Identification

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

Buprenorphine is a weak partial mu-opioid receptor agonist and a weak kappa-opioid receptor antagonist used for the treatment of severe pain.12,15 It is also commonly used as an alternative to methadone for the treatment of severe opioid addiction.19,20 Buprenorphine is commercially available as the brand name product Suboxone which is formulated in a 4:1 fixed-dose combination product along with naloxone, a non-selective competitive opioid receptor antagonist. Combination with naloxone is intended to reduce the abuse potential of Suboxone, as naloxone is poorly absorbed by the oral route (and has no effect when taken orally), but would reverse the opioid agonist effects of buprenorphine if injected intravenously.14,19,20 Buprenorphine has poor gastrointestinal absorption and is therefore formulated as a sublingual tablet.

Buprenorphine has a number of unique pharmacokinetic and pharmacodynamic properties that make it a preferred agent for the treatment of conditions requiring high doses of strong opioids.13 For example, buprenorphine dissociates from opioid receptors very slowly, resulting in a long duration of action and relief from pain or withdrawal symptoms for upwards of 24-36 hours. Use of once-daily buprenorphine may benefit individuals who have developed tolerance to other potent opioids and who require larger and more frequent doses. Buprenorphine may also be a preferred agent over methadone (which is also commonly used to treat severe pain and opioid use disorder), as it has less effect on Qtc interval prolongation,9,10 fewer drug interactions, reduced risk of sexual side effects,17 and an improved safety profile with a lower risk of overdose and respiratory depression.6,7,8

Buprenorphine acts as a partial mu-opioid receptor agonist with a high affinity for the receptor, but lower intrinsic activity compared to other full mu-opioid agonists such as heroin, oxycodone, or methadone.15 This means that buprenorphine preferentially binds the opioid receptor and displaces lower affinity opioids without activating the receptor to a comparable degree. Clinically, this results in a slow onset of action and a clinical phenomenon known as the "ceiling effect" where once a certain dose is reached, buprenorphine's effects plateau. This effect can be beneficial, however, as dose-related side effects such as respiratory depression, sedation, and intoxication also plateau at around 32mg, resulting in a lower risk of overdose compared to methadone and other full agonist opioids.4,5 It also means that opioid-dependent patients do not experience sedation or euphoria at the same rate that they might experience with more potent opioids, improving quality of life for patients with severe pain and reducing the reinforcing effects of opioids which can lead to drug-seeking behaviours.11

Treatment of opioid addiction with buprenorphine, methadone, or slow-release oral morphine (SROM) is termed Opioid Agonist Treatment (OAT) or Opioid Substitution Therapy (OST). The intention of substitution of illicit opioids with the long-acting opioids used in OAT is to prevent withdrawal symptomns for 24-36 hours following dosing to ultimately reduce cravings and drug-seeking behaviours. Use of OAT is also intended to improved social stabilization including a reduction in crime rates, marginalization, incarceration, and use of illicit substances such as heroin or fentanyl. Illegally purchased opioids can often be injected and may be laced with other substances that increase the risk of harm or overdose. Provision of OAT is often combined with education about harm reduction including use of clean needles and injection supplies in an effort to reduce the risks associated with injection drug use which includes contraction of HIV and Hepatitis C and other complications including skin infections, abscesses, or endocarditis.16

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
  • Buprenorphine
  • Buprenorphinum
Product Ingredients
IngredientUNIICASInChI Key
Buprenorphine hydrochloride56W8MW3EN153152-21-9UAIXRPCCYXNJMQ-RZIPZOSSSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BelbucaFilm, soluble750 ug/1BuccalBioDelivery Sciences International Inc2017-10-01Not applicableUs
BelbucaFilm, soluble75 ug/1BuccalBioDelivery Sciences International Inc2017-09-01Not applicableUs
BelbucaFilm, soluble900 mcgBuccalPurdue PharmaNot applicableNot applicableCanada
BelbucaFilm, soluble75 mcgBuccalPurdue Pharma2018-01-172019-05-31Canada
BelbucaFilm450 ug/1BuccalEndo Pharmaceuticals2015-06-012018-10-31Us
BelbucaFilm, soluble600 ug/1BuccalBioDelivery Sciences International Inc2017-08-24Not applicableUs
BelbucaFilm, soluble750 mcgBuccalPurdue PharmaNot applicableNot applicableCanada
BelbucaFilm300 ug/1BuccalEndo Pharmaceuticals2015-06-012018-10-31Us
BelbucaFilm, soluble450 ug/1BuccalBioDelivery Sciences International Inc2017-08-21Not applicableUs
BelbucaFilm, soluble450 mcgBuccalPurdue Pharma2018-01-172019-05-31Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BuprenorphineTablet8 mg/1SublingualContract Pharmacy Services Pa2015-04-10Not applicableUs
BuprenorphinePatch, extended release5 ug/1hTransdermalTeva Pharmaceuticals USA, Inc.2017-05-302019-03-31Us
BuprenorphineTablet2 mg/1SublingualREMEDYREPACK INC.2017-08-24Not applicableUs
BuprenorphinePatch, extended release5 ug/1hTransdermalTeva Pharmaceuticals USA, Inc.2018-11-26Not applicableUs
BuprenorphineTablet2 mg/1SublingualContract Pharmacy Services Pa2010-05-25Not applicableUs
BuprenorphineTablet2 mg/1SublingualTeva Pharmaceuticals USA, Inc.2010-05-25Not applicableUs0093 537820180907 15195 hb0lc9
BuprenorphineTablet8 mg/1SublingualRhodes Pharmaceuticals L.P.2017-10-25Not applicableUs
BuprenorphineTablet2 mg/1Sublingualbryant ranch prepack2015-02-19Not applicableUs
BuprenorphinePatch10 ug/1hTransdermalRhodes Pharmaceuticals L.P.2017-07-03Not applicableUs
BuprenorphineTablet2 mg/1SublingualContract Pharmacy Services Pa2015-04-10Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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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 (6.3 mg/1) + Naloxone hydrochloride dihydrate (1 mg/1)FilmBuccalBioDelivery Sciences International, Inc.2014-09-30Not applicableUs
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
Buprenorphine and NaloxoneBuprenorphine hydrochloride (4 mg/1) + Naloxone hydrochloride (1 mg/1)Film, solubleBuccal; SublingualIndivior Inc.2019-02-19Not applicableUs
Buprenorphine and NaloxoneBuprenorphine hydrochloride (2 mg/1) + Naloxone hydrochloride dihydrate (0.5 mg/1)TabletSublingualActavis Pharma, Inc.2015-10-01Not applicableUs
Buprenorphine and NaloxoneBuprenorphine hydrochloride (8 mg/1) + Naloxone hydrochloride dihydrate (2 mg/1)FilmBuccal; SublingualMylan Pharmaceuticals Inc.2019-02-20Not applicableUs
Buprenorphine and NaloxoneBuprenorphine hydrochloride (8 mg/1) + Naloxone (2 mg/1)Film, solubleBuccal; SublingualDr. Reddy’s Laboratories Inc.2018-06-14Not applicableUs
Buprenorphine and NaloxoneBuprenorphine (2 mg/1) + Naloxone (0.5 mg/1)TabletSublingualREMEDYREPACK INC.2019-09-26Not applicableUs
International/Other Brands
Addnok (Rusan Pharma Ltd.) / Buprel / Buprigesic (Neon Laboratories) / Morgesic (Samarth Pharma) / Norphin (Unichem Laboratories) / Norspan / 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

Buprenorphine is indicated for the management of pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate. Buprenorphine is also used in combination with naloxone in a fixed-dose combination product for the treatment of moderate to severe opioid use disorder.19,20

Associated Conditions
Pharmacodynamics

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. 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.

Dependence

Buprenorphine is a partial agonist at the mu-opioid receptor and chronic administration produces physical dependence of the opioid type, characterized by withdrawal signs and symptoms upon abrupt discontinuation or rapid taper. The withdrawal syndrome is typically milder than seen with full agonists and may be delayed in onset. Buprenorphine can be abused in a manner similar to other opioids. This should be considered when prescribing or dispensing buprenorphine in situations when the clinician is concerned about an increased risk of misuse, abuse, or diversion.20

Withdrawal

Abrupt discontinuation of treatment is not recommended as it may result in an opioid withdrawal syndrome that may be delayed in onset. Signs and symptoms may include body aches, diarrhea, gooseflesh, loss of appetite, nausea, nervousness or restlessness, anxiety, runny nose, sneezing, tremors or shivering, stomach cramps, tachycardia, trouble with sleeping, unusual increase in sweating, palpitations, unexplained fever, weakness and yawning.20

Risk of Respiratory and Central Nervous System (CNS) Depression and Overdose

Buprenorphine has been associated with life-threatening respiratory depression and death. Many, but not all, post-marketing reports regarding coma and death involved misuse by self-injection or were associated with the concomitant use of buprenorphine and benzodiazepines or other CNS depressant, including alcohol. Use buprenorphine and naloxone sublingual tablets with caution in patients with compromised respiratory function (e.g., chronic obstructive pulmonary disease, cor pulmonale, decreased respiratory reserve, hypoxia, hypercapnia, or pre-existing respiratory depression).19,20

Risk of Overdose in Opioid Naïve Patients

There have been reported deaths of opioid-naïve individuals who received a 2 mg dose of buprenorphine as a sublingual tablet for analgesia. Buprenorphine and naloxone sublingual tablets are not appropriate as an analgesic in opioid-naïve patients.19,20

Precipitation of Opioid Withdrawal Signs and Symptoms

If buprenorphine is started in opioid-dependent individuals, it will displace the other opioids and cause a phenomenon known as "precipitated withdrawal" which is characterized by a rapid and intense onset of withdrawal symptoms. Individuals must therefore be in a state of mild to moderate withdrawal before starting therapy with buprenorphine.

Because it contains naloxone, buprenorphine and naloxone sublingual tablets are also highly likely to produce marked and intense withdrawal signs and symptoms if misused parenterally by individuals dependent on full opioid agonists such as heroin, morphine, or methadone.19,20

Gastrointestinal Effects

Buprenorphine and other morphine-like opioids have been shown to decrease bowel motility and cause constipation. Buprenorphine may obscure the diagnosis or clinical course of patients with acute abdominal conditions and should be administered with caution to patients with dysfunction of the biliary tract.19,20

Effects on the Endocrine System

Opioids inhibit the secretion of adrenocorticotropic hormone (ACTH), cortisol, and luteinizing hormone (LH) in humans. They also stimulate prolactin, growth hormone (GH) secretion, and pancreatic secretion of insulin and glucagon. Chronic use of opioids may influence the hypothalamic-pituitary-gonadal axis, leading to androgen deficiency that may manifest as low libido, impotence, erectile dysfunction, amenorrhea, or infertility. The causal role of opioids in the clinical syndrome of hypogonadism is unknown because the various medical, physical, lifestyle, and psychological stressors that may influence gonadal hormone levels have not been adequately controlled for in studies conducted to date. Patients presenting with symptoms of androgen deficiency should undergo laboratory evaluation.19,20

Adrenal Insufficiency

Cases of adrenal insufficiency have been reported with opioid use, more often following greater than one month of use. Presentation of adrenal insufficiency may include non-specific symptoms and signs including nausea, vomiting, anorexia, fatigue, weakness, dizziness, and low blood pressure. If adrenal insufficiency is suspected, confirm the diagnosis with diagnostic testing as soon as possible. If adrenal insufficiency is diagnosed, treat with physiologic replacement doses of corticosteroids. Wean the patient off of the opioid to allow adrenal function to recover and continue corticosteroid treatment until adrenal function recovers. Other opioids may be tried as some cases reported use of a different opioid without recurrence of adrenal insufficiency. The information available does not identify any particular opioids as being more likely to be associated with adrenal insufficiency.19,20

Use in Patients With Impaired Hepatic Function

Buprenorphine/naloxone products are not recommended in patients with severe hepatic impairment and may not be appropriate for patients with moderate hepatic impairment. The doses of buprenorphine and naloxone in this fixed-dose combination product cannot be individually titrated, and hepatic impairment results in a reduced clearance of naloxone to a much greater extent than buprenorphine. Therefore, patients with severe hepatic impairment will be exposed to substantially higher levels of naloxone than patients with normal hepatic function. This may result in an increased risk of precipitated withdrawal at the beginning of treatment (induction) and may interfere with buprenorphine’s efficacy throughout treatment. In patients with moderate hepatic impairment, the differential reduction of naloxone clearance compared to buprenorphine clearance is not as great as in subjects with severe hepatic impairment. However, buprenorphine/naloxone products are not recommended for initiation of (treatment induction) in patients with moderate hepatic impairment due to the increased risk of precipitated withdrawal. Buprenorphine/naloxone products may be used with caution for maintenance treatment in patients with moderate hepatic impairment who have initiated treatment on a buprenorphine product without naloxone. However, patients should be carefully monitored and consideration given to the possibility of naloxone interfering with buprenorphine’s efficacy.19,20

Risk of Hepatitis, Hepatic Events

Cases of cytolytic hepatitis and hepatitis with jaundice have been observed in individuals receiving buprenorphine in clinical trials and through post-marketing adverse event reports. The spectrum of abnormalities ranges from transient asymptomatic elevations in hepatic transaminases to case reports of death, hepatic failure, hepatic necrosis, hepatorenal syndrome, and hepatic encephalopathy. In many cases, the presence of pre-existing liver enzyme abnormalities, infection with hepatitis B or hepatitis C virus, concomitant usage of other potentially hepatotoxic drugs, and ongoing injecting drug use may have played a causative or contributory role. In other cases, insufficient data were available to determine the etiology of the abnormality. Withdrawal of buprenorphine has resulted in amelioration of acute hepatitis in some cases; however, in other cases no dose reduction was necessary. The possibility exists that buprenorphine had a causative or contributory role in the development of the hepatic abnormality in some cases. Liver function tests, prior to initiation of treatment is recommended to establish a baseline. Periodic monitoring of liver function during treatment is also recommended. A biological and etiological evaluation is recommended when a hepatic event is suspected. Depending on the case, buprenorphine and naloxone sublingual tablets may need to be carefully discontinued to prevent withdrawal signs and symptoms and a return by the patient to illicit drug use, and strict monitoring of the patient should be initiated.19,20

Orthostatic Hypotension

Like other opioids, buprenorphine and naloxone sublingual tablets may produce orthostatic hypotension in ambulatory patients.

Elevation of Cerebrospinal Fluid Pressure

Buprenorphine, like other opioids, may elevate cerebrospinal fluid pressure and should be used with caution in patients with head injury, intracranial lesions, and other circumstances when cerebrospinal pressure may be increased. Buprenorphine can produce miosis and changes in the level of consciousness that may interfere with patient evaluation.

Elevation of Intracholedochal Pressure

Buprenorphine has been shown to increase intracholedochal pressure, as do other opioids, and thus should be administered with caution to patients with dysfunction of the biliary tract.

Mechanism of action

Buprenorphine is a partial agonist at the mu-opioid receptor and an antagonist at the kappa-opioid receptor. It demonstrates a high affinity for the mu-opioid receptor but has lower intrinsic activity compared to other full mu-opioid agonists such as heroin, oxycodone, or methadone.15 This means that buprenorphine preferentially binds the opioid receptor and displaces lower affinity opioids without activating the receptor to a comparable degree. Clinically, this results in a slow onset of action and a clinical phenomenon known as the "ceiling effect" where once a certain dose is reached buprenorphine's effects plateau. This effect can be beneficial, however, as dose-related side effects such as respiratory depression, sedation, and intoxication also plateau at around 32mg, resulting in a lower risk of overdose compared to methadone and other full agonist opioids.4,5 It also means that opioid-dependent patients do not experience sedation or euphoria at the same rate that they might experience with more potent opioids, improving quality of life for patients with severe pain and reducing the reinforcing effects of opioids which can lead to drug-seeking behaviours.11

Buprenorphine's high affinity, but low intrinsic activity for the mu-opioid receptor also means that if it is started in opioid-dependent individuals, it will displace the other opioids without creating an equal opioid effect and cause a phenomenon known as "precipitated withdrawal" which is characterized by a rapid and intense onset of withdrawal symptoms (i.e. anxiety, restlessness, gastrointestinal distress, diaphoresis, intense drug cravings, and tachycardia). Individuals must therefore be in a state of mild to moderate withdrawal before starting therapy with buprenorphine.

Buprenorphine is commercially available as the brand name product Suboxone which is formulated in a 4:1 fixed-dose combination product along with naloxone, a non-selective competitive opioid receptor antagonist. Combination of an opioid agonist with an opioid antagonist may seem counterintuitive, however this combination with naloxone is intended to reduce the abuse potential of Suboxone, as naloxone is poorly absorbed by the oral route (and has no effect when taken orally), but would reverse the opioid agonist effects of buprenorphine if injected intravenously.14,19,20

TargetActionsOrganism
AMu-type opioid receptor
partial agonist
Humans
AKappa-type opioid receptor
antagonist
Humans
UDelta-type opioid receptor
antagonist
Humans
UNociceptin receptorNot AvailableHumans
Additional Data Available
Adverse Effects

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Contraindications

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Absorption

Bioavailablity of buprenorphine/naloxone is very high following intravenous or subcutaneous administration, lower by the sublingual or buccal route, and very low when administered by the oral route. It is therefore provided as a sublingual tablet that is absorbed from the oral mucosa directly into systemic circulation.18

Clinical pharmacokinetic studies found that there was wide inter-patient variability in the sublingual absorption of buprenorphine and naloxone, but within subjects the variability was low. Both Cmax and AUC of buprenorphine increased in a linear fashion with the increase in dose (in the range of 4 to 16 mg), although the increase was not directly dose-proportional. Buprenorphine combination with naloxone (2mg/0.5mg) provided in sublingual tablets demonstrated a Cmax of 0.780 ng/mL with a Tmax of 1.50 hr and AUC of 7.651 ng.hr/mL.19,20

Coadministration with naloxone does not effect the pharmacokinetics of buprenorphine.

Volume of distribution

Buprenorphine is highly lipophilic, and therefore extensively distributed, with rapid penetration through the blood-brain barrier. 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

Buprenorphine is approximately 96% protein-bound, primarily to alpha- and beta-globulin.19,20

Metabolism

Buprenorphine is metabolized to norbuprenorphine via Cytochrome P450 3A4/3A5-mediated N-dealkylation. Buprenorphine and norbuprenorphine both also undergo glucuronidation to the inactive metabolites buprenorphine-3-glucuronide and norbuprenorphine-3-glucuronide, respectively.18,19,20

While norbuprenorphine has been found to bind to opioid receptors in-vitro, brain concentrations are very low which suggests that it does not contribute to the clinical effects of buprenorphine.18

Naloxone undergoes direct glucuronidation to naloxone-3-glucuronide as well as N-dealkylation, and reduction of the 6-oxo group.19,20

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).19,20

The overall mean elimination half-life of buprenorphine in plasma ranges from 31 to 42 hours, although the levels are very low 10 hours after dosing (majority of AUC of buprenorphine is captured within 10 hours), indicating that the effective half-life may be shorter.19,20

Half life

Buprenorphine demonstrates slow dissociation kinetics (~166 min), which contributes to its long duration of action and allows for once-daily or even every-second-day dosing.18 In clinical trial studies, the half-life of sublingually administered buprenorphine/naloxone 2mg/0.5mg was found to be 30.75 hours.19,20

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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Buprenorphine.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Buprenorphine.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Buprenorphine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may increase the analgesic activities of Buprenorphine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
7-Nitroindazole7-Nitroindazole may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of serotonin syndrome and opioid toxicity can be increased when Buprenorphine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
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    Severity

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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]
  4. Dahan A, Yassen A, Bijl H, Romberg R, Sarton E, Teppema L, Olofsen E, Danhof M: Comparison of the respiratory effects of intravenous buprenorphine and fentanyl in humans and rats. Br J Anaesth. 2005 Jun;94(6):825-34. doi: 10.1093/bja/aei145. Epub 2005 Apr 15. [PubMed:15833777]
  5. Walsh SL, Preston KL, Stitzer ML, Cone EJ, Bigelow GE: Clinical pharmacology of buprenorphine: ceiling effects at high doses. Clin Pharmacol Ther. 1994 May;55(5):569-80. doi: 10.1038/clpt.1994.71. [PubMed:8181201]
  6. Bruneau J, Ahamad K, Goyer ME, Poulin G, Selby P, Fischer B, Wild TC, Wood E: Management of opioid use disorders: a national clinical practice guideline. CMAJ. 2018 Mar 5;190(9):E247-E257. doi: 10.1503/cmaj.170958. [PubMed:29507156]
  7. Luty J, O'Gara C, Sessay M: Is methadone too dangerous for opiate addiction? BMJ. 2005 Dec 10;331(7529):1352-3. doi: 10.1136/bmj.331.7529.1352. [PubMed:16339224]
  8. Marteau D, McDonald R, Patel K: The relative risk of fatal poisoning by methadone or buprenorphine within the wider population of England and Wales. BMJ Open. 2015 May 29;5(5):e007629. doi: 10.1136/bmjopen-2015-007629. [PubMed:26024998]
  9. Wedam EF, Bigelow GE, Johnson RE, Nuzzo PA, Haigney MC: QT-interval effects of methadone, levomethadyl, and buprenorphine in a randomized trial. Arch Intern Med. 2007 Dec 10;167(22):2469-75. doi: 10.1001/archinte.167.22.2469. [PubMed:18071169]
  10. Anchersen K, Clausen T, Gossop M, Hansteen V, Waal H: Prevalence and clinical relevance of corrected QT interval prolongation during methadone and buprenorphine treatment: a mortality assessment study. Addiction. 2009 Jun;104(6):993-9. doi: 10.1111/j.1360-0443.2009.02549.x. Epub 2009 Apr 9. [PubMed:19392907]
  11. Tzschentke TM: Behavioral pharmacology of buprenorphine, with a focus on preclinical models of reward and addiction. Psychopharmacology (Berl). 2002 Apr;161(1):1-16. doi: 10.1007/s00213-002-1003-8. Epub 2002 Mar 6. [PubMed:11967625]
  12. Lutfy K, Eitan S, Bryant CD, Yang YC, Saliminejad N, Walwyn W, Kieffer BL, Takeshima H, Carroll FI, Maidment NT, Evans CJ: Buprenorphine-induced antinociception is mediated by mu-opioid receptors and compromised by concomitant activation of opioid receptor-like receptors. J Neurosci. 2003 Nov 12;23(32):10331-7. [PubMed:14614092]
  13. Johnson RE, Strain EC, Amass L: Buprenorphine: how to use it right. Drug Alcohol Depend. 2003 May 21;70(2 Suppl):S59-77. doi: 10.1016/s0376-8716(03)00060-7. [PubMed:12738351]
  14. Orman JS, Keating GM: Buprenorphine/naloxone: a review of its use in the treatment of opioid dependence. Drugs. 2009;69(5):577-607. doi: 10.2165/00003495-200969050-00006. [PubMed:19368419]
  15. Lutfy K, Cowan A: Buprenorphine: a unique drug with complex pharmacology. Curr Neuropharmacol. 2004 Oct;2(4):395-402. doi: 10.2174/1570159043359477. [PubMed:18997874]
  16. Toce MS, Chai PR, Burns MM, Boyer EW: Pharmacologic Treatment of Opioid Use Disorder: a Review of Pharmacotherapy, Adjuncts, and Toxicity. J Med Toxicol. 2018 Dec;14(4):306-322. doi: 10.1007/s13181-018-0685-1. Epub 2018 Oct 30. [PubMed:30377951]
  17. Yee A, Loh HS, Hisham Hashim HM, Ng CG: Clinical factors associated with sexual dysfunction among men in methadone maintenance treatment and buprenorphine maintenance treatment: a meta-analysis study. Int J Impot Res. 2014 Sep-Oct;26(5):161-6. doi: 10.1038/ijir.2014.18. Epub 2014 Jul 3. [PubMed:24990199]
  18. Coe MA, Lofwall MR, Walsh SL: Buprenorphine Pharmacology Review: Update on Transmucosal and Long-acting Formulations. J Addict Med. 2019 Mar/Apr;13(2):93-103. doi: 10.1097/ADM.0000000000000457. [PubMed:30531584]
  19. FDA Label - buprenorphine/naloxone [File]
  20. Health Canada Monograph - buprenorphine/naloxone [File]
External Links
Human Metabolome Database
HMDB0015057
KEGG Drug
D07132
KEGG Compound
C08007
PubChem Compound
644073
PubChem Substance
46505782
ChemSpider
559124
BindingDB
50026603
ChEBI
3216
ChEMBL
CHEMBL560511
Therapeutic Targets Database
DAP001353
PharmGKB
PA448685
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Buprenorphine
ATC Codes
N07BC01 — BuprenorphineN07BC51 — Buprenorphine, combinationsN02AE01 — Buprenorphine
AHFS Codes
  • 28:08.08 — Opiate Agonists
  • 28:08.12 — Opiate Partial Agonists
FDA label
Download (345 KB)
MSDS
Download (196 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceBasic Science1
0CompletedTreatmentDrug Overdose / Opiate withdrawal symptoms / Opioid-use Disorder1
0CompletedTreatmentOpioid Use Disorders1
0CompletedTreatmentOpioid-use Disorder1
1CompletedNot AvailableCocaine Abuse1
1CompletedNot AvailableHealthy Volunteers3
1CompletedNot AvailableHepatitis C Viral Infection1
1CompletedNot AvailablePain1
1CompletedNot AvailablePostoperative pain1
1CompletedBasic ScienceOpiate Dependence1
1CompletedOtherHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
1CompletedPreventionHealthy Volunteers / Opioids Use1
1CompletedTreatmentAddictions / Opioid Dependence / Pain1
1CompletedTreatmentBuprenorphine Withdrawal Syndrome / Opioid Dependence1
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
1CompletedTreatmentOpiate Addiction / Opiate Dependence / Substance Withdrawal Syndrome1
1CompletedTreatmentOpioid Dependence1
1CompletedTreatmentOpioid Use Disorders2
1CompletedTreatmentOpioid-Related Disorders5
1CompletedTreatmentOpioid-Related Disorders / Pain, Chronic1
1CompletedTreatmentOpioid-Related Disorders / Substance-Related Disorders2
1CompletedTreatmentOpioid-use Disorder1
1CompletedTreatmentOsteoarthritis Disorders1
1CompletedTreatmentPain3
1CompletedTreatmentSubstance-Related Disorders1
1Not Yet RecruitingTreatmentPostoperative pain1
1RecruitingBasic SciencePain, Chronic1
1RecruitingBasic ScienceRespiratory Depression1
1RecruitingTreatmentHeroin Dependence / Opioid Use Disorders1
1RecruitingTreatmentOpioid-use Disorder1
1TerminatedTreatmentHealthy Volunteers4
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, 2CompletedTreatmentDrug withdrawal syndrome neonatal / Neonatal Opiate Withdrawal Syndrome1
1, 2CompletedTreatmentOpiate Addiction1
1, 2CompletedTreatmentOpioid Addiction / Opioid Dependence / Opioid Related Disorders1
1, 2CompletedTreatmentOpioid-Related Disorders2
1, 2RecruitingTreatmentDrug; Withdrawal Symptoms, Neonatal / Fetus and Newborn Affected by Other Maternal Medication / Withdrawal1
1, 2RecruitingTreatmentOpioid Dependence1
1, 2RecruitingTreatmentOpioid-use Disorder2
1, 2TerminatedTreatmentChemotherapy Induced Mucositis / Orofacial Pain1
1, 2Unknown StatusTreatmentOpiate Dependence / Pain, Chronic1
2Active Not RecruitingTreatmentOpioid Use Disorders / Pain, Chronic1
2CompletedSupportive CarePain1
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 Dependence3
2CompletedTreatmentOpioid Dependency1
2CompletedTreatmentOpioid Related Disorders2
2CompletedTreatmentOpioid Use Disorders1
2CompletedTreatmentOpioid-Related Disorders30
2CompletedTreatmentOpioid-Related Disorders / Substance-Related Disorders5
2CompletedTreatmentPostoperative pain2
2CompletedTreatmentPrescription Opioid Dependence1
2Enrolling by InvitationTreatmentPain, Chronic1
2Enrolling by InvitationTreatmentSickle Cell Disorders1
2Not Yet RecruitingTreatmentAlcohol Abuse / Post Traumatic Stress Disorder (PTSD)1
2Not Yet RecruitingTreatmentOpioids Use1
2RecruitingBasic ScienceMaternal Opioid Use Disorder / Opioid Exposed Infant1
2RecruitingTreatmentHigh Dosage Buprenorphine1
2RecruitingTreatmentOpiate Addiction / Pregnancy1
2RecruitingTreatmentOpiate Addiction / Syringe-exchange Programs1
2RecruitingTreatmentOpiate Use Disorder / Post Traumatic Stress Disorder (PTSD)1
2RecruitingTreatmentOpioid-use Disorder1
2RecruitingTreatmentPain1
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, 3CompletedTreatmentAgitation / Dementias / Pain1
2, 3CompletedTreatmentDependence, Cocaine1
2, 3CompletedTreatmentHeroin Dependence / Opioid-Related Disorders1
2, 3CompletedTreatmentOpioid Dependence3
2, 3RecruitingTreatmentAnalgesics, Opioid / Buprenorphine / Rotator Cuff Injury / Rotator Cuff Syndrome1
2, 3RecruitingTreatmentOpioid-use Disorder2
2, 3RecruitingTreatmentSubstance, Addiction1
3Active Not RecruitingTreatmentBack Pain Lower Back Chronic / Pain, Chronic1
3CompletedNot AvailablePain1
3CompletedBasic ScienceHeroin Dependence1
3CompletedBasic ScienceOpioid-Related Disorders1
3CompletedHealth Services ResearchHeroin Addiction1
3CompletedTreatmentBack Pain Lower Back4
3CompletedTreatmentBack Pain Lower Back Chronic1
3CompletedTreatmentBack Pain Lower Back / Osteoarthritis (OA) / Pain, Neuropathic1
3CompletedTreatmentBack Pain Lower Back / Osteoarthritis (OA) / Pain / Pain, Neuropathic1
3CompletedTreatmentBack Pain Lower Back / Pain1
3CompletedTreatmentBack Pain, Unspecified2
3CompletedTreatmentChronic Non-Malignant Pain1
3CompletedTreatmentChronic Nonmalignant Pain1
3CompletedTreatmentCocaine-Related Disorders / Opioid-Related Disorders / Substance-Related Disorders2
3CompletedTreatmentDepression / Depressive Disorders / Major Depressive Disorder (MDD)1
3CompletedTreatmentDisease (or Disorder); Intervertebral Disc, With Myelopathy (Manifestation)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 Dependence5
3CompletedTreatmentOpioid Dependence, on Agonist Therapy1
3CompletedTreatmentOpioid Dependence / Opioid Related Disorders1
3CompletedTreatmentOpioid Dependence / Opioid Related Disorders / Pregnancy1
3CompletedTreatmentOpioid Dependency2
3CompletedTreatmentOpioid Use Disorders3
3CompletedTreatmentOpioid Use Disorders / Opioid-Related Disorders2
3CompletedTreatmentOpioid-Related Disorders5
3CompletedTreatmentOsteoarthritis (OA)5
3CompletedTreatmentOsteoarthritis (OA) / Pain1
3CompletedTreatmentPain2
3CompletedTreatmentPain, Chronic1
3Not Yet RecruitingTreatmentDrug Abuse in Pregnancy / Drug withdrawal syndrome neonatal / Neonatal Opiate Withdrawal Syndrome / Opioid-Related Disorders / Pregnancy Related / Substance Abuse / Substance, Addiction1
3Not Yet RecruitingTreatmentDrug Abuse in Pregnancy / Drug withdrawal syndrome neonatal / Neonatal Opioid Withdrawal Syndrome / Opioid-Related Disorders / Pregnancy Related / Substance Abuse / Substance, Addiction2
3Not Yet RecruitingTreatmentMajor Depressive Disorder (MDD)1
3Not Yet RecruitingTreatmentMajor Depressive Episode / Suicidal Thoughts1
3Not Yet RecruitingTreatmentOpioids Use1
3RecruitingHealth Services ResearchOpioid Dependence1
3RecruitingOtherOpioid Addiction1
3RecruitingTreatmentHeroin Dependence1
3RecruitingTreatmentOpioid Use Disorders1
3RecruitingTreatmentOpioid-use Disorder1
3RecruitingTreatmentPain1
3RecruitingTreatmentPain, Cancer1
3TerminatedPreventionHuman Immunodeficiency Virus (HIV) Infections / Opioid-Related Disorders1
3TerminatedTreatmentBack Pain Lower Back Chronic2
3TerminatedTreatmentOpioid Dependence1
3TerminatedTreatmentOpioid Dependency1
3TerminatedTreatmentOsteoarthritis (OA)4
3TerminatedTreatmentPost-Operative Pain1
3Unknown StatusTreatmentDepression / Suicidal Thoughts / Suicide, Attempted1
3WithdrawnNot AvailableOpioid Dependence1
3WithdrawnTreatmentBack Pain Lower Back / Pain1
3WithdrawnTreatmentOpiate withdrawal symptoms / Opioid-Related Disorders1
3WithdrawnTreatmentOpioid Dependence1
3WithdrawnTreatmentOther Acute Postoperative Pain / Prolonged Endotracheal Intubation1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedSupportive CareOsteoarthritis (OA)1
4CompletedSupportive CareSpinal Disorders1
4CompletedTreatmentAcute Pain Management / Renal Colic1
4CompletedTreatmentArthroplasties, Hip Replacement1
4CompletedTreatmentBack Pain Lower Back1
4CompletedTreatmentBack Pain Lower Back / Joint Pain / Muscle Soreness / Osteoarthritis (OA) / Rheumatoid Arthritis2
4CompletedTreatmentChronic Hepatitis C Infection With Hepatic Coma / Hepatic Failure / Hepatic Impairment1
4CompletedTreatmentHeroin Dependence1
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
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Substance Related Disorders1
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) / Pain2
4CompletedTreatmentOsteoarthritis Pain of the Hip and or Knee1
4CompletedTreatmentPain1
4CompletedTreatmentPain, Acute1
4CompletedTreatmentPostoperative pain1
4CompletedTreatmentPostoperative pain / Spinal Stenosis1
4CompletedTreatmentSubstance, Addiction1
4Enrolling by InvitationTreatmentOpioid Use Disorder, Moderate / Opioid Use Disorder, Severe1
4Not Yet RecruitingOtherEvaluation of QTc Interval1
4Not Yet RecruitingTreatmentGeneral Surgery / Opioid-use Disorder / Pain, Acute1
4Not Yet RecruitingTreatmentOpioid Dependence1
4Not Yet RecruitingTreatmentOpioid Use Disorder, Mild / Opioid-use Disorder1
4RecruitingTreatmentDrug Overdose / Opioid-use Disorder1
4RecruitingTreatmentOpioid Dependence1
4RecruitingTreatmentOpioid Use Disorders1
4RecruitingTreatmentOpioid-use Disorder2
4SuspendedTreatmentPain, Chronic1
4TerminatedBasic ScienceHealthy Volunteers1
4TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection1
4TerminatedTreatmentOpiate Addiction / Refractory Pains1
4TerminatedTreatmentPain1
4Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Opioid-Related Disorders1
4Unknown StatusTreatmentDementias / Depression / Pain1
4Unknown StatusTreatmentHeroin Addiction1
4Unknown StatusTreatmentOpioid Dependence1
4WithdrawnTreatmentOpiate Addiction1
4WithdrawnTreatmentRestless Legs Syndrome (RLS)1
Not AvailableActive Not RecruitingOtherOpioid-Related Disorders / Pregnancy1
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 AvailableBuprenorphine / Naloxone / Opiate Dependence / Opiate-Related Disorders / Substance Abuse1
Not AvailableCompletedNot AvailableCancer Related Pain (Breakthrough Pain) / Pain, Cancer / Pain, Neuropathic / Tumors1
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 ScienceDepression1
Not AvailableCompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedBasic SciencePain1
Not AvailableCompletedOtherHealthy Volunteers1
Not AvailableCompletedTreatmentHepatitis C Viral Infection / Heroin Dependence1
Not AvailableCompletedTreatmentOpiate Addiction2
Not AvailableCompletedTreatmentOpioid-Related Disorders4
Not AvailableCompletedTreatmentPain1
Not AvailableCompletedTreatmentPatients Undergoing Ankle Surgery1
Not AvailableNot Yet RecruitingNot AvailableKnee Osteoarthritis (Knee OA)1
Not AvailableNot Yet RecruitingNot AvailableOpioid Overdose1
Not AvailableRecruitingNot AvailableBuprenorphine Dependence / Opioid Use, Unspecified / Opioid-use Disorder1
Not AvailableRecruitingNot AvailableCardiovascular Disease (CVD) / Human Immunodeficiency Virus (HIV) Infections / Opioid-use Disorder1
Not AvailableRecruitingNot AvailableComplex Regional Pain Syndromes (CRPS)1
Not AvailableRecruitingNot AvailableObesity, Morbid1
Not AvailableRecruitingOtherHealthy Volunteers1
Not AvailableRecruitingTreatmentOpioid Pain Medication / Pain, Chronic1
Not AvailableRecruitingTreatmentOpioid-use Disorder1
Not AvailableTerminatedNot AvailableBuprenorphine / Pain1
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 mcg
Film, solubleBuccal150 ug/1
Film, solubleBuccal300 ug/1
Film, solubleBuccal300 mcg
Film, solubleBuccal450 mcg
Film, solubleBuccal450 ug/1
Film, solubleBuccal600 ug/1
Film, solubleBuccal600 mcg
Film, solubleBuccal75 ug/1
Film, solubleBuccal75 mcg
Film, solubleBuccal750 ug/1
Film, solubleBuccal750 mcg
Film, solubleBuccal900 ug/1
Film, solubleBuccal900 mcg
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
Film, solubleBuccal; Sublingual
FilmBuccal; Sublingual
InjectionIntramuscular; Intravenous0.3 mg/1mL
InjectionIntramuscular; Intravenous0.324 mg/1mL
Injection, solutionIntramuscular; Intravenous0.3 mg/1mL
Injection, solutionIntramuscular; Intravenous0.324 mg/1mL
PowderNot applicable1 kg/1kg
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
PatchTransdermal
ImplantSubcutaneous80 mg/1
ImplantSubcutaneous80 mg
SolutionSubcutaneous100 mg/1
SolutionSubcutaneous300 mg/1
Solution, gel forming, extended releaseSubcutaneous100 mg
Solution, gel forming, extended releaseSubcutaneous300 mg
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
US10198218No2019-02-052031-06-06Us
US10285910No2002-10-112022-10-11Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

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
Humans
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
Humans
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
Humans
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
Humans
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]
  2. Lutfy K, Eitan S, Bryant CD, Yang YC, Saliminejad N, Walwyn W, Kieffer BL, Takeshima H, Carroll FI, Maidment NT, Evans CJ: Buprenorphine-induced antinociception is mediated by mu-opioid receptors and compromised by concomitant activation of opioid receptor-like receptors. J Neurosci. 2003 Nov 12;23(32):10331-7. [PubMed:14614092]

Enzymes

Kind
Protein
Organism
Humans
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. 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]
  3. McCance-Katz EF, Sullivan LE, Nallani S: Drug interactions of clinical importance among the opioids, methadone and buprenorphine, and other frequently prescribed medications: a review. Am J Addict. 2010 Jan-Feb;19(1):4-16. doi: 10.1111/j.1521-0391.2009.00005.x. [PubMed:20132117]
  4. 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. doi: 10.1124/dmd.31.6.768. [PubMed:12756210]
Kind
Protein
Organism
Humans
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]
  2. Coe MA, Lofwall MR, Walsh SL: Buprenorphine Pharmacology Review: Update on Transmucosal and Long-acting Formulations. J Addict Med. 2019 Mar/Apr;13(2):93-103. doi: 10.1097/ADM.0000000000000457. [PubMed:30531584]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
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
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Moody DE, Chang Y, Huang W, McCance-Katz EF: The in vivo response of novel buprenorphine metabolites, M1 and M3, to antiretroviral inducers and inhibitors of buprenorphine metabolism. Basic Clin Pharmacol Toxicol. 2009 Sep;105(3):211-5. doi: 10.1111/j.1742-7843.2009.00432.x. Epub 2009 Jun 4. [PubMed:19500085]
  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
Humans
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]
  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
Humans
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. 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]
  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. doi: 10.1124/dmd.31.6.768. [PubMed:12756210]
  3. Umehara K, Shimokawa Y, Miyamoto G: Inhibition of human drug metabolizing cytochrome P450 by buprenorphine. Biol Pharm Bull. 2002 May;25(5):682-5. doi: 10.1248/bpb.25.682. [PubMed:12033517]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
  1. 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]
  2. Joseph D, Schobelock MJ, Riesenberg RR, Vince BD, Webster LR, Adeniji A, Elgadi M, Huang F: Effect of steady-state faldaprevir on the pharmacokinetics of steady-state methadone and buprenorphine-naloxone in subjects receiving stable addiction management therapy. Antimicrob Agents Chemother. 2015 Jan;59(1):498-504. doi: 10.1128/AAC.04046-14. Epub 2014 Nov 10. [PubMed:25385094]
  3. Kacinko SL, Jones HE, Johnson RE, Choo RE, Huestis MA: Correlations of maternal buprenorphine dose, buprenorphine, and metabolite concentrations in meconium with neonatal outcomes. Clin Pharmacol Ther. 2008 Nov;84(5):604-12. doi: 10.1038/clpt.2008.156. Epub 2008 Aug 13. [PubMed:18701886]
Kind
Protein
Organism
Humans
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. Umehara K, Shimokawa Y, Miyamoto G: Inhibition of human drug metabolizing cytochrome P450 by buprenorphine. Biol Pharm Bull. 2002 May;25(5):682-5. doi: 10.1248/bpb.25.682. [PubMed:12033517]
  2. Bomsien S, Skopp G: An in vitro approach to potential methadone metabolic-inhibition interactions. Eur J Clin Pharmacol. 2007 Sep;63(9):821-7. doi: 10.1007/s00228-007-0327-z. Epub 2007 Jun 28. [PubMed:17598095]
  3. 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]

Transporters

Kind
Protein
Organism
Humans
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
Humans
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 14, 2019 19:45