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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
  • (2-chloroethyl)({6-[(2-chloroethyl)amino]-2,3,4,5-tetrahydroxyhexyl})amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.008.551 Edit this at Wikidata
Chemical and physical data
FormulaC10H24Cl4N2O4
Molar mass378.11 g·mol−1
3D model (JSmol)
  • ClCCNC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNCCCl
  • 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

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]

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

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References

[edit]
  1. ^ Vargha L, Toldy L, Fehér Ö, Lendvai S (1957). "151. Synthesis of new sugar derivatives of potential antitumour activity. Part I. Ethyleneimino-and 2-chloroethylamino-derivatives". Journal of the Chemical Society (Resumed).: 805–809. doi:10.1039/JR9570000805.
  2. ^ Scherf HR, Krüger C, Karsten C (1970). "Untersuchungen an Ratten über immunosuppressive Eigenschaften von Cytostatica unter besonderer Berücksichtigung der carcinogenen Wirkung" [Studies on rats regarding the immunosuppressive properties of cytostatics, with particular consideration of the carcinogenic effect.]. Arzneimittel-Forsch. (in German). 20: 1467.