Ritodrine

Ritodrine
Clinical data


AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral (tablets), parenteral (IV)
ATC code	G02CA01 (WHO)
Legal status
Legal status	US: Discontinued
Pharmacokinetic data
Protein binding	~56%
Metabolism	Hepatic, metabolites are inactive^[1]
Biological half-life	1.7–2.6 hours
Identifiers
IUPAC name 4-[2-[[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol
CAS Number	26652-09-5^Y
PubChem (CID)	33572
IUPHAR/BPS	7294
DrugBank	DB00867^Y
ChemSpider	30971^Y
UNII	I0Q6O6740J^Y
KEGG	D02359^Y
ChEMBL	CHEMBL785^Y
ECHA InfoCard	100.043.512
Chemical and physical data
Formula	C₁₇H₂₁NO₃
Molar mass	287.354 g/mol
3D model (Jmol)	Interactive image
SMILES O[C@H](c1ccc(O)cc1)[C@@H](NCCc2ccc(O)cc2)C
InChI InChI=1S/C17H21NO3/c1-12(17(21)14-4-8-16(20)9-5-14)18-11-10-13-2-6-15(19)7-3-13/h2-9,12,17-21H,10-11H2,1H3/t12-,17-/m0/s1^Y Key:IOVGROKTTNBUGK-SJCJKPOMSA-N^Y
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Ritodrine RYE-to-dreen (trade name Yutopar) is a tocolytic drug used to stop premature labor.^[2] This drug has been removed from the US market, according to FDA Orange Book. It was available in oral tablets or as an injection and was typically used as the hydrochloride salt, ritodrine hydrochloride.

Mechanism

Ritodrine is a short-acting β₂ adrenoreceptor agonist — a class of medication used for smooth muscle relaxation (other similar drugs are used in asthma or other pulmonary diseases such as salbutamol (albuterol)). Since ritodrine has a bulky N-substituent, it has high β₂ selectivity. Also, the 4-hydroxy group on the benzene ring is important for activity as it is needed to form hydrogen bonds. However, the 4-hydroxy group makes it susceptible to metabolism by catechol-O-methyl transferase (COMT). Since it is β₂-selective it is used for premature labor.^[3]

Side effects and potential contraindications

Most side effects of β₂ agonists result from their concurrent β₁ activity, and include increase in heart rate, rise in systolic pressure, decrease in diastolic pressure, chest pain secondary to myocardial infarction, and arrhythmia. Beta agonists may also cause fluid retention secondary to decrease in water clearance, which when added to the tachycardia and increased myocardial work, may result in heart failure. In addition, they increase gluconeogenesis in the liver and muscle resulting in hyperglycemia, which increases insulin requirements in diabetic patients. The passage of β agonists through the placenta does occur and may be responsible for fetal tachycardia, as well as hypoglycemia or hyperglycemia at birth.

Patients with type 2 diabetes, high blood pressure or migraines should bring this to their doctor's attention before receiving care.

It has also been associated with postpartum bleeding.

References

↑ Finkelstein, BW (1981). "Ritodrine (Yutopar, Merrell Dow Pharmaceuticals Inc.)". Drug Intelligence & Clinical Pharmacy. 15: 425–33. |access-date= requires |url= (help)
↑ Li X, Zhang Y, Shi Z (February 2005). "Ritodrine in the treatment of preterm labour: a meta-analysis" (PDF). The Indian journal of medical research. 121 (2): 120–7. PMID 15756046.
↑ Medicinal Chemistry of Adrenergics and Cholinergics

Tocolytics/labor repressants (G02CA)

β₂ adrenoreceptor agonists	Buphenine Fenoterol Hexoprenaline Ritodrine Terbutaline

Oxytocin antagonists	Atosiban

NSAIDs	Indometacin

Calcium channel blockers	Nifedipine

Myosin inhibitors	Magnesium sulfate

Adrenergic receptor modulators

α₁

Agonists 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline

Antagonists Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, risperidone) Benoxathian Buflomedil Bunazosin Carvedilol Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride) Etoperidone Eugenodilol Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 Labetalol mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Nefazodone Neldazosin Niaprazine Nicergoline Niguldipine Pardoprunox Pelanserin Phendioxan Phenoxybenzamine Phentolamine Piperoxan Prazosin Quinazosin Ritanserin Silodosin Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Trazodone Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine) Trimazosin Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Urapidil WB-4101 Zolertine

α₂

Agonists (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rilmenidine Romifidine Talipexole Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil XP21279 Xylazine Xylometazoline

Antagonists 1-PP Adimolol Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine) Azapirones (e.g., buspirone, tandospirone) BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan mCPP Mianserin Mirtazapine NAN-190 Olanzapine Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269970 Setiptiline Spiroxatrine Sunepitron Tolazoline Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Yohimbine

Agonists Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol

Antagonists Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

See also: Dopaminergics

Melatonergics

Serotonergics

Monoamine reuptake and release modulators

Monoamine metabolism modulators

Monoamine neurotoxins

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