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;

Last updated March 31, 2025

Fosopamine (INN Tooltip 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

1 2 3 4 5 6 "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.

This drug article relating to the cardiovascular system is a stub. You can help Wikipedia by expanding it.

This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.

[AdisInsight-1] 1 2 3 4 5 6 "Fosopamine". AdisInsight. 7 April 1999. Retrieved 27 February 2025.

[Negwer1994-2] Negwer M (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. ISBN 978-3-05-500156-7 . Retrieved 27 February 2025.

[SupuranAngeliTanini2024-3] 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.

[1]

[2]

[3]

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: Biscaline BOH Buscaline DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone Propylone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

Clinical data

Other names	Fosfenamine; N-Methyldopamine 4-O-phosphate; Epinine 4-O-phosphate; SIM-2055; Z-2055
Routes of administration	Oral ^[1]
Drug class	Dopamine receptor agonist ^[1]
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

See also

References