular Weight	454.4 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Physical Description	Methotrexate is an odorless yellow to orange-brown crystalline powder. (NTP, 1992) It is a chemotherapy drug that interferes with DNA and RNA synthesis., Solid, Bright yellow-orange, odorless, crystalline powder.	Source
Record name	METHOTREXATE
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Record name	Methotrexate
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Record name	METHOTREXATE
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URL	https://www.osha.gov/chemicaldata/874
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Solubility	less than 1 mg/mL at 66 °F (NTP, 1992), Insoluble in water , alcohol, chloroform, ether; slightly soluble in dilute hydrochloric acid; soluble in dil solns of alkali hydroxides and carbonates., Practically insoluble in water and in alcohol., In water, 2.6X10+3 mg/L at 25 °C /Estimated/, 1.71e-01 g/L	Source
Record name	METHOTREXATE
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Record name	METHOTREXATE
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Record name	Methotrexate
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014703
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Vapor Pressure	2.1X10-19 mm Hg at 25 °C /Estimated/	Source
Record name	METHOTREXATE
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Mechanism of Action	Methotrexate enters tissues and is converted to a methotrexate polyglutamate by folylpolyglutamate. Methotrexate's mechanism of action is due to its inhibition of enzymes responsible for nucleotide synthesis including dihydrofolate reductase, thymidylate synthase, aminoimidazole caboxamide ribonucleotide transformylase (AICART), and amido phosphoribosyltransferase. Inhibtion of nucleotide synthesis prevents cell division. In rheumatoid arthritis, methotrexate polyglutamates inhibit AICART more than methotrexate. This inhibition leads to accumulation of AICART ribonucleotide, which inhibits adenosine deaminase, leading to an accumulation of adenosine triphosphate and adenosine in the extracellular space, stimulating adenosine receptors, leading to anti-inflammatory action., Methotrexate and its polyglutanate metabolites reversibly inhibits dihydrofolate reductase, the enzyme that reduces folic acid to tetrahydrofolic acid. Inhibition of tetrahydrofolate formation limits the availability of one-carbon fragments necessary for synthesis of purines and the conversion of deoxyuridylate to thymidylate in the synthesis of DNA and cell reproduction. The affinity of dihydrofolate reductase for methotrexate is far greater than its affinity for folic acid or dihydrofolic acid. and, therefore, even very large doses of folic acid given simultaneously will not reverse the effects of methotrexate. Leucovorin calcium, a derivative of tetrahydrofolic acid, may block the effects of methotrexate if given shortly after the antineoplastic agent. Results of one study indicate that methotrexate also causes an increase in intracellular deoxyadenosine triphosphate, which is thought to inhibit ribonucleotide reduction, and polynucleotide ligase, an enzyme concerned in DNA synthesis and repair. Tissues with high rates of cellular proliferation such as neoplasms, psoriatic epidermis, bone marrow, the lining of the GI tract, hair matrix, and fetal cells are most sensitive to the effects of methotrexate., Methotrexate ... has immunosuppressive activity, in part possibly as a result of inhibition of lymphocyte multiplication. The mechanism(s) of action in the management of rheumatoid arthritis of the drug is not known, although suggested mechanisms have included immunosuppressive and/or antiinflammatory effects.	Source
Record name	Methotrexate
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Record name	METHOTREXATE
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Color/Form	Orange-brown, crystalline powder
CAS No.	59-05-2	Source
Record name	METHOTREXATE
Source	CAMEO Chemicals
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Record name	Methotrexate
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Record name	Methotrexate [USAN:USP:INN:BAN:JAN]
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Record name	Methotrexate
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Record name	methotrexate
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Record name	L-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-
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Record name	Methotrexate
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Record name	Methotrexate
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Record name	METHOTREXATE
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Record name	METHOTREXATE
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Record name	Methotrexate
Source	Human Metabolome Database (HMDB)
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Record name	METHOTREXATE
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Melting Point	365 to 399 °F (decomposes) (NTP, 1992), Melting point: 185-204 °C. /Methotrexate monohydrate/, 195 °C, 356-399 °F	Source
Record name	METHOTREXATE
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Record name	Methotrexate
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Record name	METHOTREXATE
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Record name	Methotrexate
Source	Human Metabolome Database (HMDB)
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Record name	METHOTREXATE
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URL	https://www.osha.gov/chemicaldata/874
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Retrosynthesis Analysis

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Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Methotrexate

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Methotrexate

Reactant of Route 3

Methotrexate

Reactant of Route 4

Methotrexate

Reactant of Route 5

Methotrexate

Reactant of Route 6

Methotrexate

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