Production Method 1

132388-59-1

29022-11-5

162502-65-0

103213-32-7

109425-55-0

27144-18-9

71989-23-6

71989-35-0

71989-31-6

90779-69-4

Reaction Conditions

1.1 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Solvents: Dimethylformamide ;  5 min, 25 °C; 45 min, 25 °C; 45 min, 25 °C
1.2 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Solvents: Dimethylformamide ;  5 min, 25 °C; 45 min, 25 °C; 45 min, 25 °C
1.3 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Solvents: Dimethylformamide ;  5 min, 25 °C; 45 min, 25 °C; 45 min, 25 °C
1.4 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Solvents: Dimethylformamide ;  5 min, 25 °C; 45 min, 25 °C; 45 min, 25 °C
1.5 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Solvents: Dimethylformamide ;  5 min, 25 °C; 45 min, 25 °C; 45 min, 25 °C
1.6 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Solvents: Dimethylformamide ;  5 min, 25 °C; 45 min, 25 °C; 45 min, 25 °C
1.7 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Solvents: Dimethylformamide ;  5 min, 25 °C; 45 min, 25 °C; 45 min, 25 °C
1.8 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Solvents: Dimethylformamide ;  5 min, 25 °C; 45 min, 25 °C; 45 min, 25 °C
1.9 Reagents: Diisopropylcarbodiimide ,  1-Hydroxybenzotriazole Solvents: Dimethylformamide ;  5 min, 25 °C; 45 min, 25 °C; 45 min, 25 °C
1.10 Reagents: Iodine Solvents: Dimethylformamide ;  < 1 min, 25 °C; 3 h, 25 °C
1.11 Reagents: Trifluoroacetic acid ,  Triisopropylsilane Solvents: Dimethylformamide ,  Water ;  10 °C → rt; 1.5 h, rt

Reference

Investigation of On-Resin Disulfide Formation for Large-Scale Manufacturing of Cyclic Peptides: A Case Study

Yang, Yi ; Hansen, Lena; Badalassi, Fabrizio, Organic Process Research & Development, 2020, 24(7), 1281-1293

Production Method 2

132388-59-1

29022-11-5

162502-65-0

103213-32-7

109425-55-0

27144-18-9

71989-23-6

71989-35-0

71989-31-6

90779-69-4

Reaction Conditions

Reference

Synthesis of Oxytocin Analogues with Replacement of Sulfur by Carbon Gives Potent Antagonists with Increased Stability

Stymiest, Jake L.; Mitchell, Bryan F.; Wong, Susan; Vederas, John C., Journal of Organic Chemistry, 2005, 70(20), 7799-7809

Atosiban Raw materials

• (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-[(triphenylmethyl)carbamoyl]propanoic acid
• Fmoc-Gly-OH
• Fmoc-O-ethyl-D-tyrosine
• Fmoc-Cys(Trt)-OH
• Fmoc-Orn(Boc)-OH
• 3-Tritylsulfanylpropionic Acid
• Fmoc-Ile-OH
• Fmoc-Thr(tBu)-OH
• Fmoc-Pro-OH

Atosiban Preparation Products

• Atosiban (90779-69-4)

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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Peptides
• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Peptides
• Other Chemical Reagents

Atosiban and CAS No 90779-69-4: A Comprehensive Overview in Modern Pharmaceutical Research

Atosiban, a synthetic peptide analog, is widely recognized for its significant role in the realm of obstetrics and gynecology. The compound is specifically engineered to mimic the natural human peptide OCR120, which plays a crucial role in the inhibition of uterine contractions. This pharmacological agent has garnered considerable attention due to its unique mechanism of action and its potential applications in managing preterm labor. The chemical identity of Atosiban is firmly established by its CAS number, CAS No 90779-69-4, which serves as a unique identifier in the scientific community.

The development of Atosiban represents a significant advancement in the treatment of preterm labor, a condition that poses substantial risks to both newborns and pregnant women. By targeting the specific pathways involved in uterine contractility, Atosiban offers a promising alternative to traditional treatments such as non-stimulant oxytocin receptor antagonists. Recent studies have highlighted the compound's efficacy in reducing the frequency and duration of contractions, thereby providing healthcare providers with a valuable tool for managing this critical condition.

One of the most compelling aspects of Atosiban is its selectivity. Unlike some other agents that may have broader effects on smooth muscle tissue, Atosiban exhibits high specificity for the oxytocin receptors in the uterus. This selectivity not only enhances its therapeutic index but also minimizes potential side effects associated with less targeted treatments. The synthetic structure of Atosiban, as defined by CAS No 90779-69-4, has been meticulously designed to optimize its pharmacokinetic properties, ensuring that it remains effective over prolonged periods.

Recent clinical trials have provided further evidence of Atosiban's efficacy and safety profile. These trials have demonstrated that when administered appropriately, Atosiban can significantly delay preterm delivery without compromising maternal or fetal health. The results from these studies have been instrumental in guiding regulatory approvals and clinical guidelines worldwide, solidifying Atosiban's position as a cornerstone in modern obstetric care.

The pharmacological properties of Atosiban are deeply rooted in its molecular structure and interactions with biological targets. The compound's ability to bind to oxytocin receptors with high affinity and specificity is key to its therapeutic effects. This interaction leads to a reduction in uterine contractility, which is essential for preventing preterm labor. The synthetic pathways used to produce Atosiban have been optimized over several years to ensure high yield and purity, meeting stringent pharmaceutical standards.

In addition to its primary role in obstetrics, research into Atosiban is exploring potential applications in other areas of medicine. Studies are ongoing to investigate its effects on other smooth muscle tissues and its potential use in conditions such as hypertension and gastrointestinal disorders. These exploratory studies highlight the versatility of Atosiban and underscore its significance beyond its initial clinical applications.

The synthesis and characterization of Atosiban have been subjects of extensive research efforts. The molecular formula and structural details provided by CAS No 90779-69-4 have facilitated detailed studies on its pharmacodynamics and pharmacokinetics. Advanced analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and X-ray crystallography have been employed to elucidate the compound's structure-function relationships.

The regulatory landscape for Atosiban has evolved significantly since its initial approval. Regulatory agencies worldwide have recognized the compound's therapeutic value and have implemented guidelines that ensure its safe and effective use. These regulations cover aspects such as manufacturing standards, clinical trial protocols, and post-marketing surveillance. Compliance with these regulations is essential for maintaining the highest levels of patient safety and treatment efficacy.

The future prospects for Atosiban are bright, with ongoing research aimed at expanding its therapeutic applications. Innovations in drug delivery systems are being explored to enhance the compound's bioavailability and reduce dosing frequency. Additionally, combination therapies involving Atosiban with other pharmacological agents are being investigated to address complex clinical scenarios more effectively.

In conclusion, Atosiban stands as a testament to the advancements in peptide-based therapeutics. Its unique mechanism of action, coupled with its well-established safety profile, makes it an invaluable asset in modern medicine. The continued research into this compound promises further refinements in its application spectrum, ensuring that it remains at the forefront of therapeutic interventions for preterm labor and potentially other conditions.

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