Benzhydrocodone hydrochlorideProduct ingredient for Benzhydrocodone

Name
Benzhydrocodone hydrochloride
Drug Entry
Benzhydrocodone

Benzhydrocodone is a benzylic prodrug of hydrocodone.5 It was developed in an effort to reduce parenteral bioavailability of the active metabolite as a deterrent to abuse.4 Benzhydrocodone is indicated for use in the short-term management of pain. It was first approved by the FDA in February 2018 in combination with acetaminophen under the trade name Apadaz, marketed by KVK Tech and developed by KemPharm.6,7

Accession Number
DBSALT002879
Structure
Synonyms
Benzhydrocodone HCl / Benzhydrocodone hydrochloride
External IDs
KP 201 / KP-201 / KP201
UNII
I894QAU7FJ
CAS Number
1379679-42-1
Weight
Average: 439.94
Monoisotopic: 439.155036
Chemical Formula
C25H26ClNO4
InChI Key
VVCUIDHKAHHSAN-JJHQWJQCSA-N
InChI
InChI=1S/C25H25NO4.ClH/c1-26-13-12-25-17-9-11-20(29-24(27)15-6-4-3-5-7-15)23(25)30-22-19(28-2)10-8-16(21(22)25)14-18(17)26;/h3-8,10-11,17-18,23H,9,12-14H2,1-2H3;1H/t17-,18-,23+,25+;/m1./s1
IUPAC Name
(1S,5R,13R,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,14-tetraen-14-yl benzoate hydrochloride
SMILES
Cl.[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CC=C2OC(=O)C1=CC=CC=C1
ChemSpider
34222064
ChEMBL
CHEMBL3137310
Wikipedia
Benzhydrocodone
Predicted Properties
PropertyValueSource
logP3.71Chemaxon
pKa (Strongest Basic)9.36Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area48 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity114.96 m3·mol-1Chemaxon
Polarizability43.92 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon