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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:40:01 UTC
HMDB IDHMDB0014631
Secondary Accession Numbers
  • HMDB14631
Metabolite Identification
Common NameAltretamine
DescriptionAltretamine, also known as hexalen or hexastat, belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group. Altretamine is a drug which is used 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. It also acts as a chemosterilant for male houseflies and other insects. Metabolism of altretamine is a requirement of cytotoxicity. Structurally, altretamine resembles the alkylating agent triethylenemelamine, yet in vitro tests for alkylating activity of altretamine and its metabolitics have been negative. Altretamine is a very strong basic compound (based on its pKa). The precise mechanism by which altretamine exerts its cytotoxic effect is unknown although it is classified as an alkylating anti-neoplastic agent. These alkylating species consequently damage tumor cells. It is an alkylating agent proposed as an antineoplastic.
Structure
Data?1582753201
Synonyms
ValueSource
2,4,6-Tris(dimethylamino)-1,3,5-triazineChEBI
2,4,6-Tris(dimethylamino)-S-triazineChEBI
AltretaminaChEBI
AltretaminumChEBI
HexalenChEBI
HexastatChEBI
HMMChEBI
HEXAMETHYLMELAMINEHMDB
HTMHMDB
HXMHMDB
Bellon brand OF altretamineHMDB
Chiesi brand OF altretamineHMDB
MGI pharma brand OF altretamineHMDB
Rhône poulenc rorer brand OF altretamineHMDB
Altretamine bellon brandHMDB
Altretamine chiesi brandHMDB
HexinawasHMDB
Wassermann brand OF altretamineHMDB
HemelHMDB
Altretamine wassermann brandHMDB
Rhône-poulenc rorer brand OF altretamineHMDB
AltretamineChEBI
Chemical FormulaC9H18N6
Average Molecular Weight210.2794
Monoisotopic Molecular Weight210.159294606
IUPAC NameN2,N2,N4,N4,N6,N6-hexamethyl-1,3,5-triazine-2,4,6-triamine
Traditional Namealtretamine
CAS Registry Number645-05-6
SMILES
CN(C)C1=NC(=NC(=N1)N(C)C)N(C)C
InChI Identifier
InChI=1S/C9H18N6/c1-13(2)7-10-8(14(3)4)12-9(11-7)15(5)6/h1-6H3
InChI KeyUUVWYPNAQBNQJQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylarylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • N-aliphatic s-triazine
  • Aminotriazine
  • Amino-1,3,5-triazine
  • 1,3,5-triazine
  • Triazine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point172 - 174 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.1 g/LNot Available
LogP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.1 g/LALOGPS
logP2.43ALOGPS
logP2.22ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)7.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.39 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity65.65 m³·mol⁻¹ChemAxon
Polarizability23.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-7790000000-e6026ce486911f432231Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03dj-9781100000-4553bbbe9a30a0391bb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-3490000000-4af5631898604d2cec10Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dj-9781100000-4553bbbe9a30a0391bb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-d69cd870b4294e5bc170Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-eab4cf11b3d7c71c506aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1890000000-772056487934c472a76fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-72599b7d9a667dc24339Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-18a5954520aa78e7f71aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-0940000000-1d4df681882fc50a1202Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00488 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00488 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00488
Phenol Explorer Compound IDNot Available
FooDB IDFDB001629
KNApSAcK IDC00008231
Chemspider ID2038
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAltretamine
METLIN IDNot Available
PubChem Compound2123
PDB IDNot Available
ChEBI ID24564
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Damia G, D'Incalci M: Clinical pharmacokinetics of altretamine. Clin Pharmacokinet. 1995 Jun;28(6):439-48. [PubMed:7656502 ]
  2. 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:11302345 ]
  3. 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:12586589 ]
  4. 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:14751188 ]