Identification

Name
Buprenorphine
Accession Number
DB00921  (APRD00670)
Type
Small Molecule
Groups
Approved, Illicit, Investigational, Vet approved
Description

Buprenorphine is a derivative of the opioid alkaloid thebaine that is a more potent (25 - 40 times) and longer lasting analgesic than morphine. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use.

Structure
Thumb
Synonyms
  • (−)-buprenorphine
  • 17-cyclopropylmethyl-4,5α-epoxy-7α-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol
  • 2-(N-cyclopropylmethyl-4,5α-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6α-yl)-3,3-dimethyl-2-butanol
  • 2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-(14R)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-3,3-dimethyl-2-butanol
  • 21-cyclopropyl-7α-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine
  • Buprenophine
  • Buprenorfina
  • Buprenorphinum
Product Ingredients
IngredientUNIICASInChI Key
Buprenorphine hydrochloride56W8MW3EN153152-21-9UAIXRPCCYXNJMQ-RZIPZOSSSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BelbucaFilm75 ug/1BuccalEndo Pharmaceuticals2015-06-012018-10-31Us
BelbucaFilm, soluble900 ug/1BuccalBioDelivery Sciences International Inc2017-08-11Not applicableUs
BelbucaFilm, soluble450 ug/1BuccalBioDelivery Sciences International Inc2017-08-21Not applicableUs
BelbucaFilm, soluble150 ug/1BuccalBioDelivery Sciences International Inc2017-10-01Not applicableUs
BelbucaFilm750 ug/1BuccalEndo Pharmaceuticals2015-06-012018-10-31Us
BelbucaFilm, soluble450 mcgBuccalPurdue Pharma2018-01-17Not applicableCanada
BelbucaFilm300 ug/1BuccalEndo Pharmaceuticals2015-06-012018-10-31Us
BelbucaFilm, soluble75 mcgBuccalPurdue Pharma2018-01-17Not applicableCanada
BelbucaFilm, soluble750 ug/1BuccalBioDelivery Sciences International Inc2017-10-01Not applicableUs
BelbucaFilm, soluble900 mcgBuccalPurdue PharmaNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BuprenorphineTablet8 mg/1SublingualContract Pharmacy Services Pa2015-04-10Not applicableUs
BuprenorphineTablet2 mg/1Sublingualbryant ranch prepack2015-02-19Not applicableUs
BuprenorphineTablet2 mg/1SublingualREMEDYREPACK INC.2018-10-19Not applicableUs
BuprenorphinePatch10 ug/1hTransdermalRhodes Pharmaceuticals L.P.2017-07-03Not applicableUs
BuprenorphineTablet8 mg/1SublingualA-S Medication Solutions2015-04-10Not applicableUs
BuprenorphineTablet8 mg/1SublingualRhodes Pharmaceuticals L.P.2017-10-25Not applicableUs
BuprenorphineTablet2 mg/1SublingualRemedy Repack2017-08-24Not applicableUs
BuprenorphineTablet8 mg/1SublingualTeva Pharmaceuticals USA, Inc.2010-05-25Not applicableUs00093 5379 56 nlmimage10 35421ad0
BuprenorphineTablet8 mg/1SublingualActavis Pharma, Inc.2015-02-19Not applicableUs
BuprenorphineTablet2 mg/1SublingualRemedy Repack2016-10-042018-10-22Us
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Act Buprenorphine/naloxoneBuprenorphine (8 mg) + Naloxone (2 mg)TabletSublingualActavis Pharma Company2017-09-28Not applicableCanada
Act Buprenorphine/naloxoneBuprenorphine (2 mg) + Naloxone (0.5 mg)TabletSublingualActavis Pharma Company2017-09-28Not applicableCanada
BunavailBuprenorphine hydrochloride (4.2 mg/1) + Naloxone hydrochloride dihydrate (0.7 mg/1)FilmBuccalBioDelivery Sciences International, Inc.2014-09-30Not applicableUs
BunavailBuprenorphine hydrochloride (2.1 mg/1) + Naloxone hydrochloride dihydrate (0.3 mg/1)FilmBuccalBioDelivery Sciences International, Inc.2014-09-30Not applicableUs
BunavailBuprenorphine hydrochloride (6.3 mg/1) + Naloxone hydrochloride dihydrate (1 mg/1)FilmBuccalBioDelivery Sciences International, Inc.2014-09-30Not applicableUs
Buprenorphine and NaloxoneBuprenorphine hydrochloride (2 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletSublingualbryant ranch prepack2016-01-07Not applicableUs
Buprenorphine and NaloxoneBuprenorphine hydrochloride (12 mg/1) + Naloxone (3 mg/1)Film, solubleBuccal; SublingualDr. Reddy’s Laboratories Inc.2018-06-14Not applicableUs
Buprenorphine and NaloxoneBuprenorphine hydrochloride (8 mg/1) + Naloxone hydrochloride (2 mg/1)TabletSublingualAidarex Pharmaceuticals LLC2015-12-10Not applicableUs
Buprenorphine and NaloxoneBuprenorphine hydrochloride (8 mg/1) + Naloxone hydrochloride dihydrate (2 mg/1)TabletSublingualActavis Pharma, Inc.2013-03-05Not applicableUs
Buprenorphine and NaloxoneBuprenorphine hydrochloride (8 mg/1) + Naloxone hydrochloride dihydrate (2 mg/1)TabletSublingualSun Pharmaceutical Industries, Inc.2017-07-18Not applicableUs
International/Other Brands
Addnok (Rusan Pharma Ltd.) / Buprel / Buprigesic (Neon Laboratories) / Morgesic (Samarth Pharma) / Norphin (Unichem Laboratories) / Norspan / Probuphine (Titan Pharmaceuticals, Inc.) / Subutex / Temgesic / Tidigesic (Sun Pharmaceuticals)
Categories
UNII
40D3SCR4GZ
CAS number
52485-79-7
Weight
Average: 467.6401
Monoisotopic: 467.303558805
Chemical Formula
C29H41NO4
InChI Key
RMRJXGBAOAMLHD-IHFGGWKQSA-N
InChI
InChI=1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26+,27-,28+,29-/m1/s1
IUPAC Name
(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol
SMILES
CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=C5C(O[C@@H]2[C@@]35CCN1CC1CC1)=C(O)C=C4

Pharmacology

Indication

For the treatment of moderate to severe pain, peri-operative analgesia, and opioid dependence.

Associated Conditions
Pharmacodynamics

Buprenorphine is a synthetic opioid analgesic and thebaine derivative, with a longer duration of action than morphine. Buprenorphine interacts predominately with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, buprenorphine exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Buprenorphine may increase the patient's tolerance for pain and decrease the perception of suffering, 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. Buprenorphine depresses the respiratory centers, depresses the cough reflex, and constricts the pupils. Pharmacological effects peaks at 15 minutes and persists for 6 hours or longer when given intramuscularly. When given intravenously, the time to onset and peak effect are shortened.

Mechanism of action

Buprenorphine's analgesic effect is due to partial agonist activity at mu-opioid receptors. Buprenorphine is also a kappa-opioid receptor antagonist. The partial agonist activity means that opioid receptor antagonists (e.g., an antidote such as naloxone) only partially reverse the effects of buprenorphine. The binding to the mu and kappa receptors results in hyperpolarization and reduced neuronal excitability. Furthermore, buprenorphine slowly dissociates from its receptor. This observation would account for the longer duration of action compared to morphine, the unpredictability of its reversal by opioid antagonists, and its low level of manifest physical dependence. Its receptor fixation half life is 40 minutes which is significantly longer than morphine (milliseconds).

TargetActionsOrganism
AMu-type opioid receptor
partial agonist
Human
AKappa-type opioid receptor
antagonist
Human
UDelta-type opioid receptor
antagonist
Human
UNociceptin receptorNot AvailableHuman
Absorption

31% bioavailability (sublingual). Sublingual absorption is also dependent on pH. The length of time the tablet is under the tongue has little effect on absorption. Although buprenorphine is rapidly absorbed from the oral mucosa, the absorption into the systemic is slower. The time to reach peak plasma concentration (Tmax) varies between individuals (range of 40 minutes to 3.5 hours). How buprenorphine is formulated does not affect this pharmacokinetic parameter. It also undergoes extensive first-pass metabolism and as a consequence, has very low oral bioavailability. Coadministration with naloxone does not effect the pharmacokinetics of buprenorphine.

Volume of distribution

Buprenorphine is very lipophillic and is thus highly distributed. The estimated volume of distribution is 188 - 335 L when given intravenously. It is able to cross into the placenta and breast milk.

Protein binding

96% protein bound to alpha- and beta-globulin.

Metabolism

Hepatic. Buprenorphine undergoes both N-dealkylation to norbuprenorphine and glucuronidation. The N-dealkylation pathway is mediated by cytochrome P-450 3A4 isozyme. Norbuprenorphine, an active metabolite and has one-fifth of the pharmacologic activity of the parent compound, can further undergo glucuronidation.

Route of elimination

Buprenorphine, like morphine and other phenolic opioid analgesics, is metabolized by the liver and its clearance is related to hepatic blood flow. It is primarily eliminated via feces (as free forms of buprenorphine and norbuprenorphine) while 10 - 30% of the dose is excreted in urine (as conjugated forms of buprenorphine and norbuprenorphine).

Half life

IV administration, 0.3 mg = 1.2 - 7.2 hours (mean 2.2 hours); Sublingual administration = 37 hours.

Clearance

Clearance may be higher in children than in adults. Plasma clearance rate, IV administration, anaesthetized patients = 901.2 ± 39.7 mL/min; Plasma clearance rate, IV administration, healthy subjects = 1042 - 1280 mL/min.

Toxicity

Manifestations of acute overdose include pinpoint pupils, sedation, hypotension, respiratory depression and death.

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

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Buprenorphine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Buprenorphine.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Buprenorphine 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 Buprenorphine.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Buprenorphine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Buprenorphine.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Buprenorphine.
Food Interactions
Not Available

References

Synthesis Reference

Kazuhisa Ninomiya, Yasuhiro Fukushima, Mutsuo Okumura, Yuko Hosokawa, "Buprenorphine percutaneous absorption preparation." U.S. Patent US6090405, issued August, 1992.

US6090405
General References
  1. Huang P, Kehner GB, Cowan A, Liu-Chen LY: Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist. J Pharmacol Exp Ther. 2001 May;297(2):688-95. [PubMed:11303059]
  2. Bodkin JA, Zornberg GL, Lukas SE, Cole JO: Buprenorphine treatment of refractory depression. J Clin Psychopharmacol. 1995 Feb;15(1):49-57. [PubMed:7714228]
  3. Elkader A, Sproule B: Buprenorphine: clinical pharmacokinetics in the treatment of opioid dependence. Clin Pharmacokinet. 2005;44(7):661-80. [PubMed:15966752]
External Links
Human Metabolome Database
HMDB0015057
KEGG Drug
D07132
KEGG Compound
C08007
PubChem Compound
644073
PubChem Substance
46505782
ChemSpider
559124
ChEBI
3216
ChEMBL
CHEMBL560511
Therapeutic Targets Database
DAP001353
PharmGKB
PA448685
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Buprenorphine
ATC Codes
N02AE01 — BuprenorphineN07BC01 — BuprenorphineN07BC51 — Buprenorphine, combinations
AHFS Codes
  • 28:08.12 — Opiate Partial Agonists
FDA label
Download (345 KB)
MSDS
Download (196 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentDrug Overdose / Opiate withdrawal symptoms / Opioid-use Disorder1
0RecruitingTreatmentOpioid Use Disorders1
1CompletedNot AvailableHealthy Volunteers3
1CompletedNot AvailableHepatitis C Viral Infection1
1CompletedNot AvailablePostoperative pain1
1CompletedBasic ScienceOpiate Dependence1
1CompletedOtherHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentAddictions / Opioid Dependence / Pain NOS1
1CompletedTreatmentCocaine-Related Disorders1
1CompletedTreatmentCocaine-Related Disorders / Heroin Dependence / Human Immunodeficiency Virus (HIV)1
1CompletedTreatmentDrug withdrawal syndrome neonatal2
1CompletedTreatmentECG Effects1
1CompletedTreatmentHIV Risk Behaviors / Substance-Related Disorders1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHepatitis C Viral Infection1
1CompletedTreatmentHepatitis C Viral Infection / Opioid-Related Disorders1
1CompletedTreatmentHepatitis C Virus (HCV) Infection1
1CompletedTreatmentHeroin Dependence / Opioid-Related Disorders1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Opioid Dependency1
1CompletedTreatmentOpioid Dependence1
1CompletedTreatmentOpioid Use Disorders2
1CompletedTreatmentOpioid-Related Disorders5
1CompletedTreatmentOpioid-Related Disorders / Pain, Chronic1
1CompletedTreatmentOpioid-Related Disorders / Substance-Related Disorders2
1CompletedTreatmentOpioid-use Disorder1
1CompletedTreatmentOsteoarthritis Disorders1
1CompletedTreatmentPain NOS2
1CompletedTreatmentSubstance-Related Disorders1
1Not Yet RecruitingTreatmentPostoperative pain1
1RecruitingTreatmentHeroin Dependence / Opioid Use Disorders1
1TerminatedTreatmentHealthy Volunteers2
1Unknown StatusTreatmentDepression1
1Unknown StatusTreatmentHealthy Volunteers1
1Unknown StatusTreatmentHeroin Dependence / Opioid-Related Disorders / Substance-Related Disorders1
1, 2Active Not RecruitingTreatmentOpioid Abuse / Opioid Dependence1
1, 2CompletedNot AvailableMajor Depressive Disorder (MDD)1
1, 2CompletedTreatmentDepression / Major Depressive Disorder (MDD)2
1, 2CompletedTreatmentOpiate Addiction1
1, 2CompletedTreatmentOpioid Addiction / Opioid Dependence / Opioid Related Disorders1
1, 2CompletedTreatmentOpioid-Related Disorders1
1, 2Not Yet RecruitingTreatmentDrug withdrawal syndrome neonatal / Neonatal Opiate Withdrawal Syndrome1
1, 2RecruitingTreatmentDrug; Withdrawal Symptoms, Neonatal / Fetus and Newborn Affected by Other Maternal Medication / Withdrawal1
1, 2RecruitingTreatmentOpioid Dependence1
1, 2TerminatedTreatmentChemotherapy Induced Mucositis / Orofacial Pain1
1, 2Unknown StatusTreatmentOpiate Dependence / Pain, Chronic1
2Active Not RecruitingTreatmentOpioid Use Disorders / Pain, Chronic1
2CompletedSupportive CarePain NOS1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentCocaine-Related Disorders / Heroin Dependence2
2CompletedTreatmentCocaine-Related Disorders / Opioid-Related Disorders1
2CompletedTreatmentDental Pain1
2CompletedTreatmentDepression1
2CompletedTreatmentDepression / Major Depressive Disorder (MDD)1
2CompletedTreatmentDrug withdrawal syndrome neonatal / Neonatal Withdrawal Syndrome1
2CompletedTreatmentHeroin Dependence / Opioid-Related Disorders / Substance-Related Disorders1
2CompletedTreatmentOpiate Dependence2
2CompletedTreatmentOpiate withdrawal symptoms / Opioid Dependence / Opioid Detoxification1
2CompletedTreatmentOpioid Dependence1
2CompletedTreatmentOpioid Dependency1
2CompletedTreatmentOpioid Related Disorders2
2CompletedTreatmentOpioid Use Disorders1
2CompletedTreatmentOpioid-Related Disorders29
2CompletedTreatmentOpioid-Related Disorders / Substance-Related Disorders5
2Enrolling by InvitationTreatmentSickle Cell Disorders1
2Not Yet RecruitingTreatmentOpiate Addiction / Syringe-exchange Programs1
2Not Yet RecruitingTreatmentOpioids Use1
2RecruitingBasic ScienceMaternal Opioid Use Disorder / Opioid Exposed Infant1
2RecruitingTreatmentHigh Dosage Buprenorphine1
2RecruitingTreatmentOpiate Use Disorder / Post Traumatic Stress Disorder (PTSD)1
2RecruitingTreatmentPain NOS1
2TerminatedTreatmentDental Pain1
2TerminatedTreatmentOpioid-Related Disorders1
2TerminatedTreatmentPostoperative pain1
2Unknown StatusTreatmentHeroin Dependence / Opioid-Related Disorders / Substance Abuse, Intravenous1
2Unknown StatusTreatmentOpioid-Dependence Among Adolescents1
2Unknown StatusTreatmentOpioid-Related Disorders1
2Unknown StatusTreatmentPain, Chronic1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Opiate Dependence1
2, 3CompletedBasic ScienceDrug withdrawal syndrome neonatal1
2, 3CompletedTreatmentDependence, Cocaine1
2, 3CompletedTreatmentHeroin Dependence / Opioid-Related Disorders1
2, 3CompletedTreatmentOpioid Dependence1
2, 3RecruitingTreatmentAnalgesics, Opioid / Buprenorphine / Rotator Cuff Injury / Rotator Cuff Syndrome1
2, 3RecruitingTreatmentOpioid-use Disorder1
2, 3RecruitingTreatmentSubstance, Addiction1
2, 3Unknown StatusTreatmentOpioid Dependence1
3Active Not RecruitingTreatmentBack Pain Lower Back Chronic / Pain, Chronic1
3CompletedNot AvailablePain NOS1
3CompletedBasic ScienceHeroin Dependence1
3CompletedBasic ScienceOpioid-Related Disorders1
3CompletedHealth Services ResearchHeroin Addiction1
3CompletedTreatmentBack Pain1
3CompletedTreatmentBack Pain Lower Back3
3CompletedTreatmentBack Pain Lower Back / Pain NOS1
3CompletedTreatmentChronic Non-Malignant Pain1
3CompletedTreatmentChronic Nonmalignant Pain1
3CompletedTreatmentCocaine-Related Disorders / Opioid-Related Disorders / Substance-Related Disorders2
3CompletedTreatmentDepression / Depressive Disorders / Major Depressive Disorder (MDD)1
3CompletedTreatmentDrug withdrawal syndrome neonatal1
3CompletedTreatmentHeroin Dependence1
3CompletedTreatmentHeroin Dependence / Morphine Dependence / Substance Withdrawal Syndrome2
3CompletedTreatmentHeroin Dependence / Substance-Related Disorders1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentKnee Osteoarthritis (Knee OA) / Pain, Chronic1
3CompletedTreatmentOpiate Dependence / Opioid-Related Disorders1
3CompletedTreatmentOpioid Dependence3
3CompletedTreatmentOpioid Dependence, on Agonist Therapy1
3CompletedTreatmentOpioid Dependence / Opioid Related Disorders1
3CompletedTreatmentOpioid Dependence / Opioid Related Disorders / Pregnancy1
3CompletedTreatmentOpioid Dependency2
3CompletedTreatmentOpioid Use Disorders1
3CompletedTreatmentOpioid Use Disorders / Opioid-Related Disorders1
3CompletedTreatmentOpioid-Related Disorders4
3CompletedTreatmentOsteoarthritis (OA)3
3CompletedTreatmentPain NOS2
3Enrolling by InvitationTreatmentOpioid Dependence1
3Not Yet RecruitingTreatmentHeroin Dependence1
3Not Yet RecruitingTreatmentMajor Depressive Episode / Suicidal Thoughts1
3Not Yet RecruitingTreatmentOpiate withdrawal symptoms / Opioid-Related Disorders1
3Not Yet RecruitingTreatmentOpioids Use1
3RecruitingOtherOpioid Addiction1
3RecruitingTreatmentOpioid-Related Disorders1
3RecruitingTreatmentOpioid-use Disorder1
3RecruitingTreatmentPain NOS1
3TerminatedPreventionHuman Immunodeficiency Virus (HIV) Infections / Opioid-Related Disorders1
3TerminatedTreatmentBack Pain Lower Back Chronic2
3TerminatedTreatmentOpioid Dependence1
3TerminatedTreatmentOpioid Dependency1
3TerminatedTreatmentOsteoarthritis (OA)4
3Unknown StatusTreatmentDepression / Suicidal Thoughts / Suicide, Attempted1
3WithdrawnNot AvailableOpioid Dependence1
3WithdrawnTreatmentOpioid Dependence1
3WithdrawnTreatmentOther Acute Postoperative Pain / Prolonged Endotracheal Intubation1
4Active Not RecruitingTreatmentSubstance, Addiction1
4CompletedBasic ScienceBasic Science1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedSupportive CareOsteoarthritis (OA)1
4CompletedSupportive CareSpinal Disorders1
4CompletedTreatmentAcute Pain Management / Renal Colic1
4CompletedTreatmentBack Pain Lower Back1
4CompletedTreatmentArthralgia/joint pain / Back Pain Lower Back / Muscle pains / Osteoarthritis (OA) / Rheumatoid Arthritis2
4CompletedTreatmentChronic Hepatitis C Infection With Hepatic Coma / Hepatic Failure / Hepatic Impairment1
4CompletedTreatmentHeroin Dependence / Opioid Dependence / Substance-Related Disorders1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections / Opioid-Related Disorders1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Opioid Dependence1
4CompletedTreatmentLocal Anesthesia1
4CompletedTreatmentMalignancies / Pain, Cancer1
4CompletedTreatmentOpiate Addiction1
4CompletedTreatmentOpiate Dependence2
4CompletedTreatmentOpiate Dependence / Opiate-Related Disorders / Substance Abuse1
4CompletedTreatmentOpiate Dependence / Substance Dependence / Substance, Addiction1
4CompletedTreatmentOpiate Dependence / Substance Withdrawal Syndrome / Substance, Addiction1
4CompletedTreatmentOpiate Dependence / Substance, Addiction1
4CompletedTreatmentOpiate withdrawal symptoms / Opioid-use Disorder1
4CompletedTreatmentOpiate-Related Disorders1
4CompletedTreatmentOpioid Dependence, on Agonist Therapy1
4CompletedTreatmentOpioid Dependency1
4CompletedTreatmentOpioid Use Disorders1
4CompletedTreatmentOsteoarthritis (OA)1
4CompletedTreatmentOsteoarthritis (OA) / Pain NOS2
4CompletedTreatmentOsteoarthritis Pain of the Hip and or Knee1
4CompletedTreatmentPain NOS1
4CompletedTreatmentPain, Acute1
4CompletedTreatmentPostoperative pain1
4CompletedTreatmentPostoperative pain / Spinal Stenosis1
4Not Yet RecruitingTreatmentGeneral Surgery / Opioid-use Disorder / Pain, Acute1
4Not Yet RecruitingTreatmentOpioid Dependence1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Substance Related Disorders1
4RecruitingTreatmentOpioid Dependence1
4RecruitingTreatmentOpioid Use Disorders1
4RecruitingTreatmentOpioid-use Disorder1
4SuspendedTreatmentPain, Chronic1
4TerminatedBasic ScienceHealthy Volunteers1
4TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection1
4TerminatedTreatmentOpiate Addiction / Refractory Pains1
4TerminatedTreatmentPain NOS1
4Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Opioid-Related Disorders1
4Unknown StatusTreatmentDementias / Depression / Pain NOS1
4Unknown StatusTreatmentHeroin Addiction1
4Unknown StatusTreatmentOpioid Dependence1
4WithdrawnTreatmentOpiate Addiction1
4WithdrawnTreatmentRestless Legs Syndrome (RLS)1
Not AvailableActive Not RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Opiate Addiction / Substance, Addiction1
Not AvailableCompletedNot AvailableAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Opiate Dependence / Post Traumatic Stress Disorder (PTSD)1
Not AvailableCompletedNot AvailableBreakthrough Cancer Pain / Pain, Cancer / Pain, Neuropathic / Tumors1
Not AvailableCompletedNot AvailableBuprenorphine / Naloxone / Opiate Dependence / Opiate-Related Disorders / Substance Abuse1
Not AvailableCompletedNot AvailableChronic Hepatitis C Virus (HCV) Infection / Depression / Human Immunodeficiency Virus (HIV) Infections / Opioid-Related Disorders1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedNot AvailableHeroin Dependence / Opioid-Related Disorders / Substance Abuse, Intravenous1
Not AvailableCompletedNot AvailableOpiate Dependence / Opioid-Related Disorders / Substance Abuse2
Not AvailableCompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedBasic SciencePain NOS1
Not AvailableCompletedOtherHealthy Volunteers1
Not AvailableCompletedTreatmentHepatitis C Viral Infection / Heroin Dependence1
Not AvailableCompletedTreatmentOpiate Addiction1
Not AvailableCompletedTreatmentOpioid-Related Disorders4
Not AvailableCompletedTreatmentPain NOS1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingBasic ScienceDepression1
Not AvailableRecruitingOtherHealthy Volunteers1
Not AvailableRecruitingOtherOpioid-Related Disorders / Pregnancy1
Not AvailableRecruitingTreatmentOpioid-use Disorder1
Not AvailableTerminatedNot AvailableBuprenorphine / Pain NOS1
Not AvailableTerminatedTreatmentBlock Additive / Regional Block for Pain Control / Supraclavicular Block / Ultrasound Guided Block1
Not AvailableTerminatedTreatmentOpioid Use Disorders1
Not AvailableTerminatedTreatmentOpioid-Related Disorders2
Not AvailableUnknown StatusNot AvailableAnalgesic Response1
Not AvailableUnknown StatusNot AvailableOpiate Dependent / Previous Illicit Drug Use1

Pharmacoeconomics

Manufacturers
  • Purdue pharma lp
  • Reckitt benckiser pharmaceuticals inc
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Pharmaforce inc
  • Barr laboratories inc
  • Roxane laboratories inc
Packagers
  • A-S Medication Solutions LLC
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bryant Ranch Prepack
  • Hospira Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Pharmaforce Inc.
  • Prepak Systems Inc.
  • Purdue Pharma LP
  • Rebel Distributors Corp.
  • Reckitt Benckiser Inc.
  • Remedy Repack
  • Roxane Labs
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
FilmBuccal150 ug/1
FilmBuccal300 ug/1
FilmBuccal450 ug/1
FilmBuccal600 ug/1
FilmBuccal75 ug/1
FilmBuccal750 ug/1
FilmBuccal900 ug/1
Film, solubleBuccal150 ug/1
Film, solubleBuccal150 mcg
Film, solubleBuccal300 ug/1
Film, solubleBuccal300 mcg
Film, solubleBuccal450 mcg
Film, solubleBuccal450 ug/1
Film, solubleBuccal600 mcg
Film, solubleBuccal600 ug/1
Film, solubleBuccal75 ug/1
Film, solubleBuccal75 mcg
Film, solubleBuccal750 mcg
Film, solubleBuccal750 ug/1
Film, solubleBuccal900 mcg
Film, solubleBuccal900 ug/1
FilmBuccal
PatchTransdermal10 ug/1h
PatchTransdermal15 ug/1h
PatchTransdermal20 ug/1h
PatchTransdermal5 ug/1h
PatchTransdermal7.5 ug/1h
Patch, extended releaseTransdermal15 ug/1h
Patch, extended releaseTransdermal5 ug/1h
FilmBuccal; Sublingual
Film, solubleBuccal; Sublingual
InjectionIntramuscular; Intravenous0.3 mg/1mL
InjectionIntramuscular; Intravenous0.324 mg/1mL
Injection, solutionIntramuscular; Intravenous0.3 mg/1mL
Injection, solutionIntramuscular; Intravenous0.324 mg/1mL
TabletOral2 mg/1
TabletOral8 mg/1
TabletSublingual2 mg/1
TabletSublingual8 mg/1
Patch, extended releaseTransdermal10 ug/1h
Patch, extended releaseTransdermal2.5 ug/1h
Patch, extended releaseTransdermal20 ug/1h
Patch, extended releaseTransdermal7.5 ug/1h
PatchTransdermal10 mcg
PatchTransdermal15 mcg
PatchTransdermal20 mcg
PatchTransdermal5 mcg
ImplantSubcutaneous80 mg/1
ImplantSubcutaneous80 mg
SolutionSubcutaneous100 mg/1
SolutionSubcutaneous300 mg/1
Film, solubleSublingual
TabletOral
TabletSublingual
Tablet, orally disintegratingSublingual
Prices
Unit descriptionCostUnit
Buprenex 0.3 mg/ml Solution (1 Box Contains Five 1ml Box)46.39USD box
Subutex 8 mg Sublingual Tabs10.2USD tab
Subutex 8 mg tablet sl9.4USD tablet
Buprenorphine 8 mg tablet sl7.74USD tablet
Buprenex 0.3 mg/ml ampul6.96USD ml
Subutex 2 mg Sublingual Tabs5.59USD tab
Subutex 2 mg tablet sl5.0USD tablet
Buprenorphine 2 mg tablet sl4.14USD tablet
Buprenorphine 0.3 mg/ml vial2.96USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5968547No1999-10-192017-09-29Us
US5240711No1993-08-312010-11-28Us
CA2276170No2007-12-042018-02-24Canada
CA2030178No1995-08-152010-11-16Canada
US6344211No2002-02-052015-12-18Us
USRE41489No2010-08-102017-09-29Us
USRE41408No2010-06-292017-09-29Us
USRE41571No2010-08-242017-09-29Us
US6264980No2001-07-242015-12-18Us
US7579019No2009-08-252020-01-22Us
US6159498No2000-12-122016-10-18Us
US8475832No2013-07-022030-03-26Us
US8603514No2013-12-102024-04-03Us
US8017150No2011-09-132023-02-13Us
US8147866No2012-04-032027-07-23Us
US8703177No2014-04-222032-08-20Us
US8470361No2013-06-252030-05-22Us
US8454996No2013-06-042019-09-24Us
US8658198No2014-02-252027-12-03Us
US8940330No2015-01-272032-09-18Us
US9259421No2016-02-162032-09-18Us
US9642850No2017-05-092017-09-29Us
US9522188No2016-12-202035-04-24Us
US9655843No2017-05-232027-07-23Us
US9439900No2016-09-132032-09-18Us
US7736665No2010-06-152024-04-25Us
US9687454No2017-06-272029-08-07Us
US9827241No2017-11-282031-06-06Us
US9498432No2016-11-222031-06-06Us
US9782402No2017-10-102031-06-06Us
US9272044No2016-03-012031-06-06Us
US8975270No2015-03-102031-09-05Us
US8921387No2014-12-302032-01-06Us
US9855221No2018-01-022022-02-14Us
US9901539No2018-02-272032-12-21Us
US9931305No2018-04-032022-02-14Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP4.98AVDEEF,A ET AL. (1996)
pKa8.31 (at 25 °C)AVDEEF,A ET AL. (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.0168 mg/mLALOGPS
logP4.53ALOGPS
logP3.55ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.5ChemAxon
pKa (Strongest Basic)12.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.16 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity131.76 m3·mol-1ChemAxon
Polarizability53.11 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9055
Blood Brain Barrier+0.9401
Caco-2 permeable+0.6893
P-glycoprotein substrateSubstrate0.9126
P-glycoprotein inhibitor IInhibitor0.5192
P-glycoprotein inhibitor IINon-inhibitor0.6992
Renal organic cation transporterInhibitor0.5797
CYP450 2C9 substrateNon-substrate0.8366
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.8142
CYP450 1A2 substrateNon-inhibitor0.9153
CYP450 2C9 inhibitorNon-inhibitor0.8692
CYP450 2D6 inhibitorNon-inhibitor0.6721
CYP450 2C19 inhibitorNon-inhibitor0.7801
CYP450 3A4 inhibitorNon-inhibitor0.8322
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9212
Ames testNon AMES toxic0.7448
CarcinogenicityNon-carcinogens0.9391
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.1511 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8366
hERG inhibition (predictor II)Non-inhibitor0.586
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenanthrenes and derivatives
Sub Class
Not Available
Direct Parent
Phenanthrenes and derivatives
Alternative Parents
Tetralins / Azaspirodecane derivatives / Coumarans / Aralkylamines / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Tertiary alcohols / Trialkylamines / Oxacyclic compounds
show 4 more
Substituents
Phenanthrene / Azaspirodecane / Tetralin / Coumaran / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Piperidine / Tertiary alcohol / Tertiary amine
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
morphinane alkaloid (CHEBI:3216)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Partial 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. Kishioka S, Paronis CA, Lewis JW, Woods JH: Buprenorphine and methoclocinnamox: agonist and antagonist effects on respiratory function in rhesus monkeys. Eur J Pharmacol. 2000 Mar 17;391(3):289-97. [PubMed:10729371]
  2. Zubieta J, Greenwald MK, Lombardi U, Woods JH, Kilbourn MR, Jewett DM, Koeppe RA, Schuster CR, Johanson CE: Buprenorphine-induced changes in mu-opioid receptor availability in male heroin-dependent volunteers: a preliminary study. Neuropsychopharmacology. 2000 Sep;23(3):326-34. [PubMed:10942856]
  3. Sanchez-Blazquez P, Gomez-Serranillos P, Garzon J: Agonists determine the pattern of G-protein activation in mu-opioid receptor-mediated supraspinal analgesia. Brain Res Bull. 2001 Jan 15;54(2):229-35. [PubMed:11275413]
  4. Mizoguchi H, Wu HE, Narita M, Hall FS, Sora I, Uhl GR, Nagase H, Tseng LF: Antagonistic property of buprenorphine for putative epsilon-opioid receptor-mediated G-protein activation by beta-endorphin in pons/medulla of the mu-opioid receptor knockout mouse. Neuroscience. 2002;115(3):715-21. [PubMed:12435410]
  5. Ide S, Minami M, Satoh M, Uhl GR, Sora I, Ikeda K: Buprenorphine antinociception is abolished, but naloxone-sensitive reward is retained, in mu-opioid receptor knockout mice. Neuropsychopharmacology. 2004 Sep;29(9):1656-63. [PubMed:15100703]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Boothby LA, Doering PL: Buprenorphine for the treatment of opioid dependence. Am J Health Syst Pharm. 2007 Feb 1;64(3):266-72. [PubMed:17244875]
  2. Robinson SE: Buprenorphine-containing treatments: place in the management of opioid addiction. CNS Drugs. 2006;20(9):697-712. [PubMed:16953647]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
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. Induru RR, Davis MP: Buprenorphine for neuropathic pain--targeting hyperalgesia. Am J Hosp Palliat Care. 2009 Dec-2010 Jan;26(6):470-3. doi: 10.1177/1049909109341868. Epub 2009 Aug 7. [PubMed:19666890]
  2. Lester PA, Traynor JR: Comparison of the in vitro efficacy of mu, delta, kappa and ORL1 receptor agonists and non-selective opioid agonists in dog brain membranes. Brain Res. 2006 Feb 16;1073-1074:290-6. Epub 2006 Jan 27. [PubMed:16443205]
  3. Megarbane B, Marie N, Pirnay S, Borron SW, Gueye PN, Risede P, Monier C, Noble F, Baud FJ: Buprenorphine is protective against the depressive effects of norbuprenorphine on ventilation. Toxicol Appl Pharmacol. 2006 May 1;212(3):256-67. Epub 2005 Sep 16. [PubMed:16169027]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nociceptin receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for the endogenous neuropeptide nociceptin. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-b...
Gene Name
OPRL1
Uniprot ID
P41146
Uniprot Name
Nociceptin receptor
Molecular Weight
40692.775 Da
References
  1. Bloms-Funke P, Gillen C, Schuettler AJ, Wnendt S: Agonistic effects of the opioid buprenorphine on the nociceptin/OFQ receptor. Peptides. 2000 Jul;21(7):1141-6. [PubMed:10998549]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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]
  3. Kobayashi K, Yamamoto T, Chiba K, Tani M, Shimada N, Ishizaki T, Kuroiwa Y: Human buprenorphine N-dealkylation is catalyzed by cytochrome P450 3A4. Drug Metab Dispos. 1998 Aug;26(8):818-21. [PubMed:9698298]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
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
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Picard N, Cresteil T, Djebli N, Marquet P: In vitro metabolism study of buprenorphine: evidence for new metabolic pathways. Drug Metab Dispos. 2005 May;33(5):689-95. doi: 10.1124/dmd.105.003681. Epub 2005 Mar 2. [PubMed:15743975]
Kind
Protein
Organism
Human
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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
Oxygen binding
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
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. 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]
  2. Umeda S, Harakawa N, Yamamoto M, Ueno K: Effect of nonspecific binding to microsomes and metabolic elimination of buprenorphine on the inhibition of cytochrome P4502D6. Biol Pharm Bull. 2005 Feb;28(2):212-6. [PubMed:15684471]
  3. Zhang W, Ramamoorthy Y, Tyndale RF, Sellers EM: Interaction of buprenorphine and its metabolite norbuprenorphine with cytochromes p450 in vitro. Drug Metab Dispos. 2003 Jun;31(6):768-72. [PubMed:12756210]
Kind
Protein
Organism
Human
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
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Picard N, Cresteil T, Djebli N, Marquet P: In vitro metabolism study of buprenorphine: evidence for new metabolic pathways. Drug Metab Dispos. 2005 May;33(5):689-95. doi: 10.1124/dmd.105.003681. Epub 2005 Mar 2. [PubMed:15743975]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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. 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]
  2. Inhibition of Human Drug Metabolizing Cytochrome P450 by Buprenorphine [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Zhang W, Ramamoorthy Y, Tyndale RF, Sellers EM: Interaction of buprenorphine and its metabolite norbuprenorphine with cytochromes p450 in vitro. Drug Metab Dispos. 2003 Jun;31(6):768-72. [PubMed:12756210]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Dancygier H. (2010). Clinical Hepatology. Springer-Verlag. [ISBN:978-3-642-04509-7]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Tournier N, Chevillard L, Megarbane B, Pirnay S, Scherrmann JM, Decleves X: Interaction of drugs of abuse and maintenance treatments with human P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2). Int J Neuropsychopharmacol. 2010 Aug;13(7):905-15. doi: 10.1017/S1461145709990848. Epub 2009 Nov 4. [PubMed:19887017]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Tournier N, Chevillard L, Megarbane B, Pirnay S, Scherrmann JM, Decleves X: Interaction of drugs of abuse and maintenance treatments with human P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2). Int J Neuropsychopharmacol. 2010 Aug;13(7):905-15. doi: 10.1017/S1461145709990848. Epub 2009 Nov 4. [PubMed:19887017]

Drug created on June 13, 2005 07:24 / Updated on November 20, 2018 00:48