2-N,2-N,4-N,4-N,6-N,6-N-hexamethyl-1,3,5-triazine-2,4,6-triamine

• ChemBase编号: 371
• 分子式: C9H18N6
• 平均质量: 210.27942
• 单一同位素质量: 210.15929461
• SMILES: N(c1nc(N(C)C)nc(N(C)C)n1)(C)C
• Canonical SMILES: CN(c1nc(nc(n1)N(C)C)N(C)C)C
• InChI: InChI=1S/C9H18N6/c1-13(2)7-10-8(14(3)4)12-9(11-7)15(5)6/h1-6H3
• InChIKey: UUVWYPNAQBNQJQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-N,2-N,4-N,4-N,6-N,6-N-hexamethyl-1,3,5-triazine-2,4,6-triamine
• IUPAC传统名: altretamine
• 商标名: Hemel; Hexalen; Hexastat
• 别名: 六甲蜜胺; 六甲三聚氰胺; 六甲蜜胺; 2,4,6-三(二甲氨基)均三嗪; Altretaminum [INN-Latin]; HEXAMETHYLMELAMINE; HMM; HTM; HXM; Altretamine; 2-N,2-N,4-N,4-N,6-N,6-N-hexamethyl-1,3,5-triazine-2,4,6-triamine; N,N,N′,N′,N′′,N′′-Hexamethyl-1,3,5-triazine-2,4,6-triamine; Altretamine; N2,N2,N4,N4,N6,N6-Hexamethyl-1,3,5-triazine-2,4,6-triamine; 1,3,5-Tris(dimethylamino)-s-triazine; 2,4,6-Tris(dimethylamino)-1,3,5-triazine; ENT 50852; Hemel; Hexylen; NSC 13875; Altretamine; 2,4,6-Tris(dimethylamino)-1,3,5-triazine; Hexalen

登记号

• CAS号: 645-05-6
• EC号: 211-428-4
• MDL号: MFCD00549245
• PubChem SID: 24874728; 46505760; 160963834; 24278242
• PubChem CID: 2123
• CHEBI ID: 24564
• ATC码: L01XX03
• CHEMBL: 1455
• Chemspider ID: 2038
• DrugBank ID: DB00488
• KEGG ID: D02841
• 美国药典/FDA物质标识码: Q8BIH59O7H
• 维基百科标题: Altretamine
• Medline Plus: a601200

理论计算性质

JChem

• 质子受体: 6
• 质子供体: 0
• LogD (pH = 5.5): 0.43392327
• LogD (pH = 7.4): 1.7163193
• Log P: 2.2162216
• 摩尔折射率: 65.6454 cm^3
• 极化性: 22.128712 Å^3
• 极化表面积: 48.39 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.43
• LOG S: -1.83
• 溶解度: 3.10e+00 g/l

分子性质

理化性质

• 溶解度: 91 mg/L; Chloroform; Methanol
• 外观: solid; White Solid
• 熔点: 171-175 °C(lit.); 172-174°C
• 疏水性(logP): 1.665; 1.7

安全信息

• 保存条件: -20°C; Refrigerator
• RTECS编号: OS1050000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

药理学性质

• 半衰期: 4.7-10.2 hours
• 蛋白结合率: 94%
• 法定药品分级: Rx-only (US)
• 妊娠期药物分类: D (US)

产品相关信息

• 纯度: 95%; 96%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C9H18N6

详细说明

DrugBank - DB00488

• Drug Groups: approved
• Description: An alkylating agent proposed as an antineoplastic. It also acts as a chemosterilant for male houseflies and other insects. [PubChem]
• Indication: For use as a single agent in the palliative treatment of patients with persistent or recurrent ovarian cancer following first-line therapy with a cisplatin and/or alkylating agent-based combination.
• Pharmacology: Altretamine is a novel antineoplastic agent. The precise mechanism by which altretamine exerts its cytotoxic effect is unknown, although a number of theoretical possibilities have been studied. Structurally, altretamine resembles the alkylating agent triethylenemelamine, yet in vitro tests for alkylating activity of altretamine and its metabolitics have been negative. Altretamine has been demonstrated to be efficacious for certain ovarian tumors resistant to classical alkylating agents. Metabolism of altretamine is a requirement of cytotoxicity. Synthetic monohydroxymethylmelamines, and products of altretamine metabolism, in vitro and in vivo, can form covalent adducts with tissue macromolecules including DNA, but the relevance of these reactions to antitumor activity is unknown.
• Affected Organisms: Humans and other mammals
• Half Life: 4.7-10.2 hours
• Protein Binding: 94%
• Elimination: Human urinary metabolites were Ndemethylated homologues of altretamine with <1% unmetabolized altretamine excreted at 24 hours.
• References: Keldsen N, Havsteen H, Vergote I, Bertelsen K, Jakobsen A: Altretamine (hexamethylmelamine) in the treatment of platinum-resistant ovarian cancer: a phase II study. Gynecol Oncol. 2003 Feb;88(2):118-22. [Pubmed] ; Chan JK, Loizzi V, Manetta A, Berman ML: Oral altretamine used as salvage therapy in recurrent ovarian cancer. Gynecol Oncol. 2004 Jan;92(1):368-71. [Pubmed] ; Malik IA: Altretamine is an effective palliative therapy of patients with recurrent epithelial ovarian cancer. Jpn J Clin Oncol. 2001 Feb;31(2):69-73. [Pubmed] ; Damia G, D'Incalci M: Clinical pharmacokinetics of altretamine. Clin Pharmacokinet. 1995 Jun;28(6):439-48. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1278

Research Area: Cancer
Biological Activity:
Altretamine(Hexalen) is an anti-neoplastic agent. The precise mechanism by which altretamine exerts its anti-cancer effect is unknown but it is classified by MeSH as an alkylating anti-neoplastic agent.It is used to treat refractory ovarian cancer. [1]

Sigma Aldrich - A8723

Biochem/physiol Actions
抗肿瘤药

Sigma Aldrich - 549835

包装
25 g in glass bottle

Toronto Research Chemicals - A575765

An antitumor agent which also acts as a chemosterilant for male houseflies and other insects. Antineoplastic.

参考文献

• Keldsen N, Havsteen H, Vergote I, Bertelsen K, Jakobsen A: Altretamine (hexamethylmelamine) in the treatment of platinum-resistant ovarian cancer: a phase II study. Gynecol Oncol. 2003 Feb;88(2):118-22. Pubmed
• Chan JK, Loizzi V, Manetta A, Berman ML: Oral altretamine used as salvage therapy in recurrent ovarian cancer. Gynecol Oncol. 2004 Jan;92(1):368-71. Pubmed
• Malik IA: Altretamine is an effective palliative therapy of patients with recurrent epithelial ovarian cancer. Jpn J Clin Oncol. 2001 Feb;31(2):69-73. Pubmed
• Damia G, D'Incalci M: Clinical pharmacokinetics of altretamine. Clin Pharmacokinet. 1995 Jun;28(6):439-48. Pubmed
• http://www.rxlist.com/hexalen-drug.htm
• Chang, S.C., et al.: Science, 144, 57 (1964)
• Ames, M.M., et al.: Cancer Res., 39, 5016 (1964)
• D’Incalci, M., et al.: Br. J. Cancer, 41, 630 (1964)