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 names	Degranol
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	Intramuscular
ATC code	L01
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name (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^Y
UNII	E60VWA40D2
CompTox Dashboard (EPA)	DTXSID80922756 DTXSID40970470, DTXSID80922756
Chemical and physical data
Formula	C10H24Cl4N2O4
Molar mass	378.11 g·mol^−1
3D model (JSmol)	Interactive image
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

• Mannitol

References

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