Chemistry:Ritodrine

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Ritodrine, formerly sold under the brand name Yutopar among others, is a tocolytic drug used to stop premature labor.[1][2] It was withdrawn from the US market, according to the FDA Orange Book. It was available in oral tablets or as an injection and was typically used as the hydrochloride salt.

The drug acts as a selective β2-adrenergic receptor agonist.[3]

It was first approved for medical use in the United States in 1984.[4]

Medical uses

Ritodrine is used to treat preterm labor.[1]

Contraindications

Possible contraindications of ritodrine include type 2 diabetes, high blood pressure, and migraines.

Side effects

Ritodrine has been reported rarely to cause serious side effects including rhabdomyolysis, hepatotoxicity, leukopenia, pulmonary edema, and psychiatric symptoms, among others.[5][6][7][8][9]

Pharmacology

Pharmacodynamics

Ritodrine is a short-acting β2-adrenergic receptor agonist – a class of medication used for smooth muscle relaxation (other similar drugs are used in asthma or other pulmonary diseases such as salbutamol [albuterol]). Since ritodrine has a bulky N-substituent, it has high β2-adrenergic receptor selectivity. Also, the 4-hydroxy group on the benzene ring is important for activity as it is needed to form hydrogen bonds. Since the drug is β2-selective, it is used for premature labor.[10]

Pharmacokinetics

The 4-hydroxy group of ritodrine makes it susceptible to metabolism by catechol-O-methyl transferase (COMT).

Chemistry

Ritodrine, also known as 4-hydroxy-β-hydroxy-N-(4-hydroxyphenylethyl)amphetamine or as N-(4-hydroxyphenylethyl)-4-hydroxynorephedrine, is a substituted phenethylamine and amphetamine derivative.[11][12][13]

The experimental log P of ritodrine is 2.4 and its predicted ranges from 1.53 to 2.3.[11][12][13]

History

Ritodrine was first approved for medical use in the United States in 1984.[4]

Society and culture

Names

Ritodrine is the generic name of the drug and its INN, USAN, BAN, and DCF.[14][15] In the case of the hydrochloride salt, its generic name is ritodrine hydrochloride and this is its USAN and BANM.[14][15] It is also known by its developmental code name DU-21220.[14] The drug has been sold under brand names including Pre-Par, Utopar, and Yutopar, among others.[14][15]

See also

References

  1. ↑ 1.0 1.1 "Effectiveness and safety of ritodrine hydrochloride for the treatment of preterm labour: a systematic review". Pharmacoepidemiol Drug Saf 15 (11): 813–822. November 2006. doi:10.1002/pds.1317. PMID 16981213. 
  2. ↑ "Ritodrine in the treatment of preterm labour: a meta-analysis". The Indian Journal of Medical Research 121 (2): 120–7. February 2005. PMID 15756046. http://www.icmr.nic.in/ijmr/2005/February/0207.pdf. Retrieved 2008-10-05. 
  3. ↑ "[Pharmacology of ritodrine]" (in Italian). Minerva Ginecol 51 (6): 233–244. June 1999. PMID 10479875. 
  4. ↑ 4.0 4.1 Ullmann's Pharmaceuticals. Wiley. 2022. p. 4-PA9. ISBN 978-3-527-80733-8. https://books.google.com/books?id=94JlEAAAQBAJ&pg=RA4-PA9. Retrieved 30 August 2024. 
  5. ↑ "Ritodrine-induced rhabdomyolysis and psychiatric symptoms: a case report and literature review". BMC Pregnancy Childbirth 23 (1): 11. January 2023. doi:10.1186/s12884-022-05299-2. PMID 36611175. 
  6. ↑ "Ritodrine-related liver injury. Case reports and review of the literature". Ital J Gastroenterol Hepatol 30 (3): 315–317. June 1998. PMID 9759604. 
  7. ↑ "Ritodrine-induced leukopenia: a case report and literature review". Changgeng Yi Xue Za Zhi 19 (4): 388–391. December 1996. PMID 9041773. 
  8. ↑ "[Acute hepatitis due to ritodrine]" (in Spanish). Med Clin (Barc) 113 (6): 239. September 1999. PMID 10472614. 
  9. ↑ "Pulmonary edema associated with ritodrine and dexamethasone treatment of threatened premature labor. A case report". J Reprod Med 28 (5): 349–352. May 1983. PMID 6152991. 
  10. ↑ Medicinal Chemistry of Adrenergics and Cholinergics
  11. ↑ 11.0 11.1 "Ritodrine". https://pubchem.ncbi.nlm.nih.gov/compound/33572. 
  12. ↑ 12.0 12.1 "C17H21NO3". 2024-08-30. https://www.chemspider.com/Chemical-Structure.30971.html. 
  13. ↑ 13.0 13.1 "Ritodrine: Uses, Interactions, Mechanism of Action". 31 December 1984. https://go.drugbank.com/drugs/DB00867. 
  14. ↑ 14.0 14.1 14.2 14.3 Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 923. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA923. Retrieved 30 August 2024. 
  15. ↑ 15.0 15.1 15.2 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. 1999. p. 249. ISBN 978-0-7514-0499-9. https://books.google.com/books?id=mqaOMOtk61IC&pg=PA249. Retrieved 30 August 2024. 



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