Fosopamine

Fosopamine
Clinical data
Other names	Fosfenamine; N-Methyldopamine 4-O-phosphate; Epinine 4-O-phosphate; SIM-2055; Z-2055
Routes of; administration	Oral
Drug class	Dopamine receptor agonist
Identifiers
	IUPAC name [2-hydroxy-4-[2-(methylamino)ethyl]phenyl] dihydrogen phosphate;
CAS Number	103878-96-2;
PubChem CID	65878;
ChemSpider	59287;
UNII	50Q2Q042YR;
ChEMBL	ChEMBL2104671;
CompTox Dashboard (EPA)	DTXSID70869409 ;
Chemical and physical data
Formula	C9H14NO5P
Molar mass	247.187 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CNCCC1=CC(=C(C=C1)OP(=O)(O)O)O;
	InChI InChI=1S/C9H14NO5P/c1-10-5-4-7-2-3-9(8(11)6-7)15-16(12,13)14/h2-3,6,10-11H,4-5H2,1H3,(H2,12,13,14); Key:WHEGQKBWPSOMHG-UHFFFAOYSA-N;

Fosopamine (INNTooltip International Nonproprietary Name; developmental code names SIM-2055, Z-2055; also known as fosfenamine or N-methyldopamine 4-O-phosphate) is a dopamine receptor agonist of the phenethylamine and catecholamine families which was under development for the treatment of hypertension but was never marketed.^[1]^[2] It is taken orally.^[1] Fosopamine is a prodrug of epinine (N-methyldopaine) and is said to be selectively metabolized into epinine in the kidneys.^[3] The drug was being developed by AstraZeneca and Zambon Group SpA.^[1] It reached phase 2 clinical trials prior to the discontinuation of its development.^[1]

References

^ ^a ^b ^c ^d ^e ^f "Fosopamine". AdisInsight. 7 April 1999. Retrieved 27 February 2025.
^ Negwer M (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. ISBN 978-3-05-500156-7. Retrieved 27 February 2025.
^ Supuran C, Angeli A, Tanini D (2024). Advances in Prodrugs: Design and Therapeutic Applications. Elsevier. p. 296. ISBN 978-0-443-15634-2. Retrieved 27 February 2025.