Hydromorphone hydrochlorideProduct ingredient for Hydromorphone

Name
Hydromorphone hydrochloride
Drug Entry
Hydromorphone

Hydromorphone is a pure opioid,1 a semi-synthetic hydrogenated ketone derivative of morphine that has been available clinically since 1920. Structurally, hydromorphone derived from morphine in the modification of the hydroxyl group in the carbon 6 to a carbonyl and the absence of a double bond between the carbon 7 and 8. Due to these modifications, it presents a very high potency and comparable side effect profile to the parent compound.2 Even though hydromorphone does not present a 6-hydroxyl group, it is categorized under the family of phenanthrenes and it is considered a chemical under the schedule II (medical purposes with high addiction potential).3

The first reported approved product containing hydromorphone in the form of hydromorphone hydrochloride was developed by Fresenius Kabi USA and FDA approved in 1984.9

Accession Number
DBSALT000444
Structure
Synonyms
Hydromorphone HCl
UNII
L960UP2KRW
CAS Number
71-68-1
Weight
Average: 321.799
Monoisotopic: 321.113171218
Chemical Formula
C17H20ClNO3
InChI Key
XHILEZUETWRSHC-NRGUFEMZSA-N
InChI
InChI=1S/C17H19NO3.ClH/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;1H/t10-,11+,16-,17-;/m0./s1
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 hydrochloride
SMILES
Cl.[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CCC2=O
PubChem Compound
5462347
ChemSpider
4575386
ChEBI
5791
ChEMBL
CHEMBL1237055
Wikipedia
Hydromorphone
Predicted Properties
PropertyValueSource
Water Solubility4.39 mg/mLALOGPS
logP1.69ALOGPS
logP1.47Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.17Chemaxon
pKa (Strongest Basic)9.08Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area49.77 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity78.26 m3·mol-1Chemaxon
Polarizability30.06 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon