(1S,5R,13R,17R)-10-hydroxy-4-methyl-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: 212
• Molecular Formular: C17H19NO3
• Molecular Mass: 285.33766
• Monoisotopic Mass: 285.13649347
• SMILES: O1[C@@H]2[C@]34[C@H]([C@H](N(CC3)C)Cc3c4c1c(O)cc3)CCC2=O
• Canonical SMILES: O=C1CC[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O
• InChI: InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1
• InChIKey: WVLOADHCBXTIJK-YNHQPCIGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one; (1S,5R,13R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-14-one
• IUPAC Traditional name: hydromorphone
• Brand Name: DiMo; Dilaudid; Dilaudid Oros; Dilaudid-hp; Dimorphone; Hymorphan; Idromorfone; Laudacon; Laudicon; Novolaudon; Palladone; Paramorphan
• Synonyms: Dihydromorfinon [Czech]; Dihydromorphinone; Hidromorfona [INN-Spanish]; Hydromorfona [Spanish]; Hydromorphon; Hydromorphone HCL; Hydromorphonum [INN-Latin]; Hydromorphone

Database IDs

• CAS Number: 466-99-9
• PubChem SID: 160963675; 46508700
• PubChem CID: 5284570
• CHEBI ID: 5790
• ATC CODE: N02AA03
• CHEMBL: 398707
• Chemspider ID: 4447624
• DrugBank ID: DB00327
• KEGG ID: D08047
• Unique Ingredient Identifier: Q812464R06
• Wikipedia Title: Hydromorphone
• Medline Plus: a682013

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.107628
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.1500992
• LogD (pH = 7.4): 0.57617587
• Log P: 1.6227497
• Molar Refractivity: 78.2624 cm^3
• Polarizability: 30.4739 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.69
• LOG S: -1.81
• Solubility (Water): 4.39e+00 g/l

PROPERTIES

Physical Property

• Solubility: HCl: 333 mg/mL (20°C)
• Hydrophobicity(logP): 0.9

Pharmacology Properties

• Admin Routes: oral, intramuscular, intravenous, subcutaneous, intranasal, rectal, sublingual, transmucosal, buccal, transdermal (experimental)
• Bioavailability: Oral: 30–35%, Intranasal: 52–58%
• Excretion: Renal
• Half Life: 2–3 hours
• Metabolism: Hepatic
• Protein Bound: 20%
• Legal Status: Class A—Non-Clinical use—and Schedule II—Clinical use (UK), ; DEA Schedule II (USA), S8 (AU)
• Pregnancy Category: C

DETAILS

DrugBank - DB00327

• Drug Groups: illicit; approved
• Description: An opioid analgesic derived from morphine and used mainly as an analgesic. It has a shorter duration of action and is more potent than morphine. [PubChem]
• Indication: For the relief of moderate to severe pain such as that due to surgery, cancer, trauma/injury, or burns.
• Pharmacology: Hydromorphone is a hydrogenated ketone derivative of morphine that acts as a narcotic analgesic. It has a shorter duration of action than morphine. Hydromorphone is approximately 8 times more potent on a milligram basis than morphine. In addition, hydromorphone is better absorbed orally than is morphine. In clinical settings, Hydromorphone exerts its principal pharmacological effect on the central nervous system and gastrointestinal tract. Its primary actions of therapeutic value are analgesia and sedation. Hydromorphone appears to increase the patient's tolerance for pain and to decrease discomfort, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Opioids also produce respiratory depression by direct action on brain stem respiratory centers.
• Toxicity: Hydromorphone is a schedule II narcotic which can lead to physical dependence or addiction. High doses lead to respiratory depression, nausea, and vomiting. Overdoses lead to extreme somnolence progressing to stupor or coma, skeletal muscle flaccidity, cold and clammy skin, and sometimes bradycardia and hypotension. In severe overdosage, apnea, circulatory collapse, cardiac arrest and death may occur.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic. After absorption hydromorphone is metabolized by the liver to the glucuronide conjugate which is then excreted in the urine. Hydromorphone is metabolized to the major metabolites hydromorphone-3-glucuronide, hydromorphone-3-glucoside and dihydroisomorphine-6-glucuronide.
• Absorption: Better absorbed orally than morphine
• Half Life: 2.6 hours (oral); 18.6 hours for sustained release Palladone
• Protein Binding: 20%
• Elimination: Only a small amount of the hydromorphone dose is excreted unchanged in the urine. ; Most of the dose is excreted as hydromorphone-3-glucuronide along with minor amounts of 6-hydroxy reduction metabolites.
• Clearance: * 1.96 L/min
• References: Coda BA, Rudy AC, Archer SM, Wermeling DP: Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers. Anesth Analg. 2003 Jul;97(1):117-23, table of contents. [Pubmed] ; Vallner JJ, Stewart JT, Kotzan JA, Kirsten EB, Honigberg IL: Pharmacokinetics and bioavailability of hydromorphone following intravenous and oral administration to human subjects. J Clin Pharmacol. 1981 Apr;21(4):152-6. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Coda BA, Rudy AC, Archer SM, Wermeling DP: Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers. Anesth Analg. 2003 Jul;97(1):117-23, table of contents. Pubmed
• Vallner JJ, Stewart JT, Kotzan JA, Kirsten EB, Honigberg IL: Pharmacokinetics and bioavailability of hydromorphone following intravenous and oral administration to human subjects. J Clin Pharmacol. 1981 Apr;21(4):152-6. Pubmed