naloxone   Click here for help

GtoPdb Ligand ID: 1638

Synonyms: (-)-naloxone | Kloxxado® (naloxone hydrochloride nasal spray) | l-naloxone | Narcan® | Nyxoid®
Approved drug
naloxone is an approved drug (FDA (1971), EMA (2017))
Compound class: Synthetic organic
Comment: The approved drug naloxone INN-assigned preparation is the (-)-enantiomer. For a summary of the (+)-enantiomer, see the ligand page for (+)-naloxone. (-)-naloxone is the active enantiomer. The (+) isomer is inactive at the opioid receptors.
Marketed formulations may contain naloxone hydrochloride (PubChem CID 5464092).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 70
Molecular weight 327.15
XLogP 0.31
No. Lipinski's rules broken 0
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Canonical SMILES C=CCN1CCC23C4(C1Cc1c3c(OC2C(=O)CC4)c(cc1)O)O
Isomeric SMILES C=CCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)O)O
InChI 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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1971), EMA (2017))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
1526 naloxone
Synonyms Click here for help
(-)-naloxone | Kloxxado® (naloxone hydrochloride nasal spray) | l-naloxone | Narcan® | Nyxoid®
Database Links Click here for help
Specialist databases
GPCRdb Ligand naloxone
Other databases
CAS Registry No. 465-65-6 (source: Scifinder)
DrugBank Ligand DB01183
DrugCentral Ligand 1878
GtoPdb PubChem SID 135650684
PubChem CID 5284596
Search Google for chemical match using the InChIKey UZHSEJADLWPNLE-GRGSLBFTSA-N
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UniChem Compound Search for chemical match using the InChIKey UZHSEJADLWPNLE-GRGSLBFTSA-N
UniChem Connectivity Search for chemical match using the InChIKey UZHSEJADLWPNLE-GRGSLBFTSA-N
Wikipedia Naloxone