Meluadrine

Meluadrine
Clinical data
Other names	HSR-81; (R)-4-Hydroxytulobuterol
Drug class	Sympathomimetic; Tocolytic; β2-Adrenergic receptor agonist
Identifiers
	IUPAC name 4-[(1R)-2-(tert-butylamino)-1-hydroxyethyl]-3-chlorophenol;
CAS Number	134865-33-1 ; 134865-37-5 (tartrate);
PubChem CID	3045414;
ChemSpider	142963;
UNII	FYC8314117;
ChEMBL	ChEMBL2104709;
CompTox Dashboard (EPA)	DTXSID8048810 ;
Chemical and physical data
Formula	C12H18ClNO2
Molar mass	243.73 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C)NC[C@@H](C1=C(C=C(C=C1)O)Cl)O;
	InChI InChI=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; Key:LIXBJWRFCNRAPA-NSHDSACASA-N;

Meluadrine (INNTooltip International Nonproprietary Name), also known as meluadrine tartrate (JANTooltip 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.^[1]^[2]^[3]^[4]^[5] It was first described in the literature by 1994.^[6] The drug is also known as (R)-4-hydroxytulobuterol and is an active metabolite of tulobuterol.^[7]

References

^ Ballard A, Narduolo S, Ahmad HO, Cosgrove DA, Leach AG, Buurma NJ (June 2019). "The problem of racemization in drug discovery and tools to predict it". Expert Opinion on Drug Discovery. 14 (6): 527–539. doi:10.1080/17460441.2019.1588881. PMID 30882254.
^ "-drine sympathomimetics" (PDF). The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2018 (Stem Book 2018). World Health Organization.
^ Matsuda Y, Kouno S, Sakamoto H, Ikenoue T (October 2002). "Effects of meluadrine tartrate and ritodrine hydrochloride on oxytocin-induced uterine contraction, uterine arterial blood flow and maternal cardiovascular function in pregnant goats". Japanese Journal of Pharmacology. 90 (2): 107–113. doi:10.1254/jjp.90.107. PMID 12419879.
^ Matsuda Y, Kouno S, Sakamoto H, Ikenoue T (October 2002). "Effects of meluadrine tartrate on maternal metabolic responses and fetal hemodynamics in pregnant goats". Japanese Journal of Pharmacology. 90 (2): 114–120. doi:10.1254/jjp.90.114. PMID 12419880.
^ Ohashi T, Hashimoto S, Morikawa K, Kato H, Ito Y, Asano M, et al. (July 1996). "Potent inhibition of spontaneous rhythmic contraction by a novel beta 2-adrenoceptor agonist, HSR-81, in pregnant rat uterus". European Journal of Pharmacology. 307 (3): 315–322. doi:10.1016/0014-2999(96)00277-4. PMID 8836620.
^ Hashimoto S, Kawaguchi T, Yamauchi T, Ohashi T, Hosotani T, Morikawa K, et al. (1994). "Inhibitory effect of HSR-81, a novel β2-adrenoceptor agonist, on uterine contraction in late pregnancy". Japanese Journal of Pharmacology. 64: 211. doi:10.1016/S0021-5198(19)50479-6.
^ Glushkova MA, Popkov SV, Burdeinyi ML (2020). "Synthesis of the β2-Agonist Tulobuterol and Its Metabolite 4-Hydroxytulobuterol". Russian Journal of Organic Chemistry. 56 (3). Pleiades Publishing Ltd: 390–394. doi:10.1134/s1070428020030045. ISSN 1070-4280.

[BallardNarduoloAhmad2019-1] Ballard A, Narduolo S, Ahmad HO, Cosgrove DA, Leach AG, Buurma NJ (June 2019). "The problem of racemization in drug discovery and tools to predict it". Expert Opinion on Drug Discovery. 14 (6): 527–539. doi:10.1080/17460441.2019.1588881. PMID 30882254.

[WHO-INN-2018-2] "-drine sympathomimetics" (PDF). The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2018 (Stem Book 2018). World Health Organization.

[MatsudaKounoSakamoto2002a-3] Matsuda Y, Kouno S, Sakamoto H, Ikenoue T (October 2002). "Effects of meluadrine tartrate and ritodrine hydrochloride on oxytocin-induced uterine contraction, uterine arterial blood flow and maternal cardiovascular function in pregnant goats". Japanese Journal of Pharmacology. 90 (2): 107–113. doi:10.1254/jjp.90.107. PMID 12419879.

[MatsudaKounoSakamoto2002b-4] Matsuda Y, Kouno S, Sakamoto H, Ikenoue T (October 2002). "Effects of meluadrine tartrate on maternal metabolic responses and fetal hemodynamics in pregnant goats". Japanese Journal of Pharmacology. 90 (2): 114–120. doi:10.1254/jjp.90.114. PMID 12419880.

[OhashiHashimotoMorikawa1996-5] Ohashi T, Hashimoto S, Morikawa K, Kato H, Ito Y, Asano M, et al. (July 1996). "Potent inhibition of spontaneous rhythmic contraction by a novel beta 2-adrenoceptor agonist, HSR-81, in pregnant rat uterus". European Journal of Pharmacology. 307 (3): 315–322. doi:10.1016/0014-2999(96)00277-4. PMID 8836620.

[Hashimoto1994-6] Hashimoto S, Kawaguchi T, Yamauchi T, Ohashi T, Hosotani T, Morikawa K, et al. (1994). "Inhibitory effect of HSR-81, a novel β2-adrenoceptor agonist, on uterine contraction in late pregnancy". Japanese Journal of Pharmacology. 64: 211. doi:10.1016/S0021-5198(19)50479-6.

[GlushkovaPopkovBurdeinyi2020-7] Glushkova MA, Popkov SV, Burdeinyi ML (2020). "Synthesis of the β2-Agonist Tulobuterol and Its Metabolite 4-Hydroxytulobuterol". Russian Journal of Organic Chemistry. 56 (3). Pleiades Publishing Ltd: 390–394. doi:10.1134/s1070428020030045. ISSN 1070-4280.

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Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
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