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 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9618424 \| https://www.ncbi.nlm.nih.gov/pubmed/6304563	Agonist 2752		0.15 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 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 8583	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
0.81 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
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
0.93 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

AUC

Value	Dose	Analyte	Population
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
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
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

T_1/2

Value	Dose	Analyte	Population
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
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
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

Doses

Dose	Population	Adverse events
6 mg single, transdermal Overdose Dose: 6 mg Route: transdermal Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/22561319	healthy, 15 Health Status: healthy Age Group: 15 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/22561319	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
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 Health Status: unknown Age Group: 31 Sex: M 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	unhealthy, 32 Health Status: unhealthy Age Group: 32 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/25736329	Disc. AE: Syncope, Acute coronary syndrome... AEs leading to discontinuation/dose reduction: Syncope Acute coronary syndrome Sources: https://pubmed.ncbi.nlm.nih.gov/25736329
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	healthy, 33.4 Health Status: healthy Age Group: 33.4 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28942715	Other AEs: Hypoxia, Nausea... Other AEs: Hypoxia (50%) Nausea (75%) Sources: https://pubmed.ncbi.nlm.nih.gov/28942715
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	healthy, 33.4 Health Status: healthy Age Group: 33.4 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28942715	Other AEs: Somnolence... Other AEs: Somnolence (87.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/28942715
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	healthy, 33.4 Health Status: healthy Age Group: 33.4 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28942715	Other AEs: Vomiting... Other AEs: Vomiting (50%) Sources: https://pubmed.ncbi.nlm.nih.gov/28942715
1600 ug 1 times / 15 min multiple, sublingual 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	unhealthy, 53±12 Health Status: unhealthy Age Group: 53±12 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10068176	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
5 mg single, intravenous Accidental dose Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9060031	unhealthy, 62 Health Status: unhealthy Age Group: 62 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9060031	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
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020747s030lbl.pdf	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

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 926 CYP1A2 2153 CYP2A6 879 CYP2C8/9 42 CYP2E1 1060 P-gp 1741 OCT1 620 OATP1B1 1079 OATP1B3 961 OATP2B1 157	CYP1A1 389 CYP1A2 1197 CYP2C8 810 CYP2C18 149 CYP2C19 1119 CYP2E1 729 CYP3A5 446 CYP3A7 109 P-gp 2052 OATP1A2 67 OATP1B1 503 OCT1 393

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP2C8/9 42	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	likely
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	likely
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	no
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	weak
CYP2A6 911	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	weak
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	weak
OATP2B1 162	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	weak
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/31597043/	yes [IC50 117.7 uM]	NORFENTANYL 3
OCT1 656	inhibitor 4027 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 1932	inhibitor 4027 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 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	yes
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	likely
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	likely
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	likely
CYP3A4 1946	substrate 4014 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 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	minor
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	minor
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	minor
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	minor
OATP1B1 503	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23480028/	no
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31597043/	no
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11964599/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	yes
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9264313/	yes
CYP3A7 109	substrate 4014 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 67	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31746415/	yes
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31597043/	yes	NORFENTANYL 3

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 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
eMolecules	901881	https://www.emolecules.com/cgi-bin/more?vid=901881
ZINC	ZINC000002522669	http://zinc15.docking.org/substances/ZINC000002522669

PubMed

Title	Date	PubMed
Potentiation of narcosis after intravenous lidocaine in a patient given spinal opioids.	1999 Sep	10475320
Fentanyl-induced chest wall rigidity and laryngospasm in preterm and term infants.	2000 Mar	10752838
A comparison of minidose lidocaine-fentanyl and conventional-dose lidocaine spinal anesthesia.	2000 Oct	11004039
Computerised advice on drug dosage to improve prescribing practice.	2001	11279772
Abuse of topical analgesic.	2001 Apr	11282708
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
Effect of midazolam pretreatment on induction dose requirements of propofol in combination with fentanyl in younger and older adults.	2001 Feb	11167469
Evidence that postoperative pain is a mediator of the tumor-promoting effects of surgery in rats.	2001 Feb 1	11166986
Spinal and supraspinal components of opioid antinociception in streptozotocin induced diabetic neuropathy in rats.	2001 Feb 1	11166970
High concentration sevoflurane induction of anesthesia accelerates onset of vecuronium neuromuscular blockade.	2001 Jan	11212046
[Anesthesia for a patient with cardiac sarcoidosis].	2001 Jan	11211755
Ultrarapid opioid detoxification: effects on cardiopulmonary physiology, stress hormones and clinical outcomes.	2001 Jan 1	11137281
Combined spinal and epidural anesthesia with low doses of intrathecal bupivacaine in women with severe preeclampsia: a preliminary report.	2001 Jan-Feb	11172511
Cannabinoidergic and opioidergic inhibition of spinal reflexes in the decerebrated, spinalized rabbit.	2001 Mar	11249966

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 `Mon Mar 31 18:47:59 GMT 2025` Edited by `admin` on `Mon Mar 31 18:47:59 GMT 2025`
Record UNII	MUN5LYG46H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENTANYL CITRATE CII

Preferred Name

English

FENTANYL CITRATE

Official Name

English

LEPTANAL

Brand Name

English

FENTANYL CITRATE [EMA EPAR]

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 [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