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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Ritodrine
- Accession Number
- DB00867 (APRD00541)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
Adrenergic beta-agonist used to control premature labor.
- Structure
Structure for Ritodrine (DB00867)
- Synonyms
- p-Hydroxy-alpha-(1-((p-hydroxyphenethyl)amino)ethyl)benzyl alcohol
- Ritodrina
- Ritodrine
- Ritodrinium
- External IDs
- DU-21220
- Product Ingredients
Ingredient UNII CAS InChI Key Ritodrine hydrochloride ESJ56Q60GC 23239-51-2 IDLSITKDRVDKRV-UHFFFAOYSA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Yutopar Inj 50mg/5ml Liquid 10 mg Intravenous Bristol Labs Division Of Bristol Myers Squibb 1984-12-31 2001-07-30 Canada 
Yutopar Tab 10mg Tablet 10 mg Oral Bristol Labs Division Of Bristol Myers Squibb 1984-12-31 2001-07-30 Canada - International/Other Brands
- Yutopar
- Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Agents producing tachycardia
- Agents that produce hypertension
- Alcohols
- Amines
- Amino Alcohols
- Autonomic Agents
- Ethylamines
- Genito Urinary System and Sex Hormones
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Phenethylamines
- Propanolamines
- Propanols
- Reproductive Control Agents
- Sympathomimetics
- Sympathomimetics, Labour Repressants
- Tocolytic Agents
- UNII
- I0Q6O6740J
- CAS number
- 26652-09-5
- Weight
- Average: 287.3535
Monoisotopic: 287.152143543 - Chemical Formula
- C17H21NO3
- InChI Key
- IOVGROKTTNBUGK-SJCJKPOMSA-N
- 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
- IUPAC Name
- 4-(2-{[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)phenol
- SMILES
- C[C@H](NCCC1=CC=C(O)C=C1)[C@H](O)C1=CC=C(O)C=C1
Pharmacology
- Indication
For the treatment and prophylaxis of premature labour
- Pharmacodynamics
Beta-2 adrenergic receptors are located at sympathetic neuroeffector junctions of many organs, including uterus. Ritodrine is beta-2 adrenergic agonist. It stimulates beta-2 adrenergic receptor, increases cAMP level and decreases intracellular calcium concentration. The decrease of calcium concentration leads to a relaxation of uterine smooth muscle and, therefore, a decrease in premature uterine contractions.
- Mechanism of action
Ritodrine is beta-2 adrenergic agonist. It binds to beta-2 adrenergic receptors on outer membrane of myometrial cell, activates adenyl cyclase to increase the level of cAMP which decreases intracellular calcium and leads to a decrease of uterine contractions.
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
~56%
- Metabolism
Hepatic, by both the mother and fetus
- Route of elimination
- Not Available
- Half life
1.7-2.6 hours
- Clearance
- Not Available
- Toxicity
LD50=64mg/kg (mice, IV); LD50=540 mg/kg (mice, oral); LD50=85 mg/kg (rat, IV)
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid The risk or severity of hypertension can be increased when Ritodrine is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid. 1-benzylimidazole The risk or severity of hypertension can be increased when Ritodrine is combined with 1-benzylimidazole. 2,5-Dimethoxy-4-ethylamphetamine The risk or severity of adverse effects can be increased when Ritodrine is combined with 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of adverse effects can be increased when Ritodrine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 3-isobutyl-1-methyl-7H-xanthine The risk or severity of adverse effects can be increased when Ritodrine is combined with 3-isobutyl-1-methyl-7H-xanthine. 3,4-Methylenedioxyamphetamine The risk or severity of adverse effects can be increased when Ritodrine is combined with 3,4-Methylenedioxyamphetamine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of adverse effects can be increased when Ritodrine is combined with 4-Bromo-2,5-dimethoxyamphetamine. 4-Methoxyamphetamine The risk or severity of hypertension can be increased when Ritodrine is combined with 4-Methoxyamphetamine. 5-methoxy-N,N-dimethyltryptamine The risk or severity of hypertension can be increased when Ritodrine is combined with 5-methoxy-N,N-dimethyltryptamine. 6-O-benzylguanine The risk or severity of adverse effects can be increased when Ritodrine is combined with 6-O-benzylguanine. - Food Interactions
- Not Available
References
- Synthesis Reference
Naoki Yamazaki, Yoshimasa Fukuda, Yoshiaki Shibazaki, Tetsutarou Niizato, Isao Kosugi, Shin Yoshioka, "(-)-ritodrine, therapeutic compositions and use, and method of preparation." U.S. Patent US5449694, issued July, 1992.
US5449694- General References
- Not Available
- External Links
- ATC Codes
- G02CA01 — Ritodrine
- MSDS
- Download (48 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Treatment Healthy Volunteers 1 4 Completed Prevention Premature Births 1 4 Recruiting Prevention Preterm Labor Without Delivery 1 Not Available Recruiting Treatment Premature Labour 1
Pharmacoeconomics
- Manufacturers
- Abraxis pharmaceutical products
- Hospira inc
- Astrazeneca lp
- Packagers
- Solvay Pharmaceuticals
- Dosage forms
Form Route Strength Liquid Intravenous 10 mg Tablet Oral 10 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 88-90 °C Not Available water solubility Complete Not Available logP 2.4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.179 mg/mL ALOGPS logP 1.53 ALOGPS logP 1.82 ChemAxon logS -3.2 ALOGPS pKa (Strongest Acidic) 9.15 ChemAxon pKa (Strongest Basic) 9.81 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 72.72 Å2 ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 83.02 m3·mol-1 ChemAxon Polarizability 31.56 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9871 Blood Brain Barrier - 0.8115 Caco-2 permeable - 0.5546 P-glycoprotein substrate Substrate 0.692 P-glycoprotein inhibitor I Non-inhibitor 0.953 P-glycoprotein inhibitor II Non-inhibitor 0.8732 Renal organic cation transporter Non-inhibitor 0.6134 CYP450 2C9 substrate Non-substrate 0.6367 CYP450 2D6 substrate Substrate 0.5054 CYP450 3A4 substrate Non-substrate 0.5874 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9442 CYP450 2D6 inhibitor Non-inhibitor 0.6034 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8351 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7277 Ames test Non AMES toxic 0.7799 Carcinogenicity Non-carcinogens 0.9177 Biodegradation Not ready biodegradable 0.8862 Rat acute toxicity 2.2303 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7534 hERG inhibition (predictor II) Inhibitor 0.5409
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as phenethylamines. These are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenethylamines
- Direct Parent
- Phenethylamines
- Alternative Parents
- Phenylpropanes / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- Phenethylamine / Phenylpropane / Phenol / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Secondary alcohol / 1,2-aminoalcohol / Secondary amine / Secondary aliphatic amine / Amine
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- amphetamines (CHEBI:8872)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Protein homodimerization activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Tanaka N, Tamai T, Mukaiyama H, Hirabayashi A, Muranaka H, Akahane S, Miyata H, Akahane M: Discovery of novel N-phenylglycine derivatives as potent and selective beta(3)-adrenoceptor agonists for the treatment of frequent urination and urinary incontinence. J Med Chem. 2001 Apr 26;44(9):1436-45. [PubMed:11311067]
- Schwarz MK, Page P: Preterm labour: an overview of current and emerging therapeutics. Curr Med Chem. 2003 Aug;10(15):1441-68. [PubMed:12871140]
- Lye SJ, Dayes BA, Freitag CL, Brooks J, Casper RF: Failure of ritodrine to prevent preterm labor in the sheep. Am J Obstet Gynecol. 1992 Nov;167(5):1399-408. [PubMed:1332478]
- Bianchetti A, Manara L: In vitro inhibition of intestinal motility by phenylethanolaminotetralines: evidence of atypical beta-adrenoceptors in rat colon. Br J Pharmacol. 1990 Aug;100(4):831-9. [PubMed:1976401]
- Lenselink DR, Kuhlmann RS, Lawrence JM, Kolesari GL: Cardiovascular teratogenicity of terbutaline and ritodrine in the chick embryo. Am J Obstet Gynecol. 1994 Aug;171(2):501-6. [PubMed:8059831]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Phosphogluconate dehydrogenase (decarboxylating) activity
- Specific Function
- Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH.
- Gene Name
- PGD
- Uniprot ID
- P52209
- Uniprot Name
- 6-phosphogluconate dehydrogenase, decarboxylating
- Molecular Weight
- 53139.56 Da
References
- Akkemik E, Budak H, Ciftci M: Effects of some drugs on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro study. J Enzyme Inhib Med Chem. 2010 Aug;25(4):476-9. doi: 10.3109/14756360903257900. [PubMed:20235752]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Drug created on June 13, 2005 07:24 / Updated on January 01, 2019 11:02