Chemical compound
Pharmaceutical compound
Ritodrine , formerly sold under the brand nameYutopar among others, is atocolytic drug used to stoppremature labor .[ 2] [ 3] FDA Orange Book . It was available inoral tablets or as aninjection and was typically used as thehydrochloride salt .
The drug acts as aselective β2 -adrenergic receptor agonist .[ 4]
It was first approved for medical use in theUnited States in 1984.[ 5]
Ritodrine is used to treatpreterm labor .[ 2]
Possiblecontraindications of ritodrine includetype 2 diabetes ,high blood pressure , andmigraines .
Mostside effects of β2 -adrenergic receptor agonists result from their concurrentβ1 -adrenergic receptor agonistic activity, and include increase inheart rate , rise insystolic blood pressure , decrease indiastolic blood pressure ,chest pain secondary tomyocardial infarction , andarrhythmia . β-Adrenergic receptor agonists may also causefluid retention secondary to decrease in water clearance, which when added to thetachycardia and increasedmyocardial work, may result inheart failure . In addition, they increasegluconeogenesis in theliver andmuscle resulting inhyperglycemia , which increasesinsulin requirements indiabetic patients. The passage of β-adrenergic receptor agonists through theplacenta does occur and may be responsible for fetal tachycardia, as well ashypoglycemia or hyperglycemia at birth. It has also been associated withpostpartum bleeding .[citation needed
Ritodrine has been reported rarely to cause serious side effects includingrhabdomyolysis ,hepatotoxicity ,leukopenia ,pulmonary edema , andpsychiatric symptoms , among others.[ 6] [ 7] [ 8] [ 9] [ 10]
Ritodrine is a short-actingβ2 -adrenergic receptor agonist – a class of medication used for smooth muscle relaxation (other similar drugs are used in asthma or other pulmonary diseases such assalbutamol [albuterol]). Since ritodrine has a bulkyN -substituent, it has high β2 -adrenergic receptorselectivity . Also, the 4-hydroxy group on thebenzene ring is important for activity as it is needed to formhydrogen bonds . Since the drug is β2 -selective, it is used forpremature labor .[ 11]
The 4-hydroxy group of ritodrine makes it susceptible tometabolism bycatechol-O -methyl transferase (COMT).
Ritodrine, also known as 4-hydroxy-β-hydroxy-N -(4-hydroxyphenylethyl)amphetamine or asN -(4-hydroxyphenylethyl)-4-hydroxynorephedrine, is asubstituted phenethylamine andamphetamine derivative .[ 12] [ 13] [ 14]
The experimentallog P of ritodrine is 2.4 and its predicted ranges from 1.53 to 2.3.[ 12] [ 13] [ 14]
Ritodrine was first approved for medical use in theUnited States in 1984.[ 5]
Society and culture [ edit ] Ritodrine is thegeneric name of the drug and itsINN Tooltip International Nonproprietary Name ,USAN Tooltip United States Adopted Name ,BAN Tooltip British Approved Name , andDCF Tooltip Dénomination Commune Française .[ 15] [ 16] hydrochloride salt , its generic name isritodrine hydrochloride and this is itsUSAN Tooltip United States Adopted Name andBANM Tooltip British Approved Name .[ 15] [ 16] DU-21220 .[ 15] Pre-Par ,Utopar , andYutopar , among others.[ 15] [ 16]
^ Finkelstein BW (1981). "Ritodrine (Yutopar, Merrell Dow Pharmaceuticals Inc.)".Drug Intelligence & Clinical Pharmacy .15 (6):425– 33.doi :10.1177/106002808101500601 .S2CID 75942075 . ^a b Yaju Y, Nakayama T (November 2006). "Effectiveness and safety of ritodrine hydrochloride for the treatment of preterm labour: a systematic review".Pharmacoepidemiol Drug Saf .15 (11):813– 822.doi :10.1002/pds.1317 .PMID 16981213 . ^ 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 . Archived fromthe original (PDF) on 2019-08-25. Retrieved2008-10-05 . ^ Mangrella M, Torella M, Russo F, Rossi F, Piucci B, Cantoni V (June 1999). "[Pharmacology of ritodrine]".Minerva Ginecol (in Italian).51 (6):233– 244.PMID 10479875 . ^a b Kleemann A, Kutscher B (2022).Ullmann's Pharmaceuticals ISBN 978-3-527-80733-8 . Retrieved30 August 2024 . ^ Sun L, Tang M, Peng M, Xu P, Wang Y (January 2023)."Ritodrine-induced rhabdomyolysis and psychiatric symptoms: a case report and literature review" .BMC Pregnancy Childbirth .23 (1): 11.doi :10.1186/s12884-022-05299-2 PMC 9824990 PMID 36611175 . ^ Ceriani R, Borroni G, Bissoli F (June 1998). "Ritodrine-related liver injury. Case reports and review of the literature".Ital J Gastroenterol Hepatol .30 (3):315– 317.PMID 9759604 . ^ Wu CD, Chao AS, Cheng PJ, Soong YK (December 1996). "Ritodrine-induced leukopenia: a case report and literature review".Changgeng Yi Xue Za Zhi .19 (4):388– 391.PMID 9041773 . ^ Castro Fernández M, Romero Gómez M, Grande Santamaría L, Caballero Manzano M (September 1999). "[Acute hepatitis due to ritodrine]".Med Clin (Barc) (in Spanish).113 (6): 239.PMID 10472614 . ^ Alper M, Cohen WR (May 1983). "Pulmonary edema associated with ritodrine and dexamethasone treatment of threatened premature labor. A case report".J Reprod Med .28 (5):349– 352.PMID 6152991 . ^ Medicinal Chemistry of Adrenergics and Cholinergics Archived 2010-11-04 at theWayback Machine ^a b "Ritodrine" .PubChem . Retrieved30 August 2024 .^a b "C17H21NO3" .ChemSpider . 2024-08-30. Retrieved2024-08-30 .^a b "Ritodrine: Uses, Interactions, Mechanism of Action" .DrugBank Online . 31 December 1984. Retrieved30 August 2024 .^a b c d Schweizerischer Apotheker-Verein (2000).Index Nominum 2000: International Drug Directory ISBN 978-3-88763-075-1 . Retrieved30 August 2024 . ^a b c Morton IK, Hall JM (1999).Concise Dictionary of Pharmacological Agents: Properties and Synonyms ISBN 978-0-7514-0499-9 . Retrieved30 August 2024 .
α1
Agonists Antagonists Abanoquil ADRIANA Ajmalicine Alfuzosin Anisodamine Anisodine Atiprosin Atypical antipsychotics (e.g.,brexpiprazole ,clozapine ,olanzapine ,quetiapine ,risperidone )Benoxathian Beta blockers (e.g.,adimolol ,amosulalol ,arotinolol ,carvedilol ,eugenodilol ,labetalol )Buflomedil Bunazosin Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g.,acetergamine ,ergotamine ,dihydroergotamine ,lisuride ,nicergoline ,terguride )Etoperidone Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Neldazosin Niaprazine Niguldipine Pardoprunox Pelanserin Perlapine Phendioxan Phenoxybenzamine Phentolamine Phenylpiperazine antidepressants (e.g.,hydroxynefazodone ,nefazodone ,trazodone ,triazoledione )Piperoxan Prazosin Quinazosin Quinidine Silodosin Spegatrine Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline 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 Antagonists 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g.,asenapine ,brexpiprazole ,clozapine ,lurasidone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,zotepine )Azapirones (e.g.,buspirone ,gepirone ,ipsapirone ,tandospirone )BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan Ketanserin Lisuride mCPP Mianserin Mirtazapine NAN-190 Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine Setiptiline Spegatrine Spiroxatrine Sunepitron Terguride Tolazoline Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,loxapine ,thioridazine )Yohimbine
β
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted 1-Aminomethylindanes (e.g.,2CB-Ind ,AMMI ,bromojimscaline ,jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam ,lorcaserin ,7-chlorolorcaserin ,SCHEMBL5334361 )3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine ,3-PPP ,OSU-6162 (PNU-96391) ,LPH-5 ,LPH-48 ,Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g.,adrenochrome ,adrenolutin )Benzocyclobutenes (e.g.,2CBCB-NBOMe ,bromotomscaline ,S33005 ,TCB-2 ,tomscaline )Benzoxepins (e.g.,BBOX ,IBOX ,TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g.,LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI ,RU-27849 ,DEIMDHPCA ,DEMPDHPCA ,DEMPDHPCA-2C-D ,RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA ,TMT ,tranylcypromine )Phenylpiracetams (e.g.,phenylpiracetam ,MRZ-9547 ,RGPU-95 )Pyridopyrroloquinoxalines (e.g.,lumateperone ,deulumateperone ,IHCH-7079 ,IHCH-7086 ,IHCH-7113 ,ITI-1549 )Tetrahydrobenzopyranylamines (e.g.,CT-5126 )Tolazoline Tricyclics (e.g.,AMDA ,AMDH ,benzoctamine ,dizocilpine ,SpAMDA )ZC-B
Related compounds 2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g.,1,3-DMBA Tooltip 1,3-dimethylbutylamine ,1,4-DMAA Tooltip 1,4-dimethylamylamine ,heptaminol ,iproheptine ,isometheptene ,methylhexanamine/ 1,3-DMAA ,octodrine ,oenethyl ,tuaminoheptane )Benzylamines (e.g.,benzylamine ,α-methylbenzylamine ,MDM1EA ,ALPHA ,M-ALPHA ,pargyline )Benzylpiperazines (e.g.,benzylpiperazine ,MDBZP ,fipexide )Cyclohexylaminopropanes (e.g.,propylhexedrine ,norpropylhexedrine )Cyclopentylaminopropanes (e.g.,isocyclamine ,cyclopentamine )Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine ,CT-4719 ,ORG-37684 )Phenylalkenylamines (e.g.,phenylbutenamine )Phenylalkynylamines (e.g.,phenylbutynamine )Phenylpiperazines (e.g.,1-phenylpiperazine ,mCPP Tooltip meta-chlorophenylpiperazine ,TFMPP Tooltip trifluoromethylphenylpiperazine ,oMPP Tooltip ortho-methylphenylpiperazine ,pFPP Tooltip para-fluorophenylpiperazine ,pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g.,phenylpropylamine ,homo-MDA ,homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine ,methiopropamine ,thiothinone )
