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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
HEXALEN

Cmax

ValueDoseCo-administeredAnalytePopulation
790 ng/mL
200 mg single, oral
ALTRETAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1147 ng × h/mL
200 mg single, oral
ALTRETAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.2 h
200 mg single, oral
ALTRETAMINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
ALTRETAMINE plasma
Homo sapiens

Doses

AEs

PubMed

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
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
Record UNII
Q8BIH59O7H
Record Status Validated (UNII)
Record Version