Naloxone
- naloxone
- 465-65-6
- l-Naloxone
- n-Allylnoroxymorphone
- (-)-Naloxone
- Create:2005-03-26
- Modify:2025-01-11
- Abello, Naloxone
- Curamed, Naloxon
- Dihydride, Naloxone Hydrochloride
- Hydrobromide, Naloxone
- Hydrochloride Dihydride, Naloxone
- Hydrochloride, Naloxone
- MRZ 2593
- MRZ 2593 Br
- MRZ 2593-Br
- MRZ 2593Br
- MRZ-2593
- MRZ2593
- Nalone
- Naloxon Curamed
- Naloxon ratiopharm
- Naloxon-ratiopharm
- Naloxone
- Naloxone Abello
- Naloxone Hydrobromide
- Naloxone Hydrochloride
- Naloxone Hydrochloride Dihydride
- Naloxone Hydrochloride, (5 beta,9 alpha,13 alpha,14 alpha)-Isomer
- Naloxone, (5 beta,9 alpha,13 alpha,14 alpha)-Isomer
- Narcan
- Narcanti
- naloxone
- 465-65-6
- l-Naloxone
- n-Allylnoroxymorphone
- (-)-Naloxone
- Narcan
- EN 1530 base
- Naloxona
- Naloxonum
- Nalossone [DCIT]
- Naloxonum [INN-Latin]
- Nalossone
- Naloxona [INN-Spanish]
- N-Allyl-noroxymorphone
- DBL Naloxone
- 1-N-Allyl-14-hydroxynordihydromorphinone
- HSDB 3279
- Naloxone Nasal Spray
- Nyxoid
- 1-N-Allyl-7,8-dihydro-14-hydroxynormorphinone
- l-N-Allyl-14-hydroxynordihydromorphinone
- EINECS 207-365-7
- UNII-36B82AMQ7N
- NSC 70413
- NSC-70413
- 17-Allyl-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one
- Naloxone (INN)
- 17-Allyl-4,5-alpha-epoxy-3,14-dihydroxymorphinan-6-one
- l-N-Allyl-7,8-dihydro-14-hydroxynormorphinone
- BRN 1089071
- 36B82AMQ7N
- CHEBI:7459
- DTXSID8023349
- N-Allyl-4,5alpha-epoxy-3,14-dihydroxy-6-morphinanon
- Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5alpha)-
- 12-Allyl-7,7a,8,9-tetrahydro-3,7a-dihydroxy-4aH-8,9c-iminoethanophenanthro(4,5-bcd)furanone
- Morphinan-6-one, 17-allyl-4,5alpha-epoxy-3,14-dihydroxy-
- Morphinan-6-one, 4,5alpha-epoxy-3,14-dihydroxy-17-(2-propenyl)-
- 17-allyl-3,14-dihydroxy-4,5alpha-epoxymorphinan-6-one
- Normorphinone, N-allyl-7,8-dihydro-14-hydroxy-, (-)-
- DTXCID703349
- NIOSH/QD2135000
- Nalone
- RAM-301
- (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
- Naloxonum (INN-Latin)
- Narcon
- NALOXONE [INN]
- Naloxona (INN-Spanish)
- 7,8-Dihydro-N-allyl-14-hydroxynormorphinone
- Naloxone [INN:BAN]
- QD21350000
- 3,14-dihydroxy-17-(prop-2-en-1-yl)-4,5alpha-epoxymorphinan-6-one
- Morphinan-6-one, 4,5-alpha-epoxy-3,14-dihydroxy-17-(2-propenyl)-
- NALOXONE (USP-RS)
- NALOXONE [USP-RS]
- Normorphinone, 7,8-dihydro-N-allyl-14-hydroxy-
- (-)-N-ALLYL-14-HYDROXYNORDIHYDROMORPHINONE
- (1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one
- 17-Allyl-3,14-dihydroxy-4,5-alpha-epoxymorphinan-6-one
- 17-ALLYL-4,5A-EPOXY-3,14-DIHYDROXYMORPHINAN-6-ONE
- Morphinan-6-one, 17-allyl-3,14-dihydroxy-4,5-alpha-epoxy-
- MLS000069540
- MORPHINAN-6-ONE, 4,5-EPOXY-3,14-DIHYDROXY-17-(2-PROPENYL)-
- (5alpha)-3,14-dihydroxy-17-prop-2-en-1-yl-4,5-epoxymorphinan-6-one
- [3H]naloxone
- CAS-465-65-6
- NSC70413
- DBL Naloxone (TN)
- MLS000736771
- SMR000058766
- [N-allyl-2,3-3H]naloxone
- NCGC00162267-02
- Naloxonum (Latin)
- NLX
- Normorphinone, N-allyl-dihydro-14-hydroxy-
- naloxoni hydrochloridum
- NALOXONE [HSDB]
- NALOXONE [MI]
- CHEMBL80
- NALOXONE [VANDF]
- Prestwick0_000111
- Prestwick1_000111
- Prestwick2_000111
- Prestwick3_000111
- NALOXONE [WHO-DD]
- NALOXONE [EMA EPAR]
- SCHEMBL34284
- BSPBio_000122
- (-)-N-allyl-14-hydroxynordihydroxymorphinan-6-one
- BIDD:GT0110
- SPBio_002061
- NALOXONE [ORANGE BOOK]
- BPBio1_000136
- GTPL1638
- GTPL1676
- BDBM54795
- cid_5464092
- A06AH04
- V03AB15
- Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5.alpha.)-
- BDBM579486
- HMS2090F20
- US11484525, Compound Naloxone
- Tox21_112006
- (5alpha)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-one
- BDBM50000788
- HY-17417A
- PDSP2_001520
- AKOS016009988
- Tox21_112006_1
- DB01183
- SMP1_000205
- NCGC00024674-02
- NCGC00024674-03
- NCGC00024674-14
- NCGC00274058-01
- 12-Allyl-7,7a,8,9-tetrahydro-3,7a-dihydroxy-4aH-8,9c-iminoethanophenanthro[4,5-bcd]furan-5(6H)-one
- DA-65917
- 4683B
- CS-0012343
- Kloxxado (naloxone hydrochloride nasal spray)
- NS00002914
- C07252
- D08249
- EN300-19748912
- Morphinan-6-one,5.alpha.-epoxy-3,14-dihydroxy-
- Q282902
- BRD-K67511046-001-02-3
- BRD-K67511046-003-03-7
- BRD-K67511046-003-14-4
- BRD-K67511046-003-15-1
- BRD-K67511046-003-16-9
- Morphinan-6-one, 17-allyl-4,5alpha-epoxy-3,14-dihydroxy- (8CI)
- Morphinan-6-one,5.alpha.-epoxy-3,14-dihydroxy-17-(2-propenyl)-
- (5alpha)-4,5-Epoxy-3,14-dihydroxy-17-(2-propen-1-yl)morphinan-6-one
- [17-(2,3-3H-2-propenyl)]-4, 5a -epoxy-3,14-dihydroxymorphinan-6-one
- Morphinan-6-one,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5.alpha.)-
- 4aH-8,5-bcd]furan-5(6H)-one, N-allyl-7,7a,8,9-tetrahydro-3,7a-dihydroxy-
- Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5alpha)- (9CI)
- (4R,4aS,7aR,12bS)-3-allyl-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;hydrochloride
- (4R,4aS,7aR,12bS)-4a,9-bis(oxidanyl)-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;hydrochloride
- (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-prop-2-enyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;hydrochloride
- (naloxone) 4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one
- (naloxone)4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one
- (naloxone)4-allyl-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one
- 4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one
- 4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one (naloxone)
- 4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one( Naloxone)
- 4-allyl-10,17-dihydroxy-(1S,5R,13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one(Naxolone)
- 4-allyl-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one
- 4-allyl-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one(naloxone)C2H2O4
177 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
166.12 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
169.33 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
171.08107 38336
172.084396 2996
128.06189 1556
228.113098 820
156.057419 816
328.156586 100
310.144501 43.25
329.158752 20.11
253.109604 9.93
311.146881 8.12
328.1555 100
310.1450 30.13
253.1103 1.01
310.1434 100
328.1541 34.53
253.1094 11.29
268.1333 7.26
269.1162 4.38
91.05385049003485 0.14
77.03663749003485 0.09
115.05244349003485 0.06
65.03781849003484 0.05
308.09160931777086 0.04
140.05770428255178 9.82
225.05629886216207 9.72
219.11312316056228 9.62
308.10349638805997 9.52
262.089614834573 9.21
- Naloxone Hydrochloride (has salt form)
- Naloxone hydrochloride dihydrate (is active moiety of)
- Cytoplasm
- Membrane
Use (kg; approx.) in Germany (2009): >2500
Consumption (g per capita; approx.) in Germany (2009): 0.0305
Excretion rate: 0.5
Calculated removal (%): 2.3
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (89.1%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (87%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (87%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Acute Tox. 4 (100%)
Skin Irrit. 2 (89.1%)
Eye Irrit. 2 (87%)
STOT SE 3 (87%)
IMAP assessments - Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-,(5.alpha.)-: Environment tier I assessment
IMAP assessments - Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-,(5.alpha.)-: Human health tier I assessment
Therapy with naloxone has not been linked to serum enzyme elevations or to idiosyncratic acute, clinically apparent liver injury. Patients with opioid overdose often have underlying chronic liver diseases such as alcoholic liver disease, hepatitis B or C, but treatment with naloxone does not appear to exacerbate those conditions. Naloxone is extensively metabolized in the liver, but largely by conjugation with glucuronide followed by its urinary excretion.
Likelihood score: E (unlikely cause of clinically apparent liver injury).
Drug Class: Opioid Antagonists; see also Substance Abuse Treatment Agents
Other Drugs in the Class: Nalmefene; Naloxegol, Naltrexone
M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007
M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015
◉ Summary of Use during Lactation
Naloxone is excreted into milk in very small amounts and is not detectable in the plasma of breastfed infants because of its very poor oral bioavailability. Routine use of naloxone in combination products is of no concern during breastfeeding. However, if naloxone is required by the mother for an opioid overdose, she should withhold nursing until the opioid is out of her system.
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
In contrast to its effect in some animal species, naloxone does not affect suckling-induced secretion of oxytocin or prolactin in postpartum women.
◈ What is naloxone?
Naloxone is a medication used to block the effects of opioids. Examples of some opioids are heroin, morphine, codeine, oxycodone, and hydrocodone. Naloxone has also been used to stop someone from dying from an opioid overdose. Brand names for naloxone are Narcan® (nasal spray) and Evzio® (auto-injector).Naloxone combined with buprenorphine (https://mothertobaby.org/fact-sheets/buprenorphine/) is a medication whose brand name is Suboxone®. This combination drug is used to treat opioid use disorder (“OUD”). Much of the information on naloxone in pregnancy involves studies where this combination of medication (naloxone and buprenorphine) was used rather than the study of naloxone used on its own.Naloxone is added to the opioid pain medication pentazocine (Talwin NX®) to prevent pentazocine abuse.Sometimes when people find out they are pregnant, they think about changing how they take their medication, or stopping their medication altogether. However, it is important to talk with your healthcare providers before making any changes to how you take this medication. Your healthcare providers can talk with you about the benefits of treating your condition and the risks of untreated illness during pregnancy.
◈ I take naloxone. Can it make it harder for me to get pregnant?
Studies have not been done to see if taking naloxone can make it harder for to get pregnant.
◈ Does taking naloxone increase the chance for miscarriage?
Miscarriage can occur in any pregnancy. There is limited information on naloxone and pregnancy loss. One study found that there was not a greater chance for a stillbirth in pregnancies in which naloxone was used. Overdosing with an opioid might increase the chances for pregnancy loss.
◈ Does taking naloxone increase the chance of birth defects?
Every pregnancy starts out with a 3-5% chance of having a birth defect. This is called the background risk. Very little naloxone from buprenorphine/naloxone gets into the blood when it is taken by mouth. This suggests that only very small amounts of naloxone would be likely to reach the developing baby. There are limited studies on the use of buprenorphine/naloxone combination during their first trimester; these studies did not find an increased chance of birth defects above the background risk in their babies.No studies have been done to see if treatment with naloxone for an opioid overdose in the first trimester can increase the chance for birth defects.
◈ Does taking naloxone in pregnancy increase the chance of other pregnancy related problems?
Studies on the combination buprenorphine/naloxone did not find an increased chance for pregnancy-related problems such as preterm delivery (birth before week 37) or low birth weight (weighing less than 5 pounds, 8 ounces [2500 grams] at birth).
◈ Could being treated with naloxone for an overdose cause other pregnancy complications?
Studies have not been done to see if naloxone causes pregnancy complications when it is used to treat an overdose. However, people who misuse opioids could have a greater chance for pregnancy complications. During an opioid overdose a person’s breathing slows down. If a person who is pregnant is not breathing well, the developing baby might not get enough oxygen during that time. Low oxygen might have a harmful effect on the baby’s development. Naloxone helps return breathing to normal. Naloxone can also cause symptoms of withdrawal from the opiod that was being misued. The effects of opioid withdrawal while pregnant are not well understood. After treatment with naloxone for opioid overdose, let your healthcare providers know about it as soon as possible.
◈ Does taking naloxone in pregnancy affect future behavior or learning for the child?
Studies have not been done to see if naloxone can cause behavior or learning issues for the child.
◈ Breastfeeding while taking naloxone:
It is not known if naloxone gets into breastmilk in significant amounts. But if naloxone does get into breastmilk, it is thought that a nursing baby would not be able to absorb it into their body very well from their stomach.If naloxone is used to treat opioid overdose, it may be suggested to stop breastfeeding until the opiate is out of the body of the person who is breastfeeding. If any opioids have been used while breastfeeding, it has been recommended to closely monitor the breastfeeding infant for side effects. If there is an opioid in breastmilk the baby might be sleepy, could have problems with feeding, and might have problems breathing. Be sure to talk to your healthcare provider about all of your breastfeeding questions.
◈ If a male takes naloxone, could it affect fertility (ability to get partner pregnant) or increase the chance of birth defects?
Studies have not been done to see if naloxone could affect male fertility or increase the chance of birth defects.In general, exposures that fathers or sperm donors have are unlikely to increase the risks to a pregnancy. For more information, please see the MotherToBaby fact sheet Paternal Exposures at https://mothertobaby.org/fact-sheets/paternal-exposures-pregnancy/.
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Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=UZHSEJADLWPNLE-GRGSLBFTSA-N
- Australian Industrial Chemicals Introduction Scheme (AICIS)Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-,(5.alpha.)-https://services.industrialchemicals.gov.au/search-assessments/
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_use
- DTP/NCILICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuse
- EPA DSSToxCompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- European Chemicals Agency (ECHA)LICENSEUse of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.https://echa.europa.eu/web/guest/legal-noticeNaloxone (EC: 207-365-7)https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/39621
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- Hazardous Substances Data Bank (HSDB)
- Human Metabolome Database (HMDB)LICENSEHMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.http://www.hmdb.ca/citingHMDB0015314_msms_374520https://hmdb.ca/metabolites/HMDB0015314#spectra
- CCSbaseCCSbase Classificationhttps://ccsbase.net/
- ChEBI
- FDA Pharm ClassesLICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linkingFDA Pharmacological Classificationhttps://www.fda.gov/ForIndustry/DataStandards/StructuredProductLabeling/ucm162549.htm
- LiverTox
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