Naloxone HCl
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MedKoo CAT#: 329670

CAS#: 357-08-4 (HCl)

Description: Naloxone is a μ-opioid receptor (MOR) inverse agonist. Naloxone has an extremely high affinity for μ-opioid receptors in the central nervous system (CNS). 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). 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. Naloxone was approved for opioid overdose by the Food and Drug Administration in 1971


Price and Availability

Size
Price

500mg
USD 160
5g
USD 1350
Size
Price

1g
USD 350
10g
USD 2450
Size
Price

2g
USD 650
20g
USD 3850

Naloxone HCl, purity > 99%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 329670
Name: Naloxone HCl
CAS#: 357-08-4 (HCl)
Chemical Formula: C19H22ClNO4
Exact Mass:
Molecular Weight: 363.838
Elemental Analysis: C, 62.72; H, 6.10; Cl, 9.74; N, 3.85; O, 17.59


Related CAS #: 465-65-6 (free base)   357-08-4 (HCl)   51481-60-8 (HCl dihydrate)    

Synonym: Naloxone HCl; EN-15304; EN15304; EN 15304; NIH7890; Naloxone hydrochloride; Narcan; Narcanti; Nalonee;

IUPAC/Chemical Name: (4R,4aS,7aR,12bS)-3-allyl-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one hydrochloride

InChi Key: RGPDIGOSVORSAK-STHHAXOLSA-N

InChi Code: InChI=1S/C19H21NO4.ClH/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;1H/t14-,17+,18+,19-;/m1./s1

SMILES Code: O=C1[C@@](OC2=C(O)C=CC3=C24)([H])[C@@]54CCN(CC=C)[C@@](C3)([H])[C@]5(O)CC1.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>99% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.90.01


Additional Information

Naloxone was patented in 1961 and approved for opioid overdose by the Food and Drug Administration in 1971. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Naloxone is available as a generic medication. Its wholesale price in the developing world is between US$0.50 and 5.30 per dose. The vials of medication are not very expensive (less than 25 USD) in the United States. The price for a package of two auto-injectors in the US, however, has increased from $690 in 2014 to $4,500 in 2016.

The Ki affinity values of (−)-naloxone for the MOR, KOR, and DOR have been reported as 0.559 nM, 4.91 nM, and 36.5 nM, respectively, whereas for (+)-naloxone, 3,550 nM, 8,950 nM, and 122,000 nM, respectively, have been reported. As such, (−)-naloxone appears to be the active isomer. Moreover, these data suggest that naloxone binds to the MOR with approximately 9-fold greater affinity relative to the KOR and around 60-fold greater affinity relative to the DOR.


References

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10: Candy B, Jones L, Vickerstaff V, Larkin PJ, Stone P. Mu-opioid antagonists for opioid-induced bowel dysfunction in people with cancer and people receiving palliative care. Cochrane Database Syst Rev. 2018 Jun 5;6:CD006332. doi: 10.1002/14651858.CD006332.pub3. Review. PubMed PMID: 29869799.

11: Musy SN, Ausserhofer D, Schwendimann R, Rothen HU, Jeitziner MM, Rutjes AW, Simon M. Trigger Tool-Based Automated Adverse Event Detection in Electronic Health Records: Systematic Review. J Med Internet Res. 2018 May 30;20(5):e198. doi: 10.2196/jmir.9901. Review. PubMed PMID: 29848467; PubMed Central PMCID: PMC6000482.

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15: Anguelova GV, Vlak MHM, Kurvers AGY, Rijsman RM. Pharmacologic and Nonpharmacologic Treatment of Restless Legs Syndrome. Sleep Med Clin. 2018 Jun;13(2):219-230. doi: 10.1016/j.jsmc.2018.02.005. Review. PubMed PMID: 29759272.

16: Winkelmann J, Allen RP, Högl B, Inoue Y, Oertel W, Salminen AV, Winkelman JW, Trenkwalder C, Sampaio C. Treatment of restless legs syndrome: Evidence-based review and implications for clinical practice (Revised 2017)(§). Mov Disord. 2018 Jul;33(7):1077-1091. doi: 10.1002/mds.27260. Epub 2018 May 14. Review. PubMed PMID: 29756335.

17: Ragguett RM, Rong C, Rosenblat JD, Ho RC, McIntyre RS. Pharmacodynamic and pharmacokinetic evaluation of buprenorphine + samidorphan for the treatment of major depressive disorder. Expert Opin Drug Metab Toxicol. 2018 Apr;14(4):475-482. doi: 10.1080/17425255.2018.1459564. Epub 2018 Apr 6. Review. PubMed PMID: 29621905.

18: Ostling PS, Davidson KS, Anyama BO, Helander EM, Wyche MQ, Kaye AD. America's Opioid Epidemic: a Comprehensive Review and Look into the Rising Crisis. Curr Pain Headache Rep. 2018 Apr 4;22(5):32. doi: 10.1007/s11916-018-0685-5. Review. PubMed PMID: 29619569.

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