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645-05-6 molecular structure
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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 and InChIs

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

Cite this record

CBID:371 http://www.chembase.cn/molecule-371.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
Hexalen
Altretamine
2,4,6-Tris(dimethylamino)-1,3,5-triazine
N,N,N′,N′,N′′,N′′-Hexamethyl-1,3,5-triazine-2,4,6-triamine
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
2-N,2-N,4-N,4-N,6-N,6-N-hexamethyl-1,3,5-triazine-2,4,6-triamine
Altretamine
六甲三聚氰胺
六甲蜜胺
2,4,6-三(二甲氨基)均三嗪
六甲蜜胺
CAS Number
645-05-6
EC Number
211-428-4
MDL Number
MFCD00549245
PubChem SID
160963834
24278242
46505760
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 0.43392327  LogD (pH = 7.4) 1.7163193 
Log P 2.2162216  Molar Refractivity 65.6454 cm3
Polarizability 22.128712 Å3 Polar Surface Area 48.39 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 2.43  LOG S -1.83 
Solubility (Water) 3.10e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
91 mg/L expand Show data source
Chloroform expand Show data source
Methanol expand Show data source
Apperance
solid expand Show data source
White Solid expand Show data source
Melting Point
171-175 °C(lit.) expand Show data source
172-174°C expand Show data source
Hydrophobicity(logP)
1.665 expand Show data source
1.7 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
RTECS
OS1050000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Half Life
4.7-10.2 hours expand Show data source
Protein Bound
94% expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
D (US) expand Show data source
Purity
95% expand Show data source
96% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C9H18N6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia TRC TRC
DrugBank - DB00488 external link
Item Information
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
Sigma Aldrich - 549835 external link
Packaging
25 g in glass bottle
Sigma Aldrich - A8723 external link
Biochem/physiol Actions
Antineoplastic
Selleck Chemicals - S1278 external link
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]
Toronto Research Chemicals - A575765 external link
An antitumor agent which also acts as a chemosterilant for male houseflies and other insects. Antineoplastic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://www.rxlist.com/hexalen-drug.htm
  • • 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
  • • 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)
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PATENTS

PATENTS

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INTERNET

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