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Record Information
Version4.0
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-10-23 19:06:20 UTC
HMDB IDHMDB0014631
Secondary Accession Numbers
  • HMDB14631
Metabolite Identification
Common NameAltretamine
DescriptionAltretamine is only found in individuals that have used or taken this drug. It is an alkylating agent proposed as an antineoplastic. It also acts as a chemosterilant for male houseflies and other insects. [PubChem]The precise mechanism by which altretamine exerts its cytotoxic effect is unknown although it is classified as an alkylating anti-neoplastic agent. Through this mechanism, the drug is metabolized into alkylating agents by N-demethylation. These alkylating species consequently damage tumor cells.
Structure
Thumb
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 altretamineMeSH
Chiesi brand OF altretamineMeSH
MGI pharma brand OF altretamineMeSH
Rhône poulenc rorer brand OF altretamineMeSH
Altretamine bellon brandMeSH
Altretamine chiesi brandMeSH
HexinawasMeSH
Wassermann brand OF altretamineMeSH
HemelMeSH
Altretamine wassermann brandMeSH
Rhône-poulenc rorer brand OF altretamineMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
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:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-7790000000-e6026ce486911f432231View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03dj-9781100000-4553bbbe9a30a0391bb4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-3490000000-4af5631898604d2cec10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dj-9781100000-4553bbbe9a30a0391bb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-d69cd870b4294e5bc170View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-eab4cf11b3d7c71c506aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1890000000-772056487934c472a76fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-72599b7d9a667dc24339View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-18a5954520aa78e7f71aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-0940000000-1d4df681882fc50a1202View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00488 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00488 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00488
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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 ]