Midodrine

Midodrine
	Above: molecular structure of midodrine Below: 3D representation of a midodrine molecule
Clinical data
Trade names	Amatine, Gutron, Orvaten, ProAmatine, others
Other names	ST-1085; TS-701; 3,6-Dimethoxy-β-hydroxy-N-aminoethanonyl-2-phenylethylamine; 2-Amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide; 1-2',5'-Dimethoxyphenyl-1)-2 glycinamidoethanol
AHFS/Drugs.com	Monograph
MedlinePlus	a616030
License data	US DailyMed: Midodrine;
Pregnancy; category	AU: C;
Routes of; administration	By mouth
Drug class	α1-Adrenergic receptor agonist; Antihypotensive agent
ATC code	C01CA17 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	93% (as desglymidodrine)
Metabolism	Deglycination
Metabolites	• Desglymidodrine
Onset of action	≤1 hour
Elimination half-life	Midodrine: 0.5 hours; Desglymidodrine: 2–4 hours
Duration of action	2–6 hours
Identifiers
	IUPAC name (RS)-N-[2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl]glycinamide;
CAS Number	42794-76-3 ;
PubChem CID	4195;
IUPHAR/BPS	7240;
DrugBank	DB00211 ;
ChemSpider	4050 ;
UNII	6YE7PBM15H;
KEGG	D08220 ;
ChEBI	CHEBI:6933 ;
ChEMBL	ChEMBL1201212 ;
CompTox Dashboard (EPA)	DTXSID0023321 ;
ECHA InfoCard	100.151.349 100.050.842, 100.151.349
Chemical and physical data
Formula	C12H18N2O4
Molar mass	254.286 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES O=C(NCC(O)c1cc(OC)ccc1OC)CN;
	InChI InChI=1S/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16) ; Key:PTKSEFOSCHHMPD-UHFFFAOYSA-N ;
	(verify)

Midodrine, sold under the brand names ProAmatine and Orvaten among others, is an antihypotensive medication used to treat orthostatic hypotension (low blood pressure when standing) and urinary incontinence.^[3]^[5]^[1] It is taken by mouth.^[3]^[1]

Side effects of midodrine include hypertension (high blood pressure), paresthesia, itching, goosebumps, chills, urinary urgency, urinary retention, and urinary frequency.^[3] Midodrine is a prodrug of its active metabolite desglymidodrine.^[3]^[1] This metabolite acts as a selective agonist of the α₁-adrenergic receptor.^[3]^[1] This in turn results in vasoconstriction and increased blood pressure.^[3]^[1]

Midodrine was discovered by 1971^[6] and was introduced for medical use in the United States in 1996.^[7]

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Cite error: The named reference DrugBank was invoked but never defined (see the help page).
^ "Proamatine- midodrine hydrochloride tablet". DailyMed. Retrieved 14 August 2021.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "ProAmatine® (midodrine hydrochloride) Tablets" (PDF). fda.gov. Food and Drug Administration. Archived from the original (PDF) on 5 April 2021. Retrieved 28 August 2024.
^ ^a ^b ^c ^d ^e ^f Gilden JL (2004). "Midodrine and Other Sympathomimetics". Primer on the Autonomic Nervous System. Elsevier. pp. 413–415. doi:10.1016/b978-012589762-4/50113-4. ISBN 978-0-12-589762-4.
^ "GE Healthcare". AdisInsight. 21 October 2021. Retrieved 28 August 2024.
^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
^ Kymes SM, Sullivan C, Jackson K, Raj SR (May 2020). "Real-world droxidopa or midodrine treatment persistence in patients with neurogenic orthostatic hypotension or orthostatic hypotension". Autonomic Neuroscience. 225 102659. doi:10.1016/j.autneu.2020.102659. PMID 32200263.

[DrugBank-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Cite error: The named reference DrugBank was invoked but never defined (see the help page).

[2] "Proamatine- midodrine hydrochloride tablet". DailyMed. Retrieved 14 August 2021.

[Midodrine-Label-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "ProAmatine® (midodrine hydrochloride) Tablets" (PDF). fda.gov. Food and Drug Administration. Archived from the original (PDF) on 5 April 2021. Retrieved 28 August 2024.

[Gilden2004-4] ^ ^a ^b ^c ^d ^e ^f Gilden JL (2004). "Midodrine and Other Sympathomimetics". Primer on the Autonomic Nervous System. Elsevier. pp. 413–415. doi:10.1016/b978-012589762-4/50113-4. ISBN 978-0-12-589762-4.

[AdisInsight-5] "GE Healthcare". AdisInsight. 21 October 2021. Retrieved 28 August 2024.

[Elks2014-6] Cite error: The named reference Elks2014 was invoked but never defined (see the help page).

[7] Kymes SM, Sullivan C, Jackson K, Raj SR (May 2020). "Real-world droxidopa or midodrine treatment persistence in patients with neurogenic orthostatic hypotension or orthostatic hypotension". Autonomic Neuroscience. 225 102659. doi:10.1016/j.autneu.2020.102659. PMID 32200263.

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