Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C18H21NO3.2C4H6O6.5H2O |
Molecular Weight | 988.9786 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 12 / 12 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.O.O.O[C@H]([C@@H](O)C(O)=O)C(O)=O.O[C@H]([C@@H](O)C(O)=O)C(O)=O.[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]15CCN(C)[C@H](C4)[C@]5([H])CCC2=O.[H][C@@]67OC8=C(OC)C=CC9=C8[C@@]6%10CCN(C)[C@H](C9)[C@]%10([H])CCC7=O
InChI
InChIKey=JMBRWJAVUIITGV-LNNMZZBZSA-N
InChI=1S/2C18H21NO3.2C4H6O6.5H2O/c2*1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19;2*5-1(3(7)8)2(6)4(9)10;;;;;/h2*3,6,11-12,17H,4-5,7-9H2,1-2H3;2*1-2,5-6H,(H,7,8)(H,9,10);5*1H2/t2*11-,12+,17-,18-;2*1-,2-;;;;;/m0011...../s1
Molecular Formula | C18H21NO3 |
Molecular Weight | 299.3642 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C4H6O6 |
Molecular Weight | 150.0868 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Benzhydrocodone is a prodrug of hydrocodone. Benzhydrocodone is formed by covalently bonding hydrocodone to benzoic acid. Benzhydrocodone itself is not pharmacologically active, but must be metabolized to hydrocodone by enzymes in the intestinal tract to optimally deliver its pharmacologic effects. Hydrocodone is a full agonist of the opioid receptors with a higher affinity for the mu-opioid receptor. Upon binding, hydrocodone produces an analgesic effect with no ceiling. APADAZ a combination of benzhydrocodone and acetaminophen is FDA approved and indicated for the short-term (no more than 14 days) management of acute pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate. APADAZ, even when taken as recommended, can result in addiction, abuse, and misuse, which can lead to overdose and death.
CNS Activity
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZOHYDRO ER Approved UseZOHYDRO ER is an opioid agonist indicated for the management of pain severe enough to require daily, around-the-clock, long-term opioid treatment and for which alternative treatment options are inadequate. Launch Date1.38257275E12 |
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Primary | APADAZ Approved UseAPADAZ is a combination of benzhydrocodone, a prodrug of the opioid agonist hydrocodone, and acetaminophen, and is indicated for the short-term (no more than 14 days) management of acute pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate. Launch Date1.54647357E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138027/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
23.6 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
155 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138027/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27138027/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4 h |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
55% |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCODONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
30 mg multiple, oral (total) Overdose Dose: 30 mg Route: oral Route: multiple Dose: 30 mg Co-administed with:: clarithromycin Sources: valproic acid(250 mg, 2 times per day) |
unhealthy, 5 years n = 1 Health Status: unhealthy Condition: cold Age Group: 5 years Sex: F Population Size: 1 Sources: |
Other AEs: Adverse event... |
160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Electrocardiogram QTc interval prolonged... Other AEs: Electrocardiogram QTc interval prolonged Sources: |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
Other AEs: Withdrawal syndrome neonatal... Other AEs: Withdrawal syndrome neonatal Sources: |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Respiratory depression, Addiction... Other AEs: Respiratory depression (grade 5) Sources: Addiction |
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 115 |
unhealthy, adult n = 296 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 296 Sources: Page: p. 115 |
Disc. AE: Vomiting, Nausea... AEs leading to discontinuation/dose reduction: Vomiting (1%) Sources: Page: p. 115Nausea (1%) Headache (1%) Dizziness (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Adverse event | grade 5 | 30 mg multiple, oral (total) Overdose Dose: 30 mg Route: oral Route: multiple Dose: 30 mg Co-administed with:: clarithromycin Sources: valproic acid(250 mg, 2 times per day) |
unhealthy, 5 years n = 1 Health Status: unhealthy Condition: cold Age Group: 5 years Sex: F Population Size: 1 Sources: |
Electrocardiogram QTc interval prolonged | 160 mg 1 times / day multiple, oral Highest studied dose Dose: 160 mg, 1 times / day Route: oral Route: multiple Dose: 160 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
Withdrawal syndrome neonatal | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
|
Addiction | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
Respiratory depression | grade 5 | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Dizziness | 1% Disc. AE |
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 115 |
unhealthy, adult n = 296 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 296 Sources: Page: p. 115 |
Headache | 1% Disc. AE |
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 115 |
unhealthy, adult n = 296 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 296 Sources: Page: p. 115 |
Nausea | 1% Disc. AE |
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 115 |
unhealthy, adult n = 296 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 296 Sources: Page: p. 115 |
Vomiting | 1% Disc. AE |
20 mg 1 times / day multiple, oral Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 115 |
unhealthy, adult n = 296 Health Status: unhealthy Age Group: adult Sex: M+F Population Size: 296 Sources: Page: p. 115 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/206627s007s008lbl.pdf#page=29 Page: 29.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/206627s007s008lbl.pdf#page=29 Page: 29.0 |
minor | |||
yes | yes (co-administration study) Comment: The 90% confidence interval (CI) of the geometric means for hydrocodone AUCinf (98 to 115%), AUCt (98 to 115%), and Cmax (93 to 121%) values were within the range of 80 to 125% when a single dose of HYSINGLA ER 20 mg was co-administered with CYP2D6 inhibitor paroxetine |
|||
yes | yes (co-administration study) Comment: Co-administration of HYSINGLA ER and CYP3A4 inhibitor ketoconazole increased mean hydrocodone AUC and Cmax by 135% and 78%, respectively; |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206627Orig1s000PharmR.pdf#page=33 Page: 33.0 |
PubMed
Title | Date | PubMed |
---|---|---|
[Longitudinal study of parameters of respiratory function tests and blood gas analysis in patients with progressive systemic scleroderma]. | 2001 |
|
Narcotic analgesics for dental pain: available products, strengths, and formulations. | 2001 Mar-Apr |
|
[Lung function tests and bronchoalveolar lavage (BAL) findings in patients with primary biliary cirrhosis]. | 2002 |
|
The simultaneous determination of codeine, morphine, hydrocodone, hydromorphone, 6-acetylmorphine, and oxycodone in hair and oral fluid. | 2002 Apr |
|
[Hospital maternal mortality: causes and consistency between clinical and autopsy diagnosis at the Northeastern Medical Center of the IMSS, Mexico]. | 2002 Feb |
|
A phase II study of hydrocodone for cough in advanced cancer. | 2002 Jan-Feb |
|
Effect of narcotic pain reliever on pulp tests in women. | 2002 Jul |
|
Gateways to clinical trials. | 2002 Jul-Aug |
|
Photodynamic therapy for Barrett's esophagus and high grade dysplasia: results of a patient satisfaction survey. | 2002 Jul-Aug |
|
A double-blind, single-dose comparison of the analgesic efficacy of tramadol/acetaminophen combination tablets, hydrocodone/acetaminophen combination tablets, and placebo after oral surgery. | 2002 Jun |
|
Simultaneous determination of hydrocodone and hydromorphone in human plasma by liquid chromatography with tandem mass spectrometric detection. | 2002 Mar 25 |
|
[Trends in the incidence of hepatic tumors in childhood]. | 2002 Mar-Apr |
|
Gender differences in narcotic-induced emesis in the ED. | 2002 May |
|
Exacerbation of panic disorder symptoms following Vicodin exposure. | 2002 Nov-Dec |
|
Rational use of analgesic combinations. | 2002 Oct |
|
Simultaneous quantitation of opioids in blood by GC-EI-MS analysis following deproteination, detautomerization of keto analytes, solid-phase extraction, and trimethylsilyl derivatization. | 2002 Oct |
|
A field evaluation of five on-site drug-testing devices. | 2002 Oct |
|
Detection of cocaine analytes and opiates in nails from postmortem cases. | 2002 Oct |
|
Adverse drug reactions to oxycodone and hydrocodone in CYP2D6 ultrarapid metabolizers. | 2003 Aug |
|
Quantification of the O- and N-demethylated metabolites of hydrocodone and oxycodone in human liver microsomes using liquid chromatography with ultraviolet absorbance detection. | 2003 Feb 25 |
|
I am following a health care professional who, I think, has a drug problem. | 2003 Jan |
|
Trials and tribulations: current challenges in conducting clinical trials. | 2003 Jan |
|
Hair analysis for opiates: evaluation of washing and incubation procedures. | 2003 Jun 5 |
|
Postmortem oxycodone and hydrocodone blood concentrations. | 2003 Mar |
|
Cognitive and motor function after administration of hydrocodone bitartrate plus ibuprofen, ibuprofen alone, or placebo in healthy subjects with exercise-induced muscle damage: a randomized, repeated-dose, placebo-controlled study. | 2003 Mar |
|
Misuse of prescribed controlled substances defined by urinalysis. | 2003 Mar-Apr |
|
Current concepts in acute pain management. | 2003 May |
|
Withdrawal hyperalgesia after acute opioid physical dependence in nonaddicted humans: a preliminary study. | 2003 Nov |
|
Pharmacokinetic drug interactions of morphine, codeine, and their derivatives: theory and clinical reality, Part II. | 2003 Nov-Dec |
|
Patterns and trends in opioid use among individuals with back pain in the United States. | 2004 Apr 15 |
|
1000 office-based hysteroscopies prior to in vitro fertilization: feasibility and findings. | 2004 Apr-Jun |
|
Carisoprodol withdrawal syndrome. | 2004 Dec |
|
Activation of G-proteins by morphine and codeine congeners: insights to the relevance of O- and N-demethylated metabolites at mu- and delta-opioid receptors. | 2004 Feb |
|
Dose-response relationship between opioid use and adverse effects after ambulatory surgery. | 2004 Jul |
|
Efficacy of ibuprofen-hydrocodone for the treatment of postoperative pain after periodontal surgery. | 2004 Jun |
|
Persistent nonmalignant pain and analgesic prescribing patterns in elderly nursing home residents. | 2004 Jun |
|
CYP2D6 and CYP3A4 involvement in the primary oxidative metabolism of hydrocodone by human liver microsomes. | 2004 Mar |
|
[Origin and growth of the National Program of Continuous Academic Development for the General Physician]. | 2004 May-Jun |
|
Local anesthetic infusion pumps improve postoperative pain after inguinal hernia repair: a randomized trial. | 2004 Nov |
|
6-oxo-morphinane oximes: pharmacology, chemistry and analytical application. | 2004 Oct |
|
Presurgical intravenous parecoxib sodium and follow-up oral valdecoxib for pain management after laparoscopic cholecystectomy surgery reduces opioid requirements and opioid-related adverse effects. | 2004 Oct |
|
Fracture of an endoluminal nitinol stent used in the treatment of tracheal collapse in a dog. | 2004 Oct 15 |
|
Cough suppression during flexible bronchoscopy using combined sedation with midazolam and hydrocodone: a randomised, double blind, placebo controlled trial. | 2004 Sep |
|
A 35-year-old physician with opioid dependence. | 2004 Sep 15 |
|
Selective potentiation of opioid analgesia by nonsteroidal anti-inflammatory drugs. | 2005 Apr 8 |
|
Detection of hypoventilation during thoracoscopy: combined cutaneous carbon dioxide tension and oximetry monitoring with a new digital sensor. | 2005 Feb |
|
A preclinical comparison between different opioids: antinociceptive versus adverse effects. | 2005 Feb |
|
The GC-MS detection and characterization of neopine resulting from opium use and codeine metabolism and its potential as an opiate-product-use marker. | 2005 Jun |
|
A 46-year-old man with excruciating shoulder pain. | 2005 Mar |
|
Oral analgesics for acute nonspecific pain. | 2005 Mar 1 |
Sample Use Guides
APADAZ Immediate-release tablets: 6.12 mg benzhydrocodone (equivalent to 6.67 mg benzhydrocodone hydrochloride) and 325 mg acetaminophen.
Initiate treatment with APADAZ at 1 or 2 tablets every 4 to 6 hours as needed for pain. Dosage should not exceed 12 tablets in a 24 hour period.
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 13:00:03 UTC 2023
by
admin
on
Thu Jul 06 13:00:03 UTC 2023
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Record UNII |
NO70W886KK
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C67413
Created by
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NCI_THESAURUS |
C66917
Created by
admin on Thu Jul 06 13:00:03 UTC 2023 , Edited by admin on Thu Jul 06 13:00:03 UTC 2023
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DEA NO. |
9193
Created by
admin on Thu Jul 06 13:00:03 UTC 2023 , Edited by admin on Thu Jul 06 13:00:03 UTC 2023
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NCI_THESAURUS |
C1506
Created by
admin on Thu Jul 06 13:00:03 UTC 2023 , Edited by admin on Thu Jul 06 13:00:03 UTC 2023
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Code System | Code | Type | Description | ||
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1315001
Created by
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PRIMARY | |||
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DBSALT001233
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PRIMARY | |||
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SUB02559MIG
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PRIMARY | |||
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DTXSID7091543
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PRIMARY | |||
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34195-34-1
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PRIMARY | |||
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23724881
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PRIMARY | |||
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300000040282
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NO70W886KK
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PRIMARY | |||
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CHEMBL1457
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142439
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PRIMARY | RxNorm | ||
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NO70W886KK
Created by
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PRIMARY | |||
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5780
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PRIMARY | |||
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M6093
Created by
admin on Thu Jul 06 13:00:03 UTC 2023 , Edited by admin on Thu Jul 06 13:00:03 UTC 2023
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PRIMARY | Merck Index | ||
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Hydrocodone bitartrate
Created by
admin on Thu Jul 06 13:00:03 UTC 2023 , Edited by admin on Thu Jul 06 13:00:03 UTC 2023
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PRIMARY | |||
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C29099
Created by
admin on Thu Jul 06 13:00:03 UTC 2023 , Edited by admin on Thu Jul 06 13:00:03 UTC 2023
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PRIMARY |
Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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ANHYDROUS->SOLVATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.2
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |