Mannomustine

Mannomustine (INN), also known as mannitol nitrogen mustard, tradename Degranol is an old alkylating antineoplastic agent from the group of nitrogen mustards. It was first synthesized and characterized in 1957 by Vargha et al.[1]

Mannomustine
Clinical data
Trade namesDegranol
Pregnancy
category
  • AU: D
Routes of
administration		Intramuscular
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
Identifiers
IUPAC name
  • (2-chloroethyl)({6-[(2-chloroethyl)amino]-2,3,4,5-tetrahydroxyhexyl})amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H24Cl4N2O4
Molar mass378.11 g·mol−1
3D model (JSmol)
SMILES
  • ClCCNC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNCCCl
InChI
  • InChI=1S/C10H22Cl2N2O4/c11-1-3-13-5-7(15)9(17)10(18)8(16)6-14-4-2-12/h7-10,13-18H,1-6H2/t7-,8-,9-,10-/m1/s1
  • Key:MQXVYODZCMMZEM-ZYUZMQFOSA-N

The mechanism of antineoplastic activity of mannomustine, like for all other alkylating agents, lies in its ability to alkylate DNA guanine nucleobases and, thus, to prevent uncoupling of DNA strands, which is a required step for any cell to divide.

Mannomustine was, at the time of its creation as a drug, claimed to be considerably less toxic than mechlorethamine. For example, the LD50 in rats, for intravenous mannomustine administration route, is claimed to be about 56 mg/kg.[2]

See also

References
  1. Vargha et al., J. Chem. Soc. 1957, 805.
  2. Scherf et al., Arzneim.-Forsch. 20, 1467 (1970)
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