Midodrine

Structural formula
	Structural formula without stereochemistry
General
Non-proprietary name	Midodrine
other names	(±) -1- (2,5-dimethoxyphenyl) -2-glycine amidoethanol; ( RS ) -1- (2,5-dimethoxyphenyl) -2-glycine amidoethanol; 2-Amino- N - [2- (2,5-dimethoxyphenyl) -2-hydroxyethyl] acetamide ( IUPAC ) ;
Molecular formula	C 12 H 18 N 2 O 4
External identifiers / databases
EC number	255-945-3
ECHA InfoCard	100.050.842
PubChem	4195
ChemSpider	4050
DrugBank	DB00211
Wikidata	Q415051
Drug information
ATC code	C01 CA17
Drug class	Sympathomimetic
Mechanism of action	α 1 adrenoceptor agonist
properties
Molar mass	254.28 g mol −1
Melting point	102-104 ° C (midodrine) ; 192–193 ° C (midodrine hydrochloride) ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 301
	P: 301 + 310
Toxicological data	68.8 mg kg −1 ( LD 50 , rat , oral , hydrochloride)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Midodrin ( trade name Gutron ^® ) is a drug used to treat hypotonic circulatory disorders ( orthostatic hypotension ). It is a prodrug whose metabolite desglymidodrin is the actual active ingredient.

The drug is used in the form of its hydrochloride .

Chemical structure

Midodrin contains the basic structure 2-phenylethylamine , which is also the basis of the body's own neurotransmitters adrenaline and noradrenaline .

Stereochemistry

Midodrine contains a stereocenter and consists of two enantiomers. This is a racemate , i.e. a 1: 1 mixture of ( R ) - and ( S ) -form:

Enantiomers of midodrine
CAS number: 133163-25-4	CAS number: 133267-39-7

Pharmacokinetics and Effect

Structural formula of desglymidodrine

By amide cleavage ( deglycination ), the active substance desglymidodrine is produced in the organism from the precursor midodrine . This can only cross the blood-brain barrier with difficulty. Desglymidodrine is an agonist at α ₁ -adrenoceptors (direct sympathomimetic ) and causes an increase in the tone of the arterial and venous vascular muscles and thereby increases blood pressure ( vasoconstriction ).

Trade names

Gutron (D, A, CH)

Individual evidence

↑ ^a ^b ^c Entry on midodrin. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
↑ ^a ^b Datasheet Midodrine hydrochloride from Sigma-Aldrich , accessed on October 16, 2016 ( PDF ).
↑ Red List online, as of October 12, 2017.
↑ AM comp. d. Switzerland, as of October 2009.
↑ AGES-PharmMed, as of October 2009.
↑ HJ Roth u. H. Fenner: Drugs . Thieme, Stuttgart a. New York 1988, pp. 408-409.
↑ Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) . Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10-9 , p. 196.

[RÖMPP_Online-1] Entry on midodrin. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.

[Sigma-2] Datasheet Midodrine hydrochloride from Sigma-Aldrich , accessed on October 16, 2016 ( PDF ).

[3] Red List online, as of October 12, 2017.

[4] AM comp. d. Switzerland, as of October 2009.

[5] AGES-PharmMed, as of October 2009.

[6] HJ Roth u. H. Fenner: Drugs . Thieme, Stuttgart a. New York 1988, pp. 408-409.

[Rote_Liste-7] Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) . Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10-9 , p. 196.