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

• ChemBase ID: 371
• Molecular Formular: C9H18N6
• Molecular Mass: 210.27942
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-N,2-N,4-N,4-N,6-N,6-N-hexamethyl-1,3,5-triazine-2,4,6-triamine
• IUPAC Traditional name: altretamine
• Brand Name: Hemel; Hexalen; Hexastat
• Synonyms: 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; 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

Database IDs

• CAS Number: 645-05-6
• EC Number: 211-428-4
• MDL Number: MFCD00549245
• PubChem SID: 46505760; 24278242; 160963834; 24874728
• PubChem CID: 2123
• CHEBI ID: 24564
• ATC CODE: L01XX03
• CHEMBL: 1455
• Chemspider ID: 2038
• DrugBank ID: DB00488
• KEGG ID: D02841
• Unique Ingredient Identifier: Q8BIH59O7H
• Wikipedia Title: Altretamine
• Medline Plus: a601200

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.43392327
• LogD (pH = 7.4): 1.7163193
• Log P: 2.2162216
• Molar Refractivity: 65.6454 cm^3
• Polarizability: 22.128712 Å^3
• Polar Surface Area: 48.39 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.43
• LOG S: -1.83
• Solubility (Water): 3.10e+00 g/l

PROPERTIES

Physical Property

• Solubility: 91 mg/L; Chloroform; Methanol
• Apperance: solid; White Solid
• Melting Point: 171-175 °C(lit.); 172-174°C
• Hydrophobicity(logP): 1.665; 1.7

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: OS1050000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Half Life: 4.7-10.2 hours
• Protein Bound: 94%
• Legal Status: Rx-only (US)
• Pregnancy Category: D (US)

Product Information

• Purity: 95%; 96%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C9H18N6

DETAILS

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
Antineoplastic

Sigma Aldrich - 549835

Packaging
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.

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
• 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)