U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H18N6
Molecular Weight 210.2794
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALTRETAMINE

SMILES

CN(C)C1=NC(=NC(=N1)N(C)C)N(C)C

InChI

InChIKey=UUVWYPNAQBNQJQ-UHFFFAOYSA-N
InChI=1S/C9H18N6/c1-13(2)7-10-8(14(3)4)12-9(11-7)15(5)6/h1-6H3

HIDE SMILES / InChI
Molecular Formula C9H18N6
Molecular Weight 210.2794
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.rxlist.com/hexalen-drug/warnings-precautions.htm http://www.survivorlibrary.com/library/anticancer-therapeutics.pdf#page=146 https://books.google.ru/books?hl=ru&lr=&id=VEibBwAAQBAJ&oi=fnd&pg=PP1&dq=Hexamethylmelamine+formaldehide&ots=-eXXGg_pDu&sig=H4nRJZrJvcJ4rK6AIQe68qCP_KI&redir_esc=y#v=onepage&q&f=false https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8456a8db-a7f6-4bc0-86be-e9c8c374140b

Altretamine is structurally similar to the alkylating agent triethylenemelamine (tretamine). Although Altretamine structurally resembles an alkylating agent, it has not been found to have alkylating activity in vitro. The precise mechanism of Altretamine cytotoxicity is unknown, although several proposals have been made. Altretamine requires N-demethylation in the liver to produce reactive intermediates (formaldehyde and/or iminium species) which covalently bind to DNA, resulting in DNA damage, or act as alkylating agents. Altretamine is used as a palliative treatment for persistent or recurrent ovarian cancer following treatment failure with a cisplatin- or alkylating agent-based combination. Side effects of Altretamine include nausea and vomiting, neurotoxicity (mood disorders, disorders of consciousness, ataxia, dizziness, vertigo), mild to moderate dose-related myelosuppression. Altretamine has been shown to be embryotoxic and teratogenic in rats and rabbits and may cause fetal damage when administered to a pregnant woman. Under the trade name Hexalen, Altretamine, is an antineoplastic agent. It is indicated 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.

CNS Activity

CNS Active
4002
Curator's Comment: Altretamine itself has poor CNS penetration. Its demethylated metabolites occur in high concentrations in cerebrospinal fluid and may be concentrated in the brain. Altretamine side effects include central neurotoxicity (rare) and peripheral neurotoxicity. Additional resources: https://books.google.ru/books?id=rRP-Wvc5uDgC&pg=PA89&lpg=PA89&dq=altretamine+blood+brain+barrier&source=bl&ots=V11TobJZil&sig=jAHs-S6mwG8qRRIHq1u185BIRuA&hl=ru&sa=X&sqi=2&ved=0ahUKEwiz1pfW5NbLAhUlAHMKHY-DDwgQ6AEITjAH#v=onepage&q=altretamine%20blood%20brain%20barrier&f=false

Originator

Kaiser, D.W. et al.
2
Curator's Comment: The synthesis of hexamethylmelamine (Altretamine) was first reported in 1951 (Kaiser et al., 1951).

Approval Year

1990
111
Targets

Targets

Primary TargetPharmacologyConditionPotency
Interacts
323
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8583
HEXALEN

Approved Use

INDICATIONS and USAGE HEXALEN® (altretamine) capsules is indicated 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.

Launch Date

1990
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.77 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/109196/
200 mg/m² single, oral
dose: 200 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
ALTRETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
0.61 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/109196/
300 mg/m² single, oral
dose: 300 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
ALTRETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
790 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/2515524
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALTRETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
503 μg × min/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/109196/
200 mg/m² single, oral
dose: 200 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
ALTRETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
119.7 μg × min/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/109196/
300 mg/m² single, oral
dose: 300 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
ALTRETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
1147 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/2515524
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALTRETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.35 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/109196/
200 mg/m² single, oral
dose: 200 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
ALTRETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
6.59 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/109196/
300 mg/m² single, oral
dose: 300 mg/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
ALTRETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
2.2 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/2515524
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALTRETAMINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
OTHER GOV
https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8456a8db-a7f6-4bc0-86be-e9c8c374140b
single, oral
 ALTRETAMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
260 mg/m2 1 times / day multiple, oral
Recommended
Dose: 260 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 260 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
unhealthy, 62.0 years (range: 33–81 years)
Health Status: unhealthy
Age Group: 62.0 years (range: 33–81 years)
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
Other AEs: Granulocytopenia, Anxiety...
Other AEs:
Granulocytopenia (grade 4, 2 patients)
Anxiety (grade 4, 1 patient)
Depression (grade 4, 1 patient)
Malaise (grade 3, 7%)
Fatigue (grade 3, 7%)
Lethargy (grade 3, 7%)
Nausea (grade 3, 6%)
Vomiting (grade 3, 3%)
Paresthesia (grade 3, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
630 mg/m2 1 times / day multiple, parenteral
MTD
Dose: 630 mg/m2, 1 times / day
Route: parenteral
Route: multiple
Dose: 630 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2104537
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://pubmed.ncbi.nlm.nih.gov/2104537
Sources:
https://pubmed.ncbi.nlm.nih.gov/2104537
850 mg/m2 single, parenteral
MTD
Dose: 850 mg/m2
Route: parenteral
Route: single
Dose: 850 mg/m2
Sources:
https://pubmed.ncbi.nlm.nih.gov/2104537
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://pubmed.ncbi.nlm.nih.gov/2104537
Sources:
https://pubmed.ncbi.nlm.nih.gov/2104537
AEs

AEs

AESignificanceDosePopulation
Paresthesia grade 3, 1 patient
260 mg/m2 1 times / day multiple, oral
Recommended
Dose: 260 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 260 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
unhealthy, 62.0 years (range: 33–81 years)
Health Status: unhealthy
Age Group: 62.0 years (range: 33–81 years)
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
Vomiting grade 3, 3%
260 mg/m2 1 times / day multiple, oral
Recommended
Dose: 260 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 260 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
unhealthy, 62.0 years (range: 33–81 years)
Health Status: unhealthy
Age Group: 62.0 years (range: 33–81 years)
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
Nausea grade 3, 6%
260 mg/m2 1 times / day multiple, oral
Recommended
Dose: 260 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 260 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
unhealthy, 62.0 years (range: 33–81 years)
Health Status: unhealthy
Age Group: 62.0 years (range: 33–81 years)
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
Fatigue grade 3, 7%
260 mg/m2 1 times / day multiple, oral
Recommended
Dose: 260 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 260 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
unhealthy, 62.0 years (range: 33–81 years)
Health Status: unhealthy
Age Group: 62.0 years (range: 33–81 years)
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
Lethargy grade 3, 7%
260 mg/m2 1 times / day multiple, oral
Recommended
Dose: 260 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 260 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
unhealthy, 62.0 years (range: 33–81 years)
Health Status: unhealthy
Age Group: 62.0 years (range: 33–81 years)
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
Malaise grade 3, 7%
260 mg/m2 1 times / day multiple, oral
Recommended
Dose: 260 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 260 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
unhealthy, 62.0 years (range: 33–81 years)
Health Status: unhealthy
Age Group: 62.0 years (range: 33–81 years)
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
Anxiety grade 4, 1 patient
260 mg/m2 1 times / day multiple, oral
Recommended
Dose: 260 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 260 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
unhealthy, 62.0 years (range: 33–81 years)
Health Status: unhealthy
Age Group: 62.0 years (range: 33–81 years)
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
Depression grade 4, 1 patient
260 mg/m2 1 times / day multiple, oral
Recommended
Dose: 260 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 260 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
unhealthy, 62.0 years (range: 33–81 years)
Health Status: unhealthy
Age Group: 62.0 years (range: 33–81 years)
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
Granulocytopenia grade 4, 2 patients
260 mg/m2 1 times / day multiple, oral
Recommended
Dose: 260 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 260 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
unhealthy, 62.0 years (range: 33–81 years)
Health Status: unhealthy
Age Group: 62.0 years (range: 33–81 years)
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11531286
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY565266
https://www.001chemical.com/chem/645-05-6
3B Scientific (Wuhan) Corp
3B2-0964
http://www.3bsc.com/index/pro_info.php?id=41869
AA Blocks
AA0034DG
https://www.aablocks.com/goods/Goods/detail?id=AA0034DG
Aaron Chemicals
AR003558
http://www.aaronchem.com/645-05-6
abcr GmbH
AB509262
http://www.abcr.com/shop/en/AB509262
AbMole Bioscience
M2242
http://www.abmole.com/products/altretamine.html
Achemtek
0104-006567
http://www.achemtek.com/645-05-6
Active Biopharma
ABP000596
http://www.activebiopharma.com/645-05-6
Adooq BioScience
A10059
https://www.adooq.com/altretamine.html
AHH Chemical co.,ltd
MT-46992
http://www.ahhchemical.com/product/MT-46992.html
AK Scientific, Inc. (AKSCI)
65631
http://www.aksci.com/item_detail.php?cat=65631
Alfa Chemistry
AP645056
https://reagents.alfa-chemistry.com/product/altretamine-cas-645-05-6-14551.html
Ambeed
A112657
https://www.ambeed.com/products/645-05-6.html
Ambinter
Amb1007035
http://www.ambinter.com/reference/1007035
Angel Pharmatech
AG252110
http://www.angelpharmatech.com/645-05-6.html
Ark Pharm
AK431828
http://www.arkpharminc.com/products/645-05-6.html
Aurora Fine Chemicals LLC
A13.142.921
http://online.aurorafinechemicals.com/info?ID=A13.142.921
Aurora Fine Chemicals LLC
K01.093.554
http://online.aurorafinechemicals.com/info?ID=K01.093.554
Aurum Pharmatech LLC
M-2093
http://www.Aurumpharmatech.com/Product/ProductDetails/M_2093
BioChemPartner
BCP27675
http://www.biochempartner.com/645-05-6-BCP27675
BioCrick
BCC1216
http://www.biocrick.com/Altretamine-BCC1216.html
BioSynth
J-523408
https://www.biosynth.com/en/products/all-products/products/J-523408.html
BLD Pharm
BD66388
http://www.bldpharm.com/products/645-05-6.html
Boerchem
BC203873
http://www.boerchem.com/?product_34242.html
Chem Scene
CS-2061
http://www.chemscene.com/645-05-6.html
ChemBridge
5148727
http://www.hit2lead.com/search.asp?db=SC&ids=5148727
Chemenu
CM110241
http://www.chemenu.com/products/CM110241
ChemMol
30101821
http://www.chemmol.com/chemmol/30101821.html
ChemMol
44001616
http://www.chemmol.com/chemmol/44001616.html
ChemMol
49428477
http://www.chemmol.com/chemmol/49428477.html
Chemspace
CSSB00000016056
https://chem-space.com/CSSB00000016056
CSNpharm
CSN18706
https://www.csnpharm.com/products/altretamine.html
DC Chemicals
DCAPI1290
http://www.dcchemicals.com//product_show-Altretamine_Hexalen_.html
Debye Scientific
DB-054676
http://www.debyesci.com/cas_645-05-6.html
Enamine
Z57931197
https://www.enaminestore.com/catalog/Z57931197
eNovation Chemicals
D672618
https://www.enovationchem.com/ProductDetails.asp?ProductID=D672618
eNovation Chemicals
D766181
https://www.enovationchem.com/ProductDetails.asp?ProductID=D766181
Finetech
FT-0651499
http://www.finetechnology-ind.com/prod/detail/pub/645-05-6.html
Glentham Life Sciences
GP0509
http://www.glentham.com/products/product/GP0509/
Hairui
HR126599
http://www.hairuichem.com/en/product/645-05-6.html
iChemical
EBD29031
http://www.ichemical.com/chemicals/cas-645-05-6
Lab Network
LN00195151
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00195151
mcule
MCULE-1605383293
https://mcule.com/MCULE-1605383293/
MedChem Express
HY-B0181
https://www.medchemexpress.com/Altretamine.html
Molcore
MC565266
https://www.molcore.com/product/645-05-6
Oakwood
358119
http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=197309&ExtHyperLink=1
OChem
249
http://www.ocheminc.com/index.php?act=psearch&pid=645A056
Parchem
28163
http://www.parchem.com/chemical-supplier-distributor/Altretamine-018163.aspx
Renno Tech
RP18094
http://www.rennotech.com/product_show.asp?id=23962
Selleck Chemicals
S1278
http://www.selleckchem.com/products/Altretamine.html
Sigma-Aldrich
1017105_USP
https://www.sigmaaldrich.com/catalog/product/usp/1017105?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich
549835_ALDRICH
https://www.sigmaaldrich.com/catalog/product/aldrich/549835?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich
A8723_SIGMA
https://www.sigmaaldrich.com/catalog/product/sigma/a8723?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule
S518191
http://www.smolecule.com/products/s518191
THE BioTek
bt-258581
https://www.thebiotek.com/product/inhibitors/bt-258581
THE BioTek
bt-318379
https://www.thebiotek.com/product/others/bt-318379
Vesino Industrial Co Ltd
VA10242
http://www.vsnchem.com/goto/product/23743/
Yuhao Chemical
JZ4099
http://www.chemyuhao.com/645-05-6.html
PubMed

PubMed

TitleDatePubMed
Clinical trials and progress with paclitaxel in ovarian cancer.
2010-11-19
Cancer-drug associations: a complex system.
2010-04-02
Liposomes incorporating sodium deoxycholate for hexamethylmelamine (HMM) oral delivery: development, characterization, and in vivo evaluation.
2010-04
Hexamethylmelamine as consolidation treatment for patients with advanced epithelial ovarian cancer in complete response after first-line chemotherapy.
2009-08
Enhancing the efficacy of cisplatin in ovarian cancer treatment - could arsenic have a role.
2009-01-14
Synergy of irofulven in combination with other DNA damaging agents: synergistic interaction with altretamine, alkylating, and platinum-derived agents in the MV522 lung tumor model.
2008-12
Relationship between frailty and cognitive decline in older Mexican Americans.
2008-10
Atom efficient cyclotrimerization of dimethylcyanamide catalyzed by aluminium amide: a combined experimental and theoretical investigation.
2008-08-21
Lessons from a time capsule: evolution, not revolution, in therapy for advanced non-small-cell lung cancer.
2008-07-01
Pretreatment CA-125 and risk of relapse in advanced ovarian cancer.
2006-03-20
Topotecan: weighing in when there are many options.
2005-10
Better treatments improve survival of CHD patients.
2005-09
Emerging drugs for ovarian cancer.
2005-05
Recurrent ovarian cancer: how important is it to treat to disease progression?
2004-11-15
Carboplatin, doxorubicin and etoposide in the treatment of tumours of unknown primary site.
2004-05-17
Long-term follow-up of a phase II trial of oral altretamine for consolidation of clinical complete remission in women with stage III epithelial ovarian cancer in the Southwest Oncology Group.
2004-04-17
A phase II study of sequential carboplatin, paclitaxel and topotecan in patients with previously untreated advanced ovarian cancer.
2004-02-23
Do CA125 response criteria overestimate tumour response in second-line treatment of epithelial ovarian carcinoma?
2004-01-26
Medication sheets for patients. Oral chemotherapy.
2004-01-07
Oral altretamine used as salvage therapy in recurrent ovarian cancer.
2004-01
Outcome of ATP-based tumor chemosensitivity assay directed chemotherapy in heavily pre-treated recurrent ovarian carcinoma.
2003-07-03
Oral melphalan as a treatment for platinum-resistant ovarian cancer.
2003-06-16
Altretamine (hexamethylmelamine) in the treatment of platinum-resistant ovarian cancer: a phase II study.
2003-02
Oral cancer treatment: developments in chemotherapy and beyond.
2002-10-21
Part II: chemotherapy for epithelial ovarian cancer-treatment of recurrent disease.
2002-09
A phase II study of mitomycin C, cisplatin and continuous infusion 5-fluorouracil (MCF) in the treatment of patients with carcinoma of unknown primary site.
2002-04-22
Solvent, emulsifier and drug concentration factors in poly(D,L-lactic acid) microspheres containing hexamethylmelamine.
2002-01-29
Recent advances in the treatment of epithelial ovarian cancer.
2001-09
A phase I study of paclitaxel and altretamine as second-line therapy to cisplatin regimens for ovarian cancer.
2001-08
Phase II trial of oral altretamine for consolidation of clinical complete remission in women with stage III epithelial ovarian cancer: a Southwest Oncology Group trial (SWOG-9326).
2001-08
Phase II study of vinorelbine in the treatment of platinum-resistant ovarian carcinoma.
2001-04
Altretamine is an effective palliative therapy of patients with recurrent epithelial ovarian cancer.
2001-02
A rapid and systematic review of the clinical effectiveness and cost-effectiveness of topotecan for ovarian cancer.
2001
Altretamine for the treatment of metastatic renal cell carcinoma. A Hoosier Oncology Group trial.
2001
Clinical pharmacokinetics of altretamine.
1995-06
The w/w+ SMART is a useful tool for the evaluation of pesticides.
1994-07
Incidence of neuropathy in 395 patients with ovarian cancer treated with or without cisplatin.
1990-10-15
Randomised trial comparing two combination chemotherapy regimens (Hexa-CAF vs CHAP-5) in advanced ovarian carcinoma.
1984-09-15
Orthostatic hypotension as a complication of hexamethylmelamine antidepressant interaction.
1983-05
Hexamethylmelamine chemotherapy for disseminated endometrial cancer.
1981-09
Single-agent chemotherapy for recurrent carcinoma of the cervix.
1980
Phase II evaluation of hexamethylmelamine in advanced breast cancer: a Southwest Oncology Group study.
1979-08
Hexamethylmelamine: an evaluation of its role in the treatment of ovarian cancer.
1979-04-01
Patents

Patents

20010004454
41
JP2006502184A
41
JP2008533019A
34
JP2011528275A
456
JP4397691B2
21
US3424752
2

Sample Use Guides

In Vivo Use Guide
HEXALEN® (altretamine) capsules are administered orally. Doses are calculated on the basis of body surface area. HEXALEN® (altretamine) capsules may be administered either for 14 or 21 consecutive days in a 28-day cycle at a dose of 260 mg/m²/day. The total daily dose should be given as 4 divided oral doses after meals and at bedtime.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Hexamethylmelamine inhibited colony formation when incubated with A204 cells for 1 hour (short-term exposure) in the presence of the hepatic metabolizing system (S-9).
Long-term (10-day) exposure of Hexamethylmelamine (Altretamine) inhibited colony formation by human rhabdomyosarcoma cell line A204 by 70% at a concentration of 150 ug/ml.
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:53:15 GMT 2025
Edited
by admin
on Wed Apr 02 09:53:15 GMT 2025
Record UNII
Q8BIH59O7H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALTRETAMINE [HSDB]
Preferred Name English
ALTRETAMINE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
Altretamine [WHO-DD]
Common Name English
1,3,5-TRIAZINE-2,4,6-TRIAMINE, N,N,N',N',N'',N''-HEXAMETHYL-
Systematic Name English
Hexamethylmelamine
Common Name English
ALTRETAMINE [MI]
Common Name English
ALTRETAMINE [USP-RS]
Common Name English
ALTRETAMINE [MART.]
Common Name English
ALTRETAMINE [ORANGE BOOK]
Common Name English
NSC-13875
Code English
ALTRETAMINE [USAN]
Common Name English
HEXALEN
Systematic Name English
altretamine [INN]
Common Name English
ALTRETAMINE [VANDF]
Common Name English
ALTRETAMINE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548524
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
NCI_THESAURUS C292
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
FDA ORPHAN DRUG 983
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
NDF-RT N0000175558
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
WHO-VATC QL01XX03
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
WHO-ATC L01XX03
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
NDF-RT N0000000236
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
Code System Code Type Description
RXCUI
5296
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY RxNorm
SMS_ID
100000087660
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
ALANWOOD
altretamine
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
HSDB
7559
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
211-428-4
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
CAS
645-05-6
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
MESH
D006585
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
DRUG BANK
DB00488
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
USAN
CC-25
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
WIKIPEDIA
ALTRETAMINE
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL1455
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
RS_ITEM_NUM
1017105
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
IUPHAR
7112
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
INN
4825
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
EVMPD
SUB05382MIG
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID4022579
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
FDA UNII
Q8BIH59O7H
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
MERCK INDEX
m1586
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY Merck Index
DRUG CENTRAL
141
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
PUBCHEM
2123
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
NCI_THESAURUS
C544
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
CHEBI
24564
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
NSC
13875
Created by admin on Wed Apr 02 09:53:15 GMT 2025 , Edited by admin on Wed Apr 02 09:53:15 GMT 2025
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of ALTRETAMINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of N-(HYDROXYMETHYL)PENTAMETHYLMELAMINE
METABOLITE -> PARENT
Structure of 4,6-BIS(DIMETHYLAMINO)-N-METHYL-N-METHYLENE-1,3,5-TRIAZIN-2-AMINIUM
METABOLITE -> PARENT
CYP450-mediated metabolism generated this electrophilic iminium species that is capaple of reacting covalently with DNA guanine and cytosine residues, as well as protein.
URINE
Structure of PENTAMETHYLMELAMINE
METABOLITE -> PARENT
Structure of 2,4,6-TRIMETHYLMELAMINE
METABOLITE -> PARENT
Related Record Type Details
Structure of 4,6-BIS(DIMETHYLAMINO)-1,3,5-TRIAZINE-2(1H)-ONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 6-(DIMETHYLAMINO)-1,3,5-TRIAZINE-2,4(1H,3H)-DIONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 4-CHLORO-6-(DIMETHYLAMINO)-1,3,5-TRIAZINE-2(1H)-ONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 4,6-DICHLORO-N,N-DIMETHYL-1,3,5-TRIAZINE-2-AMINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 6-CHLORO-N2,N2,N4,N4-TETRAMETHYL-1,3,5-TRIAZINE-2,4-DIAMINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of ALTRETAMINE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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