U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21NO4
Molecular Weight 327.3743
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NALOXONE

SMILES

[H][C@@]12OC3=C4C(C[C@H]5N(CC=C)CC[C@@]14[C@@]5(O)CCC2=O)=CC=C3O

InChI

InChIKey=UZHSEJADLWPNLE-GRGSLBFTSA-N
InChI=1S/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1

HIDE SMILES / InChI
Naloxone, sold under the brand name Narcan among others, is a medication used to block the effects of opioids, especially in overdose. Naloxone has an extremely high affinity for μ-opioid receptors in the central nervous system (CNS). Naloxone is a μ-opioid receptor (MOR) inverse agonist, and its rapid blockade of those receptors often produces rapid onset of withdrawal symptoms. Naloxone also has an antagonist action, though with a lower affinity, at κ- (KOR) and δ-opioid receptors (DOR). If administered in the absence of concomitant opioid use, no functional pharmacological activity occurs (except the inability for the body to combat pain naturally). In contrast to direct opiate agonists, which elicit opiate withdrawal symptoms when discontinued in opiate-tolerant people, no evidence indicates the development of tolerance or dependence on naloxone. The mechanism of action is not completely understood, but studies suggest it functions to produce withdrawal symptoms by competing for opiate receptor sites within the CNS (a competitive antagonist, not a direct agonist), thereby preventing the action of both endogenous and xenobiotic opiates on these receptors without directly producing any effects itself. When administered parenterally (e.g. intravenously or by injection), as is most common, naloxone has a rapid distribution throughout the body. The mean serum half-life has been shown to range from 30 to 81 minutes, shorter than the average half-life of some opiates, necessitating repeat dosing if opioid receptors must be stopped from triggering for an extended period. Naloxone is primarily metabolized by the liver. Its major metabolite is naloxone-3-glucuronide, which is excreted in the urine. Naloxone is useful both in acute opioid overdose and in reducing respiratory or mental depression due to opioids. Whether it is useful in those in cardiac arrest due to an opioid overdose is unclear. Naloxone is poorly absorbed when taken by mouth, so it is commonly combined with a number of oral opioid preparations, including buprenorphine and pentazocine, so that when taken orally, just the opioid has an effect, but if misused by injecting, the naloxone blocks the effect of the opioid. In a meta-analysis of people with shock, including septic, cardiogenic, hemorrhagic, or spinal shock, those who received naloxone had improved blood flow. Naloxone is also experimentally used in the treatment for congenital insensitivity to pain with anhidrosis, an extremely rare disorder (one in 125 million) that renders one unable to feel pain or differentiate temperatures. Naloxone can also be used as an antidote in overdose of clonidine, a medication that lowers blood pressure.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.3 nM [IC50]
49.8 nM [IC50]
138.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NARCAN

Approved Use

Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for the relief of moderate to severe pain. Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for oral use only.

Launch Date

1971
Primary
NARCAN

Approved Use

Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for the relief of moderate to severe pain. Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for oral use only.

Launch Date

1971
Primary
NARCAN

Approved Use

Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for the relief of moderate to severe pain. Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for oral use only.

Launch Date

1971
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.09 ng/mL
10 mg/kg single, nasal
dose: 10 mg/kg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.87 ng/mL
0.4 mg single, intramuscular
dose: 0.4 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
9.62 ng/mL
8 mg single, nasal
dose: 8 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.83 ng/mL
4 mg single, nasal
dose: 4 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
37.1 ng × min/mL
10 mg/kg single, nasal
dose: 10 mg/kg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.68 ng × h/mL
0.4 mg single, intramuscular
dose: 0.4 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
15 ng × h/mL
8 mg single, nasal
dose: 8 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
7.9 ng × h/mL
4 mg single, nasal
dose: 4 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
28.2 min
10 mg/kg single, nasal
dose: 10 mg/kg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.2 h
0.4 mg single, intramuscular
dose: 0.4 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.1 h
8 mg single, nasal
dose: 8 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NALOXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.8 mg single, intramuscular
Dose: 0.8 mg
Route: intramuscular
Route: single
Dose: 0.8 mg
Sources:
healthy, 23.8 years (range: 22.6–25 years)
n = 12
Health Status: healthy
Age Group: 23.8 years (range: 22.6–25 years)
Sex: M+F
Population Size: 12
Sources:
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
Disc. AE: Hypotension, Bradycardia...
Other AEs: Nausea, Emesis...
AEs leading to
discontinuation/dose reduction:
Hypotension (3 patients)
Bradycardia (2 patients)
Myoclonus (1 patient)
Hypertension (1 patient)
Other AEs:
Nausea (32%)
Emesis (5%)
Seizures (5%)
Headache (5%)
Confusion (5%)
Agitation (3%)
Sources:
8 mg single, intranasal
Dose: 8 mg
Route: intranasal
Route: single
Dose: 8 mg
Sources:
healthy, adult
n = 28
Health Status: healthy
Age Group: adult
Population Size: 28
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypertension 1 patient
Disc. AE
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
Myoclonus 1 patient
Disc. AE
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
Bradycardia 2 patients
Disc. AE
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
Hypotension 3 patients
Disc. AE
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
Agitation 3%
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
Nausea 32%
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
Confusion 5%
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
Emesis 5%
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
Headache 5%
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
Seizures 5%
160 mg/m2 single, intravenous (starting)
Highest studied dose
Dose: 160 mg/m2
Route: intravenous
Route: single
Dose: 160 mg/m2
Sources:
unhealthy, 35-85 years
n = 38
Health Status: unhealthy
Condition: acute ischemic stroke
Age Group: 35-85 years
Population Size: 38
Sources:
PubMed

PubMed

TitleDatePubMed
Prevention by morphine of apomorphine- and oxytocin-induced penile erection and yawning: site of action in the brain.
1992 Jan
Modification of naloxone-induced withdrawal signs by dextromethorphan in morphine-dependent mice.
1999 Jul 14
Seizure and electroencephalographic changes in the newborn period induced by opiates and corrected by naloxone infusion.
1999 Mar
Effects of SCH 23390, raclopride, and haloperidol on morphine withdrawal-induced aggression in male mice.
1999 Sep
Morphine inhibits human microglial cell production of, and migration towards, RANTES.
2000
Acute detoxification of opioid-addicted patients with naloxone during propofol or methohexital anesthesia: a comparison of withdrawal symptoms, neuroendocrine, metabolic, and cardiovascular patterns.
2000 Apr
The effect of spinal ibuprofen on opioid withdrawal in the rat.
2000 Aug
Phenytoin, midazolam, and naloxone protect against fentanyl-induced brain damage in rats.
2000 Dec
Fentanyl-induced chest wall rigidity and laryngospasm in preterm and term infants.
2000 Mar
Differential cardiorespiratory effects of endomorphin 1, endomorphin 2, DAMGO, and morphine.
2000 Sep
Opioid-induced hyperalgesia and incisional pain.
2001 Jul
Inverse agonists and neutral antagonists at mu opioid receptor (MOR): possible role of basal receptor signaling in narcotic dependence.
2001 Jun
Naloxone improves arterial blood pressure and hypoxic ventilatory depression, but not survival, of rats during acute hypoxia.
2001 Mar
Effects of Ferula gummosa Boiss. fractions on morphine dependence in mice.
2001 Sep
Environment associated with morphine and experience of aggression modulate behaviors of postdependent mice.
2002 Jan 15
Safety of enteral naloxone and i.v. neostigmine when used to relieve constipation.
2003 Jun 15
Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme.
2003 May
Systemic morphine-induced release of serotonin in the rostroventral medulla is not mimicked by morphine microinjection into the periaqueductal gray.
2003 Sep
Influence of sweet tasting solutions on opioid withdrawal.
2004 Dec 15
Magnesium influence on morphine--induced pharmacodependence in rats.
2004 Mar
[Effect of nitric oxide synthase inhibitor on the testis cell apoptosis in morphine-dependent rats].
2004 Nov
Testosterone and luteinizing hormone responses to naloxone help predict sexual performance in rams.
2004 Nov
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
Potentiated startle and hyperalgesia during withdrawal from acute morphine: effects of multiple opiate exposures.
2004 Nov
Effect of agmatine on the development of morphine dependence in rats: potential role of cAMP system.
2004 Nov 19
Effects of L-745,870, a dopamine D4 receptor antagonist, on naloxone-induced morphine dependence in mice.
2004 Oct
Rapid, transient, and dose-dependent expression of hsp70 messenger RNA in the rat brain after morphine treatment.
2004 Summer
Calcitonin gene-related peptide-induced suppression of luteinizing hormone pulses in the rat: the role of endogenous opioid peptides.
2005 Aug 1
Effect of fentanyl on lidocaine-induced convulsions in mice.
2005 Dec
Morphine-induced chemotaxis and brain-derived neurotrophic factor expression in microglia.
2005 Jan 12
Naloxone increases ketamine-induced hyperactivity in the open field in female rats.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Effective opiate-receptor antagonist therapy of cholestatic pruritus induced by an oral contraceptive.
2005 May
Patents

Sample Use Guides

Opioid Overdose–Known or Suspected: An initial dose of 0.4 mg to 2 mg of NARCAN may be administered intravenously. If the desired degree of counteraction and improvement in respiratory functions are not obtained, it may be repeated at two- to three-minute intervals. If no response is observed after 10 mg of NARCAN have been administered, the diagnosis of opioid-induced or partial opioid-induced toxicity should be questioned. Intramuscular or subcutaneous administration may be necessary if the intravenous route is not available. Postoperative Opioid Depression: For the partial reversal of opioid depression following the use of opioids during surgery, smaller doses of NARCAN are usually sufficient. The dose of NARCAN should be titrated according to the patient’s response. For the initial reversal of respiratory depression, NARCAN should be injected in increments of 0.1 to 0.2 mg intravenously at two- to three-minute intervals to the desired degree of reversal, i.e., adequate ventilation and alertness without significant pain or discomfort. Larger than necessary dosage of NARCAN may result in significant reversal of analgesia and increase in blood pressure. Similarly, too rapid reversal may induce nausea, vomiting, sweating or circulatory stress. Repeat doses of NARCAN may be required within one- to two-hour intervals depending upon the amount, type (i.e., short or long acting) and time interval since last administration of an opioid. Supplemental intramuscular doses have been shown to produce a longer lasting effect.
Route of Administration: Other
MDCKII-MDR1 assay. Stock solutions of Naloxone (20 mM) were prepared in 100% DMSO and then diluted to the final concentration of 10 mkM, in Dulbecco’s PBS. Naloxone were tested in both directions, apicalto-basolateral (A→B) and basolateral-to-apical (B→A), in duplicate. The ratio BA/AB >2 indicates an efflux phenomena. Permeability studies were conducted at 37 ◦C in incubator for 60 min. The monolayer integrity was evaluated by measuring the TransEpithelial Electrical Resistance (TEER) by using the Millicell-ERS system (Millipore Corporation) and it was considered integer if the resistancewas between 200 and 300 cm2. After the transport study the monolayer integrity was measured in each well by adding a 0.02 mg/mL solution of lucifer yellow (LY); the test was conducted at 37 ◦C for 60 min, and the fluorescence (RFU) was measured at 485/535 nm.
Name Type Language
NALOXONE
EMA EPAR   HSDB   INN   MI   ORANGE BOOK   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
17-ALLYL-4,5A-EPOXY-3,14-DIHYDROXYMORPHINAN-6-ONE
Common Name English
NALOXONE [MI]
Common Name English
DBL NALOXONE
Brand Name English
Naloxone [WHO-DD]
Common Name English
(-)-N-ALLYL-14-HYDROXYNORDIHYDROMORPHINONE
Common Name English
MORPHINAN-6-ONE, 4,5-EPOXY-3,14-DIHYDROXY-17-(2-PROPENYL)-
Systematic Name English
NALOXONE [VANDF]
Common Name English
NALOXONE [USP-RS]
Common Name English
NALOXONE [EMA EPAR]
Common Name English
NSC-70413
Code English
naloxone [INN]
Common Name English
NALOXONE [ORANGE BOOK]
Common Name English
NALOXONE [HSDB]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 280209
Created by admin on Fri Dec 15 15:12:56 GMT 2023 , Edited by admin on Fri Dec 15 15:12:56 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 4.2
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NDF-RT N0000000154
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EMA ASSESSMENT REPORTS SUBOXONE (AUTHORIZED: OPIOID-RELATED DISEASES)
Created by admin on Fri Dec 15 15:12:56 GMT 2023 , Edited by admin on Fri Dec 15 15:12:56 GMT 2023
WHO-VATC QV03AB15
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FDA ORPHAN DRUG 79093
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WHO-ATC V03AB15
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WHO-ATC A06AH04
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LIVERTOX NBK548244
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NDF-RT N0000175691
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WHO-ATC N02AA53
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NCI_THESAURUS C681
Created by admin on Fri Dec 15 15:12:56 GMT 2023 , Edited by admin on Fri Dec 15 15:12:56 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL80
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PRIMARY
LACTMED
Naloxone
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PRIMARY
CHEBI
7459
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PRIMARY
PUBCHEM
5284596
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PRIMARY
SMS_ID
100000085468
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PRIMARY
WIKIPEDIA
NALOXONE
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PRIMARY
DRUG CENTRAL
1878
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PRIMARY
RXCUI
7242
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PRIMARY RxNorm
DAILYMED
36B82AMQ7N
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PRIMARY
EVMPD
SUB09142MIG
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PRIMARY
INN
1526
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PRIMARY
EPA CompTox
DTXSID8023349
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PRIMARY
MESH
D009270
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PRIMARY
FDA UNII
36B82AMQ7N
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PRIMARY
DRUG BANK
DB01183
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PRIMARY
NCI_THESAURUS
C62054
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PRIMARY
RS_ITEM_NUM
1453005
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PRIMARY
IUPHAR
1638
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PRIMARY
HSDB
3279
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PRIMARY
ECHA (EC/EINECS)
207-365-7
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PRIMARY
NSC
70413
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PRIMARY
MERCK INDEX
m7717
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PRIMARY Merck Index
CAS
465-65-6
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PRIMARY