Droxidopa
[CAS# 23651-95-8]

Identification

• Classification: API >> Circulatory system medication >> Antihypertensive drug
• Name: Droxidopa
• Synonyms: (-)-(2S,3R)-2-Amino-3-hydroxy-3-(3,4-dihydroxyphenyl)propionic acid
• Molecular Formula: C₉H₁₁NO₅
• Molecular Weight: 213.19
• CAS Registry Number: 23651-95-8
• EC Number: 688-528-3
• SMILES: C1=CC(=C(C=C1[C@H]([C@@H](C(=O)O)N)O)O)O

Properties

• Boiling Point: 549.8±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 286.3±30.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Droxidopa is a medication used primarily to treat symptomatic orthostatic hypotension, a condition where blood pressure drops significantly upon standing, leading to dizziness, lightheadedness, or fainting. Discovered in the 1980s and approved by the U.S. Food and Drug Administration (FDA) in 2014, droxidopa represents a significant advancement in the management of this challenging condition.

Droxidopa is a prodrug that is metabolized in the body to norepinephrine, a neurotransmitter involved in regulating blood pressure and other autonomic functions. Its discovery was aimed at developing a treatment for patients with neurogenic orthostatic hypotension, which can result from conditions such as Parkinson's disease, multiple system atrophy, and pure autonomic failure. These conditions impair the body's ability to regulate blood pressure properly, leading to the symptoms droxidopa is designed to alleviate.

The mechanism of droxidopa involves its conversion to norepinephrine, which then acts on alpha-adrenergic receptors in the blood vessels, causing vasoconstriction. This action increases blood pressure and helps prevent the significant drops in blood pressure that occur upon standing. By improving vascular tone and enhancing the body's ability to maintain stable blood pressure, droxidopa helps mitigate the symptoms associated with orthostatic hypotension.

Droxidopa is administered orally in the form of capsules. The dosage is typically adjusted based on the patient's response and tolerance, with the goal of achieving effective symptom relief while minimizing side effects. Clinical studies have demonstrated that droxidopa is effective in increasing blood pressure and improving symptoms of dizziness and lightheadedness in patients with neurogenic orthostatic hypotension.

One of the main advantages of droxidopa is its targeted action on the underlying mechanism of orthostatic hypotension. Unlike some other treatments that may have broad effects or are less specific, droxidopa directly addresses the low levels of norepinephrine that contribute to the condition. This specificity helps improve patient outcomes and quality of life.

Despite its benefits, droxidopa can have side effects. Common adverse effects include headache, dizziness, and nausea. There may also be a risk of elevated blood pressure if the dosage is not properly managed, particularly in patients with pre-existing hypertension. Regular monitoring is necessary to ensure that the medication is effectively controlling symptoms without causing excessive increases in blood pressure.

In summary, droxidopa has provided a valuable therapeutic option for patients with neurogenic orthostatic hypotension. Its development has filled an important gap in the treatment of this condition, offering a targeted approach to managing symptoms and improving patients' quality of life.