Mannomustine

Chemical compound
  • AU: D
Routes of
administrationIntramuscularATC code
  • L01
Legal statusLegal status
  • In general: ℞ (Prescription only)
Pharmacokinetic dataMetabolismHepaticExcretionRenalIdentifiers
  • (2-chloroethyl)({6-[(2-chloroethyl)amino]-2,3,4,5-tetrahydroxyhexyl})amine
CAS Number
  • 576-68-1 551-74-6
PubChem CID
  • 3033867
ChemSpider
  • 2298447 checkY
UNII
  • E60VWA40D2
CompTox Dashboard (EPA)
  • DTXSID9020798 Edit this at Wikidata
ECHA InfoCard100.008.551 Edit this at WikidataChemical and physical dataFormulaC10H24Cl4N2O4Molar mass378.11 g·mol−13D model (JSmol)
  • Interactive image
  • 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

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

References

  1. ^ Vargha et al., J. Chem. Soc. 1957, 805.
  2. ^ Scherf et al., Arzneim.-Forsch. 20, 1467 (1970)
  • v
  • t
  • e
SPs/MIs
(M phase)
Block microtubule assembly
Block microtubule disassembly
DNA replication
inhibitor
DNA precursors/
antimetabolites
(S phase)
Folic acid
Purine
Pyrimidine
Deoxyribonucleotide
Topoisomerase inhibitors
(S phase)
I
II
II+Intercalation
Crosslinking of DNA
(CCNS)
Alkylating
Platinum-based
Nonclassical
Intercalation
Photosensitizers/PDTOther
Enzyme inhibitors
Receptor antagonists
Other/ungrouped
  • v
  • t
  • e
Vesicants
  • HN1
  • HN2
  • HN3
  • TL-301
  • TL-481
  • TL-512
  • TL-513
  • TL-695
  • TL-995
Antineoplastic agents
Neurotoxins
Other