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Identification
NameMorphine
Accession NumberDB00295  (APRD00215)
TypeSmall Molecule
GroupsApproved, Investigational
Description

The principal alkaloid in opium and the prototype opiate analgesic and narcotic. Morphine has widespread effects in the central nervous system and on smooth muscle. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(-)-MorphineNot AvailableNot Available
(−)-morphineNot AvailableNot Available
(5alpha,6alpha)-17-Methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diolNot AvailableNot Available
(5alpha,6alpha)-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diolNot AvailableNot Available
(5R,6S,9R,13S,14R)-4,5-Epoxy-N-methyl-7-morphinen-3,6-diolNot AvailableNot Available
(7R,7AS,12bs)-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline-7,9-diolNot AvailableNot Available
MorfinaNot AvailableNot Available
MorphiaNot AvailableNot Available
MorphinGermanNot Available
MorphineNot AvailableNot Available
MorphinumLatinNot Available
MorphiumNot AvailableNot Available
Salts
Name/CAS Structure Properties
Morphine Sulfate
Thumb
  • InChI Key: USAHOPJHPJHUNS-IFCNUISUSA-N
  • Monoisotopic Mass: 668.2403662
  • Average Mass: 668.754
DBSALT000122
Brand names
NameCompany
AvinzaNot Available
DuramorphNot Available
KadianNot Available
KapanolNot Available
MS ContinNot Available
MSIRNot Available
OramorphNot Available
RoxanolNot Available
Brand mixtures
Brand NameIngredients
Camphorated Opium TinctureBenzoic Acid + Camphor + Morphine
ParegoriqueCamphor + Morphine
Categories
CAS number57-27-2
WeightAverage: 285.3377
Monoisotopic: 285.136493479
Chemical FormulaC17H19NO3
InChI KeyBQJCRHHNABKAKU-KBQPJGBKSA-N
InChI
InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1
IUPAC Name
(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraene-10,14-diol
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O
Mass Specshow(9.42 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassAlkaloids and Derivatives
ClassMorphinans
SubclassNot Available
Direct parentMorphinans
Alternative parentsBenzylisoquinolines; Phenanthrenes and Derivatives; Tetralins; Benzofurans; Phenols and Derivatives; Alkyl Aryl Ethers; Piperidines; Secondary Alcohols; Tertiary Amines; Polyamines; Enols
Substituentsphenanthrene; tetralin; benzofuran; phenol derivative; alkyl aryl ether; benzene; piperidine; tertiary amine; secondary alcohol; polyamine; enol; ether; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
Pharmacology
IndicationFor the relief and treatment of severe pain.
PharmacodynamicsMorphine is a narcotic pain management agent indicated for the relief of pain in patients who require opioid analgesics for more than a few days. Morphine interacts predominantly with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, with high densities in the posterior amygdala, hypothalamus, thalamus, nucleus caudatus, putamen, and certain cortical areas. They are also found on the terminal axons of primary afferents within laminae I and II (substantia gelatinosa) of the spinal cord and in the spinal nucleus of the trigeminal nerve. In clinical settings, morphine exerts its principal pharmacological effect on the central nervous system and gastrointestinal tract. Its primary actions of therapeutic value are analgesia and sedation. Morphine appears to increase the patient's tolerance for pain and to decrease discomfort, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Opioids also produce respiratory depression by direct action on brain stem respiratory centers.
Mechanism of actionThe precise mechanism of the analgesic action of morphine is unknown. However, specific CNS opiate receptors have been identified and likely play a role in the expression of analgesic effects. Morphine first acts on the mu-opioid receptors. The mechanism of respiratory depression involves a reduction in the responsiveness of the brain stem respiratory centers to increases in carbon dioxide tension and to electrical stimulation. It has been shown that morphine binds to and inhibits GABA inhibitory interneurons. These interneurons normally inhibit the descending pain inhibition pathway. So, without the inhibitory signals, pain modulation can proceed downstream.
AbsorptionBioavailability is approximately 30%.
Volume of distribution
  • 1 to 6 L/kg
Protein binding30-40%
Metabolism

Primarily hepatic (90%), converted to dihydromorphinone and normorphine. Also converted to morphine-3-glucuronide (M3G) and morphine-6-glucuronide. Virtually all morphine is converted to glucuronide metabolites; only a small fraction (less than 5%) of absorbed morphine is demethylated.

SubstrateEnzymesProduct
Morphine
morphine-6-glucuronideDetails
Morphine
morphine-3-glucuronideDetails
Morphine
Not Available
NormorphineDetails
Route of eliminationA small amount of glucuronide conjugates are excreted in bile, with minor enterohepatic recycling. Seven to 10% of administered morphine sulfate is excreted in the feces.
Half life2-4 hours
Clearance
  • 20 – 30 mL/min/kg [Adult]
  • 1852 +/- 116 mL/min [Chinese]
  • 1495 +/- 80 mL/min [Caucasian]
ToxicityLD50 = 461 mg/kg (rat, oral), 600 mg/kg (mouse, oral). Human lethal dose by ingestion is 120-250 mg of morphine sulfate. Symptoms of overdose include cold, clammy skin, flaccid muscles, fluid in the lungs, lowered blood pressure, "pinpoint" or dilated pupils, sleepiness leading to stupor and coma, slowed breathing, and slow pulse rate.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Morphine Metabolism PathwayDrug metabolismSMP00622
Codeine Metabolism PathwayDrug metabolismSMP00621
Heroin Metabolism PathwayDrug metabolismSMP00623
Heroin Action PathwayDrug actionSMP00407
Codeine Action PathwayDrug actionSMP00405
Morphine Action PathwayDrug actionSMP00406
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Multidrug resistance protein 1
Gene symbol: ABCB1
UniProt: P08183
rs1045642 Not AvailableT AlleleBetter response to pain relief drugs17898703
Mu-type opioid receptor
Gene symbol: OPRM1
UniProt: P35372
rs1799971 Not AvailableA AlleleBetter response to pain relief drugs17898703
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9971
Blood Brain Barrier + 0.9882
Caco-2 permeable + 0.8867
P-glycoprotein substrate Substrate 0.8787
P-glycoprotein inhibitor I Non-inhibitor 0.8782
P-glycoprotein inhibitor II Non-inhibitor 0.956
Renal organic cation transporter Inhibitor 0.6221
CYP450 2C9 substrate Non-substrate 0.7451
CYP450 2D6 substrate Substrate 0.8919
CYP450 3A4 substrate Substrate 0.7375
CYP450 1A2 substrate Non-inhibitor 0.5191
CYP450 2C9 substrate Non-inhibitor 0.9046
CYP450 2D6 substrate Non-inhibitor 0.647
CYP450 2C19 substrate Non-inhibitor 0.8155
CYP450 3A4 substrate Non-inhibitor 0.9176
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7503
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.9634
Biodegradation Not ready biodegradable 0.9944
Rat acute toxicity 2.8989 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8367
hERG inhibition (predictor II) Non-inhibitor 0.874
Pharmacoeconomics
Manufacturers
  • King pharmaceuticals inc
  • Actavis elizabeth llc
  • Ekr therapeutics inc
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia and critical care
  • Hospira inc
  • Mallinckrodt chemical inc
  • Meridian medical technologies inc
  • Watson laboratories inc
  • Roxane laboratories inc
  • Clonmel healthcare ltd
  • Endo pharmaceuticals inc
  • Kv pharmaceutical co
  • Mallinckrodt inc
  • Purdue pharma lp
  • Xanodyne pharmaceutics inc
  • Actavis
Packagers
Dosage forms
FormRouteStrength
Capsule, extended releaseOral
LiquidIntramuscular
LiquidIntravenous
SoapTopical
SolutionEpidural
SolutionIntramuscular
SolutionIntravenous
Solution / dropsOral
SuppositoryRectal
SyrupOral
TabletOral
Tablet, extended releaseOral
Prices
Unit descriptionCostUnit
Depodur 15 mg/1.5 ml vial618.18USDml
Roxanol 20 mg/ml Solution 120ml Bottle95.98USDbottle
Morphine Sulfate 20 mg/5ml Solution 500ml Bottle65.05USDbottle
Apokyn 30 mg/3 ml cartridge52.48USDml
Morphine Sulfate 10 mg/5ml Solution 500ml Bottle38.55USDbottle
Kadian er 200 mg capsule35.43USDcapsule
Kadian er 100 mg capsule23.01USDcapsule
Roxanol 20 mg/ml Solution 30ml Bottle22.99USDbottle
Morphine Sulfate 10 mg/5ml Solution 100ml Bottle21.99USDbottle
Oramorph sr 60 mg tablet21.76USDtablet
Ms contin 200 mg tablet21.5USDtablet
Kadian er 80 mg capsule18.66USDcapsule
Roxanol 20 mg/ml Solution 240ml Bottle17.99USDbottle
Avinza 90 mg capsule17.56USDcapsule
Oramorph sr 100 mg tablet17.16USDtablet
Kadian 100 mg 24 Hour Capsule16.93USDcapsule
MS Contin 200 mg 12 Hour tablet16.32USDtablet
Kadian 100 mg capsule sr16.25USDcapsule
Kadian er 60 mg capsule14.31USDcapsule
AVINza 90 mg 24 Hour Capsule13.21USDcapsule
Kadian 80 mg capsule sr12.96USDcapsule
Avinza 120 mg capsule12.07USDcapsule
Kadian er 50 mg capsule11.76USDcapsule
Ms contin 100 mg tablet11.75USDtablet
Avinza 60 mg capsule11.58USDcapsule
AVINza 120 mg 24 Hour Capsule11.33USDcapsule
Avinza 75 mg capsule10.79USDcapsule
Morphine sulfate powder10.61USDg
Avinza 45 mg capsule10.22USDcapsule
Kadian 60 mg 24 Hour Capsule9.06USDcapsule
Morphine Sulfate CR 200 mg 12 Hour tablet8.97USDtablet
MS Contin 100 mg 12 Hour tablet8.89USDtablet
Morphine sulf 30 mg suppository8.44USDsuppository
AVINza 60 mg 24 Hour Capsule8.36USDcapsule
Ms contin 60 mg tablet7.95USDtablet
Infumorph 10 mg/ml ampul p-f7.8USDml
Kadian 50 mg 24 Hour Capsule7.71USDcapsule
Kadian er 30 mg capsule7.13USDcapsule
Oramorph sr 30 mg tablet6.83USDtablet
Morphine sulf 20 mg suppository6.71USDsuppository
Kadian er 10 mg capsule6.35USDcapsule
Morphine sulf 10 mg suppository6.25USDsuppository
Avinza 30 mg capsule6.0USDcapsule
MS Contin 60 mg 12 Hour tablet5.71USDtablet
Kadian er 20 mg capsule5.69USDcapsule
Ms Contin 200 mg Sustained-Release Tablet5.62USDtablet
Kadian 30 mg 24 Hour Capsule4.8USDcapsule
Kadian 20 mg 24 Hour Capsule4.76USDcapsule
AVINza 30 mg 24 Hour Capsule4.47USDcapsule
Morphine sulf 5 mg suppository4.45USDsuppository
Morphine Sulfate CR 100 mg 12 Hour tablet4.33USDtablet
M-Eslon 200 mg Extended-Release Capsule4.3USDcapsule
Oramorph sr 15 mg tablet4.12USDtablet
Ms contin cr 30 mg tablet4.09USDtablet
Kadian 10 mg capsule sr4.05USDcapsule
Morphine Hp 50 50 mg/ml4.01USDml
Kadian 10 mg 24 Hour Capsule4.0USDcapsule
Ms contin 15 mg tablet3.58USDtablet
MS Contin 30 mg 12 Hour tablet3.26USDtablet
Novo-Morphine Sr 200 mg Sustained-Release Tablet3.09USDtablet
Pms-Morphine Sulfate Sr 200 mg Sustained-Release Tablet3.09USDtablet
Ms Contin 100 mg Sustained-Release Tablet3.02USDtablet
Morphine Sulfate CR 60 mg 12 Hour tablet3.0USDtablet
Morphine Hp 25 25 mg/ml2.9USDml
Statex 30 mg Suppository2.55USDsuppository
Kadian 100 mg Sustained-Release Capsule2.35USDcapsule
Statex 20 mg Suppository2.32USDsuppository
Morphine Lp Epidural 1 mg/ml2.24USDml
M-Eslon 100 mg Extended-Release Capsule2.15USDcapsule
MS Contin 15 mg 12 Hour tablet2.13USDtablet
Ms Contin 60 mg Sustained-Release Tablet1.98USDtablet
Statex 10 mg Suppository1.95USDsuppository
Morph sulf 5 mg/0.25 ml vial1.83USDvial
Statex 5 mg Suppository1.75USDsuppository
Novo-Morphine Sr 100 mg Sustained-Release Tablet1.66USDtablet
Pms-Morphine Sulfate Sr 100 mg Sustained-Release Tablet1.66USDtablet
Morphine Sulfate CR 30 mg 12 Hour tablet1.63USDtablet
Morphine 8 mg/ml ampule1.56USDml
Kadian 50 mg Sustained-Release Capsule1.35USDcapsule
Duramorph 0.5 mg/ml ampul1.31USDml
Astramorph-pf 1 mg/ml ampul1.15USDml
Ms Contin 30 mg Sustained-Release Tablet1.13USDtablet
Morphine Lp Epidural 0.5 mg/ml1.12USDml
Morphine Sulfate 15 mg/ml1.03USDml
Morphine Sulfate 10 mg/ml1.02USDml
Novo-Morphine Sr 60 mg Sustained-Release Tablet1.01USDtablet
Pms-Morphine Sulfate Sr 60 mg Sustained-Release Tablet1.01USDtablet
Ratio-Morphine Sulfate Sr 60 mg Sustained-Release Tablet1.01USDtablet
M-Eslon 60 mg Extended-Release Capsule1.0USDcapsule
Statex 50 mg/ml Drops0.99USDml
Morphine Sulfate CR 15 mg 12 Hour tablet0.93USDtablet
Duramorph 1 mg/ml ampul0.91USDml
M.O.S.-Sr 60 mg Sustained-Release Tablet0.89USDtablet
Morphine 50 mg/25 ml-d5w syr0.86USDml
Morphine-ns 10 mg/ml syringe0.86USDml
Morphine-ns 5 mg/ml syringe0.8USDml
Ms Contin 15 mg Sustained-Release Tablet0.75USDtablet
Morphine 5 mg/ml vial0.74USDml
Kadian 20 mg Sustained-Release Capsule0.73USDcapsule
Astramorph-pf 0.5 mg/ml amp0.72USDml
Morphine Sulfate 15 mg tablet0.65USDtablet
Morphine Sulfate 30 mg tablet0.65USDtablet
Morphine 1 mg/ml vial p-f0.6USDml
Morphine-ns 1 mg/ml syringe0.58USDml
Novo-Morphine Sr 30 mg Sustained-Release Tablet0.57USDtablet
Pms-Morphine Sulfate Sr 30 mg Sustained-Release Tablet0.57USDtablet
Ratio-Morphine Sulfate Sr 30 mg Sustained-Release Tablet0.57USDtablet
M-Eslon 30 mg Extended-Release Capsule0.56USDcapsule
Morphine 0.5 mg/ml vial0.55USDml
Morphine sulfate 50 mg/ml vial0.55USDml
Morphine sulfate ir 30 mg tablet0.55USDtablet
Ratio-Morphine 20 mg/ml Syrup0.55USDsyrup
Statex 20 mg/ml Drops0.52USDml
M.O.S.-Sr 30 mg Sustained-Release Tablet0.51USDtablet
Morphine 1 mg/ml syringe0.48USDml
Morphine 10 mg/ml vial0.48USDml
Ms.Ir 30 mg Tablet0.48USDtablet
Morphine sulfate 25 mg/ml vial0.43USDml
Morphine sulf 1 mg/ml vial0.4USDml
M.O.S. Sulfate 50 mg Tablet0.39USDtablet
Statex 50 mg Tablet0.39USDtablet
Kadian 10 mg Sustained-Release Capsule0.38USDcapsule
M-Eslon 15 mg Extended-Release Capsule0.38USDcapsule
Ms.Ir 20 mg Tablet0.38USDtablet
Novo-Morphine Sr 15 mg Sustained-Release Tablet0.37USDtablet
Pms-Morphine Sulfate Sr 15 mg Sustained-Release Tablet0.37USDtablet
Ratio-Morphine Sulfate Sr 15 mg Sustained-Release Tablet0.37USDtablet
M-Eslon 10 mg Extended-Release Capsule0.33USDcapsule
Morphine sulfate ir 15 mg tablet0.32USDtablet
Morphine 15 mg/ml vial0.3USDml
Morphine-ns 25 mg/25 ml syr0.26USDml
M.O.S. Sulfate 25 mg Tablet0.25USDtablet
Statex 25 mg Tablet0.25USDtablet
Ms.Ir 10 mg Tablet0.21USDtablet
Ratio-Morphine 10 mg/ml Syrup0.19USDsyrup
M.O.S. Sulfate 10 mg Tablet0.19USDtablet
Statex 10 mg Tablet0.19USDtablet
Morphine-ns 5 mg/ml0.16USDml
Morphine-ns 55 mg/55 ml syr0.14USDml
Ms.Ir 5 mg Tablet0.14USDtablet
M.O.S. Sulfate 5 mg Tablet0.12USDtablet
Statex 5 mg Tablet0.12USDtablet
Morphine 1 mg/ml-d5w 100 ml0.1USDml
Morphine-ns 150 mg/150 ml0.1USDml
Statex 5 mg/ml Syrup0.08USDml
Morphine 1 mg/ml-d5w 250 ml0.06USDml
Ratio-Morphine 5 mg/ml Syrup0.05USDsyrup
Ratio-Morphine 1 mg/ml Syrup0.02USDsyrup
Statex 1 mg/ml Syrup0.02USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States60663391997-11-252017-11-25
United States53784741993-03-232010-03-23
Canada20652102000-08-292012-04-06
Canada21285911999-03-232014-07-21
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point255 °CPhysProp
water solubility149 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.89AVDEEF,A ET AL. (1996)
logS-3.28ADME Research, USCD
pKa8.21 (at 25 °C)LIDE,DR (1995)
Predicted Properties
PropertyValueSource
Water Solubility10.2ALOGPS
logP0.99ALOGPS
logP0.9ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.26ChemAxon
pKa (Strongest Basic)9.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.93 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.12 m3·mol-1ChemAxon
Polarizability29.95 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Nagaraj R. Ayyangar, Anil R. Choudhary, Uttam R. Kalkote, Vasant K. Sharma, “Process for the preparation of codeine from morphine.” U.S. Patent US4764615, issued May, 1912.

US4764615
General Reference
  1. Kilpatrick GJ, Smith TW: Morphine-6-glucuronide: actions and mechanisms. Med Res Rev. 2005 Sep;25(5):521-44. Pubmed
  2. Loguinov AV, Anderson LM, Crosby GJ, Yukhananov RY: Gene expression following acute morphine administration. Physiol Genomics. 2001 Aug 28;6(3):169-81. Pubmed
External Links
ResourceLink
KEGG DrugD00842
KEGG CompoundC01516
PubChem Compound5288826
PubChem Substance46505161
ChemSpider4450907
ChEBI17303
ChEMBLCHEMBL70
Therapeutic Targets DatabaseDAP000071
PharmGKBPA450550
HETMOI
Drug Product Database2245286
RxListhttp://www.rxlist.com/cgi/generic/ms.htm
Drugs.comhttp://www.drugs.com/morphine.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/msc1277.shtml
WikipediaMorphine
ATC CodesG04BE07N02AA01N02AA04N04BC07R05DA01R05DA05S01XA06D10AX30
AHFS Codes
  • 84:24.12
  • 28:08.08
PDB EntriesNot Available
FDA labelshow(1.2 MB)
MSDSshow(51.7 KB)
Interactions
Drug Interactions
Drug
AlvimopanIncreases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
EltrombopagEltrombopag increases Morphine levels via decreasing metabolism. UDP-glucuronosyltransferase inhibition with unclear significance.
RifampicinRifampin decreases the effect of morphine/codeine
TriprolidineThe CNS depressants, Triprolidine and Morphine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
TrovafloxacinMorphine may reduce serum levels of Trovafloxacin decreasing the efficacy of the antibiotic. IV doses of morphine should be administered at least 2 hours after a dose of Trovafloxacin given in a fasting state or 4 hours after if given in a fed state.
Food Interactions
  • Avoid alcohol.
  • Take with food.
  • To avoid constipation: increase your daily intake of fiber (beans, whole grains, vegetables).

Targets

1. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

References:

  1. Yamada H, Shimoyama N, Sora I, Uhl GR, Fukuda Y, Moriya H, Shimoyama M: Morphine can produce analgesia via spinal kappa opioid receptors in the absence of mu opioid receptors. Brain Res. 2006 Apr 14;1083(1):61-9. Epub 2006 Mar 10. Pubmed
  2. Kasai S, Han W, Ide S, Hata H, Takamatsu Y, Yamamoto H, Uhl GR, Sora I, Ikeda K: Involvement of the 3’ non-coding region of the mu opioid receptor gene in morphine-induced analgesia. Psychiatry Clin Neurosci. 2006 Apr;60 Suppl 1:S11-7. doi:10.1111/j.1440-1819.2006.01523.x-i1
  3. Choi HS, Kim CS, Hwang CK, Song KY, Wang W, Qiu Y, Law PY, Wei LN, Loh HH: The opioid ligand binding of human mu-opioid receptor is modulated by novel splice variants of the receptor. Biochem Biophys Res Commun. 2006 May 19;343(4):1132-40. Epub 2006 Mar 23. Pubmed
  4. Castro RR, Cunha FQ, Silva FS Jr, Rocha FA: A quantitative approach to measure joint pain in experimental osteoarthritis—evidence of a role for nitric oxide. Osteoarthritis Cartilage. 2006 Aug;14(8):769-76. Epub 2006 Mar 31. Pubmed
  5. Johnson EA, Oldfield S, Braksator E, Gonzalez-Cuello A, Couch D, Hall KJ, Mundell SJ, Bailey CP, Kelly E, Henderson G: Agonist-selective mechanisms of mu-opioid receptor desensitization in human embryonic kidney 293 cells. Mol Pharmacol. 2006 Aug;70(2):676-85. Epub 2006 May 8. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  7. Yekkirala AS, Kalyuzhny AE, Portoghese PS: Standard opioid agonists activate heteromeric opioid receptors: evidence for morphine and [d-Ala2-MePhe4-Glyol5] enkephalin as selective μ−δ agonists. ACS Chem. Neurosci. 2010; 1(2):146-154 doi:10.1021/cn9000236

2. Kappa-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Kappa-type opioid receptor P41145 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Leventhal L, Silva RM, Rossi GC, Pasternak GW, Bodnar RJ: Morphine-6beta-glucuronide-induced hyperphagia: characterization of opioid action by selective antagonists and antisense mapping in rats. J Pharmacol Exp Ther. 1998 Nov;287(2):538-44. Pubmed
  4. Kozak CA, Filie J, Adamson MC, Chen Y, Yu L: Murine chromosomal location of the mu and kappa opioid receptor genes. Genomics. 1994 Jun;21(3):659-61. Pubmed
  5. Teodorov E, Modena CC, Sukikara MH, Felicio LF: Preliminary study of the effects of morphine treatment on opioid receptor gene expression in brain structures of the female rat. Neuroscience. 2006 Sep 1;141(3):1225-31. Epub 2006 Jun 6. Pubmed
  6. Yekkirala AS, Kalyuzhny AE, Portoghese PS: Standard opioid agonists activate heteromeric opioid receptors: evidence for morphine and [d-Ala2-MePhe4-Glyol5] enkephalin as selective μ−δ agonists. ACS Chem. Neurosci. 2010; 1(2):146-154 doi:10.1021/cn9000236

3. Delta-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Delta-type opioid receptor P41143 Details

References:

  1. Yamada H, Shimoyama N, Sora I, Uhl GR, Fukuda Y, Moriya H, Shimoyama M: Morphine can produce analgesia via spinal kappa opioid receptors in the absence of mu opioid receptors. Brain Res. 2006 Apr 14;1083(1):61-9. Epub 2006 Mar 10. Pubmed
  2. Dortch-Carnes J, Russell KR: Morphine-induced reduction of intraocular pressure and pupil diameter: role of nitric oxide. Pharmacology. 2006;77(1):17-24. Epub 2006 Mar 13. Pubmed
  3. Koch T, Wu DF, Yang LQ, Brandenburg LO, Hollt V: Role of phospholipase D2 in the agonist-induced and constitutive endocytosis of G-protein coupled receptors. J Neurochem. 2006 Apr;97(2):365-72. Epub 2006 Mar 15. Pubmed
  4. Galeotti N, Stefano GB, Guarna M, Bianchi E, Ghelardini C: Signaling pathway of morphine induced acute thermal hyperalgesia in mice. Pain. 2006 Aug;123(3):294-305. Epub 2006 May 2. Pubmed
  5. Asensio VJ, Miralles A, Garcia-Sevilla JA: Stimulation of mitogen-activated protein kinase kinases (MEK1/2) by mu-, delta- and kappa-opioid receptor agonists in the rat brain: regulation by chronic morphine and opioid withdrawal. Eur J Pharmacol. 2006 Jun 6;539(1-2):49-56. Epub 2006 Apr 6. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  7. Kieffer BL, Gaveriaux-Ruff C: Exploring the opioid system by gene knockout. Prog Neurobiol. 2002 Apr;66(5):285-306. Pubmed
  8. Yekkirala AS, Kalyuzhny AE, Portoghese PS: Standard opioid agonists activate heteromeric opioid receptors: evidence for morphine and [d-Ala2-MePhe4-Glyol5] enkephalin as selective μ−δ agonists. ACS Chem. Neurosci. 2010; 1(2):146-154 doi:10.1021/cn9000236

Enzymes

1. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. 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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. 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. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. 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. Epub 2009 Nov 24. Pubmed

4. UDP-glucuronosyltransferase 2B7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 2B7 P16662 Details

References:

  1. Coffman BL, Rios GR, King CD, Tephly TR: Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos. 1997 Jan;25(1):1-4. Pubmed
  2. Takeda S, Ishii Y, Iwanaga M, Mackenzie PI, Nagata K, Yamazoe Y, Oguri K, Yamada H: Modulation of UDP-glucuronosyltransferase function by cytochrome P450: evidence for the alteration of UGT2B7-catalyzed glucuronidation of morphine by CYP3A4. Mol Pharmacol. 2005 Mar;67(3):665-72. Epub 2004 Dec 20. Pubmed
  3. Yamada H, Ishii K, Ishii Y, Ieiri I, Nishio S, Morioka T, Oguri K: Formation of highly analgesic morphine-6-glucuronide following physiologic concentration of morphine in human brain. J Toxicol Sci. 2003 Dec;28(5):395-401. Pubmed
  4. Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. Epub 2010 Jan 13. Pubmed

5. UDP-glucuronosyltransferase 1-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-1 P22309 Details

References:

  1. Ohno S, Kawana K, Nakajin S: Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties. Drug Metab Dispos. 2008 Apr;36(4):688-94. Epub 2008 Jan 10. Pubmed

6. UDP-glucuronosyltransferase 1-8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-8 Q9HAW9 Details

References:

  1. Ohno S, Kawana K, Nakajin S: Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties. Drug Metab Dispos. 2008 Apr;36(4):688-94. Epub 2008 Jan 10. Pubmed

7. UDP-glucuronosyltransferase 2B15

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 2B15 P54855 Details

References:

  1. Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. Epub 2010 Jan 13. Pubmed

8. UDP-glucuronosyltransferase 2B4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 2B4 P06133 Details

References:

  1. Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. Epub 2010 Jan 13. Pubmed

9. UDP-glucuronosyltransferase 1-3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-3 P35503 Details

References:

  1. Green MD, King CD, Mojarrabi B, Mackenzie PI, Tephly TR: Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos. 1998 Jun;26(6):507-12. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. Pubmed
  2. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09