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Ritodrine
Identification
- Name
- Ritodrine
- Accession Number
- DB00867
- Description
Adrenergic beta-agonist used to control premature labor.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Ritodrine (DB00867)
- Weight
- Average: 287.3535
Monoisotopic: 287.152143543 - Chemical Formula
- C17H21NO3
- Synonyms
- p-Hydroxy-alpha-(1-((p-hydroxyphenethyl)amino)ethyl)benzyl alcohol
- Ritodrina
- Ritodrine
- Ritodrinium
- External IDs
- DU-21220
Pharmacology
- Indication
For the treatment and prophylaxis of premature labour
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- 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
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbaloparatide The risk or severity of adverse effects can be increased when Ritodrine is combined with Abaloparatide. Acebutolol The therapeutic efficacy of Ritodrine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Ritodrine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Ritodrine is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Ritodrine is combined with Acetylsalicylic acid. Aclidinium The risk or severity of Tachycardia can be increased when Ritodrine is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Ritodrine. Alclofenac The risk or severity of hypertension can be increased when Ritodrine is combined with Alclofenac. Alfentanil The risk or severity of hypertension can be increased when Alfentanil is combined with Ritodrine. Alfuzosin The therapeutic efficacy of Ritodrine can be decreased when used in combination with Alfuzosin. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Ritodrine hydrochloride ESJ56Q60GC 23239-51-2 IDLSITKDRVDKRV-UHFFFAOYSA-N - International/Other Brands
- Yutopar
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataYutopar Inj 50mg/5ml Liquid Intravenous Bristol Labs Division Of Bristol Myers Squibb 1984-12-31 2001-07-30 Canada 
Yutopar Tab 10mg Tablet Oral Bristol Labs Division Of Bristol Myers Squibb 1984-12-31 2001-07-30 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- G02CA01 — Ritodrine
- Drug 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
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- amphetamines (CHEBI:8872)
Chemical Identifiers
- UNII
- I0Q6O6740J
- CAS number
- 26652-09-5
- 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
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
- Human Metabolome Database
- HMDB0015005
- KEGG Drug
- D02359
- KEGG Compound
- C07239
- PubChem Compound
- 33572
- PubChem Substance
- 46505273
- ChemSpider
- 30971
- BindingDB
- 97162
- 9392
- ChEBI
- 8872
- ChEMBL
- CHEMBL785
- ZINC
- ZINC000000057480
- Therapeutic Targets Database
- DAP000937
- PharmGKB
- PA451258
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ritodrine
- MSDS
- Download (48 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Premature Births 1 4 Recruiting Prevention Preterm Labor Without Delivery 1 1 Completed Treatment Healthy Volunteers 1 Not Available Completed Treatment Pregnancy 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 Tablet Oral - 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
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 July 02, 2020 07:23
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