 Home > Encyclopedia > Fentanyl citrate

Fentanyl citrate

Fentanyl citrate structure

CAS No:
990-73-8
Formula:
C22H28N2O.C6H8O7
Chemical Name:
Fentanyl citrate
Synonyms:
Propanamide,N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-,2-hydroxy-1,2,3-propanetricarboxylate (1:1);Propionanilide,N-(1-phenethyl-4-piperidyl)-,citrate (1:1);McN-JR 4263-49;Fentanyl citrate;N-(1-Phenethyl-4-piperidinyl)propionanilide dihydrogen citrate;N-(1-Phenethyl-4-piperidyl)propionanilide citrate;Phentanyl citrate;Sublimaze;Leptanal;R 5240;McN-JR 4263;Fentaz;Duragesic;Actiq;Leptanol;Pentanyl;Oralet;Oravescent;Fentanil citrate;NasalFent;Onsolis;Fentos Tape;Instanyl
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

Description

White Powder

Fentanyl citrate is the citric acid salt of fentanyl, comprising equimolar amounts of citric acid and fentanyl. A mu-opioid receptor agonist, it is a potent opioid analgesic used in the management of labour pain, postoperative pain, and chronic intractable cancer pain. It is also widely used as the analgesic component of balanced anaesthesia. It has a role as a mu-opioid receptor agonist and an opioid analgesic. It contains a fentanyl.|Oralet is a DEA Schedule II controlled substance. Substances in the DEA Schedule II have a high potential for abuse which may lead to severe psychological or physical dependence.|Fentanyl Citrate is the citrate salt of fentanyl, a synthetic opioid related to the phenylpiperidines with analgesic and anesthetic properties. Fentanyl exerts its analgesic effect by selectively binding to the mu-opioid receptor in the central nervous system (CNS), thereby mimicking the effects of endogenous opiates. Additional pharmacological effects of fentanyl include anxiolysis, euphoria, feelings of relaxation, respiratory depression, constipation, miosis, and cough suppression.|A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078)

Fentanyl citrate Basic Attributes

Molecular Weight：

528.59

Exact Mass：

528.247192

EC Number：

213-588-0

UNII：

MUN5LYG46H

DEA Code Number：

9801

DSSTox ID：

DTXSID80243933

NCI Thesaurus Code：

C47994

ATC Code：

N02AB03

HScode：

2933330000

Characteristics

PSA：

155.68000

XLogP3：

2.82610

Melting Point：

149-151 °C

Boiling Point：

466.2ºC at 760 mmHg

Flash Point：

11 °C

Storage Conditions：

2-8°C

Toxicity：

LD50 in mice (mg/kg): 11.2 i.v.; 62 s.c. (Gardocki, Yelnosky)

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2811 6.1/PG 2

wgk germany：

hazard class code：

26/27/28-42/43-39/23/24/25-23/24/25-11-36/37

safety instructions：

7-16-36/37-45-36/37/39-26

RTECS Number：

UE5600000

Marks：

T+,T,F

Precautionary statement(s)：

Missing Phrase - N15.00950417-P260-P280-P284-P302 + P352 + P310-P304 + P340 + P310

Hazard Statements：

H300 + H310 + H330-H317-H334

GHS Classification：

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P261, P262, P264, P270, P271, P272, P280, P284, P285, P301+P310, P302+P350, P302+P352, P304+P340, P304+P341, P310, P312, P320, P321, P322, P330, P333+P313, P342+P311, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 66 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Instanyl is indicated for the management of breakthrough pain in adults already receiving maintenance opioid therapy for chronic cancer pain. Breakthrough pain is a transitory exacerbation of pain that occurs on a background of otherwise controlled persistent pain. Patients receiving maintenance opioid therapy are those who are taking at least 60 mg of oral morphine daily, at least 25 micrograms of transdermal fentanyl per hour, at least 30 mg oxycodone daily, at least 8 mg of oral hydromorphone daily or an equianalgesic dose of another opioid for a week or longer.|Treatment of acute pain, Prevention of acute pain|Acute pain

MeSH：

Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS. (See all compounds classified as Narcotics.)|Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)|Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174) (See all compounds classified as Anesthetics, Intravenous.)|Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)

MeSH Entry Terms：

Duragesic

DEA Controlled Substances：

Fentanyl|Duragesic, Oralet, Actiq, Sublimaze, Innovar|9801|Schedule II - Substances in the DEA Schedule II have a high potential for abuse which may lead to severe psychological or physical dependence.|Yes

Fentanyl citrate Use and Manufacturing

Methods of Manufacturing

Fentanyl base is made from phenethylamine through addition, cyclization, condensation, reduction, and propionylation, and it forms a salt with citric acid to obtain a finished product.

Uses

Used as an analgesic. Controlled substance

Use Classification：

Human drugs -> Instanyl -> EMA Drug Category|Analgesics -> Human pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:528.6
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:11
Exact Mass:528.24716611
Monoisotopic Mass:528.24716611
Topological Polar Surface Area:156
Heavy Atom Count:38
Complexity:618
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes