| Identification | More | [Name]
Midodrine hydrochloride | [CAS]
3092-17-9 | [Synonyms]
[+/-]-1-[2,5-DIMETHOXYPHENYL]-2-GLYCINAMIDOETHANOL HYDROCHLORIDE
AMATINE
GUTRON
HIPERTAN
METLIGINE
MIDODRINE
MIDODRINE HCL
MIDODRINE HYDROCHLORIDE
PROAMATINE
ST-1085
2-amino-n-(2-(2,5-dimethoxyphenyl)-2-hydroxyethyl)-acetamidmonohydrochlo
acetamide,2-amino-n-(beta-hydroxy-2,5-dimethoxyphenethyl)-,monohydrochloride,
ST-1085, Amatine, Gutron, Hipertan, Metligine, ProAmatine,
(±)-1-(2,5-dimethoxyphenyl)-2-glycinamidoethanol
(+/-)-1-(2,5-Dimethoxyphenyl)-2-glycinamidoethanol hydrochloride | [EINECS(EC#)]
622-590-4 | [Molecular Formula]
C12H19ClN2O4 | [MDL Number]
MFCD00079455 | [Molecular Weight]
290.74 | [MOL File]
3092-17-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
192-193°C | [storage temp. ]
-20°C Freezer | [form ]
neat | [Usage]
A phenylalkanolamine derivative which has been found to be effective in treating hypertensive conditions due to their long lasting blood pressure increasing effects | [InChIKey]
MGCQZNBCJBRZDT-UHFFFAOYSA-N | [CAS DataBase Reference]
3092-17-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed. | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
AB4343000
| [HS Code ]
29242990 |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Originator]
Gutron,Hormonchemie,W. Germany,1977 | [Uses]
A phenylalkanolamine derivative which has been found to be effective in treating hypertensive conditions due to their long lasting blood pressure increasing effects | [Uses]
morphine antagonist | [Definition]
ChEBI: A hydrochloride resulting from the combination of equimolar amounts of midodrine and hydrogen chloride. Midodrine is a direct-acting sympathomimetic with selective alpha-adrenergic agonist activity. The hydrochloride salt is used as a periph
ral vasoconstrictor in the treatment of certain hypotensive states. The main active moiety is its major metabolite, deglymidodrine. | [Manufacturing Process]
19.5 parts of carbobenzoxyglycine, 7.1 parts of triethylamine and 162 parts ofdry toluene are mixed with 11.2 parts of isovaleric acid chloride at 0°C toform the mixed anhydride and the mixture is agitated for two hours at 0°C.32.4 parts of 1-(2',5'-dimethoxyphenyl)-2-aminoethanol-(1) are then added,the mixture is agitated for four hours at a temperature between 0°C and+10°C and then left to stand overnight at that temperature. A thick crystalpaste forms. The reaction product is dissolved in 450 parts of ethyl acetateand 200 parts of water. The ethyl acetate solution is separated, washed withhydrochloric acid, sodium bicarbonate solution and water, dried over sodiumsulfate and inspissated. The inspissation residue is digested with 342 parts ofxylene, the required product crystallizing out. 34.9 parts of 1-(2',5'-dimethoxyphenyl)-2-(N-carbobenzoxyglycineamido)-ethanol-(1) are obtained.66.2 parts of 1-(2',5'-dimethoxyphenyl)-2-(N-carbobenzoxyglycineamido)-ethanol-(1) are hydrogenated in the presence of 6.6 parts of palladium carbon(10%) in 2,000 parts of glacial acetic acid. When no more hydrogen isabsorbed (3 mols of hydrogen are used), hydrogenation stops. The catalyst isremoved by suction and the equivalent quantity of hydrochloric acid in ethanolis added to the filtrate with agitation. During further agitation at roomtemperature 28.6 parts of crude 1-(2',5'-dimethoxyphenyl)-2-glycineamidoethanol-(1)hydrochloride crystallize, and are isolated andrecrystallized from water-methanol for purification. 22.1 parts of pure productare obtained with a melting point of 192°C to 193°C.
An alternative synthesis route is described by Kleeman and Engel. | [Brand name]
Orvaten (UpsherSmith); Proamatine (Shire). | [Therapeutic Function]
Peripheral vasotonic, Antihypotensive | [General Description]
Midodrine is the N-glycyl prodrug ofthe selectiveα1-agonist desglymidodrine. Removal of theN-glycyl moiety from midodrine occurs readily in the liver aswell as throughout the body, presumably by amidases.Midodrine is orally active and represents another example ofa dimethoxy-β-phenylethylamine derivative that is used therapeuticallyfor its vasoconstrictor properties. Specifically, it isused in the treatment of symptomatic orthostatic hypotension. | [Clinical Use]
Treatment of orthostatic hypotension, including dialysis
related hypotension | [Drug interactions]
Potentially hazardous interactions with other drugs
Adrenergic neurone blockers: midodrine antagonises
hypotensive effect.
Anaesthetics: risk of arrhythmias if given with
volatile anaesthetics.
Antidepressants: risk of arrhythmias and
hypertension if given with tricyclic antidepressants,
MAOIs and moclobemide.
Antihypertensives: antagonise hypertensive effect of
midodrine; risk of severe hypertension if given with
beta-blockers.
Dopaminergics: avoid with rasagiline and selegiline.
Other drugs which increase blood pressure:
enhanced hypertensive effect. | [Metabolism]
Undergoes enzymatic hydrolysis in the systemic
circulation to an active metabolite (desglymidodrine) |
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