Mannomustine

Mannomustine

Systematic (IUPAC) name
(2-chloroethyl)({6-[(2-chloroethyl)amino]-2,3,4,5-tetrahydroxyhexyl})amine
Clinical data
Trade names	Degranol
Pregnancy category	AU: D US: D (Evidence of risk) D
Dependence liability	not capable to cause dependency
Routes of administration	intramuscular only
Legal status	℞ (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
CAS Number	576-68-1 551-74-6
ATC code	L01
PubChem	CID 3033867
ChemSpider	2298447
Chemical data
Formula	C10H24Cl4N2O4
Molar mass	378.12 g/mol
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

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]

References

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