Fentanyl citrate
[CAS# 990-73-8]

Identification

• Classification: API >> Antipyretic analgesics >> Analgesics
• Name: Fentanyl citrate
• Synonyms: N-(Phenyl)-N-(1-[2-phenylethyl]-4-piperidinyl)propanamide citrate
• Molecular Formula: C₂₂H₂₈N₂O^.C₆H₈O₇
• Molecular Weight: 528.59
• CAS Registry Number: 990-73-8
• EC Number: 213-588-0
• SMILES: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

Properties

• Solubility: Soluble 40 mg/mL (water)

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Hazard Statements: H300-H310-H317-H330-H334-H336
• Precautionary Statements: P233-P260-P261-P262-P264-P270-P271-P272-P280-P284-P301+P316-P302+P352-P304+P340-P316-P319-P320-P321-P330-P333+P317-P342+P316-P361+P364-P362+P364-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	2	H330
Respiratory sensitization	Resp. Sens.	1	H334
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	2	H310
Acute toxicity	Acute Tox.	1	H310
Reproductive toxicity	Lact.	-	H362
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	3	H336
Acute toxicity	Acute Tox.	1	H330
Reproductive toxicity	Repr.	2	H361
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	1	H300
Specific target organ toxicity - single exposure	STOT SE	1	H370
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Fentanyl citrate, a potent synthetic opioid analgesic, was first synthesized in 1960 by Dr. Paul Janssen, a Belgian pharmacologist. Working at Janssen Pharmaceutica, Dr. Janssen and his team were exploring novel compounds for pain relief when they developed fentanyl as part of their efforts to create a series of potent analgesics. Fentanyl citrate, derived from fentanyl, was subsequently synthesized to improve its solubility and pharmacokinetic properties, making it suitable for intravenous administration. The discovery of fentanyl citrate marked a significant advancement in pain management, offering a highly effective opioid medication for alleviating severe pain in medical settings.

Fentanyl citrate is commonly used as an adjunct to general anesthesia during surgical procedures. Its rapid onset and potent analgesic properties make it an ideal choice for achieving intraoperative pain control and ensuring patient comfort. When administered intravenously, fentanyl citrate induces rapid and profound analgesia, allowing for smooth induction and maintenance of anesthesia.

Following surgery, fentanyl citrate is frequently utilized for postoperative pain management. Its high potency and relatively short duration of action make it well-suited for controlling acute pain in the immediate postoperative period. Patient-controlled analgesia (PCA) systems often incorporate fentanyl citrate, allowing patients to self-administer doses within prescribed limits to achieve optimal pain relief while minimizing side effects.

Fentanyl citrate is an essential medication for managing breakthrough cancer pain, which refers to sudden and intense episodes of pain that occur despite ongoing opioid therapy. Its rapid onset of action and potent analgesic effects make it particularly effective for providing rapid relief during these episodes, improving the quality of life for cancer patients experiencing debilitating pain.

In chronic pain conditions, such as severe back pain or neuropathic pain, fentanyl citrate may be prescribed for patients who require strong opioid analgesics for long-term pain control. Transdermal fentanyl patches are commonly used for continuous pain relief in these cases, offering a convenient and controlled delivery of the medication over an extended period.

Fentanyl citrate plays a crucial role in emergency medicine for managing acute pain in various settings, including trauma, burns, and myocardial infarction. Its rapid onset, potent analgesic effects, and versatility in administration routes (intravenous, intranasal, transmucosal) make it invaluable for providing effective pain relief in critical situations.

Fentanyl citrate is an essential component of palliative care for patients with advanced illness or terminal conditions. It helps alleviate severe pain and discomfort, allowing patients to maintain dignity and quality of life during the end-of-life stage.

References

2000. Duragesic(R) Transdermal Patch: Postmortem Tissue Distribution of Fentanyl in 25 Cases. Journal of Analytical Toxicology, 24(7).
DOI: 10.1093/jat/24.7.627

2003. Intrathecal Magnesium Prolongs Fentanyl Analgesia. Anesthesia and Analgesia, 96(5).
DOI: 10.1213/01.ane.0000058162.70154.bd

2005. Intrathecal fentanyl added to intrathecal bupivacaine for day case surgery: a randomized study. European Journal of Anaesthesiology, 20(4).
DOI: 10.1017/s0265021503000462