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465-65-6 molecular structure
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(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

ChemBase ID: 1054
Molecular Formular: C19H21NO4
Molecular Mass: 327.37434
Monoisotopic Mass: 327.14705816
SMILES and InChIs

SMILES:
O1[C@@H]2[C@]34[C@](O)([C@H](N(CC3)CC=C)Cc3c4c1c(O)cc3)CCC2=O
Canonical 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
InChIKey:
UZHSEJADLWPNLE-GRGSLBFTSA-N

Cite this record

CBID:1054 http://www.chembase.cn/molecule-1054.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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
IUPAC Traditional name
naloxone
Brand Name
Nalone
Narcan
Narcanti
Narcon
Synonyms
L-Naloxone
N-Allylnoroxymorphone
EN 1530 Base
Nalossone [Dcit]
Naloxona [INN-Spanish]
Naloxone HCl
Naloxonum [INN-Latin]
Naloxone
CAS Number
465-65-6
PubChem SID
46508816
160964517
PubChem CID
5284596

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.066371  H Acceptors
H Donor LogD (pH = 5.5) -0.6951441 
LogD (pH = 7.4) 1.0430377  Log P 1.6202211 
Molar Refractivity 88.7222 cm3 Polarizability 34.542297 Å3
Polar Surface Area 70.0 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.47  LOG S -1.76 
Solubility (Water) 5.64e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Soluble expand Show data source
Hydrophobicity(logP)
0.6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01183 external link
Item Information
Drug Groups approved
Description A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors. [PubChem]
Indication For the complete or partial reversal of narcotic depression, including respiratory depression, induced by opioids including natural and synthetic narcotics, propoxyphene, methadone and the narcotic-antagonist analgesics: nalbuphine, pentazocine and butorphanol.
Pharmacology Naloxone is an opiate antagonist and prevents or reverses the effects of opioids including respiratory depression, sedation and hypotension. Also, it can reverse the psychotomimetic and dysphoric effects of agonist-antagonists such as pentazocine. Naloxone is an essentially pure narcotic antagonist, i.e., it does not possess the "agonistic" or morphine-like properties characteristic of other narcotic antagonists; naloxone does not produce respiratory depression, psychotomimetic effects or pupillary constriction. In the absence of narcotics or agonistic effects of other narcotic antagonists, it exhibits essentially no pharmacologic activity.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption Well absorbed following intramuscular injection.
Half Life 30-81 minutes
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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PATENTS

PATENTS

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