(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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 465-65-6
• PubChem SID: 46508816; 160964517
• PubChem CID: 5284596

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.066371
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.6951441
• LogD (pH = 7.4): 1.0430377
• Log P: 1.6202211
• Molar Refractivity: 88.7222 cm^3
• Polarizability: 34.542297 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.47
• LOG S: -1.76
• Solubility (Water): 5.64e+00 g/l

PROPERTIES

Physical Property

• Solubility: Soluble
• Hydrophobicity(logP): 0.6

DETAILS

DrugBank - DB01183

• 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