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 Historically, hydrocodone has been used as a cough suppressant although this has largely been replaced by dextromethorphan in current cough and cold formulations.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
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

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 TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageAcute painCombination Product in combination with: Ibuprofen (DB01050)••••••••••••••••••
Used in combination for symptomatic treatment ofCoughCombination Product in combination with: Sodium citrate (DB09154), Doxylamine (DB00366), Ethanol (DB00898), Etafedrine (DB11587)•••••••••••••••••
Symptomatic treatment ofCough•••••••••••••••••
Used in combination for symptomatic treatment ofCoughCombination Product in combination with: Homatropine (DB11181)•••••••••••••••••• ••••••
Used in combination for symptomatic treatment ofCough caused by allergic rhinitisCombination Product in combination with: Guaifenesin (DB00874), Brompheniramine (DB00835), Phenylephrine (DB00388)•••••••••••••••••
Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
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

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
PathwayCategory
Hydrocodone Action PathwayDrug action
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

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.
DrugInteraction
1,2-Benzodiazepine1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
AbametapirThe serum concentration of Hydrocodone can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Hydrocodone can be increased when combined with Abatacept.
AbirateroneThe metabolism of Hydrocodone can be decreased when combined with Abiraterone.
AcebutololThe 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
IngredientUNIICASInChI Key
Hydrocodone bitartrateNO70W886KK34195-34-1JMBRWJAVUIITGV-LNNMZZBZSA-N
Hydrocodone hydrochlorideQKZ0920OV325968-91-6GCJAEXSZUXBMFS-RNWHKREASA-N
Hydrocodone polistirexNot AvailableNot AvailableNot applicable
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Hycodan SyrupSyrup5 mg / 5 mLOralBristol Myers Squibb1992-12-312017-07-14Canada flag
Hycodan TabletsTablet5 mgOralBristol Myers Squibb1992-12-312017-08-18Canada flag
Hysingla ERTablet, extended release120 mg/1OralPurdue Pharma LP2015-01-15Not applicableUS flag
Hysingla ERTablet, extended release60 mg/1OralPurdue Pharma LP2015-01-15Not applicableUS flag
Hysingla ERTablet, extended release30 mg/1OralPurdue Pharma LP2015-01-15Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Hydrocodone BitartrateTablet, extended release30 mg/1OralAlvogen Inc.2021-03-03Not applicableUS flag
Hydrocodone BitartrateCapsule, extended release40 mg/1OralPersion Pharmaceuticals LLC2013-10-25Not applicableUS flag
Hydrocodone BitartrateCapsule, extended release15 mg/1OralPersion Pharmaceuticals LLC2013-10-25Not applicableUS flag
Hydrocodone BitartrateTablet, extended release120 mg/1OralAlvogen Inc.2021-03-03Not applicableUS flag
Hydrocodone BitartrateCapsule, extended release10 mg/1OralAlvogen Inc.2020-01-21Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ACETAMINOFÉN / HIDROCODONA BITARTRATO 325 MG / 5 MG TABLETASHydrocodone bitartrate (5 mg) + Acetaminophen (325 mg)TabletOralSANOFI - AVENTIS DE COLOMBIA S.A2021-09-02Not applicableColombia flag
Antitussive hydrocodone bitartrate and homatropine methylbromideHydrocodone bitartrate (5 mg/1) + Homatropine methylbromide (1.5 mg/1)TabletOralActavis Totowa LLC2001-01-012008-08-20US flag
BALANDOF® 5 - 325TABLETASHydrocodone bitartrate (5 mg) + Acetaminophen (325 mg)TabletOralCLARIPACK S.A2017-11-14Not applicableColombia flag
BALANDOF® 7.5 - 325Hydrocodone bitartrate (7.5 mg) + Acetaminophen (325 mg)TabletOralCLARIPACKS.A2017-11-14Not applicableColombia flag
Caldomine Dh AdulteHydrocodone 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)LiquidOralTechnilab Pharma Inc.1981-12-312001-04-04Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Atuss HS TannateHydrocodone bitartrate (5 mg/5mL) + Chlorpheniramine maleate (4 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)SuspensionOralAtley Pharmaceuticals2006-11-212009-08-03US flag
Hydrocodone/GuaifenesinHydrocodone bitartrate (2.5 mg/1) + Guaifenesin (300 mg/1)TabletOralPhysicians Total Care, Inc.2005-12-202007-10-31US flag
HyTanHydrocodone (5 mg/5mL) + Chlorpheniramine tannate (4 mg/5mL)SuspensionOralPrasco, Laboratories2006-05-312007-12-31US flag
P-TussHydrocodone bitartrate (5 mg/5mL) + Potassium guaiacolsulfonate (300 mg/5mL)LiquidOralPrasco, Laboratories2010-12-012011-01-21US flag
Pancof HCHydrocodone bitartrate (3 mg/5mL) + Pseudoephedrine hydrochloride (15 mg/5mL)SyrupOralPhysicians Total Care, Inc.2007-02-022007-10-31US flag

Categories

ATC Codes
R05DA03 — Hydrocodone
Drug Categories
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
show 5 more
Substituents
Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Coumaran / Ether
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]
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);">
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableChronic Pain1
4CompletedBasic ScienceDriving Behavior1
4CompletedSupportive CareCarpal Tunnel Syndrome (CTS)1
4CompletedTreatmentAlzheimer's Disease (AD) / Dementia / Pain / Vascular Dementia (VaD)1
4CompletedTreatmentChronic Pain1

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
FormRouteStrength
SuspensionOral
TabletOral5 mg
CapsuleOral
ElixirOral
SolutionOral
TabletOral
TabletOral5 mg/1
Tablet, film coatedOral
Tablet, extended releaseOral100 mg/1
Tablet, extended releaseOral120 mg/1
Tablet, extended releaseOral20 mg/1
Tablet, extended releaseOral40 mg/1
Tablet, extended releaseOral80 mg/1
SyrupOral
SyrupOral5 mg / 5 mL
SyrupOral1 mg / mL
KitOral
CreamTopical
Capsule, extended releaseOral
Tablet, extended releaseOral
Suspension, extended releaseOral
Tablet, extended releaseOral15 mg/1
Tablet, extended releaseOral30 mg/1
Tablet, extended releaseOral45 mg/1
Tablet, extended releaseOral60 mg/1
Tablet, extended releaseOral90 mg/1
Tablet, coatedOral
LiquidOral
Capsule, extended releaseOral10 mg/1
Capsule, extended releaseOral15 mg/1
Capsule, extended releaseOral20 mg/1
Capsule, extended releaseOral30 mg/1
Capsule, extended releaseOral40 mg/1
Capsule, extended releaseOral50 mg/1
Prices
Unit descriptionCostUnit
Hydrocodone-Acetaminophen 7.5-500 mg/15ml Solution 473ml Bottle60.97USD bottle
Hydrocodone-Ibuprofen 7.5-200 mg tablet1.13USD tablet
Hydrocodone-Acetaminophen 10-750 mg tablet1.1USD tablet
Hydrocodone-Acetaminophen 7.5-325 mg tablet0.63USD tablet
Hydrocodone-Acetaminophen 10-325 mg tablet0.57USD tablet
Hydrocodone-Acetaminophen 5-325 mg tablet0.57USD tablet
Hydrocodone-Acetaminophen 10-660 mg tablet0.53USD tablet
Hydrocodone-Acetaminophen 10-500 mg tablet0.5USD tablet
Hydrocodone-Acetaminophen 10-650 mg tablet0.47USD tablet
Hydrocodone-Acetaminophen 7.5-500 mg tablet0.47USD tablet
Hydrocodone-Acetaminophen 2.5-500 mg tablet0.43USD tablet
Hydrocodone-Acetaminophen 7.5-750 mg tablet0.43USD tablet
Hydrocodone-Acetaminophen 5-500 mg tablet0.4USD tablet
Hydrocodone-Acetaminophen 7.5-650 mg tablet0.16USD tablet
Hydrocodone-Homatropine 5-1.5 mg/5ml Syrup0.15USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9265760No2016-02-232033-07-23US flag
US6599531No2003-07-292017-06-10US flag
US6348216No2002-02-192017-06-10US flag
US6228398No2001-05-082019-11-01US flag
US8309060No2012-11-132023-11-20US flag
US6488963No2002-12-032017-06-24US flag
US9060940No2015-06-232021-10-30US flag
US8808740No2014-08-192031-12-21US flag
US6733783No2004-05-112021-10-30US flag
US9095614No2015-08-042027-08-24US flag
US9095615No2015-08-042027-08-24US flag
US8361499No2013-01-292021-10-30US flag
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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)198 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.797 mg/mLALOGPS
logP2.13ALOGPS
logP1.96Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)19.44Chemaxon
pKa (Strongest Basic)9.17Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area38.77 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity82.74 m3·mol-1Chemaxon
Polarizability32.03 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9984
Caco-2 permeable+0.8621
P-glycoprotein substrateSubstrate0.8253
P-glycoprotein inhibitor IInhibitor0.6425
P-glycoprotein inhibitor IINon-inhibitor0.8664
Renal organic cation transporterInhibitor0.6604
CYP450 2C9 substrateNon-substrate0.8546
CYP450 2D6 substrateSubstrate0.8997
CYP450 3A4 substrateSubstrate0.8168
CYP450 1A2 substrateNon-inhibitor0.8207
CYP450 2C9 inhibitorNon-inhibitor0.9412
CYP450 2D6 inhibitorInhibitor0.6629
CYP450 2C19 inhibitorNon-inhibitor0.8402
CYP450 3A4 inhibitorNon-inhibitor0.7625
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8675
Ames testNon AMES toxic0.7735
CarcinogenicityNon-carcinogens0.9419
BiodegradationNot ready biodegradable0.984
Rat acute toxicity3.0914 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9024
hERG inhibition (predictor II)Non-inhibitor0.8165
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.3 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-2090000000-117774746c444c4e0488
Mass Spectrum (Electron Ionization)MSsplash10-0005-6970000000-3ba3e105098639cd6091
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0009000000-f21858df54194757e2d9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0009000000-9b129b5d29df52345272
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0649000000-82623b23b75f0a0b232d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0920000000-b67ff5a32d0ddd40c4c7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-006t-0900000000-0277ba7435a4081ab333
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0g6v-0900000000-b335c52fad1274cd28cb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0019000000-aa23ab8086639840d8ad
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-67bdd165e4243700f6bd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0049000000-f5c49c0eb373590ae494
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-56200b77e5b0e013fa63
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfu-1091000000-61c4098af41188200440
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fgk-0090000000-71691da5d4aaf685e185
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[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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Details
1. 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]
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]
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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. 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]
  2. Monte AA, Heard KJ, Campbell J, Hamamura D, Weinshilboum RM, Vasiliou V: The effect of CYP2D6 drug-drug interactions on hydrocodone effectiveness. Acad Emerg Med. 2014 Aug;21(8):879-85. doi: 10.1111/acem.12431. Epub 2014 Aug 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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]
  2. Monte AA, Heard KJ, Campbell J, Hamamura D, Weinshilboum RM, Vasiliou V: The effect of CYP2D6 drug-drug interactions on hydrocodone effectiveness. Acad Emerg Med. 2014 Aug;21(8):879-85. doi: 10.1111/acem.12431. Epub 2014 Aug 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. FDA Label: Hydrocodone Tab ER [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. FDA Label: Hydrocodone Tab ER [Link]

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