Ritodrine

Overview

Ritodrine, formerly sold under the brand name Yutopar among others, is a tocolytic drug used to stop premature labor. It was withdrawn from the US market, according to the FDA Orange Book.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.[1][2] WP

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

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

Uses, dosage and effects

Medical uses

Ritodrine is used to treat preterm labor.[1] WP

Risks and side effects

Contraindications

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

Side effects

Most side effects of β₂-adrenergic receptor agonists result from their concurrent β₁-adrenergic receptor agonistic activity, and include increase in heart rate, rise in systolic blood pressure, decrease in diastolic blood pressure, chest pain secondary to myocardial infarction, and arrhythmia. β-Adrenergic receptor agonists may also cause fluid retention secondary to decrease in water clearance, which when added to the tachycardia and increased myocardial work, may result in heart failure. In addition, they increase gluconeogenesis in the liver and muscle resulting in hyperglycemia, which increases insulin requirements in diabetic patients. The passage of β-adrenergic receptor agonists through the placenta does occur and may be responsible for fetal tachycardia, as well as hypoglycemia or hyperglycemia at birth. It has also been associated with postpartum bleeding. WP⚠ Wikipedia itself has flagged this text: citation needed.

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

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] WP

Pharmacokinetics

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

History

History

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

Legal status

Names

Ritodrine is the generic name of the drug and its INN (International Nonproprietary Name), USAN (United States Adopted Name), BAN (British Approved Name), and DCF (Dénomination Commune Française). In the case of the hydrochloride salt, its generic name is ritodrine hydrochloride and this is its USAN (United States Adopted Name) and BANM (British Approved Name). It is also known by its developmental code name DU-21220. The drug has been sold under brand names including Pre-Par, Utopar, and Yutopar, among others.[11][12] WP

Chemistry

Formula

C17H21NO3 PC

CAS number

26652-09-5 PC

Molar mass (g/mol)

287.35 PC

IUPAC name (computed by PubChem)

4-[2-[[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol PC

SMILES

C[C@@H]([C@@H](C1=CC=C(C=C1)O)O)NCCC2=CC=C(C=C2)O PC

InChIKey

IOVGROKTTNBUGK-SJCJKPOMSA-N PC

PubChem CID

33572

IUPAC name

4-Square bracket open2-Square bracket open WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Yaju Y, Nakayama T. Effectiveness and safety of ritodrine hydrochloride for the treatment of preterm labour: a systematic review. Pharmacoepidemiol Drug Saf. November 2006. doi:10.1002/pds.1317 · PMID 16981213
2. Journal / agency Li X, Zhang Y, Shi Z. Ritodrine in the treatment of preterm labour: a meta-analysis. The Indian Journal of Medical Research. February 2005. PMID 15756046
3. Journal / agency Mangrella M, Torella M, Russo F, Rossi F, Piucci B, Cantoni V. Pharmacology of ritodrine. Minerva Ginecol. June 1999. PMID 10479875
4. Other Kleemann A, Kutscher B. Ullmann's Pharmaceuticals. 2022
5. Journal / agency Sun L, Tang M, Peng M, Xu P, Wang Y. Ritodrine-induced rhabdomyolysis and psychiatric symptoms: a case report and literature review. BMC Pregnancy Childbirth. January 2023. doi:10.1186/s12884-022-05299-2 · PMID 36611175 · PMC9824990
6. Journal / agency Ceriani R, Borroni G, Bissoli F. Ritodrine-related liver injury. Case reports and review of the literature. Ital J Gastroenterol Hepatol. June 1998. PMID 9759604
7. Journal / agency Wu CD, Chao AS, Cheng PJ, Soong YK. Ritodrine-induced leukopenia: a case report and literature review. Changgeng Yi Xue Za Zhi. December 1996. PMID 9041773
8. Journal / agency Castro Fernández M, Romero Gómez M, Grande Santamaría L, Caballero Manzano M. Acute hepatitis due to ritodrine. Med Clin (Barc). September 1999. PMID 10472614
9. Journal / agency Alper M, Cohen WR. Pulmonary edema associated with ritodrine and dexamethasone treatment of threatened premature labor. A case report. J Reprod Med. May 1983. PMID 6152991
10. Other Medicinal Chemistry of Adrenergics and Cholinergics. link 2
11. Other Schweizerischer Apotheker-Verein. Index Nominum 2000: International Drug Directory. 2000
12. Other Morton IK, Hall JM. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 1999

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.