Meluadrine

{{Short description|Abandoned tocolytic drug}}

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| class = Sympathomimetic; Tocolytic; β₂-Adrenergic receptor agonist

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| CAS_number = 134865-33-1

| CAS_supplemental =
134865-37-5 (tartrate)

| PubChem = 3045414

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| ChemSpiderID = 142963

| UNII = FYC8314117

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| ChEMBL = 2104709

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| synonyms = HSR-81; (R)-4-Hydroxytulobuterol

| IUPAC_name = 4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-3-chlorophenol

| C=12 | H=18 | Cl=1 | N=1 | O=2

| SMILES = CC(C)(C)NC[C@@H](C1=C(C=C(C=C1)O)Cl)O

| StdInChI = 1S/C12H18ClNO2/c1-12(2,3)14-7-11(16)9-5-4-8(15)6-10(9)13/h4-6,11,14-16H,7H2,1-3H3/t11-/m0/s1

| StdInChIKey = LIXBJWRFCNRAPA-NSHDSACASA-N

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Meluadrine ({{Abbrlink|INN|International Nonproprietary Name}}), also known as meluadrine tartrate ({{Abbrlink|JAN|Japanese Accepted Name}}; developmental code name HSR-81) in the case of the tartrate salt, is a sympathomimetic and β₂-adrenergic receptor agonist which was studied as a tocolytic drug but was never marketed.{{cite journal | vauthors = Ballard A, Narduolo S, Ahmad HO, Cosgrove DA, Leach AG, Buurma NJ | title = The problem of racemization in drug discovery and tools to predict it | journal = Expert Opinion on Drug Discovery | volume = 14 | issue = 6 | pages = 527–539 | date = June 2019 | pmid = 30882254 | doi = 10.1080/17460441.2019.1588881 | url = https://orca.cardiff.ac.uk/id/eprint/121600/ }}{{cite book | chapter = -drine sympathomimetics | title = The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2018 (Stem Book 2018) | chapter-url = https://cdn.who.int/media/docs/default-source/international-nonproprietary-names-(inn)/stembook-2018.pdf#page=95 | publisher = World Health Organization }}{{cite journal | vauthors = Matsuda Y, Kouno S, Sakamoto H, Ikenoue T | title = Effects of meluadrine tartrate and ritodrine hydrochloride on oxytocin-induced uterine contraction, uterine arterial blood flow and maternal cardiovascular function in pregnant goats | journal = Japanese Journal of Pharmacology | volume = 90 | issue = 2 | pages = 107–113 | date = October 2002 | pmid = 12419879 | doi = 10.1254/jjp.90.107 | doi-access = free }}{{cite journal | vauthors = Matsuda Y, Kouno S, Sakamoto H, Ikenoue T | title = Effects of meluadrine tartrate on maternal metabolic responses and fetal hemodynamics in pregnant goats | journal = Japanese Journal of Pharmacology | volume = 90 | issue = 2 | pages = 114–120 | date = October 2002 | pmid = 12419880 | doi = 10.1254/jjp.90.114 | doi-access = free }}{{cite journal | vauthors = Ohashi T, Hashimoto S, Morikawa K, Kato H, Ito Y, Asano M, Azuma H | title = Potent inhibition of spontaneous rhythmic contraction by a novel beta 2-adrenoceptor agonist, HSR-81, in pregnant rat uterus | journal = European Journal of Pharmacology | volume = 307 | issue = 3 | pages = 315–322 | date = July 1996 | pmid = 8836620 | doi = 10.1016/0014-2999(96)00277-4 }} It was first described in the literature by 1994.{{cite journal | vauthors = Hashimoto S, Kawaguchi T, Yamauchi T, Ohashi T, Hosotani T, Morikawa K, Kato H, Ito Y | title = Inhibitory effect of HSR-81, a novel β2-adrenoceptor agonist, on uterine contraction in late pregnancy. | journal = Japanese Journal of Pharmacology | date = 1994 | volume = 64 | page = 211 | doi = 10.1016/S0021-5198(19)50479-6 | url = https://cir.nii.ac.jp/crid/1362262943729883392 | doi-access = free }} The drug is also known as (R)-4-hydroxytulobuterol and is an active metabolite of tulobuterol.{{cite journal | vauthors = Glushkova MA, Popkov SV, Burdeinyi ML | title=Synthesis of the β2-Agonist Tulobuterol and Its Metabolite 4-Hydroxytulobuterol | journal=Russian Journal of Organic Chemistry | publisher=Pleiades Publishing Ltd | volume=56 | issue=3 | year=2020 | issn=1070-4280 | doi=10.1134/s1070428020030045 | pages=390–394}}