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
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
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
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ZOHYDRO ER Approved UseZOHYDRO ER is an opioid agonist indicated for the management of pain severe enough to require daily, around-the-clock, long-term opioid treatment and for which alternative treatment options are inadequate. Launch Date1.38257275E12 |
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Primary | APADAZ Approved UseAPADAZ is a combination of benzhydrocodone, a prodrug of the opioid agonist hydrocodone, and acetaminophen, and is 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. Launch Date1.54647357E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138027/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
23.6 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
155 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138027/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138027/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4 h |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
55% |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
30 mg multiple, oral (total) Overdose Dose: 30 mg Route: oral Route: multiple Dose: 30 mg Co-administed with:: clarithromycin Sources: valproic acid(250 mg, 2 times per day) |
unhealthy, 5 years n = 1 Health Status: unhealthy Condition: cold Age Group: 5 years Sex: F Population Size: 1 Sources: |
Other AEs: Adverse event... |
160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Electrocardiogram QTc interval prolonged... Other AEs: Electrocardiogram QTc interval prolonged Sources: |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
Other AEs: Withdrawal syndrome neonatal... Other AEs: Withdrawal syndrome neonatal Sources: |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Respiratory depression, Addiction... Other AEs: Respiratory depression (grade 5) Sources: Addiction |
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 115 |
unhealthy, adult n = 296 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 296 Sources: Page: p. 115 |
Disc. AE: Vomiting, Nausea... AEs leading to discontinuation/dose reduction: Vomiting (1%) Sources: Page: p. 115Nausea (1%) Headache (1%) Dizziness (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Adverse event | grade 5 | 30 mg multiple, oral (total) Overdose Dose: 30 mg Route: oral Route: multiple Dose: 30 mg Co-administed with:: clarithromycin Sources: valproic acid(250 mg, 2 times per day) |
unhealthy, 5 years n = 1 Health Status: unhealthy Condition: cold Age Group: 5 years Sex: F Population Size: 1 Sources: |
Electrocardiogram QTc interval prolonged | 160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
Withdrawal syndrome neonatal | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
|
Addiction | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
Respiratory depression | grade 5 | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Dizziness | 1% Disc. AE |
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 115 |
unhealthy, adult n = 296 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 296 Sources: Page: p. 115 |
Headache | 1% Disc. AE |
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 115 |
unhealthy, adult n = 296 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 296 Sources: Page: p. 115 |
Nausea | 1% Disc. AE |
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 115 |
unhealthy, adult n = 296 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 296 Sources: Page: p. 115 |
Vomiting | 1% Disc. AE |
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 115 |
unhealthy, adult n = 296 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 296 Sources: Page: p. 115 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/206627s007s008lbl.pdf#page=29 Page: 29.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/206627s007s008lbl.pdf#page=29 Page: 29.0 |
minor | |||
yes | yes (co-administration study) Comment: The 90% confidence interval (CI) of the geometric means for hydrocodone AUCinf (98 to 115%), AUCt (98 to 115%), and Cmax (93 to 121%) values were within the range of 80 to 125% when a single dose of HYSINGLA ER 20 mg was co-administered with CYP2D6 inhibitor paroxetine |
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yes | yes (co-administration study) Comment: Co-administration of HYSINGLA ER and CYP3A4 inhibitor ketoconazole increased mean hydrocodone AUC and Cmax by 135% and 78%, respectively; |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000PharmR.pdf#page=33 Page: 33.0 |
PubMed
Title | Date | PubMed |
---|---|---|
[Longitudinal study of parameters of respiratory function tests and blood gas analysis in patients with progressive systemic scleroderma]. | 2001 |
|
Opioid formulations: tailoring to the needs in chronic pain. | 2001 |
|
Do gender and race affect decisions about pain management? | 2001 Apr |
|
Psychosis after ultrarapid opiate detoxification. | 2001 Jun |
|
Narcotic analgesics for dental pain: available products, strengths, and formulations. | 2001 Mar-Apr |
|
[Learning from experience. Analysis of claims submitted to the National Commission of Medical Arbitration]. | 2001 Sep-Oct |
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Complications of intranasal prescription narcotic abuse. | 2002 Feb |
|
Esophageal cancer and the esophagus: challenges and potential strategies for selective cytoprotection of the tumor-bearing organ during cancer treatment. | 2002 Jan |
|
Combination hydrocodone and ibuprofen versus combination oxycodone and acetaminophen in the treatment of moderate or severe acute low back pain. | 2002 Jan |
|
The effectiveness of an anesthetic continuous-infusion device on postoperative pain control. | 2002 Jan |
|
Synthesis and biological activity of 8beta-substituted hydrocodone indole and hydromorphone indole derivatives. | 2002 Jan 21 |
|
Photodynamic therapy for Barrett's esophagus and high grade dysplasia: results of a patient satisfaction survey. | 2002 Jul-Aug |
|
Simultaneous determination of hydrocodone and hydromorphone in human plasma by liquid chromatography with tandem mass spectrometric detection. | 2002 Mar 25 |
|
Gender differences in narcotic-induced emesis in the ED. | 2002 May |
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A field evaluation of five on-site drug-testing devices. | 2002 Oct |
|
Determination of 6-oxo-morphinans, as the oximes, by difference circular dichroism spectroscopy. | 2002 Oct |
|
[Hypoxic brain damage in victims of fatal road traffic accident: prevalence, distribution and association with survival time and other head and extracranial injuries]. | 2002 Sep |
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Quantification of the O- and N-demethylated metabolites of hydrocodone and oxycodone in human liver microsomes using liquid chromatography with ultraviolet absorbance detection. | 2003 Feb 25 |
|
I am following a health care professional who, I think, has a drug problem. | 2003 Jan |
|
Trials and tribulations: current challenges in conducting clinical trials. | 2003 Jan |
|
Characterizing the subjective, psychomotor, and physiological effects of a hydrocodone combination product (Hycodan) in non-drug-abusing volunteers. | 2003 Jan |
|
[Maternal and fetal morbidity in patients with premature rupture of the membrane after 27-week gestation. Causes and costs]. | 2003 Jul |
|
Hair analysis for opiates: evaluation of washing and incubation procedures. | 2003 Jun 5 |
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Postmortem oxycodone and hydrocodone blood concentrations. | 2003 Mar |
|
Cognitive and motor function after administration of hydrocodone bitartrate plus ibuprofen, ibuprofen alone, or placebo in healthy subjects with exercise-induced muscle damage: a randomized, repeated-dose, placebo-controlled study. | 2003 Mar |
|
[Spanish scientific production in anesthesiology and resuscitation 1983-1995]. | 2003 Nov |
|
The influence of gender and race on physicians' pain management decisions. | 2003 Nov |
|
1000 office-based hysteroscopies prior to in vitro fertilization: feasibility and findings. | 2004 Apr-Jun |
|
Carisoprodol withdrawal syndrome. | 2004 Dec |
|
Refractory status epilepticus. | 2004 Feb |
|
Effective treatment of laparoscopic cholecystectomy pain with intravenous followed by oral COX-2 specific inhibitor. | 2004 Feb |
|
Postoperative pain management after anterior cruciate ligament reconstruction. | 2004 Jan |
|
Loss prevention case of the month. Monitoring remains critical. | 2004 Jan |
|
Patient characteristics and risks factors for development of dependence on hydrocodone and oxycodone. | 2004 Jan-Feb |
|
Efficacy of ibuprofen-hydrocodone for the treatment of postoperative pain after periodontal surgery. | 2004 Jun |
|
Fatal intravenous fentanyl abuse: four cases involving extraction of fentanyl from transdermal patches. | 2004 Jun |
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Persistent nonmalignant pain and analgesic prescribing patterns in elderly nursing home residents. | 2004 Jun |
|
Office visits and analgesic prescriptions for musculoskeletal pain in US: 1980 vs. 2000. | 2004 Jun |
|
Hallucinations with zolpidem and fluoxetine in an impaired driver. | 2004 Mar |
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CYP2D6 and CYP3A4 involvement in the primary oxidative metabolism of hydrocodone by human liver microsomes. | 2004 Mar |
|
[Detection of thyroid pathology during surgical exploration of the neck for primary hyperthyroidism]. | 2004 Mar-Apr |
|
[Gender and health in the daily press]. | 2004 May |
|
Patient-controlled ropivacaine analgesia after arthroscopic subacromial decompression. | 2004 May |
|
Topical metronidazole (10 percent) decreases posthemorrhoidectomy pain and improves healing. | 2004 May |
|
Fracture of an endoluminal nitinol stent used in the treatment of tracheal collapse in a dog. | 2004 Oct 15 |
|
Selective potentiation of opioid analgesia by nonsteroidal anti-inflammatory drugs. | 2005 Apr 8 |
|
Detection of hypoventilation during thoracoscopy: combined cutaneous carbon dioxide tension and oximetry monitoring with a new digital sensor. | 2005 Feb |
|
A preclinical comparison between different opioids: antinociceptive versus adverse effects. | 2005 Feb |
|
The GC-MS detection and characterization of neopine resulting from opium use and codeine metabolism and its potential as an opiate-product-use marker. | 2005 Jun |
|
Oral analgesics for acute nonspecific pain. | 2005 Mar 1 |
Sample Use Guides
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
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PARENT)
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