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52128-35-5 分子结构
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5-methyl-6-{[(3,4,5-trimethoxyphenyl)amino]methyl}quinazoline-2,4-diamine

ChemBase编号:1028
分子式:C19H23N5O3
平均质量:369.41762
单一同位素质量:369.18008962
SMILES和InChIs

SMILES:
O(c1cc(NCc2c(c3c(nc(nc3N)N)cc2)C)cc(OC)c1OC)C
Canonical SMILES:
COc1cc(NCc2ccc3c(c2C)c(N)nc(n3)N)cc(c1OC)OC
InChI:
InChI=1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)
InChIKey:
NOYPYLRCIDNJJB-UHFFFAOYSA-N

引用这个纪录

CBID:1028 http://www.chembase.cn/molecule-1028.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
5-methyl-6-{[(3,4,5-trimethoxyphenyl)amino]methyl}quinazoline-2,4-diamine
IUPAC传统名
trimetrexate
商标名
Neutrexin
别名
TMQ
TMX
Trimetrexato [INN-Spanish]
Trimetrexatum [INN-Latin]
Trimetrexate
CAS号
52128-35-5
PubChem SID
46505247
160964491
PubChem CID
5583

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB01157 external link
PubChem 5583 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 17.038574  质子受体
质子供体 LogD (pH = 5.5) 0.6246217 
LogD (pH = 7.4) 1.9100662  Log P 2.2781131 
摩尔折射率 107.698 cm3 极化性 40.20676 Å3
极化表面积 117.54 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.36  LOG S -4.08 
溶解度 3.09e-02 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
31.4 mg/L expand 查看数据来源
疏水性(logP)
2 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB01157 external link
Item Information
Drug Groups approved
Description A nonclassical folic acid inhibitor through its inhibition of the enzyme dihydrofolate reductase. It is being tested for efficacy as an antineoplastic agent and as an antiparasitic agent against pneumocystis pneumonia in AIDS patients. Myelosuppression is its dose-limiting toxic effect. [PubChem]
Indication For use, with concurrent leucovorin administration (leucovorin protection), as an alternative therapy for the treatment of moderate-to-severe Pneumocystis carinii pneumonia (PCP) in immunocompromised patients, including patients with the acquired immunodeficiency syndrome (AIDS). Also used to treat several types of cancer including colon cancer.
Pharmacology Trimetrexate, a non-classical folate antagonist, is a synthetic inhibitor of the enzyme dihydrofolate reductase (DHFR). During DNA synthesis and cellular reproduction, folic acid is reduced to tetrahydrofolic acid by the enzyme folic acid reductase. By interfering with the reduction of folic acid, trimetrexate interferes with tissue cell reproduction. Generally, the most sensitive cells to the antimetabolite effect of trimetrexate are those cells which are most actively proliferating such as malignant cells, dermal epithelium, buccal and intestinal mucosa, bone marrow, fetal cells, and cells of the urinary bladder. Because the proliferation of cells in malignant tissues is greater than in most normal tissues, trimetrexate may impair the growth of the malignant tissues without causing irreversible damage to normal tissues. Due to very serious and potentially life-threatening side-effects of this drug, leucovorin must be co-administered for at least 72 hours after the last dose.
Toxicity The LD50 of intravenous trimetrexate in mice is 62 mg/kg (186 mg/m2). Myelosuppression is a dose-limiting toxic effect.
Affected Organisms
Humans and other mammals
Bacteria and protozoa
Biotransformation Hepatic. Preclinical data strongly suggest that the major metabolic pathway is oxidative O-demethylation, followed by conjugation to either glucuronide or the sulfate.
Half Life 11 to 20 hours
Protein Binding 95% (over the concentration range of 18.75 to 1000 ng/mL)
Elimination Ten to 30% of the administered dose is excreted unchanged in the urine.
Distribution * 20 ± 8 L/m2
* 36.9 ± 6 L/m2 [cancer patients]
Clearance * 38 +/- 15 mL/min/m2 [patients with acquired immunodeficiency syndrome (AIDS) who had Pneumocystis carinii pneumonia (4 patients) or toxoplasmosis (2 patients). Trimetrexate was administered intravenously as a bolus injection at a dose of 30 mg/m2/day along with leucovorin 20 mg/m2 every 6 hours for 21 days]
* 53 +/- 41 mL/min/m2 [Cancer patients with advanced solid tumors using various dosage regimensreceiving a single-dose administration of 10 to 130 mg/m2]
* 30 +/- 8 mL/min/m2 [Cancer patients with advanced solid tumors using various dosage regimensafter a five-day infusion]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

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专利

专利

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