Identification

Name
Hydrocodone
Accession Number
DB00956  (APRD00591, DB09475)
Type
Small Molecule
Groups
Approved, Illicit, Investigational
Description

Narcotic analgesic related to codeine, but more potent and more addicting by weight. It is used also as cough suppressant.

Structure
Thumb
Synonyms
  • (-)-Dihydrocodeinone
  • 4,5-alpha-Epoxy-3-methoxy-17-methylmorphinan-6-one
  • Dihydrocodeinone
  • Hidrocodona
  • Hydrocodon
  • Hydrocodone
  • Hydrocodonum
  • Hydrocone
  • Hydroconum
  • Idrocodone
External IDs
NSC-19044
Product Ingredients
IngredientUNIICASInChI Key
Hydrocodone bitartrateNO70W886KK34195-34-1JMBRWJAVUIITGV-LNNMZZBZSA-N
Hydrocodone hydrochlorideQKZ0920OV325968-91-6GCJAEXSZUXBMFS-RNWHKREASA-N
Hydrocodone polistirexNot AvailableNot AvailableNot applicable
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hycodan SyrupSyrup5 mgOralBristol Myers Squibb1992-12-31Not applicableCanada
Hycodan TabletsTablet5 mgOralBristol Myers Squibb1992-12-31Not applicableCanada
Hysingla ERTablet, extended release60 mg/1OralPurdue Pharma LP2015-01-15Not applicableUs
Hysingla ERTablet, extended release100 mg/1OralPurdue Pharma LP2015-01-15Not applicableUs
Hysingla ERTablet, extended release20 mg/1OralPurdue Pharma LP2015-01-15Not applicableUs
Hysingla ERTablet, extended release80 mg/1OralPurdue Pharma LP2015-01-15Not applicableUs
Hysingla ERTablet, extended release30 mg/1OralPurdue Pharma LP2015-01-15Not applicableUs
Hysingla ERTablet, extended release120 mg/1OralPurdue Pharma LP2015-01-15Not applicableUs
Hysingla ERTablet, extended release40 mg/1OralPurdue Pharma LP2015-01-15Not applicableUs
Robidone 1mg/ml SyrSyrup1 mgOralWyeth Ayerst Canada Inc.1993-12-312001-11-06Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hydrocodone Bitartrate And AcetaminophenTablet5 mg/1OralRemedy Repack2013-02-202013-02-21Us
Hydrocodone Bitartrate and AcetaminophenTablet5 mg/1OralRemedy Repack2013-03-182014-03-18Us
Pdp-hydrocodoneSyrup5 mgOralPendopharm Division Of De Pharmascience Inc2009-03-21Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antitussive hydrocodone bitartrate and homatropine methylbromideHydrocodone bitartrate (5 mg/1) + Homatropine Methylbromide (1.5 mg/1)TabletOralActavis Totowa LLC2001-01-012008-08-20Us
Caldomine Dh AdulteHydrocodone bitartrate (5 mg) + Mepyramine maleate (12.5 mg) + Pheniramine maleate (12.5 mg) + Phenylpropanolamine hydrochloride (25 mg)LiquidOralTechnilab Pharma Inc.1981-12-312001-04-04Canada
Caldomine Dh EnfantHydrocodone bitartrate (1.667 mg) + Mepyramine maleate (6.25 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg)LiquidOralTechnilab Pharma Inc.1982-12-312001-04-04Canada
Co-gesicHydrocodone bitartrate (5 mg/1) + Acetaminophen (500 mg/1)TabletOralKremers Urban1982-05-312014-01-14Us
CodofenHydrocodone bitartrate (7.5 mg) + Ibuprofen (200 mg)TabletOralPaladin Labs IncNot applicableNot applicableCanada
Coristine-DH LiqHydrocodone bitartrate (1.7 mg) + Phenylephrine hydrochloride (10 mg)SyrupOralTechnilab Pharma Inc.1988-12-312006-07-28Canada
DalmacolHydrocodone bitartrate (1.65 mg) + Doxylamine succinate (6 mg) + Etafedrine hydrochloride (16.65 mg) + Ethanol (0.25 ml) + Sodium Citrate (200 mg)SyrupOralLaboratoire Riva Inc1997-03-26Not applicableCanada
DalmacolHydrocodone bitartrate (1.65 mg) + Doxylamine succinate (6 mg) + Etafedrine hydrochloride (16.65 mg) + Ethanol (0.25 ml) + Sodium Citrate (200 mg)SyrupOralLaboratoire Atlas Inc1983-12-31Not applicableCanada
Dimetane Expectorant DcHydrocodone bitartrate (1.8 mg) + Brompheniramine maleate (2 mg) + Guaifenesin (100 mg) + Phenylephrine hydrochloride (5 mg)SyrupOralPfizer Laboratories Div Pfizer Inc.2001-09-06Not applicableCanada
Dimetane Expectorant-DC SyrHydrocodone bitartrate (1.8 mg) + Brompheniramine maleate (2 mg) + Guaifenesin (100 mg) + Phenylephrine hydrochloride (5 mg) + Phenylpropanolamine hydrochloride (5 mg)SyrupOralWhitehall Robins Inc.1993-12-312001-04-10Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Atuss HS TannateHydrocodone bitartrate (5 mg/5mL) + Chlorpheniramine maleate (4 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)SuspensionOralAtley Pharmaceuticals2006-11-212009-08-03Us
Hydrocodone/GuaifenesinHydrocodone bitartrate (2.5 mg/1) + Guaifenesin (300 mg/1)TabletOralPhysicians Total Care, Inc.2005-12-202007-10-31Us
HyTanHydrocodone (5 mg/5mL) + Chlorpheniramine tannate (4 mg/5mL)SuspensionOralPrasco, Laboratories2006-05-312007-12-31Us
P-TussHydrocodone bitartrate (5 mg/5mL) + Potassium Guaiacolsulfonate (300 mg/5mL)LiquidOralPrasco, Laboratories2010-12-012011-01-21Us
Pancof HCHydrocodone bitartrate (3 mg/5mL) + Pseudoephedrine hydrochloride (15 mg/5mL)SyrupOralPhysicians Total Care, Inc.2007-02-022007-10-31Us
Theracodophen-325Hydrocodone bitartrate (10 mg/1) + Acetaminophen (325 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-02-08Not applicableUs
Theracodophen-650Hydrocodone bitartrate (10 mg/1) + Acetaminophen (650 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-03-06Not applicableUs
Theracodophen-750Hydrocodone bitartrate (7.5 mg/1) + Acetaminophen (750 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-02-09Not applicableUs
Theracodophen-Low-90Hydrocodone bitartrate (5 mg/1) + Acetaminophen (500 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-02-02Not applicableUs
Topical PainHydrocodone (0.1 g/100mL) + Diazepam (0.1 g/100mL) + Ibuprofen (0.1 g/100mL) + Tramadol (0.1 g/100mL)CreamTopicalDr Marc's Manufacturing And Sales2016-02-232018-04-18Us
Categories
UNII
6YKS4Y3WQ7
CAS number
125-29-1
Weight
Average: 299.3642
Monoisotopic: 299.152143543
Chemical Formula
C18H21NO3
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[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]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

Pharmacology

Indication

For relief of moderate to moderately severe pain. Also used for the symptomatic relief of nonproductive cough, alone or in combination with other antitussives or expectorants.

Associated Conditions
Pharmacodynamics

Hydrocodone, a semisynthetic opiate agonist and hydrogenated ketone derivative, is similar to other phenanthrene derivatives, such as codeine. Used as an analgesic, hydrocodone is combined with acetaminophen, ibuprofen, or aspirin to treat pain. Used as an antitussive, hydrocodone is combined with phenylephrine, pseudoephedrine, phenylpropanolamine, guaifenesin, pyrilamine, pheniramine, or chlorpheniramine. Opiate agonists exert their principal pharmacologic effect at specific receptor binding sites in the CNS and other tissues. There are several subtypes of opiate receptors including the mu receptor (localized in pain modulating regions of the CNS), the kappa receptor (localized in the deep layers of the cerebral cortex), the delta receptor (localized in the limbic regions of the CNS), and the sigma receptor (thought to mediate the dysphoric and psychotomimetic effects of some opiate partial agonists). Agonist activity at the mu or kappa receptor can result in analgesia, miosis, and/or decreased body temperature. Agonist activity at the mu receptor can also result in suppression of opiate withdrawal, whereas antagonist activity can result in precipitation of withdrawal. Opiate agonists act at several sites within the CNS involving several systems of neurotransmitters to produce analgesia, but the precise mechanism of action has not been fully determined. Opiate agonists do not alter the threshold or responsiveness of afferent nerve endings to noxious stimuli nor the conduction of impulses along peripheral nerves. Instead, they alter the perception of pain at the spinal cord and higher levels in the CNS and the person's emotional response to pain.

Mechanism of action

Hydrocodone acts as a weak agonist at OP1, OP2, and OP3 opiate receptors within the central nervous system (CNS). Hydrocodone primarily affects OP3 receptors, which are coupled with G-protein receptors and function as modulators, both positive and negative, of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine, and noradrenaline is inhibited. Opioids such as hydrocodone also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.

TargetActionsOrganism
AMu-type opioid receptor
agonist
Human
ADelta-type opioid receptor
agonist
Human
Absorption

Well absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

As most agents in the 5-ring morphinan group of semi-synthetic opioids bind plasma protein to a similar degree (range 19% Hydromorphone to 45% Oxycodone), hydrocodone is expected to fall within this range.

Metabolism

Hepatic and also in intestinal mucosa.

Route of elimination
Not Available
Half life

1.25-3 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include respiratory depression (a decrease in respiratory rate and/or tidal volume, Cheyne-Stokes respiration, cyanosis), extreme somnolence progressing to stupor or coma, skeletal muscle flaccidity, dizziness, ringing in the ears, confusion, blurred vision, eye problems, cold and clammy skin, and sometimes bradycardia and hypotension. In severe overdose, apnea, circulatory collapse, cardiac arrest and death may occur. LD50=85.7mg/kg (subcutaneous, in mice).

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Hydrocodone Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Hydrocodone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Hydrocodone.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Hydrocodone is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Hydrocodone.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Hydrocodone.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Hydrocodone.
Food Interactions
  • Avoid alcohol.
  • Take with food.
  • To avoid constipation: increase your daily intake of fiber (beans, whole grains, vegetables).

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
Not Available
External Links
Human Metabolome Database
HMDB0015091
KEGG Drug
D08045
KEGG Compound
C08024
PubChem Compound
5284569
PubChem Substance
46506225
ChemSpider
4447623
BindingDB
50386689
ChEBI
5779
ChEMBL
CHEMBL1457
Therapeutic Targets Database
DAP000253
PharmGKB
PA449900
RxList
RxList Drug Page
Wikipedia
Hydrocodone
ATC Codes
R05DA03 — Hydrocodone
AHFS Codes
  • 48:08.00 — Antitussives
MSDS
Download (48.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentFracture, Ankle1
0RecruitingSupportive CareMetastatic Malignant Neoplasm / Neoplasms, Malignant / Pain NOS1
0WithdrawnTreatmentPain NOS / Painful musculoskeletal conditions1
1Active Not RecruitingTreatmentHead and Neck Carcinoma / Oral Mucositis1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableHepatic Impairment1
1CompletedNot AvailableImpaired Renal Function1
1CompletedNot AvailablePain NOS1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedSupportive CareHealthy Volunteers1
1CompletedTreatmentSubstance Abuse1
1Not Yet RecruitingPreventionInfections, Respiratory Syncytial Virus1
1WithdrawnTreatmentOpioid-Related Disorders / Pain, Acute / Postoperative pain2
1, 2Not Yet RecruitingTreatmentAcute Myeloid Leukemia Arising From Previous Myelodysplastic Syndrome / Acute, recurrent Myeloid Leukemia / Refractory Acute Myeloid Leukemia / TP53 Gene Mutation Negative1
2CompletedNot AvailableDegenerative Joint Disease1
2CompletedNot AvailablePostoperative pain1
2CompletedTreatmentAdverse Drug Events / Allergic Rhinitis (AR) / Quality of Life1
2CompletedTreatmentBack Pain Lower Back Chronic1
2CompletedTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL) / Non-Hodgkin's Lymphoma (NHL)1
2CompletedTreatmentPain NOS6
2Not Yet RecruitingSupportive CarePostoperative pain1
2Not Yet RecruitingTreatmentPain NOS1
2RecruitingTreatmentCorneal Abrasions / Eye Trauma1
2RecruitingTreatmentDouble-hit Lymphoma / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Mantle Cell Lymphoma (MCL) / Peripheral T Cell Lymphoma (PTCL)1
2RecruitingTreatmentAcute, recurrent Myeloid Leukemia / Refractory Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia1
2RecruitingTreatmentPainful musculoskeletal conditions1
3Active Not RecruitingTreatmentNausea / Pain NOS / Vomiting1
3CompletedPreventionNausea / Pain NOS / Vomiting1
3CompletedSupportive CareAnalgesia After ED Discharge for Extremity Injuries1
3CompletedTreatmentAcute Nonlymphocytic Leukemia / Leukemia Acute Myeloid Leukemia (AML) / Leukemias1
3CompletedTreatmentBack Pain Lower Back1
3CompletedTreatmentBack Pain Lower Back Chronic5
3CompletedTreatmentChronic Nonmalignant and Nonneuropathic Pain1
3CompletedTreatmentModerate to Severe Chronic, Non-malignant Pain1
3CompletedTreatmentNausea / Pain NOS / Vomiting1
3CompletedTreatmentOsteoarthritis (OA)1
3CompletedTreatmentPain NOS3
3CompletedTreatmentPain, Chronic1
3RecruitingSupportive CareMalignant Head and Neck Neoplasm / Mucositis / Radiation-Induced Disorder1
3RecruitingTreatmentAcute Lymphoblastic Leukemia, Pediatric1
3RecruitingTreatmentChronic Kidney Disease Requiring Chronic Dialysis / Hyperphosphataemia1
3RecruitingTreatmentOpioids Use / Shoulder Pain1
3RecruitingTreatmentPostoperative pain / Surgery, Outpatient1
3TerminatedNot AvailablePost Operative Pain1
4CompletedNot AvailablePain, Chronic1
4CompletedBasic ScienceDriving Behavior1
4CompletedTreatmentAlzheimer's Disease (AD) / Dementia, Vascular / Dementias / Pain NOS1
4CompletedTreatmentNarcotic Use / Nausea / Occasional Constipation / Pain NOS1
4CompletedTreatmentOpioids Use / Postoperative pain1
4CompletedTreatmentPain NOS2
4CompletedTreatmentToothache1
4Not Yet RecruitingTreatmentPain NOS1
4RecruitingSupportive CareCarpal Tunnel1
4RecruitingSupportive CareColon Diverticulosis / Colonic Neoplasms / Constipation Drug Induced / Diverticulitis, Colonic / Ileus / Ileus paralytic / Ileus; Mechanical / Malignant Neoplasm of Colon / Occasional Constipation / Postoperative pain / Rectum Cancer / Rectum Neoplasm1
4RecruitingTreatmentBody Weight Changes / Post-Operative Nausea and Vomiting (PONV) / Postoperative Hemorrhages / Postoperative pain1
4RecruitingTreatmentPain Control After Functional Endoscopic Sinus Surgery and Septoplasty1
4RecruitingTreatmentPain Management1
4RecruitingTreatmentPain NOS1
4RecruitingTreatmentRib Fracture Multiple / Rib Fractures1
4SuspendedTreatmentRotator Cuff Syndrome1
4TerminatedTreatmentAdverse Reaction to Drug / Obstructive Sleep Apnea (OSA) / Recurrent Tonsillitis / Sleep Disordered Breathing (SDB)1
4TerminatedTreatmentCarpal Tunnel Syndrome (CTS)1
4TerminatedTreatmentCarpal Tunnel / Cystic tumour of the ganglia / De Quervain's Disease / Trigger Finger1
Not AvailableCompletedPreventionPost-Operative Nausea and Vomiting (PONV)1
Not AvailableCompletedTreatmentCancer, Breast / Postoperative pain1
Not AvailableCompletedTreatmentChildren / Laceration / Pain NOS / Procedures1
Not AvailableCompletedTreatmentContraception / Inhalation of Nitrous Oxide1
Not AvailableCompletedTreatmentDrug Drug Interaction (DDI)1
Not AvailableCompletedTreatmentSkin Laxity1
Not AvailableNot Yet RecruitingTreatmentNon-steroidal Ant Inflammatory Drugs / Opioids Use / Rhinoplasty1
Not AvailableUnknown StatusNot AvailableAnalgesic Response1
Not AvailableWithdrawnSupportive CareToothache1

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
LiquidOral
TabletOral5 mg
CapsuleOral
ElixirOral
SolutionOral
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
TabletOral
SyrupOral
SyrupOral5 mg
SyrupOral1 mg
Kit
CreamTopical
Capsule, extended releaseOral
SuspensionOral
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
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.
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US9861584No2018-01-092031-12-21Us
US9872837No2018-01-232031-12-21Us
US10028946No2013-07-252033-07-25Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)198 °CPhysProp
water solubilityInsolubleNot Available
logP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.797 mg/mLALOGPS
logP2.13ALOGPS
logP1.96ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)18ChemAxon
pKa (Strongest Basic)8.61ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity82.74 m3·mol-1ChemAxon
Polarizability32.05 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-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0005-6970000000-3ba3e105098639cd6091
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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

Taxonomy

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
Morphinan / Phenanthrene / Isoquinolone / Tetralin / Coumaran / Anisole / Alkyl aryl ether / Aralkylamine / Piperidine / Benzenoid
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound (CHEBI:5779)

Targets

Details
1. Mu-type opioid receptor
Kind
Protein
Organism
Human
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. [PubMed:11752352]
  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. [PubMed:10640321]
  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. [PubMed:16291875]
  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. [PubMed:2849950]
  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. [PubMed:14600248]
  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. [PubMed:20665209]
  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. [PubMed:18606504]
Kind
Protein
Organism
Human
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. 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. [PubMed:16291875]
  2. 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. [PubMed:14600248]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:14998425]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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. [PubMed:14998425]

Drug created on June 13, 2005 07:24 / Updated on December 16, 2018 23:30