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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H21NO3
Molecular Weight 299.3642
Optical Activity ( - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROCODONE

SMILES

[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]15CCN(C)[C@H](C4)[C@]5([H])CCC2=O

InChI

InChIKey=LLPOLZWFYMWNKH-CMKMFDCUSA-N
InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-12,17H,4-5,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1

HIDE SMILES / InChI

Description

Benzhydrocodone is a prodrug of hydrocodone. Benzhydrocodone is formed by covalently bonding hydrocodone to benzoic acid. Benzhydrocodone itself is not pharmacologically active, but must be metabolized to hydrocodone by enzymes in the intestinal tract to optimally deliver its pharmacologic effects. Hydrocodone is a full agonist of the opioid receptors with a higher affinity for the mu-opioid receptor. Upon binding, hydrocodone produces an analgesic effect with no ceiling. APADAZ a combination of benzhydrocodone and acetaminophen is FDA approved and indicated for the short-term (no more than 14 days) management of acute pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate. APADAZ, even when taken as recommended, can result in addiction, abuse, and misuse, which can lead to overdose and death.

CNS Activity

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZOHYDRO ER
Primary
APADAZ

Cmax

ValueDoseCo-administeredAnalytePopulation
10.1 ng/mL
15 mg single, oral
HYDROCODONE plasma
Homo sapiens
23.6 ng/mL
10 mg single, oral
HYDROCODONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
155 ng × h/mL
15 mg single, oral
HYDROCODONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10.2 h
15 mg single, oral
HYDROCODONE plasma
Homo sapiens
4 h
10 mg single, oral
HYDROCODONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
55%
10 mg single, oral
HYDROCODONE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
APADAZ Immediate-release tablets: 6.12 mg benzhydrocodone (equivalent to 6.67 mg benzhydrocodone hydrochloride) and 325 mg acetaminophen. Initiate treatment with APADAZ at 1 or 2 tablets every 4 to 6 hours as needed for pain. Dosage should not exceed 12 tablets in a 24­ hour period.
Route of Administration: Oral