HYDROCODONE

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 Search

SMILES

COC1=C2O[C@H]3C(=O)CC[C@H]4[C@H]5CC(C=C1)=C2[C@@]34CCN5C

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

Molecular Formula	C18H21NO3
Molecular Weight	299.3642
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/books/NBK501225/ | https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208653s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/30140595 | https://www.ncbi.nlm.nih.gov/pubmed/29092079

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
Pain 619 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1b89a045-d552-40b6-a717-09858b5e6239	Primary		Approved 8583	ZOHYDRO ER Approved Use ZOHYDRO 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 Date 2013
Acute pain 17 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208653s000lbl.pdf	Primary		Approved 8583	APADAZ Approved Use APADAZ 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 Date 2019

C_max

Value	Dose	Co-administered	Analyte	Population
13 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
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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/005213s039lbl.pdf	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
16.04 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/208653s007lbl.pdf#page=30	6.12 mg single, oral dose: 6.12 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
19.18 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/208653s007lbl.pdf#page=30	6.12 mg single, oral dose: 6.12 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
33.95 ng/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=25	12.24 mg 6 times / day multiple, oral dose: 12.24 mg route of administration: Oral experiment type: MULTIPLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
62.79 ng/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=25	12.24 mg 6 times / day multiple, oral dose: 12.24 mg route of administration: Oral experiment type: MULTIPLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
208 ng/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=27	73.44 mg single, oral dose: 73.44 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.4 ng/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=29	6.12 mg single, nasal dose: 6.12 mg route of administration: Nasal experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
27 ng/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=29	24.48 mg single, nasal dose: 24.48 mg route of administration: Nasal experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
25.6 ng/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=31 \| https://pubmed.ncbi.nlm.nih.gov/29092079/	12.24 mg single, nasal dose: 12.24 mg route of administration: Nasal experiment type: SINGLE co-administered:		HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
40.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29025138/	12.24 mg single, oral dose: 12.24 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
34.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29025138/	12.24 mg single, nasal dose: 12.24 mg route of administration: Nasal experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
269 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
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
130.91 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/208653s007lbl.pdf#page=30	6.12 mg single, oral dose: 6.12 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
125.73 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/208653s007lbl.pdf#page=30	6.12 mg single, oral dose: 6.12 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
92.94 ng × h/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=25	12.24 mg 6 times / day multiple, oral dose: 12.24 mg route of administration: Oral experiment type: MULTIPLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
195.07 ng × h/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=25	12.24 mg 6 times / day multiple, oral dose: 12.24 mg route of administration: Oral experiment type: MULTIPLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1272 ng × h/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=27	73.44 mg single, oral dose: 73.44 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
194.7 ng × h/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=31 \| https://pubmed.ncbi.nlm.nih.gov/29092079/	12.24 mg single, nasal dose: 12.24 mg route of administration: Nasal experiment type: SINGLE co-administered:		HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
252.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29025138/	12.24 mg single, oral dose: 12.24 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
278.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29025138/	12.24 mg single, nasal dose: 12.24 mg route of administration: Nasal experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.5 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
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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/005213s039lbl.pdf	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
4.51 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/208653s007lbl.pdf#page=30	6.12 mg single, oral dose: 6.12 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
4.33 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/208653s007lbl.pdf#page=30	6.12 mg single, oral dose: 6.12 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
4.45 h OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=25	12.24 mg 6 times / day multiple, oral dose: 12.24 mg route of administration: Oral experiment type: MULTIPLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.87 h OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=25	12.24 mg 6 times / day multiple, oral dose: 12.24 mg route of administration: Oral experiment type: MULTIPLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5 h OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=27	73.44 mg single, oral dose: 73.44 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN	ACETAMINOPHEN	HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.29 h OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/208653Orig1s000ClinPharmR.pdf#page=31 \| https://pubmed.ncbi.nlm.nih.gov/29092079/	12.24 mg single, nasal dose: 12.24 mg route of administration: Nasal experiment type: SINGLE co-administered:		HYDROCODONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
55% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/005213s039lbl.pdf	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 Overdose Dose: 30 mg Route: oral Route: multiple Dose: 30 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20837591	unhealthy, 5 years Health Status: unhealthy Age Group: 5 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/20837591	Other AEs: Adverse event... Other AEs: Adverse event (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/20837591
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf	Other AEs: Electrocardiogram QTc interval prolonged... Other AEs: Electrocardiogram QTc interval prolonged Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf	pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf	Other AEs: Withdrawal syndrome neonatal... Other AEs: Withdrawal syndrome neonatal Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf	Other AEs: Respiratory depression, Addiction... Other AEs: Respiratory depression (grade 5) Addiction Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf	Disc. AE: Vomiting, Nausea... AEs leading to discontinuation/dose reduction: Vomiting (1%) Nausea (1%) Headache (1%) Dizziness (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf
13.34 mg 1 times / day steady-state, intranasal Studied dose Dose: 13.34 mg, 1 times / day Route: intranasal Route: steady-state Dose: 13.34 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/	Other AEs: Nasal discomfort, Nasal congestion... Other AEs: Nasal discomfort (16 patients) Nasal congestion (7 patients) Rhinorrhea (7 patients) Throat irritation (6 patients) Oropharyngeal pain (1 pt) Dry throat (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946		substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2B6 776 CYP2C19 1119

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/206627s007s008lbl.pdf#page=29 Page: 29.0	minor
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/206627s007s008lbl.pdf#page=29 Page: 29.0	minor
CYP2D6 1388	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1884456/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/206627s007s008lbl.pdf#page=30	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 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1884456/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/206627s007s008lbl.pdf#page=30
CYP3A4 1946	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1884456/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/206627s007s008lbl.pdf#page=30	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; Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1884456/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/206627s007s008lbl.pdf#page=30

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000PharmR.pdf#page=33 Page: 33.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5779	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5779
eMolecules	29539213	https://www.emolecules.com/cgi-bin/more?vid=29539213
ZINC	ZINC000001280665	http://zinc15.docking.org/substances/ZINC000001280665

PubMed

Title	Date	PubMed
The GC-MS detection and characterization of neopine resulting from opium use and codeine metabolism and its potential as an opiate-product-use marker.	2005-06	15782326
Selective potentiation of opioid analgesia by nonsteroidal anti-inflammatory drugs.	2005-04-08	15804436
Oral analgesics for acute nonspecific pain.	2005-03-01	15768621
A 46-year-old man with excruciating shoulder pain.	2005-03	15764791
Detection of hypoventilation during thoracoscopy: combined cutaneous carbon dioxide tension and oximetry monitoring with a new digital sensor.	2005-02	15706000
A preclinical comparison between different opioids: antinociceptive versus adverse effects.	2005-02	15680184
[Origin and growth of the National Program of Continuous Academic Development for the General Physician].	2005-01-14	15646146
Carisoprodol withdrawal syndrome.	2004-12	15585447
Local anesthetic infusion pumps improve postoperative pain after inguinal hernia repair: a randomized trial.	2004-11	15586515
Fracture of an endoluminal nitinol stent used in the treatment of tracheal collapse in a dog.	2004-10-15	15521443
6-oxo-morphinane oximes: pharmacology, chemistry and analytical application.	2004-10	15544463
Continuous local anesthetic infusion for pain management after outpatient inguinal herniorrhaphy.	2004-10	15467660
Presurgical intravenous parecoxib sodium and follow-up oral valdecoxib for pain management after laparoscopic cholecystectomy surgery reduces opioid requirements and opioid-related adverse effects.	2004-10	15352969
A 35-year-old physician with opioid dependence.	2004-09-15	15367558
Metaxalone (Skelaxin)-related death.	2004-09	15516312
Cough suppression during flexible bronchoscopy using combined sedation with midazolam and hydrocodone: a randomised, double blind, placebo controlled trial.	2004-09	15333854
Dose-response relationship between opioid use and adverse effects after ambulatory surgery.	2004-07	15223083
[Detection of thyroid pathology during surgical exploration of the neck for primary hyperthyroidism].	2004-06-04	15175123
Efficacy of ibuprofen-hydrocodone for the treatment of postoperative pain after periodontal surgery.	2004-06	15295955
Fatal intravenous fentanyl abuse: four cases involving extraction of fentanyl from transdermal patches.	2004-06	15166776
Persistent nonmalignant pain and analgesic prescribing patterns in elderly nursing home residents.	2004-06	15161448
Office visits and analgesic prescriptions for musculoskeletal pain in US: 1980 vs. 2000.	2004-06	15157714
1000 office-based hysteroscopies prior to in vitro fertilization: feasibility and findings.	2004-05-04	15119651
[Gender and health in the daily press].	2004-05	15171880
Patient-controlled ropivacaine analgesia after arthroscopic subacromial decompression.	2004-05	15122133
Topical metronidazole (10 percent) decreases posthemorrhoidectomy pain and improves healing.	2004-05	15054681
Patterns and trends in opioid use among individuals with back pain in the United States.	2004-04-15	15082989
Hallucinations with zolpidem and fluoxetine in an impaired driver.	2004-03	15027567
CYP2D6 and CYP3A4 involvement in the primary oxidative metabolism of hydrocodone by human liver microsomes.	2004-03	14998425
Refractory status epilepticus.	2004-02	15000791
Effective treatment of laparoscopic cholecystectomy pain with intravenous followed by oral COX-2 specific inhibitor.	2004-02	14742366
Activation of G-proteins by morphine and codeine congeners: insights to the relevance of O- and N-demethylated metabolites at mu- and delta-opioid receptors.	2004-02	14600248
Patient characteristics and risks factors for development of dependence on hydrocodone and oxycodone.	2004-01-06	14704593
Postoperative pain management after anterior cruciate ligament reconstruction.	2004-01	14971669
Loss prevention case of the month. Monitoring remains critical.	2004-01	14968682
A message of hope.	2004	15503937
The synergistic analgesic interactions between hydrocodone and ibuprofen.	2003-12	14633549
Pharmacokinetic drug interactions of morphine, codeine, and their derivatives: theory and clinical reality, Part II.	2003-11-05	14597688
[Spanish scientific production in anesthesiology and resuscitation 1983-1995].	2003-11	14753139
Withdrawal hyperalgesia after acute opioid physical dependence in nonaddicted humans: a preliminary study.	2003-11	14636819
The influence of gender and race on physicians' pain management decisions.	2003-11	14636818
Evaluation of postoperative bupivacaine infusion for pain management after anterior cruciate ligament reconstruction.	2003-10	14551548
Adverse drug reactions to oxycodone and hydrocodone in CYP2D6 ultrarapid metabolizers.	2003-08	12920424
Misuse of prescribed controlled substances defined by urinalysis.	2003-07-24	12874916
[Maternal and fetal morbidity in patients with premature rupture of the membrane after 27-week gestation. Causes and costs].	2003-07	14515665
Hair analysis for opiates: evaluation of washing and incubation procedures.	2003-06-05	12726847
Current concepts in acute pain management.	2003-05	12839235
Review of the analgesic efficacy of ibuprofen.	2003-04	12723741
Rapid communication: laparoscopic Anderson-Hynes dismembered pyeloplasty using the da Vinci robot: technical considerations.	2003-03	12689399
Postmortem oxycodone and hydrocodone blood concentrations.	2003-03	12665006

Patents

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:45:35 GMT 2025` Edited by `admin` on `Mon Mar 31 17:45:35 GMT 2025`
Record UNII	6YKS4Y3WQ7
Record Status	`Validated (UNII)`
Record Version

Download

Related Record	Type

Name

Type

Language

HYDROCODONE

Official Name

English

BEKADID

Preferred Name

English

OXYCODONE HYDROCHLORIDE, HYDROCODONE- [USP IMPURITY]

Common Name

English

Hydrocodone [WHO-DD]

Common Name

English

HYDROCODONE [HSDB]

Common Name

English

hydrocodone [INN]

Common Name

English

HYDROCODON

Common Name

English

HYDROCODONE [MI]

Common Name

English

HYDROCODONE [VANDF]

Common Name

English

DIHYDROCODEINONE

Common Name

English

NSC-19044

Code

English

HYDROCODONE CII [USP-RS]

Common Name

English

HYDROCODONE-

Common Name

English

OXYCODONE HYDROCHLORIDE IMPURITY E [EP IMPURITY]

Common Name

English

MULTACODIN

Common Name

English

(5.ALPHA.)-3-METHOXY-17-METHYL-4,5-EPOXYMORPHINAN-6-ONE

Systematic Name

English

(-)-DIHYDROCODEINONE

Common Name

English

DIHYDROCODEINE HYDROGEN TARTRATE IMPURITY C [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

WHO-ATC

R05DA03

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

WHO-VATC

QR05DA03

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

NCI_THESAURUS

C66917

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

DEA NO.

9193

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

LIVERTOX

NBK548700

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

NDF-RT

N0000000174

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

NCI_THESAURUS

C1506

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

NCI_THESAURUS

C67413

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

NDF-RT

N0000175690

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

Code System Code Type Description

FDA UNII

6YKS4Y3WQ7

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

INN

1700

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

WIKIPEDIA

HYDROCODONE

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

HSDB

3097

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

DRUG CENTRAL

1386

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

MERCK INDEX

m6093

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

Merck Index

SMS_ID

100000084214

Created by admin on Mon Mar 31 17:45:36 GMT 2025 , Edited by admin on Mon Mar 31 17:45:36 GMT 2025

PRIMARY

ECHA (EC/EINECS)

204-733-9

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

EPA CompTox

DTXSID8023131

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

LACTMED

Hydrocodone

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

DRUG BANK

DB00956

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

NSC

19044

Created by admin on Mon Mar 31 17:45:36 GMT 2025 , Edited by admin on Mon Mar 31 17:45:36 GMT 2025

PRIMARY

DAILYMED

6YKS4Y3WQ7

Created by admin on Mon Mar 31 17:45:36 GMT 2025 , Edited by admin on Mon Mar 31 17:45:36 GMT 2025

PRIMARY

RXCUI

5489

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

RS_ITEM_NUM

1314960

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

CHEBI

5779

Created by admin on Mon Mar 31 17:45:36 GMT 2025 , Edited by admin on Mon Mar 31 17:45:36 GMT 2025

PRIMARY

IUPHAR

7081

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

ChEMBL

CHEMBL1457

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

EVMPD

SUB08063MIG

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

MESH

D006853

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

CAS

125-29-1

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

NCI_THESAURUS

C62033

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

PUBCHEM

5284569

Created by admin on Mon Mar 31 17:45:35 GMT 2025 , Edited by admin on Mon Mar 31 17:45:35 GMT 2025

PRIMARY

Related Record Type Details


					6D04Y0152T

HYDROCODONE HYDROIODIDE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					DC7N64C409

HYDROCODONE TEREPHTHALATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					68T7388F5H

HYDROCODONE TANNATE

SALT/SOLVATE -> PARENT


					229E1EUY20

HYDROCODONE HYDROCHLORIDE MONOHYDRATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					NO70W886KK

HYDROCODONE BITARTRATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					9GU1G05Y03

HYDROCODONE BITARTRATE ANHYDROUS

SALT/SOLVATE -> PARENT


					DC7N64C409

HYDROCODONE TEREPHTHALATE

DERIVATIVE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					PPK4BVC0DX

HYDROCODONE HYDROCHLORIDE DIHYDRATE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:

HYDROCODONE POLISTIREX

SUB_CONCEPT->SUBSTANCE


					QKZ0920OV3

HYDROCODONE HYDROCHLORIDE

SALT/SOLVATE -> PARENT

HYDROCODONE RESIN COMPLEX

SUB_CONCEPT->SUBSTANCE

Related Record Type Details


					C3S5FRP6JW

DIHYDROMORPHINE

METABOLITE -> PARENT

Comments:

trace amount

Interaction Type:

MINOR

Qualification:

URINE


					5U0JDQ5Z5U

HYDROMORPHOL, 6.BETA.-

METABOLITE -> PARENT

Comments:

Trace amount

Interaction Type:

MINOR

Qualification:

URINE


					75MS0AAZ9I

BENZHYDROCODONE

PRODRUG -> METABOLITE ACTIVE

Amount:


					18NB5F1JT4

NORHYDROCODONE

METABOLITE ACTIVE -> PARENT

Amount:

Related Record Type Details


					8LXS95BSA9

DIHYDROCODEINE BITARTRATE

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:


					C1ENJ2TE6C

OXYCODONE HYDROCHLORIDE

PARENT -> IMPURITY

Related Record Type Details


					6YKS4Y3WQ7

HYDROCODONE

ACTIVE MOIETY

Amount:

AE	Significance	Dose	Population
Adverse event	grade 5	30 mg multiple, oral Overdose Dose: 30 mg Route: oral Route: multiple Dose: 30 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20837591	unhealthy, 5 years Health Status: unhealthy Age Group: 5 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/20837591
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf	pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206627s000lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000MedR.pdf
Dry throat	1 pt	13.34 mg 1 times / day steady-state, intranasal Studied dose Dose: 13.34 mg, 1 times / day Route: intranasal Route: steady-state Dose: 13.34 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/
Oropharyngeal pain	1 pt	13.34 mg 1 times / day steady-state, intranasal Studied dose Dose: 13.34 mg, 1 times / day Route: intranasal Route: steady-state Dose: 13.34 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/
Nasal discomfort	16 patients	13.34 mg 1 times / day steady-state, intranasal Studied dose Dose: 13.34 mg, 1 times / day Route: intranasal Route: steady-state Dose: 13.34 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/
Throat irritation	6 patients	13.34 mg 1 times / day steady-state, intranasal Studied dose Dose: 13.34 mg, 1 times / day Route: intranasal Route: steady-state Dose: 13.34 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/
Nasal congestion	7 patients	13.34 mg 1 times / day steady-state, intranasal Studied dose Dose: 13.34 mg, 1 times / day Route: intranasal Route: steady-state Dose: 13.34 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/
Rhinorrhea	7 patients	13.34 mg 1 times / day steady-state, intranasal Studied dose Dose: 13.34 mg, 1 times / day Route: intranasal Route: steady-state Dose: 13.34 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29025138/

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/books/NBK501225/ | https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208653s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/30140595 | https://www.ncbi.nlm.nih.gov/pubmed/29092079

CNS Activity

Approval Year

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/books/NBK501225/ | https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/208653s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/30140595 | https://www.ncbi.nlm.nih.gov/pubmed/29092079

C_max

T_1/2

F_unbound