Hydrocodone

Identification

Summary

Hydrocodone is an opioid agonist used as an analgesic and antitussive agent.

Brand Names

Dalmacol, Hycet, Hycodan, Hydromet, Hysingla, Lorcet, Lortab, Norco, Obredon, Reprexain, Tussicaps, Tussionex, Vicoprofen, Xodol, Zamicet, Zohydro, Zydone

Generic Name

Hydrocodone

DrugBank Accession Number

DB00956

Background

Hydrocodone is a synthetic opioid derivative of codeine.¹⁴ It is commonly used in combination with acetaminophen to control moderate to severe pain. Historically, hydrocodone has been used as a cough suppressant although this has largely been replaced by dextromethorphan in current cough and cold formulations. Hydrocodone's more potent metabolite, hydromorphone has also found wide use as an analgesic and is frequently used in cases of severe pain. The FDA first approved Hydrocodone for use as part of the cough suppressant syrup Hycodan in March of 1943.¹⁷

Type

Small Molecule

Groups

Approved, Illicit, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Hydrocodone (DB00956)

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Weight

Average: 299.3642
Monoisotopic: 299.152143543

Chemical Formula

C₁₈H₂₁NO₃

Synonyms

• (-)-Dihydrocodeinone
• 4,5-alpha-Epoxy-3-methoxy-17-methylmorphinan-6-one
• Dihydrocodeinone
• Hidrocodona
• Hydrocodon
• Hydrocodone
• Hydrocodonum
• Hydrocone
• Hydroconum
• Idrocodone

External IDs

• NSC-19044

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Pharmacology

Indication

Hydrocodone is indicated for the management of acute pain, sometimes in combination with acetaminophen or ibuprofen, as well as the symptomatic treatment of the common cold and allergic rhinitis in combination with decongestants, antihistamines, and expectorants.^Label,16

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to manage	Acute pain	Combination Product in combination with: Ibuprofen (DB01050)	••••••••••••			••••••
Used in combination for symptomatic treatment of	Cough	Combination Product in combination with: Sodium citrate (DB09154), Doxylamine (DB00366), Ethanol (DB00898), Etafedrine (DB11587)	••••••••••••			•••••
Symptomatic treatment of	Cough		••••••••••••			•••••
Used in combination for symptomatic treatment of	Cough	Combination Product in combination with: Homatropine (DB11181)	••••••••••••			•••••• ••••••
Used in combination for symptomatic treatment of	Cough caused by allergic rhinitis	Combination Product in combination with: Guaifenesin (DB00874), Brompheniramine (DB00835), Phenylephrine (DB00388)	••••••••••••			•••••

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Pharmacodynamics

Hydrocodone inhibits pain signaling in both the spinal cord and brain ¹². Its actions in the brain also produce euphoria, respiratory depression, and sedation.

Mechanism of action

Hydrocodone binds to the mu opioid receptor (MOR) with the highest affinity followed by the delta opioid receptors (DOR).¹³ Hydrocodone's agonist effect at the MOR is considered to contribute the most to its analgesic effects. Both MOR and DOR are Gi/o coupled and and produces its signal through activation of inward rectifier potassium (GIRK) channels, inhibition of voltage gated calcium channel opening, and decreased adenylyl cyclase activity.¹⁴ In the dorsal horn of the spinal cord, activation of pre-synaptic MOR on primary afferents the inhibition of calcium channel opening and increased activity of GIRK channels hyperpolarizes the neuron and prevents release of neurotransmitters. Post-synaptic MOR can also prevent activation of neurons by glutamate through the aforementioned mechanisms.

Hydrocodone can also produce several actions in the brain similarly to other opioids. Activation of MOR in the periaquaductal gray (PAG) inhibits the GABAergic tone on medulo-spinal neurons.^14,12 This allows these neurons, which project to the dorsal horn of the spinal cord, to suppress pain signalling in secondary afferents by activating inhibitory interneurons. MOR can also inhibit GABAergic neurons in the ventral tegmental area, removing the inhibitory tone on dopaminergic neurons in the nucleus accumbens and contributing to the activation of the brain's reward and addiction pathway. The inhibitory action or MOR likely contributes to respiratory depression, sedation, and suppression of the cough reflex.

Activation of DOR may contribute to analgesia through the above mechanisms but has not been well studied.¹²

Target	Actions	Organism
AMu-type opioid receptor	agonist	Humans
ADelta-type opioid receptor	agonist	Humans
USigma non-opioid intracellular receptor 1	ligand	Humans

Absorption

The absolute bioavailability of hydrocodone has not been characterized due to lack of an IV formulation. The liquid formulations of hydrocodone have a Tmax of 0.83-1.33 h.^3,5 The extended release tablet formulations have a Tmax of 14-16 h.^Label The Cmax remains dose proportional over the range of 2.5-10 mg in liquid formulations and 20-120 mg in extended release formulations.^3,5,Label Administration with food increases Cmax by about 27% while Tmax and AUC remain the same.⁶ Administration with 40% ethanol has been observed to increase Cmax 2-fold with an approximate 20% increase in AUC with no change in Tmax. 20% alcohol produces no significant effect.

Volume of distribution

The apparent volume of distribution ranges widely in published literature. The official FDA labeling reports a value of 402 L.^Label Pharmacokinetic studies report values from 210-714 L with higher values associated with higher doses or single dose studies and lower values associated with lower doses and multiple dose studies.^2,3,4,5 Hydrocodone has been observed in human breast milk at levels equivalent to 1.6% of the maternal dosage.¹¹ Only 12 of the 30 women studied had detectable concentrations of hydromorphone at mean levels of 0.3 mcg/kg/day.

Protein binding

Hydrocodone is 36% bound to plasma proteins.^Label

Metabolism

Hydrocodone undergoes oxidative O-demethylation to form hydromorphone, a more potent active metabolite.⁸ Though hydromorphone is active it is not present in sufficient quantities to contribute significantly to hydrocodone's therapeutic effects.¹ Both hydrocodone and hydromorphone form 6-α- and 6-β-hydroxy metabolites through 6-ketoreduction. The hydroxy metabolites and hydromorphone can form glucuronide conjugates. Hydrocodone also undergoes oxidative N-demthylation to norhydrocodone. O-demethylation is primarily catalyzed by CYP2D6 while N-demethylation is primarily CYP3A4.⁹

Hover over products below to view reaction partners

• Hydrocodone
  • Hydromorphone
    • Hydromorphone glucuronide conjugate
    • 6-α-hydromorphol + 6-β-hydromorphol
      • 6-β-hydromorphol glucuronide conjugate 1 + 6-β-hydromorphol glucuronide conjugate 2
      • 6-α-hydromorphol glucuronide conjugate 1 + 6-α-hydromorphol glucuronide conjugate 2
  • norhydrocodone
  • 6-α-hydrocodol + 6-β-hydrocodol
    • 6-β-hydrocodol glucuronide conjugate
    • 6-β-hydromorphol
      • 6-β-hydromorphol glucuronide conjugate 1 + 6-β-hydromorphol glucuronide conjugate 2
    • 6-α-hydromorphol
      • 6-α-hydromorphol glucuronide conjugate 1 + 6-α-hydromorphol glucuronide conjugate 2

Route of elimination

Most hydrocodone appears to be eliminated via a non-renal route as renal clearance is substantially lower than total apparent clearance.^Label Hepatic metabolism may account for a portion of this, however the slight increase in serum concentration and AUC seen in hepatic impairment indicates a different primary route of elimination.

Half-life

The half-life of elimination reported for hydrocodone is 7-9 h.^Label,6,10

Clearance

Official FDA labeling reports an apparent clearance of 83 L/h.^Label Pharmacokinetic studies report values ranging from 24.5-58.8 L/h largely dependent on CYP2D6 metabolizer status.^2,3,4,5

Adverse Effects

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Toxicity

Overdosage with hydrocodone presents as opioid intoxication including respiratory depression, somnolence, coma, skeletal muscle flaccidity, cold and clammy skin, constricted pupils, pulmonary edema, bradycardia, hypotension, partial or complete airway obstruction, atypical snoring, and death.¹⁵

In case of oversdosage the foremost priority is the maintenance of a patent and protected airway with the provision of assisted ventilation if necessary. Supportive measures such as IV fluids, supplemental oxygen, and vasopressors may be used to manage circulatory shock.¹⁵ Advanced life support may be necessary in the case of cardiac arrest or arrhythmias. Opioid antagonists such as naloxone may be used to reverse the respiratory and circulatory effects of hydrocodone. Emergency monitoring is still required after naloxone administration as the opioid effects may reappear. Additionally, if used in an opioid tolerant patient, naloxone may produce opioid withdrawal symptoms.

Pathways

Pathway	Category
Hydrocodone Action Pathway	Drug action

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Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
Abametapir	The serum concentration of Hydrocodone can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Hydrocodone can be increased when combined with Abatacept.
Abiraterone	The metabolism of Hydrocodone can be decreased when combined with Abiraterone.
Acebutolol	The metabolism of Hydrocodone can be decreased when combined with Acebutolol.

Food Interactions

• Avoid alcohol. Profound CNS depression, including sedation, respiratory depression, coma, and death may occur.
• Take with or without food. Cmax and AUC are not altered by food in a clinically significant way.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Hydrocodone bitartrate	NO70W886KK	34195-34-1	JMBRWJAVUIITGV-LNNMZZBZSA-N
Hydrocodone hydrochloride	QKZ0920OV3	25968-91-6	GCJAEXSZUXBMFS-RNWHKREASA-N
Hydrocodone polistirex	Not Available	Not Available	Not applicable

Product Images

PreviousNext

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Hycodan Syrup	Syrup	5 mg / 5 mL	Oral	Bristol Myers Squibb	1992-12-31	2017-07-14
Hycodan Tablets	Tablet	5 mg	Oral	Bristol Myers Squibb	1992-12-31	2017-08-18
Hysingla ER	Tablet, extended release	120 mg/1	Oral	Purdue Pharma LP	2015-01-15	Not applicable
Hysingla ER	Tablet, extended release	60 mg/1	Oral	Purdue Pharma LP	2015-01-15	Not applicable
Hysingla ER	Tablet, extended release	30 mg/1	Oral	Purdue Pharma LP	2015-01-15	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Hydrocodone Bitartrate	Tablet, extended release	30 mg/1	Oral	Alvogen Inc.	2021-03-03	Not applicable
Hydrocodone Bitartrate	Capsule, extended release	40 mg/1	Oral	Persion Pharmaceuticals LLC	2013-10-25	Not applicable
Hydrocodone Bitartrate	Capsule, extended release	15 mg/1	Oral	Persion Pharmaceuticals LLC	2013-10-25	Not applicable
Hydrocodone Bitartrate	Tablet, extended release	120 mg/1	Oral	Alvogen Inc.	2021-03-03	Not applicable
Hydrocodone Bitartrate	Capsule, extended release	10 mg/1	Oral	Alvogen Inc.	2020-01-21	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
ACETAMINOFÉN / HIDROCODONA BITARTRATO 325 MG / 5 MG TABLETAS	Hydrocodone bitartrate (5 mg) + Acetaminophen (325 mg)	Tablet	Oral	SANOFI - AVENTIS DE COLOMBIA S.A	2021-09-02	Not applicable
Antitussive hydrocodone bitartrate and homatropine methylbromide	Hydrocodone bitartrate (5 mg/1) + Homatropine methylbromide (1.5 mg/1)	Tablet	Oral	Actavis Totowa LLC	2001-01-01	2008-08-20
BALANDOF® 5 - 325TABLETAS	Hydrocodone bitartrate (5 mg) + Acetaminophen (325 mg)	Tablet	Oral	CLARIPACK S.A	2017-11-14	Not applicable
BALANDOF® 7.5 - 325	Hydrocodone bitartrate (7.5 mg) + Acetaminophen (325 mg)	Tablet	Oral	CLARIPACKS.A	2017-11-14	Not applicable
Caldomine Dh Adulte	Hydrocodone bitartrate (5 mg / 5 mL) + Mepyramine maleate (12.5 mg / 5 mL) + Pheniramine maleate (12.5 mg / 5 mL) + Phenylpropanolamine hydrochloride (25 mg / 5 mL)	Liquid	Oral	Technilab Pharma Inc.	1981-12-31	2001-04-04

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Atuss HS Tannate	Hydrocodone bitartrate (5 mg/5mL) + Chlorpheniramine maleate (4 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)	Suspension	Oral	Atley Pharmaceuticals	2006-11-21	2009-08-03
Hydrocodone/Guaifenesin	Hydrocodone bitartrate (2.5 mg/1) + Guaifenesin (300 mg/1)	Tablet	Oral	Physicians Total Care, Inc.	2005-12-20	2007-10-31
HyTan	Hydrocodone (5 mg/5mL) + Chlorpheniramine tannate (4 mg/5mL)	Suspension	Oral	Prasco, Laboratories	2006-05-31	2007-12-31
P-Tuss	Hydrocodone bitartrate (5 mg/5mL) + Potassium guaiacolsulfonate (300 mg/5mL)	Liquid	Oral	Prasco, Laboratories	2010-12-01	2011-01-21
Pancof HC	Hydrocodone bitartrate (3 mg/5mL) + Pseudoephedrine hydrochloride (15 mg/5mL)	Syrup	Oral	Physicians Total Care, Inc.	2007-02-02	2007-10-31

Categories

ATC Codes

R05DA03 — Hydrocodone

• R05DA — Opium alkaloids and derivatives
• R05D — COUGH SUPPRESSANTS, EXCL. COMBINATIONS WITH EXPECTORANTS
• R05 — COUGH AND COLD PREPARATIONS
• R — RESPIRATORY SYSTEM

Drug Categories

• Alkaloids
• Analgesics
• Antitussive Agents
• Central Nervous System Agents
• Central Nervous System Depressants
• Cough and Cold Preparations
• Cytochrome P-450 CYP2B6 Substrates
• Cytochrome P-450 CYP2C19 Substrates
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Substrates
• Heterocyclic Compounds, Fused-Ring
• Morphinans
• Morphine Derivatives
• Narcotics
• Opiate Alkaloids
• Opioid Agonist
• Opioids
• Opium Alkaloids and Derivatives
• Peripheral Nervous System Agents
• Respiratory System Agents
• Semi-synthetic Opioids
• Sensory System Agents
• Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Phenanthrenes and derivatives / Isoquinolones and derivatives / Tetralins / Coumarans / Anisoles / Aralkylamines / Alkyl aryl ethers / Piperidines / Trialkylamines / Ketones / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives

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Substituents

Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Coumaran / Ether / Hydrocarbon derivative / Isoquinolone / Ketone / Morphinan / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Phenanthrene / Piperidine / Tertiary aliphatic amine / Tertiary amine / Tetralin

show 17 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:5779)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

6YKS4Y3WQ7

CAS number

125-29-1

InChI Key

LLPOLZWFYMWNKH-CMKMFDCUSA-N

InChI

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

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-trien-14-one

SMILES

[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CCC2=O

References

Synthesis Reference

Anne M. Hailes, Christopher E. French, Neil C. Bruce, "Morphinone reductase for the preparation of hydromorphone and hydrocodone." U.S. Patent US5571685, issued November, 1990.

US5571685

General References

1. Melhem MR, Rubino CM, Farr SJ, Robinson CY: Population pharmacokinetic analysis for hydrocodone following the administration of hydrocodone bitartrate extended-release capsules. Clin Pharmacokinet. 2013 Oct;52(10):907-17. doi: 10.1007/s40262-013-0081-6. [Article]
2. Linares OA, Fudin J, Daly AL, Boston RC: Individualized Hydrocodone Therapy Based on Phenotype, Pharmacogenetics, and Pharmacokinetic Dosing. Clin J Pain. 2015 Dec;31(12):1026-35. doi: 10.1097/AJP.0000000000000214. [Article]
3. Liu W, Dutta S, Kearns G, Awni W, Neville KA: Pharmacokinetics of hydrocodone/acetaminophen combination product in children ages 6-17 with moderate to moderately severe postoperative pain. J Clin Pharmacol. 2015 Feb;55(2):204-11. doi: 10.1002/jcph.394. Epub 2014 Sep 26. [Article]
4. Otton SV, Schadel M, Cheung SW, Kaplan HL, Busto UE, Sellers EM: CYP2D6 phenotype determines the metabolic conversion of hydrocodone to hydromorphone. Clin Pharmacol Ther. 1993 Nov;54(5):463-72. doi: 10.1038/clpt.1993.177. [Article]
5. Deng S, Huang W, Ni X, Zhang M, Lu H, Wang Z, Hu J, Zhu X, Qiu C, Shang D, Zhang Y, Xiong L, Wen Y: Pharmacokinetics of guaifenesin, pseudoephedrine and hydrocodone in a combination oral liquid formulation, administered as single and multiple doses in healthy Chinese volunteers, and comparison with data for individual compounds formulated as Antuss(R). Xenobiotica. 2017 Oct;47(10):870-878. doi: 10.1080/00498254.2016.1241451. Epub 2016 Oct 24. [Article]
6. Farr SJ, Robinson CY, Rubino CM: Effects of food and alcohol on the pharmacokinetics of an oral, extended-release formulation of hydrocodone in healthy volunteers. Clin Pharmacol. 2015 Jan 19;7:1-9. doi: 10.2147/CPAA.S70831. eCollection 2015. [Article]
7. Cardia L, Calapai G, Quattrone D, Mondello C, Arcoraci V, Calapai F, Mannucci C, Mondello E: Preclinical and Clinical Pharmacology of Hydrocodone for Chronic Pain: A Mini Review. Front Pharmacol. 2018 Oct 1;9:1122. doi: 10.3389/fphar.2018.01122. eCollection 2018. [Article]
8. Cone EJ, Darwin WD, Gorodetzky CW, Tan T: Comparative metabolism of hydrocodone in man, rat, guinea pig, rabbit, and dog. Drug Metab Dispos. 1978 Jul-Aug;6(4):488-93. [Article]
9. Hutchinson MR, Menelaou A, Foster DJ, Coller JK, Somogyi AA: CYP2D6 and CYP3A4 involvement in the primary oxidative metabolism of hydrocodone by human liver microsomes. Br J Clin Pharmacol. 2004 Mar;57(3):287-97. [Article]
10. Kapil RP, Cipriano A, Wen W, Yu Lynch S, He E, Colucci SV, Harris SC: Pharmacokinetic Profile and Sustained 24-hour Analgesia of a Once-daily Hydrocodone Bitartrate Extended-release Tablet with Abuse-deterrent Properties. Clin Ther. 2016 Feb;38(2):302-14. doi: 10.1016/j.clinthera.2015.12.003. Epub 2015 Dec 31. [Article]
11. Sauberan JB, Anderson PO, Lane JR, Rafie S, Nguyen N, Rossi SS, Stellwagen LM: Breast milk hydrocodone and hydromorphone levels in mothers using hydrocodone for postpartum pain. Obstet Gynecol. 2011 Mar;117(3):611-7. doi: 10.1097/AOG.0b013e31820ca504. [Article]
12. Trescot AM, Datta S, Lee M, Hansen H: Opioid pharmacology. Pain Physician. 2008 Mar;11(2 Suppl):S133-53. [Article]
13. Olson KM, Duron DI, Womer D, Fell R, Streicher JM: Comprehensive molecular pharmacology screening reveals potential new receptor interactions for clinically relevant opioids. PLoS One. 2019 Jun 6;14(6):e0217371. doi: 10.1371/journal.pone.0217371. eCollection 2019. [Article]
14. Brunton LL, Hilal-Dandan R, Knollmann BC. eds (2018). Goodman & Gilman's: The Pharmacological Basis of Therapeutics (13th ed.). McGraw-Hill Education. [ISBN:978-1-25-958473-2]
15. FDA Label: Hydrocodone Tab ER [Link]
16. DPD Monograph: Dimetane Syrup [Link]
17. Drugs@FDA: Hycodan [Link]
18. FDA Approved Drug Products: HYSINGLA® ER (hydrocodone bitartrate) extended-release tablets, for oral use, CII [Link]

External Links

Human Metabolome Database

HMDB0015091

KEGG Drug

D08045

KEGG Compound

C08024

PubChem Compound

5284569

PubChem Substance

46506225

ChemSpider

4447623

BindingDB

50386689

RxNav

5489

ChEBI

5779

ChEMBL

CHEMBL1457

ZINC

ZINC000001280665

Therapeutic Targets Database

DAP000253

PharmGKB

PA449900

RxList

RxList Drug Page

Wikipedia

Hydrocodone

FDA label

Download (496 KB)

MSDS

Download (48.8 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Chronic Pain	1
4	Completed	Basic Science	Driving Behavior	1
4	Completed	Supportive Care	Carpal Tunnel Syndrome (CTS)	1
4	Completed	Treatment	Alzheimer's Disease (AD) / Dementia / Pain / Vascular Dementia (VaD)	1
4	Completed	Treatment	Chronic Pain	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• Abbott Laboratories Ltd.
• Actavis Group
• AG Marin Pharmaceuticals
• Aidarex Pharmacuticals LLC
• Altura Pharmaceuticals Inc.
• Amerisource Health Services Corp.
• Amneal Pharmaceuticals
• Andrx Laboratories Inc.
• Apotheca Inc.
• A-S Medication Solutions LLC
• Auriga Pharmaceuticals LLC
• BASF Corp.
• Blenheim Pharmacal
• Brighton Pharmaceuticals
• Bristol-Myers Squibb Co.
• Bryant Ranch Prepack
• Caraco Pharmaceutical Labs
• Cardinal Health
• Caremark LLC
• Comfortpak Inc.
• Corepharma LLC
• Cypress Pharmaceutical Inc.
• D.M. Graham Laboratories Inc.
• Dartmouth Pharmaceuticals Inc.
• Deltex Pharmaceuticals Inc.
• Direct Dispensing Inc.
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Econolab Inc.
• ECR Pharmaceuticals
• Edwards Pharmaceuticals
• Endo Pharmaceuticals Inc.
• Everett Laboratories Inc.
• Gm Pharmaceuticals Inc.
• Great Southern Laboratories
• H.J. Harkins Co. Inc.
• Hampton Laine LLC
• Hawthorn Pharmaceuticals
• Heartland Repack Services LLC
• Hi Tech Pharmacal Co. Inc.
• Innoviant Pharmacy Inc.
• Iopharm Laboratories Inc.
• Ivax Pharmaceuticals
• JMI Daniels Pharmaceuticals Inc.
• Kaiser Foundation Hospital
• Keltman Pharmaceuticals Inc.
• King Pharmaceuticals Inc.
• KV Pharmaceutical Co.
• Lake Erie Medical and Surgical Supply
• Larken Laboratories Inc.
• Liberty Pharmaceuticals
• Llorens Pharmaceutical
• Magna Pharmaceuticals
• Major Pharmaceuticals
• Mallinckrodt Inc.
• Marnel Pharmaceuticals Inc.
• Mason Pharmaceuticals Inc.
• Mckesson Corp.
• MCR American Pharmaceuticals Inc.
• Medvantx Inc.
• Mikart Inc.
• Monarch Pharmacy
• Monte Sano Pharmaceuticals Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Nippon Protein Co. Ltd.
• Novartis AG
• Nucare Pharmaceuticals Inc.
• Ohm Laboratories Inc.
• Palmetto Pharmaceuticals Inc.
• Pamlab LLC
• Patient First Corp.
• PCA LLC
• PD-Rx Pharmaceuticals Inc.
• Pharmaceutical Association
• Pharmedix
• Pharmpak Inc.
• Physicians Total Care Inc.
• Poly Pharmaceuticals Inc.
• Prasco Labs
• Preferred Pharmaceuticals Inc.
• Prepackage Specialists
• Prepak Systems Inc.
• Provident Pharmaceuticals LLC
• Qualitest
• Ranbaxy Laboratories
• Rebel Distributors Corp.
• Redpharm Drug
• Remedy Repack
• Sandhills Packaging Inc.
• Sandoz
• Schwarz Pharma Inc.
• Seatrace Pharmaceuticals Inc.
• Southwood Pharmaceuticals
• Sovereign Pharmaceuticals Ltd.
• St Mary's Medical Park Pharmacy
• Stat Rx Usa
• Sun Pharmaceutical Industries Ltd.
• Superior Pharmeceuticals
• Talbert Medical Management Corp.
• Teamm Pharmaceuticals Inc.
• UCB Pharma
• UDL Laboratories
• United Research Laboratories Inc.
• Va Cmop Dallas
• Veratex Corp.
• Victory Pharma
• Vintage Pharmaceuticals Inc.
• Vistapharm Inc.
• Watson Pharmaceuticals
• Wockhardt Ltd.
• WraSer Pharmaceuticals
• Xanodyne Pharmaceuticals Inc.
• Zyber Pharmaceuticals

Dosage Forms

Form	Route	Strength
Suspension	Oral
Tablet	Oral	5 mg
Capsule	Oral
Elixir	Oral
Solution	Oral
Tablet	Oral
Tablet	Oral	5 mg/1
Tablet, film coated	Oral
Tablet, extended release	Oral	100 mg/1
Tablet, extended release	Oral	120 mg/1
Tablet, extended release	Oral	20 mg/1
Tablet, extended release	Oral	40 mg/1
Tablet, extended release	Oral	80 mg/1
Syrup	Oral
Syrup	Oral	5 mg / 5 mL
Syrup	Oral	1 mg / mL
Kit	Oral
Cream	Topical
Capsule, extended release	Oral
Tablet, extended release	Oral
Suspension, extended release	Oral
Tablet, extended release	Oral	15 mg/1
Tablet, extended release	Oral	30 mg/1
Tablet, extended release	Oral	45 mg/1
Tablet, extended release	Oral	60 mg/1
Tablet, extended release	Oral	90 mg/1
Tablet, coated	Oral
Liquid	Oral
Capsule, extended release	Oral	10 mg/1
Capsule, extended release	Oral	15 mg/1
Capsule, extended release	Oral	20 mg/1
Capsule, extended release	Oral	30 mg/1
Capsule, extended release	Oral	40 mg/1
Capsule, extended release	Oral	50 mg/1

Prices

Unit description	Cost	Unit
Hydrocodone-Acetaminophen 7.5-500 mg/15ml Solution 473ml Bottle	60.97USD	bottle
Hydrocodone-Ibuprofen 7.5-200 mg tablet	1.13USD	tablet
Hydrocodone-Acetaminophen 10-750 mg tablet	1.1USD	tablet
Hydrocodone-Acetaminophen 7.5-325 mg tablet	0.63USD	tablet
Hydrocodone-Acetaminophen 10-325 mg tablet	0.57USD	tablet
Hydrocodone-Acetaminophen 5-325 mg tablet	0.57USD	tablet
Hydrocodone-Acetaminophen 10-660 mg tablet	0.53USD	tablet
Hydrocodone-Acetaminophen 10-500 mg tablet	0.5USD	tablet
Hydrocodone-Acetaminophen 10-650 mg tablet	0.47USD	tablet
Hydrocodone-Acetaminophen 7.5-500 mg tablet	0.47USD	tablet
Hydrocodone-Acetaminophen 2.5-500 mg tablet	0.43USD	tablet
Hydrocodone-Acetaminophen 7.5-750 mg tablet	0.43USD	tablet
Hydrocodone-Acetaminophen 5-500 mg tablet	0.4USD	tablet
Hydrocodone-Acetaminophen 7.5-650 mg tablet	0.16USD	tablet
Hydrocodone-Homatropine 5-1.5 mg/5ml Syrup	0.15USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US9265760	No	2016-02-23	2033-07-23
US6599531	No	2003-07-29	2017-06-10
US6348216	No	2002-02-19	2017-06-10
US6228398	No	2001-05-08	2019-11-01
US8309060	No	2012-11-13	2023-11-20
US6488963	No	2002-12-03	2017-06-24
US9060940	No	2015-06-23	2021-10-30
US8808740	No	2014-08-19	2031-12-21
US6733783	No	2004-05-11	2021-10-30
US9095614	No	2015-08-04	2027-08-24
US9095615	No	2015-08-04	2027-08-24
US8361499	No	2013-01-29	2021-10-30
US9084816	No	2015-07-21	2027-08-24
US9205056	No	2015-12-08	2021-10-30
US8647667	No	2014-02-11	2021-10-30
US9198863	No	2015-12-01	2021-10-30
US9289391	No	2016-03-22	2021-10-30
US9056052	No	2015-06-16	2021-10-30
US8529948	No	2013-09-10	2022-08-06
US8551520	No	2013-10-08	2021-10-30
US9023401	No	2015-05-05	2021-10-30
US9326982	No	2016-05-03	2033-07-25
US6902742	No	2005-06-07	2019-11-01
US9132096	No	2015-09-15	2034-09-12
US9492389	No	2016-11-15	2027-08-24
US9492391	No	2016-11-15	2027-08-24
US9549907	No	2017-01-24	2035-11-13
US9572804	No	2017-02-21	2020-10-30
US9669023	No	2017-06-06	2020-10-30
US9486412	No	2016-11-08	2027-08-24
US9669024	No	2017-06-06	2020-10-30
US9572779	No	2017-02-21	2031-12-21
US9486413	No	2016-11-08	2027-08-24
US9517236	No	2016-12-13	2020-10-30
US9492390	No	2016-11-15	2027-08-24
US9675611	No	2017-06-13	2020-10-30
US9682077	No	2017-06-20	2020-10-30
US9545380	No	2017-01-17	2027-08-24
US9333201	No	2016-05-10	2033-07-25
US9610286	No	2017-04-04	2033-07-25
US9452163	No	2016-09-27	2034-09-12
US9486451	No	2016-11-08	2034-09-12
US9339499	No	2016-05-17	2033-07-25
US9421200	No	2016-08-23	2033-07-25
US9433619	No	2016-09-06	2033-07-25
US9675610	No	2017-06-13	2023-06-16
US9572803	No	2017-02-21	2027-09-13
US9216176	No	2015-12-22	2027-09-13
US8445018	No	2013-05-21	2029-07-31
US9713611	No	2017-07-25	2034-09-12
US9763933	No	2017-09-19	2027-08-24
US9770416	No	2017-09-26	2027-08-24
US9775809	No	2017-10-03	2027-08-24
US9750703	No	2017-09-05	2031-12-21
US9861584	No	2018-01-09	2031-12-21
US9872837	No	2018-01-23	2031-12-21
US10028946	No	2018-07-24	2033-07-25
US10092559	No	2018-10-09	2034-09-12
US10130591	No	2018-11-20	2023-11-20
US9808431	No	2017-11-07	2035-11-13
US10105324	No	2018-10-23	2035-11-13
US10369109	No	2019-08-06	2023-06-16
US10322120	No	2019-06-18	2033-07-25
US10456393	No	2019-10-29	2033-07-25
US10722511	No	2020-07-28	2033-07-25
US11304909	No	2007-08-24	2027-08-24
US11304908	No	2007-08-24	2027-08-24
US11844865	No	2005-02-13	2025-02-13

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	198 °C	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.797 mg/mL	ALOGPS
logP	2.13	ALOGPS
logP	1.96	Chemaxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	19.44	Chemaxon
pKa (Strongest Basic)	9.17	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	38.77 Å2	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	82.74 m3·mol-1	Chemaxon
Polarizability	32.03 Å3	Chemaxon
Number of Rings	5	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9984
Caco-2 permeable	+	0.8621
P-glycoprotein substrate	Substrate	0.8253
P-glycoprotein inhibitor I	Inhibitor	0.6425
P-glycoprotein inhibitor II	Non-inhibitor	0.8664
Renal organic cation transporter	Inhibitor	0.6604
CYP450 2C9 substrate	Non-substrate	0.8546
CYP450 2D6 substrate	Substrate	0.8997
CYP450 3A4 substrate	Substrate	0.8168
CYP450 1A2 substrate	Non-inhibitor	0.8207
CYP450 2C9 inhibitor	Non-inhibitor	0.9412
CYP450 2D6 inhibitor	Inhibitor	0.6629
CYP450 2C19 inhibitor	Non-inhibitor	0.8402
CYP450 3A4 inhibitor	Non-inhibitor	0.7625
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8675
Ames test	Non AMES toxic	0.7735
Carcinogenicity	Non-carcinogens	0.9419
Biodegradation	Not ready biodegradable	0.984
Rat acute toxicity	3.0914 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9024
hERG inhibition (predictor II)	Non-inhibitor	0.8165

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (10.3 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0a4i-2090000000-117774746c444c4e0488
Mass Spectrum (Electron Ionization)	MS	splash10-0005-6970000000-3ba3e105098639cd6091
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0udi-0009000000-f21858df54194757e2d9
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0udi-0009000000-9b129b5d29df52345272
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0udi-0649000000-82623b23b75f0a0b232d
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0002-0920000000-b67ff5a32d0ddd40c4c7
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-006t-0900000000-0277ba7435a4081ab333
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0g6v-0900000000-b335c52fad1274cd28cb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-0019000000-aa23ab8086639840d8ad
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0002-0090000000-67bdd165e4243700f6bd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-0049000000-f5c49c0eb373590ae494
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0002-0090000000-56200b77e5b0e013fa63
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0zfu-1091000000-61c4098af41188200440
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0fgk-0090000000-71691da5d4aaf685e185
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	175.161393	predicted	DarkChem Lite v0.1.0
[M-H]-	175.83595	predicted	DeepCCS 1.0 (2019)
[M+H]+	175.164293	predicted	DarkChem Lite v0.1.0
[M+H]+	178.38687	predicted	DeepCCS 1.0 (2019)
[M+Na]+	175.026193	predicted	DarkChem Lite v0.1.0
[M+Na]+	185.9405	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	9.5	N/A	N/A	A27655

Details

Binding Properties1. Mu-type opioid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Voltage-gated calcium channel activity

Specific Function

Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...

Gene Name

OPRM1

Uniprot ID

P35372

Uniprot Name

Mu-type opioid receptor

Molecular Weight

44778.855 Da

References

1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
2. Kotzer CJ, Hay DW, Dondio G, Giardina G, Petrillo P, Underwood DC: The antitussive activity of delta-opioid receptor stimulation in guinea pigs. J Pharmacol Exp Ther. 2000 Feb;292(2):803-9. [Article]
3. Peckham EM, Traynor JR: Comparison of the antinociceptive response to morphine and morphine-like compounds in male and female Sprague-Dawley rats. J Pharmacol Exp Ther. 2006 Mar;316(3):1195-201. Epub 2005 Nov 16. [Article]
4. Hennies HH, Friderichs E, Schneider J: Receptor binding, analgesic and antitussive potency of tramadol and other selected opioids. Arzneimittelforschung. 1988 Jul;38(7):877-80. [Article]
5. Thompson CM, Wojno H, Greiner E, May EL, Rice KC, Selley DE: 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. J Pharmacol Exp Ther. 2004 Feb;308(2):547-54. Epub 2003 Nov 4. [Article]
6. Stoops WW, Hatton KW, Lofwall MR, Nuzzo PA, Walsh SL: Intravenous oxycodone, hydrocodone, and morphine in recreational opioid users: abuse potential and relative potencies. Psychopharmacology (Berl). 2010 Oct;212(2):193-203. doi: 10.1007/s00213-010-1942-4. Epub 2010 Jul 28. [Article]
7. Walsh SL, Nuzzo PA, Lofwall MR, Holtman JR Jr: The relative abuse liability of oral oxycodone, hydrocodone and hydromorphone assessed in prescription opioid abusers. Drug Alcohol Depend. 2008 Dec 1;98(3):191-202. doi: 10.1016/j.drugalcdep.2008.05.007. Epub 2008 Jul 7. [Article]
8. Olson KM, Duron DI, Womer D, Fell R, Streicher JM: Comprehensive molecular pharmacology screening reveals potential new receptor interactions for clinically relevant opioids. PLoS One. 2019 Jun 6;14(6):e0217371. doi: 10.1371/journal.pone.0217371. eCollection 2019. [Article]

Details2. Delta-type opioid receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Opioid receptor activity

Specific Function

G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...

Gene Name

OPRD1

Uniprot ID

P41143

Uniprot Name

Delta-type opioid receptor

Molecular Weight

40368.235 Da

References

1. Thompson CM, Wojno H, Greiner E, May EL, Rice KC, Selley DE: 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. J Pharmacol Exp Ther. 2004 Feb;308(2):547-54. Epub 2003 Nov 4. [Article]
2. Olson KM, Duron DI, Womer D, Fell R, Streicher JM: Comprehensive molecular pharmacology screening reveals potential new receptor interactions for clinically relevant opioids. PLoS One. 2019 Jun 6;14(6):e0217371. doi: 10.1371/journal.pone.0217371. eCollection 2019. [Article]

Details3. Sigma non-opioid intracellular receptor 1

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Ligand

General Function

Opioid receptor activity

Specific Function

Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma m...

Gene Name

SIGMAR1

Uniprot ID

Q99720

Uniprot Name

Sigma non-opioid intracellular receptor 1

Molecular Weight

25127.52 Da

References

1. Olson KM, Duron DI, Womer D, Fell R, Streicher JM: Comprehensive molecular pharmacology screening reveals potential new receptor interactions for clinically relevant opioids. PLoS One. 2019 Jun 6;14(6):e0217371. doi: 10.1371/journal.pone.0217371. eCollection 2019. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55