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Identification
Name Ritodrine
Accession Number DB00867 (APRD00541)
Type small molecule
Groups approved
Description

Adrenergic beta-agonist used to control premature labor. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Ritodrina [INN-Spanish]
Ritodrine Hcl
Ritodrine Hydrochloride
Ritodrinium [INN-Latin]
Salts Not Available
Brand names
Name Company
Yutopar
Yutopar S.R
Brand mixtures Not Available
Categories
  • Sympathomimetics
  • Adrenergic beta-Agonists
  • Tocolytic Agents
  • Sympathomimetic
CAS number 26652-09-5
Weight Average: 287.3535
Monoisotopic: 287.152143543
Chemical Formula C17H21NO3
InChI Key InChIKey=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
Plain Text
IUPAC Name
4-[(1R,2S)-1-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]amino}propyl]phenol
SMILES
C[C@H](NCCC1=CC=C(O)C=C1)[C@H](O)C1=CC=C(O)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Amphetamines
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Alcohols and Polyols
  • Phenyl Esters
  • Amphetamines
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.
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
Pharmacoeconomics
Manufacturers
  • Abraxis pharmaceutical products
  • Hospira inc
  • Astrazeneca lp
Packagers
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 88-90 °C Not Available
water solubility Complete Not Available
logP 2.4 Not Available
Predicted Properties
Property Value Source
water solubility 1.79e-01 g/l 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 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 83.02 ChemAxon
polarizability 31.56 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D02359 Link_out
KEGG Compound C07239 Link_out
PubChem Compound 33572 Link_out
PubChem Substance 46505273 Link_out
ChemSpider 30971 Link_out
Therapeutic Targets Database DAP000937 Link_out
PharmGKB PA451258 Link_out
Drug Product Database 550140 Link_out
Drugs.com http://www.drugs.com/cons/ritodrine-oral-intravenous.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Ritodrine Link_out
ATC Codes
  • G02CA01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (48 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Beta-2 adrenergic receptor

Pharmacological action: yes
Actions: agonist

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 30-fold greater affinity than it does norepinephrine

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. Schwarz MK, Page P: Preterm labour: an overview of current and emerging therapeutics. Curr Med Chem. 2003 Aug;10(15):1441-68. Pubmed
  3. 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
  4. 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
  5. 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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. 6-phosphogluconate dehydrogenase, decarboxylating

Actions: inhibitor

6-phospho-D-gluconate + NADP(+) = D-ribulose 5-phosphate + CO(2) + NADPH

UniProt ID: P52209 Link_out
Gene: PGD Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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 Mar 17. Pubmed
  2. 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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19