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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. [PubChem]
- Structure
Structure for Ritodrine (DB00867)
- Synonyms
- DU-21220
- Ritodrina
- Ritodrine
- Ritodrinium
- 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
- 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 agonistHuman - 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 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Ritodrine. Acebutolol The therapeutic efficacy of Ritodrine can be decreased when used in combination with Acebutolol. Acepromazine Acepromazine may decrease the vasoconstricting activities of Ritodrine. Alclometasone The risk or severity of hypokalemia can be increased when Alclometasone is combined with Ritodrine. Alfuzosin The therapeutic efficacy of Ritodrine can be decreased when used in combination with Alfuzosin. Alprenolol Alprenolol may decrease the bronchodilatory activities of Ritodrine. Amcinonide The risk or severity of hypokalemia can be increased when Amcinonide is combined with Ritodrine. Amineptine The risk or severity of adverse effects can be increased when Amineptine is combined with Ritodrine. Amitriptyline The therapeutic efficacy of Ritodrine can be decreased when used in combination with Amitriptyline. Amitriptylinoxide The risk or severity of adverse effects can be increased when Amitriptylinoxide is combined with Ritodrine. - 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
- Human
- 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
- Human
- 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 October 01, 2018 16:26