3092-17-9 Usage
Description
Midodrine hydrochloride is a direct-acting sympathomimetic with selective alpha-adrenergic agonist activity. It is the N-glycyl prodrug of the selective α1-agonist desglymidodrine, which is used therapeutically for its vasoconstrictor properties. Midodrine is orally active and is rapidly metabolized in the liver and throughout the body, with its main active moiety being its major metabolite, deglymidodrine. It is a crystalline solid and is available under the brand names Orvaten (Upsher-Smith) and Proamatine (Shire).
Uses
Used in Pharmaceutical Industry:
Midodrine hydrochloride is used as a peripheral vasoconstrictor for the treatment of certain hypotensive states, specifically symptomatic orthostatic hypotension. It helps increase blood pressure and alleviate symptoms associated with low blood pressure, such as dizziness and fatigue.
Used in Morphine Antagonist Applications:
Midodrine hydrochloride is used as a morphine antagonist, which means it can counteract the effects of morphine, particularly in cases where patients experience low blood pressure as a side effect of morphine use.
Used in Hypertensive Treatment:
Midodrine hydrochloride is used as a phenylalkanolamine derivative for treating hypertensive conditions. It has been found to be effective due to its long-lasting blood pressure-increasing effects, making it a valuable option for managing high blood pressure in patients.
Originator
Gutron,Hormonchemie,W. Germany,1977
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.
Therapeutic Function
Peripheral vasotonic, Antihypotensive
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)
Check Digit Verification of cas no
The CAS Registry Mumber 3092-17-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,0,9 and 2 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 3092-17:
(6*3)+(5*0)+(4*9)+(3*2)+(2*1)+(1*7)=69
69 % 10 = 9
So 3092-17-9 is a valid CAS Registry Number.
InChI:InChI=1/C18H14ClFN3O/c1-11-22(24)10-13-9-21-18(14-4-2-3-5-16(14)20)15-8-12(19)6-7-17(15)23(11)13/h2-8,10,24H,9H2,1H3
3092-17-9Relevant articles and documents
COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS
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Page/Page column 45-49; 60, (2010/12/31)
The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.
AN IMPROVED PROCESS FOR THE SYNTHESIS OF (±) 2-AMINO-N-[2,(S,5-DIMETHOXYPHENYL)-2-HYDROXYETHYL] ACETAMIDE MONOHYDROCHLORIDE
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Page 11-12, (2008/06/13)
This invention relates to an improved process for synthesizing (±) 2-Amino-N-[2,(S,5-dimethoxyphenyl)-2-hydroxyethyl] acetamide monohydrochloride in good yield and in a cost effective manner from 1-(2,5dimethoxyphenyl)-2-bromoethanone by reacting the same
A process for the preparation of midodrine
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Example 4, (2010/01/31)
The invention provides a process for the preparation of 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide of the formula 1 by hydrogenolysis of substituted 2-dibenzylamino-N-[2-(2',5'-dimethoxyphenyl)-2-hydroxy-ethyl]acetamide having the formula (5), wherein Ar and Ar' are aryl groups.
