FENTANYL CITRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H28N2O.C6H8O7
Molecular Weight	528.594
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=CC=C3

InChI

InChIKey=IVLVTNPOHDFFCJ-UHFFFAOYSA-N

InChI=1S/C22H28N2O.C6H8O7/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-12,21H,2,13-18H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C22H28N2O
Molecular Weight	336.4705
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9618424
Curator's Comment: Description was created based on several sources, including https://www.addictioncenter.com/painkillers/fentanyl/ | https://www.ncbi.nlm.nih.gov/pubmed/24635521

Fentanyl is a potent agonist of mu opioid receptor. It is used to relieve severe pain, such as after surgery or during cancer treatment, and breakthrough pain (flare-ups of intense pain despite round-the-clock narcotic treatment). Fentanyl is an extremely powerful analgesic, 50–100-times more potent than morphine. Fentanyl harbors massive risk for addiction and abuse regardless of its prescription form. Fentanyl abuse is especially dangerous to those without a tolerance to opioids. The substance’s already elevated risk of overdose is multiplied when someone without a tolerance abuses it.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9618424 \| https://www.ncbi.nlm.nih.gov/pubmed/6304563	Agonist 2678		0.15 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/016619s034lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/19813s039lbl.pdf	Primary		Approved 8429	DURAGESIC-100 Approved Use Fentanyl transdermal system is a transdermal formulation of fentanyl indicated for the management of persistent, moderate to severe chronic pain in opioid-tolerant patients 2 years of age and older when a continuous, around-the-clock opioid analgesic is required for an extended period of time, and the patient cannot be managed by other means such as non-steroidal analgesics, opioid combination products, or immediate-release opioids. Patients considered opioid-tolerant are those who are taking at least 60 mg of morphine daily, or at least 30 mg of oral oxycodone daily, or at least 8 mg of oral hydromorphone daily, or an equianalgesic dose of another opioid for a week or longer. Fentanyl transdermal system contains fentanyl, a full opioid agonist. Fentanyl transdermal system is indicated for the management of persistent, moderate to severe chronic pain in opioid‑tolerant patients 2 years of age and older when a continuous, around-the-clock opioid analgesic is needed for an extended period of time. (1) Fentanyl transdermal system is NOT intended for use as an as-needed analgesic. (1) Launch Date 1990

C_max

Value	Dose	Analyte	Population
0.91 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23497761/	100 μg single, intravenous dose: 100 μg route of administration: Intravenous experiment type: SINGLE co-administered:	FENTANYL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.61 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23497761/	400 μg single, oral transmucosal dose: 400 μg route of administration: Oral transmucosal experiment type: SINGLE co-administered:	FENTANYL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.81 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23497761/	400 μg single, sublingual dose: 400 μg route of administration: Sublingual experiment type: SINGLE co-administered:	FENTANYL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
1.76 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23497761/	100 μg single, intravenous dose: 100 μg route of administration: Intravenous experiment type: SINGLE co-administered:	FENTANYL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.18 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23497761/	400 μg single, oral transmucosal dose: 400 μg route of administration: Oral transmucosal experiment type: SINGLE co-administered:	FENTANYL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.76 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23497761/	400 μg single, sublingual dose: 400 μg route of administration: Sublingual experiment type: SINGLE co-administered:	FENTANYL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
4.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23497761/	100 μg single, intravenous dose: 100 μg route of administration: Intravenous experiment type: SINGLE co-administered:	FENTANYL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23497761/	400 μg single, oral transmucosal dose: 400 μg route of administration: Oral transmucosal experiment type: SINGLE co-administered:	FENTANYL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
10 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23497761/	400 μg single, sublingual dose: 400 μg route of administration: Sublingual experiment type: SINGLE co-administered:	FENTANYL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
6 mg single, transdermal (total) Overdose Dose: 6 mg Route: transdermal Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463	healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463	Disc. AE: Apnea, Respiratory depression... AEs leading to discontinuation/dose reduction: Apnea Respiratory depression Bradypnea Tachycardia Diaphoresis Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463
150 ug 1 times / hour multiple, transdermal Overdose Dose: 150 ug, 1 times / hour Route: transdermal Route: multiple Dose: 150 ug, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/9695458	unknown, 31 n = 1 Health Status: unknown Age Group: 31 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9695458	Disc. AE: Respiratory arrest... AEs leading to discontinuation/dose reduction: Respiratory arrest (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/9695458
225 ug 1 times / hour multiple, transdermal Overdose Dose: 225 ug, 1 times / hour Route: transdermal Route: multiple Dose: 225 ug, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/25736329 Page: p.51	unhealthy, 32 n = 1 Health Status: unhealthy Condition: Knee pain Age Group: 32 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25736329 Page: p.51	Disc. AE: Syncope, Acute coronary syndrome... AEs leading to discontinuation/dose reduction: Syncope Acute coronary syndrome Sources: https://pubmed.ncbi.nlm.nih.gov/25736329 Page: p.51
800 ug single, sublingual Higher than recommended Dose: 800 ug Route: sublingual Route: single Dose: 800 ug Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 14	healthy, 33.4 n = 8 Health Status: healthy Age Group: 33.4 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 14	Other AEs: Hypoxia, Nausea... Other AEs: Hypoxia (50%) Nausea (75%) Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 14
800 ug single, sublingual Higher than recommended Dose: 800 ug Route: sublingual Route: single Dose: 800 ug Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 15	healthy, 33.4 n = 8 Health Status: healthy Age Group: 33.4 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 15	Other AEs: Somnolence... Other AEs: Somnolence (87.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 15
800 ug single, sublingual Higher than recommended Dose: 800 ug Route: sublingual Route: single Dose: 800 ug Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 16	healthy, 33.4 n = 8 Health Status: healthy Age Group: 33.4 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 16	Other AEs: Vomiting... Other AEs: Vomiting (50%) Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 16
1600 ug 1 times / 15 min multiple, sublingual (max) Highest studied dose Dose: 1600 ug, 1 times / 15 min Route: sublingual Route: multiple Dose: 1600 ug, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309	unhealthy, 53±12 n = 65 Health Status: unhealthy Condition: Pain Age Group: 53±12 Sex: M+F Population Size: 65 Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309	Disc. AE: Somnolence, Dizziness... AEs leading to discontinuation/dose reduction: Somnolence (3%) Dizziness (3%) Hallucinations (1.5%) Dry mouth (1.5%) Headache (1.5%) Nausea (1.5%) Vomiting (1.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309
5 mg single, intravenous Accidental dose Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199	unhealthy, 62 n = 1 Health Status: unhealthy Condition: Pain Age Group: 62 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199	Disc. AE: Confusion, Restlessness... AEs leading to discontinuation/dose reduction: Confusion (acute) Restlessness (mild) Visual hallucinations Sweating Miosis Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199
200 ug 6 times / day multiple, sublingual Recommended Dose: 200 ug, 6 times / day Route: sublingual Route: multiple Dose: 200 ug, 6 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020747s030lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Pain Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020747s030lbl.pdf Page: p.1	Disc. AE: Respiratory depression, Opioid abuse... AEs leading to discontinuation/dose reduction: Respiratory depression (grade 4) Opioid abuse Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020747s030lbl.pdf Page: p.1

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	substrate 1037	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 810 CYP1A2 1524 CYP2A6 707 CYP2C8/9 44 CYP2E1 882 P-gp 1461 OCT1 512 OATP1B1 788 OATP1B3 706 OATP2B1 123	CYP1A1 349 CYP1A2 1054 CYP2C8 693 CYP2C18 138 CYP2C19 991 CYP2E1 667 CYP3A5 395 CYP3A7 110 P-gp 1537 OATP1A2 62 OATP1B1 406 OCT1 327

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP2C8/9 44	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	likely
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	likely
CYP2E1 970	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	no
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	no
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	weak
CYP2A6 739	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	weak
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	weak
OATP2B1 126	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	weak
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/31597043/	yes [IC50 117.7 uM]	NORFENTANYL 3
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18788725/, https://pubmed.ncbi.nlm.nih.gov/31597043/, http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50008984&submit=repeat&energyterm=&column=EC50&startPg=50&Increment=50	yes [IC50 46.2 uM]
P-gp 1650	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00813, https://pubmed.ncbi.nlm.nih.gov/11964599/, https://www.ema.europa.eu/en/documents/assessment-report/instanyl-epar-public-assessment-report_en.pdf#page=10 Page: (EMA PAR) 10	yes [IC50 6.5 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	yes
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	likely
CYP2C18 138	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	likely
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	likely
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20747_Actiq_phrmr.pdf#page=17, https://pubmed.ncbi.nlm.nih.gov/9264313/, https://www.pmda.go.jp/drugs/2001/P200100034/80015500_21300AMY00455_263_1.pdf#page=17, https://pubmed.ncbi.nlm.nih.gov/10485779/ Page: (Pharm) 17, 28, (PMDA) 17	major		yes (co-administration study) Comment: Rate: 61 pmol/min/mg protein; Activity (Fentanyl): 1.03 nmol/min/nmol CYP (Biochem Pharmacol, 53, 1613 (1997)); Coadministartion of Ritonavir (strong CYP3A inhibitor, PO) increased Fentanyl (IV) AUCinf by 2.74-fold. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20747_Actiq_phrmr.pdf#page=17, https://pubmed.ncbi.nlm.nih.gov/9264313/, https://www.pmda.go.jp/drugs/2001/P200100034/80015500_21300AMY00455_263_1.pdf#page=17, https://pubmed.ncbi.nlm.nih.gov/10485779/ Page: (Pharm) 17, 28, (PMDA) 17
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	minor
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	minor
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	minor
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	minor
OATP1B1 406	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23480028/	no
OCT1 327	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/31597043/	no
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11964599/	no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	yes
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	yes
CYP3A7 110	substrate 3367 Sources: https://ncit-stage.nci.nih.gov/ncitbrowser/pages/concept_details.jsf?dictionary=NCI_Thesaurus&version=21.02d&code=C494&ns=ncit&type=relationship&key=n1099999666&b=1&n=0&vse=null	yes
OATP1A2 62	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/31746415/	yes
OCT1 327	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/31597043/	yes	NORFENTANYL 3

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/32321735/, , https://pubmed.ncbi.nlm.nih.gov/15911273/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:119915	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:119915
ZINC	ZINC000002522669	http://zinc15.docking.org/substances/ZINC000002522669
eMolecules	901881	https://www.emolecules.com/cgi-bin/more?vid=901881

PubMed

Title	Date	PubMed
Spasm and operative cholangiography.	1975 Jan	1119938
[Effects of speed of injection on anesthesia induction with propofol and fentanyl].	1999 Aug	10481417
Seizure and electroencephalographic changes in the newborn period induced by opiates and corrected by naloxone infusion.	1999 Mar	10642972
Combined spinal epidural for labour analgesia--duration, efficacy and side effects of adding sufentanil or fentanyl to bupivacaine intrathecally vs plain bupivacaine.	1999 Oct	10741192
Continuous paravertebral extrapleural infusion for post-thoracotomy pain management.	1999 Oct	10520911
Three cases with different presentation of fentanyl-induced muscle rigidity--a rare problem in intensive care of neonates.	2000	10928600
Comparison of intravenous and oral ketoprofen for postoperative pain after adenoidectomy in children.	2000 Aug	10992828
Phenytoin, midazolam, and naloxone protect against fentanyl-induced brain damage in rats.	2000 Dec	11093997
Long-lasting hyperalgesia induced by fentanyl in rats: preventive effect of ketamine.	2000 Feb	10691234
Low-dose clonidine and neostigmine prolong the duration of intrathecal bupivacaine-fentanyl for labor analgesia.	2000 Feb	10691221
An assessment of the safety, efficacy, and acceptability of intranasal fentanyl citrate in the management of cancer-related breakthrough pain: a pilot study.	2000 Oct	11027906
A comparison of minidose lidocaine-fentanyl and conventional-dose lidocaine spinal anesthesia.	2000 Oct	11004039
A comparison of ropivacaine with fentanyl to bupivacaine with fentanyl for postoperative patient-controlled epidural analgesia.	2001 Apr	11273944
The clinical use of small-dose tetracaine spinal anesthesia for transurethral prostatectomy.	2001 Apr	11273943
The effects of opioids on isolated human pregnant uterine muscles.	2001 Apr	11273940
Stress response in infants undergoing cardiac surgery: a randomized study of fentanyl bolus, fentanyl infusion, and fentanyl-midazolam infusion.	2001 Apr	11273919
Patient-controlled spinal analgesia for labour and caesarean delivery.	2001 Feb	11261914
[Anesthesia in a case of Bardet-Biedl syndrome].	2001 Feb	11257962
[Anesthetic management of two patients with insulinoma using propofol--in association with rapid radioimmunoassay for insulin].	2001 Feb	11244767
Economic evaluation of the fentanyl transdermal system for the treatment of chronic moderate to severe pain.	2001 Feb	11226764
Nociceptin/orphanin FQ exacerbates excitotoxic white-matter lesions in the murine neonatal brain.	2001 Feb	11181645
Cardiovascular effects of sevoflurane, isoflurane, halothane, and fentanyl-midazolam in children with congenital heart disease: an echocardiographic study of myocardial contractility and hemodynamics.	2001 Feb	11176085
Levobupivacaine for epidural analgesia in labor: the sparing effect of epidural fentanyl.	2001 Feb	11159242
Spinal and supraspinal components of opioid antinociception in streptozotocin induced diabetic neuropathy in rats.	2001 Feb 1	11166970
Interscalene brachial plexus anaesthesia with small volumes of ropivacaine 0.75%: effects of the injection technique on the onset time of nerve blockade.	2001 Jan	11270011
Comparative analysis of costs of total intravenous anaesthesia with propofol and remifentanil vs. balanced anaesthesia with isoflurane and fentanyl.	2001 Jan	11270005
Strong opioids for cancer pain.	2001 Jan	11220062
[Anesthesia for a patient with cardiac sarcoidosis].	2001 Jan	11211755
[Low concentration/high volume is more effective than high concentration/low volume for postoperative continuous epidural analgesia with the combination of bupivacaine and fentanyl].	2001 Jan	11211743
Serotonin syndrome: potential consequences of Meridia combined with Demerol or fentanyl.	2001 Jan	11176649
Survey of 1057 patients receiving postoperative patient-controlled epidural analgesia.	2001 Jan	11167440
Digitally assisted acromioplasty: the effect of interscalene block on this new surgical technique.	2001 Jan	11154366
The influence of halothane, isoflurane and sevoflurane on rocuronium infusion in children.	2001 Jan	11152037
Opiates, intracranial pressure, and autoregulation.	2001 Jan	11135743
The Combitube in elective surgery: a report of 200 cases.	2001 Jan	11135725
Buprenorphine substitution ameliorates spontaneous withdrawal in fentanyl-dependent rat pups.	2001 Jan	11134491
Demographic and therapeutic determinants of pain reactivity in very low birth weight neonates at 32 Weeks' postconceptional Age.	2001 Jan	11134442
Awake craniotomy for removal of intracranial tumor: considerations for early discharge.	2001 Jan	11133607
Dexamethasone facilitates discharge after outpatient anorectal surgery.	2001 Jan	11133606
A randomized, double-blinded comparison of intrathecal morphine, sufentanil and their combination versus IV morphine patient-controlled analgesia for postthoracotomy pain.	2001 Jan	11133596
Ultrarapid opioid detoxification: effects on cardiopulmonary physiology, stress hormones and clinical outcomes.	2001 Jan 1	11137281
A murine model of opioid-induced hyperalgesia.	2001 Jan 31	11165371
Surgery of the canine vagina and vulva.	2001 Mar	11265492
Comparison of midazolam with or without fentanyl for conscious sedation and hemodynamics in coronary angiography.	2001 Mar	11264560
Cannabinoidergic and opioidergic inhibition of spinal reflexes in the decerebrated, spinalized rabbit.	2001 Mar	11249966
Morphine and alternative opioids in cancer pain: the EAPC recommendations.	2001 Mar 2	11237376

Patents

Sample Use Guides

In Vivo Use Guide

Dosage should be individualized. Some of the factors to be considered in determining the dose are age, body weight, physical status, underlying pathological condition, use of other drugs, type of anesthesia to be used and the surgical procedure involved. Dosage should be reduced in elderly or debilitated patients (see PRECAUTIONS). Vital signs should be monitored routinely. I. Premedication — Premedication (to be appropriately modified in the elderly, debilitated and those who have received other depressant drugs) — 50 to 100 mcg (0.05 to 0.1 mg) (1 to 2 mL) may be administered intramuscularly 30 to 60 minutes prior to surgery. II. Adjunct to General Anesthesia — See Dosage Range Chart III. Adjunct to Regional Anesthesia - 50 to 100 mcg (0.05 to 0.1 mg) (1 to 2 mL) may be administered intramuscularly or slowly intravenously, over one to two minutes, when additional analgesia is required. IV. Postoperatively (recovery room) - 50 to 100 mcg (0.05 to 0.1 mg) (1 to 2 mL) may be administered intramuscularly for the control of pain, tachypnea and emergence delirium. The dose may be repeated in one to two hours as needed

Route of Administration: Other

In Vitro Use Guide

0.5 - 5 ng/ml fentanyl inhibited viability of SW1990 cells in vitro.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:32:29 GMT 2023` Edited by `admin` on `Fri Dec 15 17:32:29 GMT 2023`
Record UNII	MUN5LYG46H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENTANYL CITRATE

Official Name

English

LEPTANAL

Brand Name

English

FENTANYL CITRATE [EMA EPAR]

Common Name

English

FENTANYL CITRATE CII

Common Name

English

INSTANYL

Brand Name

English

KW-2246

Common Name

English

SUBLIMAZE

Brand Name

English

LAZANDA

Brand Name

English

FENTANYL CITRATE [MI]

Common Name

English

FENTANYL CITRATE [EP MONOGRAPH]

Common Name

English

FENTANYL CITRATE [ORANGE BOOK]

Common Name

English

R-4263

Code

English

EFFENTORA

Brand Name

English

ABSTRAL

Brand Name

English

INNOVAR COMPONENT FENTANYL CITRATE

Common Name

English

FENTANYL CITRATE [USAN]

Common Name

English

N-(1-Phenethyl-4-piperidyl)propionanilide citrate (1:1)

Systematic Name

English

MCN-JR-4263-49

Code

English

FENTORA

Brand Name

English

FENTANYL CITRATE [USP MONOGRAPH]

Common Name

English

PROPANAMIDE, N-PHENYL-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)

Systematic Name

English

FENTANYL CITRATE CII [USP-RS]

Common Name

English

FENTANYL CITRATE [MART.]

Common Name

English

FENTANYL CITRATE COMPONENT OF INNOVAR

Common Name

English

FENTANYL CITRATE [GREEN BOOK]

Common Name

English

ACTIQ

Brand Name

English

FENTANYL CITRATE [JAN]

Common Name

English

ONSOLIS

Brand Name

English

Fentanyl citrate [WHO-DD]

Common Name

English

FENTANYL BUCCAL

Brand Name

English

FENTANYL CITRATE [VANDF]

Common Name

English

Classification Tree Code System Code

DEA NO.

9801

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

EMA ASSESSMENT REPORTS

INSTANYL (AUTHORIZED: PAIN)

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

EMA ASSESSMENT REPORTS

EFFENTORA (AUTHORIZED: PAIN)

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

NCI_THESAURUS

C67413

Created by admin on Fri Dec 15 17:32:30 GMT 2023 , Edited by admin on Fri Dec 15 17:32:30 GMT 2023

CFR

21 CFR 522.800

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

NCI_THESAURUS

C1506

Created by admin on Fri Dec 15 17:32:30 GMT 2023 , Edited by admin on Fri Dec 15 17:32:30 GMT 2023

Code System Code Type Description

FDA UNII

MUN5LYG46H

Created by admin on Fri Dec 15 17:32:30 GMT 2023 , Edited by admin on Fri Dec 15 17:32:30 GMT 2023

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MERCK INDEX

m5298

Created by admin on Fri Dec 15 17:32:30 GMT 2023 , Edited by admin on Fri Dec 15 17:32:30 GMT 2023

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Merck Index

ECHA (EC/EINECS)

213-588-0

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

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CAS

990-73-8

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

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DAILYMED

MUN5LYG46H

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

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CHEBI

31602

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

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EPA CompTox

DTXSID80243933

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

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RS_ITEM_NUM

1270005

Created by admin on Fri Dec 15 17:32:30 GMT 2023 , Edited by admin on Fri Dec 15 17:32:30 GMT 2023

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NCI_THESAURUS

C47994

Created by admin on Fri Dec 15 17:32:30 GMT 2023 , Edited by admin on Fri Dec 15 17:32:30 GMT 2023

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PUBCHEM

13810

Created by admin on Fri Dec 15 17:32:30 GMT 2023 , Edited by admin on Fri Dec 15 17:32:30 GMT 2023

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DRUG BANK

DBSALT000301

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

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RXCUI

142436

Created by admin on Fri Dec 15 17:32:30 GMT 2023 , Edited by admin on Fri Dec 15 17:32:30 GMT 2023

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RxNorm

ChEMBL

CHEMBL596

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

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EVMPD

SUB02129MIG

Created by admin on Fri Dec 15 17:32:29 GMT 2023 , Edited by admin on Fri Dec 15 17:32:29 GMT 2023

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SMS_ID

100000092142

Created by admin on Fri Dec 15 17:32:30 GMT 2023 , Edited by admin on Fri Dec 15 17:32:30 GMT 2023

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Related Record Type Details


					XF417D3PSL

ANHYDROUS CITRIC ACID

PARENT -> SALT/SOLVATE


					UF599785JZ

FENTANYL

PARENT -> SALT/SOLVATE

Related Record Type Details


					96O442668X

PHENETHYL BROMIDE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					9BV2D1A57H

BENZYLFENTANYL

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					G344JN7CAQ

PYRUVYL FENTANYL

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:


					2MK6D8JV6J

NORFENTANYL

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					6DZ28538KS

ACETYLFENTANYL

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					7FTW970M7K

N-PHENYL-1-(PHENYLMETHYL)-4-PIPERIDINAMINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					07V1H7R6ZN

BUTYRFENTANYL

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:


					MM6ALH2F07

FENTANYL N-OXIDE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					TA269SD04T

BENZALDEHYDE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					CQ9ROS690X

4-ANILINOPIPERIDINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					Q88EHD0U8G

DESPROPIONYLFENTANYL

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

Related Record Type Details


					UF599785JZ

FENTANYL

ACTIVE MOIETY

AE	Significance	Dose	Population
Apnea	Disc. AE	6 mg single, transdermal (total) Overdose Dose: 6 mg Route: transdermal Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463	healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463
Bradypnea	Disc. AE	6 mg single, transdermal (total) Overdose Dose: 6 mg Route: transdermal Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463	healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463
Diaphoresis	Disc. AE	6 mg single, transdermal (total) Overdose Dose: 6 mg Route: transdermal Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463	healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463
Respiratory depression	Disc. AE	6 mg single, transdermal (total) Overdose Dose: 6 mg Route: transdermal Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463	healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463
Tachycardia	Disc. AE	6 mg single, transdermal (total) Overdose Dose: 6 mg Route: transdermal Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463	healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/22561319 Page: p.463
Respiratory arrest	grade 5 Disc. AE	150 ug 1 times / hour multiple, transdermal Overdose Dose: 150 ug, 1 times / hour Route: transdermal Route: multiple Dose: 150 ug, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/9695458	unknown, 31 n = 1 Health Status: unknown Age Group: 31 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9695458
Acute coronary syndrome	Disc. AE	225 ug 1 times / hour multiple, transdermal Overdose Dose: 225 ug, 1 times / hour Route: transdermal Route: multiple Dose: 225 ug, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/25736329 Page: p.51	unhealthy, 32 n = 1 Health Status: unhealthy Condition: Knee pain Age Group: 32 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25736329 Page: p.51
Syncope	Disc. AE	225 ug 1 times / hour multiple, transdermal Overdose Dose: 225 ug, 1 times / hour Route: transdermal Route: multiple Dose: 225 ug, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/25736329 Page: p.51	unhealthy, 32 n = 1 Health Status: unhealthy Condition: Knee pain Age Group: 32 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25736329 Page: p.51
Hypoxia	50%	800 ug single, sublingual Higher than recommended Dose: 800 ug Route: sublingual Route: single Dose: 800 ug Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 14	healthy, 33.4 n = 8 Health Status: healthy Age Group: 33.4 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 14
Nausea	75%	800 ug single, sublingual Higher than recommended Dose: 800 ug Route: sublingual Route: single Dose: 800 ug Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 14	healthy, 33.4 n = 8 Health Status: healthy Age Group: 33.4 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 14
Somnolence	87.5%	800 ug single, sublingual Higher than recommended Dose: 800 ug Route: sublingual Route: single Dose: 800 ug Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 15	healthy, 33.4 n = 8 Health Status: healthy Age Group: 33.4 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 15
Vomiting	50%	800 ug single, sublingual Higher than recommended Dose: 800 ug Route: sublingual Route: single Dose: 800 ug Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 16	healthy, 33.4 n = 8 Health Status: healthy Age Group: 33.4 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/28942715 Page: p.13, 16
Dry mouth	1.5% Disc. AE	1600 ug 1 times / 15 min multiple, sublingual (max) Highest studied dose Dose: 1600 ug, 1 times / 15 min Route: sublingual Route: multiple Dose: 1600 ug, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309	unhealthy, 53±12 n = 65 Health Status: unhealthy Condition: Pain Age Group: 53±12 Sex: M+F Population Size: 65 Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309
Hallucinations	1.5% Disc. AE	1600 ug 1 times / 15 min multiple, sublingual (max) Highest studied dose Dose: 1600 ug, 1 times / 15 min Route: sublingual Route: multiple Dose: 1600 ug, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309	unhealthy, 53±12 n = 65 Health Status: unhealthy Condition: Pain Age Group: 53±12 Sex: M+F Population Size: 65 Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309
Headache	1.5% Disc. AE	1600 ug 1 times / 15 min multiple, sublingual (max) Highest studied dose Dose: 1600 ug, 1 times / 15 min Route: sublingual Route: multiple Dose: 1600 ug, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309	unhealthy, 53±12 n = 65 Health Status: unhealthy Condition: Pain Age Group: 53±12 Sex: M+F Population Size: 65 Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309
Nausea	1.5% Disc. AE	1600 ug 1 times / 15 min multiple, sublingual (max) Highest studied dose Dose: 1600 ug, 1 times / 15 min Route: sublingual Route: multiple Dose: 1600 ug, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309	unhealthy, 53±12 n = 65 Health Status: unhealthy Condition: Pain Age Group: 53±12 Sex: M+F Population Size: 65 Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309
Vomiting	1.5% Disc. AE	1600 ug 1 times / 15 min multiple, sublingual (max) Highest studied dose Dose: 1600 ug, 1 times / 15 min Route: sublingual Route: multiple Dose: 1600 ug, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309	unhealthy, 53±12 n = 65 Health Status: unhealthy Condition: Pain Age Group: 53±12 Sex: M+F Population Size: 65 Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309
Dizziness	3% Disc. AE	1600 ug 1 times / 15 min multiple, sublingual (max) Highest studied dose Dose: 1600 ug, 1 times / 15 min Route: sublingual Route: multiple Dose: 1600 ug, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309	unhealthy, 53±12 n = 65 Health Status: unhealthy Condition: Pain Age Group: 53±12 Sex: M+F Population Size: 65 Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309
Somnolence	3% Disc. AE	1600 ug 1 times / 15 min multiple, sublingual (max) Highest studied dose Dose: 1600 ug, 1 times / 15 min Route: sublingual Route: multiple Dose: 1600 ug, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309	unhealthy, 53±12 n = 65 Health Status: unhealthy Condition: Pain Age Group: 53±12 Sex: M+F Population Size: 65 Sources: https://pubmed.ncbi.nlm.nih.gov/10068176 Page: p.309
Miosis	Disc. AE	5 mg single, intravenous Accidental dose Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199	unhealthy, 62 n = 1 Health Status: unhealthy Condition: Pain Age Group: 62 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199
Sweating	Disc. AE	5 mg single, intravenous Accidental dose Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199	unhealthy, 62 n = 1 Health Status: unhealthy Condition: Pain Age Group: 62 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199
Visual hallucinations	Disc. AE	5 mg single, intravenous Accidental dose Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199	unhealthy, 62 n = 1 Health Status: unhealthy Condition: Pain Age Group: 62 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199
Confusion	acute Disc. AE	5 mg single, intravenous Accidental dose Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199	unhealthy, 62 n = 1 Health Status: unhealthy Condition: Pain Age Group: 62 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199
Restlessness	mild Disc. AE	5 mg single, intravenous Accidental dose Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199	unhealthy, 62 n = 1 Health Status: unhealthy Condition: Pain Age Group: 62 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9060031 Page: p.199
Opioid abuse	Disc. AE	200 ug 6 times / day multiple, sublingual Recommended Dose: 200 ug, 6 times / day Route: sublingual Route: multiple Dose: 200 ug, 6 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020747s030lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Pain Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020747s030lbl.pdf Page: p.1
Respiratory depression	grade 4 Disc. AE	200 ug 6 times / day multiple, sublingual Recommended Dose: 200 ug, 6 times / day Route: sublingual Route: multiple Dose: 200 ug, 6 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020747s030lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Pain Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020747s030lbl.pdf Page: p.1

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/9618424Curator's Comment: Description was created based on several sources, including https://www.addictioncenter.com/painkillers/fentanyl/ | https://www.ncbi.nlm.nih.gov/pubmed/24635521

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9618424
Curator's Comment: Description was created based on several sources, including https://www.addictioncenter.com/painkillers/fentanyl/ | https://www.ncbi.nlm.nih.gov/pubmed/24635521

C_max

T_1/2

Drug as perpetrator