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Drug

D1332 | buprenorphine

Molecular Formula C29H41NO4
Molecular Weight 467.6
Structure
State solid
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.
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.
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).
Protein binding 96% protein bound to alpha- and beta-globulin.
Half life IV administration, 0.3 mg = 1.2 - 7.2 hours (mean 2.2 hours); Sublingual administration = 37 hours.
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.
Trade names Subutex
Description opioid

N

N07BC51 Buprenorphine, combinations


[N07BC] Drugs used in opioid dependence


[N07B] DRUGS USED IN ADDICTIVE DISORDERS


[N07] OTHER NERVOUS SYSTEM DRUGS


[N] Nervous system

N07BC01 Buprenorphine


[N07BC] Drugs used in opioid dependence


[N07B] DRUGS USED IN ADDICTIVE DISORDERS


[N07] OTHER NERVOUS SYSTEM DRUGS


[N] Nervous system

N02AE01 Buprenorphine


[N02AE] Oripavine derivatives


[N02A] OPIOIDS


[N02] ANALGESICS


[N] Nervous system

Toxicity Dose Time Species Model Method Action Positive criterion Reference
ELECTROPHORETIC UNCOUPLING 278
MITOCHONDRIAL FATTY ACID BETA OXIDATION 100 μM rat liver mitochondria the mitochondrial membrane potential assessed by the fluorescence of safranine. affect 235

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 90 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H301 (87.78%): Toxic if swallowed [Danger Acute toxicity, oral]


H302 (11.11%): Harmful if swallowed [Warning Acute toxicity, oral]


H315 (87.78%): Causes skin irritation [Warning Skin corrosion/irritation]


H319 (90%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (87.78%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


H361 (11.11%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P261, P264, P270, P271, P280, P281, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)


  • (-)-buprenorphine (1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7(12),8,10-trien-11-ol (1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-ol
    (2S)-2-[(5R,6R,7R,14S)-9alpha-Cyclopropylmethyl-3-hydroxy-6-methoxy-4,5-epoxy-6,14-ethanomorphinan-7-yl]-3,3-dimethylbutan-2-ol (5alpha,14beta,18R)-17-(Cyclopropylmethyl)-18-[(2S)-2-hydroxy-3,3-dimethyl-2-butanyl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol (5alpha,6beta,14beta,18R)-17-(cyclopropylmethyl)-18-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol
    17-Cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl-6-methoxy-6,14-endo-ethanomorphinan-3-ol 17-cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol 2-(N-Cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-7alpha-yl)-3,3-dimethyl-2-butanol
    2-(N-cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6alpha-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-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine
    21-cyclopropyl-7alpha-(2-hydroxy-3,3-dimethyl-2-butyl)-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine 21-cyclopropyl-7alpha-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine 40D3SCR4GZ
    52485-79-7 53152-21-9 6,14-Ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-,
    6,14-Ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-, (5-alpha,7-alpha-(S))- 6,14-Ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-, (alphaS,5alpha,7alpha)- (9CI) 6,14-ethenomorphinan-3-ol, 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-, (5alpha,7alpha)-
    6029-M BDBM50026603 BEMA
    Buprenex Buprenophine Buprenorfina
    Buprenorfina [INN-Spanish] Buprenorphine (BN) Buprenorphine (JAN/INN)
    Buprenorphine [INN:BAN:JAN] Buprenorphinum Buprenorphinum [INN-Latin]
    Butrans Buvidal C-22673
    C08007 CAM2038 CC-25269
    CHEBI:3216 CHEMBL560511 D07132
    DB00921 DEA No. 9064 DTXSID2022705
    EINECS 257-950-6 GTPL1670 Probuphenine
    Probuphine Q407721 RBP-6000
    RX 6029M SCHEMBL15821 Sixmo (buprenorphine hydrochloride)
    Sublocade Subutex Temgesic
    Temgesic (TN) UNII-40D3SCR4GZ ZINC1319780
    [5?,7?(S)]-?-tert-butyl-17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-?-methyl-6,14-ethenomorphinan-7-methanol hydrochloride;[5a,7a(S)]-a-tert-butyl-17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-a-methyl-6,14-ethenomorphinan-7-methanol hydrochloride;Buprenorphine hydrochloride [5alpha,7alpha(S)]- [5alpha,7alpha(S)]-17-(Cyclopropylmethyl)-alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-6,14-ethenomorphinan-7-methanol
    buprenorphin buprenorphine

    DrugBank DB00921
    CAS Number 52485-79-7
    PubChem Compound 644073