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Drug

D0265 | Glibenclamide

Molecular Formula C23H28ClN3O5S
Molecular Weight 494
Structure
State solid
Clearance 78 ml/hr/kg in healthy adults. Clearance may be substantially decreased in those with severe renal impairment.
Volume of distribution Steady state V<sub>d</sub>=0.125 L/kg; V<sub>d</sub> during elimination phase=0.155 L/kg.
Route of elimination Glyburide is excreted as metabolites in the bile and urine, approximately 50% by each route. This dual excretory pathway is qualitatively different from that of other sulfonylureas, which are excreted primarily in the urine.
Protein binding Unchanged drug is ~99% bound to serum proteins; 4-trans-hydroxyglyburide is greater than 97% bound to serum proteins. Protein binding is primarily nonionic making glyburide and is less likely to displace or be displaced by drugs that bind via an ionic mechanism.
Half life 1.4-1.8 hours (unchanged drug only); 10 hours (metabolites included). Duration of effect is 12-24 hours. The half-life of glyburide appears to be unaffected in those with a creatinine clearance of greater than 29 ml/min/1.73m<sup>2</sup>.
Absorption Significant absorption within 1 hour and peak plasma levels are reached in 2 to 4 hours. Onset of action occurs within one hour.
Trade names Diabeta, Flycron
Description second generation sulfonylurea; treat diabetes mellitus type II; Glyburide stimulates insulin secretion through the closure of ATP-sensitive potassium channels on beta cells

A

A10BB01 Glibenclamide


[A10BB] Sulfonylureas


[A10B] BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS


[A10] DRUGS USED IN DIABETES


[A] Alimentary tract and metabolism

Toxicity Dose Time Species Model Method Action Positive criterion Reference
TRANSPORT OF POTASSIUM affect 188
TRANSPORT OF POTASSIUM K1/2 values 1-6 microM heart and liver mitochondria from rat affect 190

Target Dose Time Species Model Method Action Positive criterion Reference
mitochondrial KATP chanel (mtKATP) inhibitor 188
mitochondrial KATP chanel (mtKATP) K1/2 values 1-6 microM heart and liver mitochondria from rat inhibitor 190

Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 220 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 1 of 220 companies. For more detailed information, please visit ECHA C&L website


Of the 9 notification(s) provided by 219 of 220 companies with hazard statement code(s):


H302 (96.35%): Harmful if swallowed [Warning Acute toxicity, oral]


H413 (97.72%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]


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.


 P264, P270, P273, P301+P312, P330, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
rat LD50 subcutaneous > 20gm/kg (20000mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969.
dog LD50 oral > 10gm/kg (10000mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1404, 1969.
mouse LD50 subcutaneous > 20gm/kg (20000mg/kg) skin and appendages (skin): "dermatitis, other: after systemic exposure" Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 247, 1970.
mouse LD50 intraperitoneal 2700mg/kg (2700mg/kg) Pharmaceutical Chemistry Journal Vol. 29, Pg. 265, 1995.
rat LD50 intraperitoneal 3750mg/kg (3750mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969.
rabbit LD oral > 20gm/kg (20000mg/kg) Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 247, 1970.
rat LD50 oral > 20gm/kg (20000mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1413, 1969.
mouse LD50 oral 3250mg/kg (3250mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1640, 1966.
guinea pig LD50 oral > 15gm/kg (15000mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1404, 1969.
women TDLo oral 147ug/kg (0.147mg/kg) Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 142, 1984.
man TDLo oral 209mg/kg/4Y-I (209mg/kg) Western Journal of Medicine. Vol. 168, Pg. 274, 1998.


  • (5-chloro-2-methoxyphenyl)-N-[2-(4-{[(cyclohexylamino)carbonylamino]sulfonyl}p henyl)ethyl]carboxamide 1-((p-(2-(5-Chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexyl urea 1-((p-(2-(5-Chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea
    1-(p-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea 1-[[p-[2-(5-Chloro-o-anisamido)ethyl]phenyl]sulfonyl]-3-cyclohexylurea 1-{4-[2-(5-chloro-2-methoxybenzamido)ethyl]benzenesulfonyl}-3-cyclohexylurea;1-{4-[2-(5-chloro-2-methoxybenzamido)ethyl]benzenesulfonyl}-3-cyclohexylurea
    10238-21-8 23047-14-5 5-Chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide
    5-Chloro-N-(2-[4-(([(cyclohexylamino)carbonyl]amino)sulfonyl)phenyl]ethyl)-2-methoxybenzamide # 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)-phenethyl)-2-methoxybenzamide 5-Chloro-N-(4-(N-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide
    5-Chloro-N-[2-[4-[[[(Cylcohexylamino)carbonyl]amino]sulphonyl]phenyl]ethyl]-2-methoxybenzamide 5-Chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]-amino]sulfonyl]phenyl]-ethyl]-2-methoxybenzamide 5-Chloro-N-[4-(3-cyclohexylureidosulfonyl)phenethyl]-2-methoxybenzamide
    5-Chloro-N-[4-(cyclohexylureidosulfonyl)phenethyl]-2-methoxybenzamide 5-chloro-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide 5-chloro-N-(2-{4-[N-(N-cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide
    5-chloro-N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide 5-chloro-N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide
    5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide. 5-chloro-N-[4-({[(cyclohexylamino)carbonyl]amino}sulfonyl)phenethyl]-2-methoxybenzamide 78637-EP2270001A1
    78637-EP2270011A1 78637-EP2272825A2 78637-EP2272841A1
    78637-EP2275414A1 78637-EP2287165A2 78637-EP2287166A2
    78637-EP2292620A2 78637-EP2298750A1 78637-EP2298776A1
    78637-EP2298779A1 78637-EP2301923A1 78637-EP2301936A1
    78637-EP2305648A1 78637-EP2308847A1 A19539
    AB00051949 AB00051949-16 AB00051949-17
    AB00051949_18 AB00051949_19 AB0012611
    AB2000243 ACMC-20a66i AKOS001487495
    ANW-58936 AOB6214 Abbenclamide
    Adiab Amglidia Apo-Glibenclamide
    Azuglucon BCP05327 BCP9000729
    BDBM50012957 BG0207 BIDD:GT0239
    BPBio1_000344 BRD-K36927236-001-06-0 BRD-K36927236-001-17-7
    BRN 2230085 BSPBio_000312 BSPBio_001351
    BSPBio_003053 Bastiverit Benclamin
    Benzamide, 5-chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxy- Benzamide, 5-chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxy- Betanase
    Betanese 5 Bio1_000076 Bio1_000565
    Bio1_001054 Bio2_000071 Bio2_000551
    C-22898 C07022 C23H28ClN3O5S
    CAS-10238-21-8 CBiol_001790 CCG-39618
    CHEBI:5441 CHEMBL472 CPD000058229
    CS-1075 CTK8B7917 Calabren
    Certified Reference Material Cytagon D00336
    DB01016 DSSTox_CID_17237 DSSTox_GSID_37237
    DSSTox_RID_79313 DTXSID0037237 Daonil
    Debtan Delmide Diabeta
    Diabeta (TN) Diabiphage Dibelet
    DivK1c_000481 Duraglucon EINECS 233-570-6
    EU-0100499 Euclamin Euglucan
    Euglucon Euglucon 5 Euglucon N
    Euglykon FT-0601608 G 0639
    G-150 G0382 GBM
    GBN 5 GIBENCLAMIDE GP8701
    GTPL2414 Gen-Glybe Gewaglucon
    Gilemal Glamide Glibadone
    Gliban Gliben Glibenbeta
    Glibenclamid AL Glibenclamid Basics Glibenclamid Fabra
    Glibenclamid Genericon Glibenclamid Heumann Glibenclamid Riker M
    Glibenclamid Riker M. Glibenclamid-Cophar Glibenclamid-Ratiopharm
    Glibenclamida Glibenclamida [INN-Spanish] Glibenclamide
    Glibenclamide (JP17/INN) Glibenclamide 1.0 mg/ml in Acetonitrile Glibenclamide B.P.
    Glibenclamide [INN] Glibenclamide for peak identification, European Pharmacopoeia (EP) Reference Standard Glibenclamide,(S)
    Glibenclamidum Glibenclamidum [INN-Latin] Glibenil
    Glibens Glibesyn Glibet
    Glibetic Glibil Gliboral
    Glicem Glidiabet Glimel
    Glimide Glisulin Glitisol
    Glubate Gluben Glucobene
    Glucohexal Glucolon Glucomid
    Glucoremed Glucoven Glyben
    Glybenclamide Glybenclamide, >=99% (HPLC) Glybenclamide, European Pharmacopoeia (EP) Reference Standard
    Glybenzcyclamide Glyburide (Diabeta) Glyburide (Glibenclamide), Pharmaceutical Secondary Standard
    Glyburide (USP) Glyburide (micronized) Glyburide [USAN:USP]
    Glyburide [USAN] Glyburide(Diabeta) Glyburide, United States Pharmacopeia (USP) Reference Standard
    Glyburide, meets USP testing specifications Glycomin Glycron
    Glynase Glynase (TN) HB 419
    HB-419 HB-420 HD 419
    HMS1361D13 HMS1568P14 HMS1791D13
    HMS1922L08 HMS1989D13 HMS2089L06
    HMS2093P04 HMS2095P14 HMS3259O12
    HMS3261D19 HMS3267A15 HMS3402D13
    HMS3411F16 HMS3428D15 HMS3651E17
    HMS3675F16 HMS3712P14 HMS501I03
    HY-15206 Hemi-Daonil Hexaglucon
    Humedia IDI1_000481 IDI1_033821
    J10021 KBio1_000481 KBio2_000071
    KBio2_000730 KBio2_002639 KBio2_003298
    KBio2_005207 KBio2_005866 KBio3_000141
    KBio3_000142 KBio3_002273 KBioGR_000071
    KBioGR_001897 KBioSS_000071 KBioSS_000730
    KS-5326 LP00499 LS-159295
    Lederglib Libanil Lisaglucon
    Lopac-G-0639 Lopac0_000499 MCULE-2351642942
    MFCD00056625 MLS000069721 MLS001077262
    Maninil Med-Glionil Melix
    Micronase Micronase (TN) Micronized glyburide
    Miglucan N-(4-(.beta.-(2-Methoxy-5-chlorbenzamido)-aethyl)-benzolsulfonyl)-N'-cyclohexyl-harnstoff N-(4-(2-(5-Chloro-2-methoxybenzamido)ethyl)phenylsulfonyl)-N'-cyclohexylurea
    N-(4-(beta-(2-Methoxy-5-chlorbenzamido)-aethyl)-benzolsulfonyl)-N'-cyclohexyl-harnstoff N-[(4-{2-[(5-chloro-2-methoxyphenyl)carbonylamino]ethyl}phenyl)sulfonyl](cyclo hexylamino)carboxamide N-p-[2-(5-Chloro-2-methoxybenzamido)ethyl]benzenesulfonyl-N'-cyclohexylurea
    N1-[4-({[(cyclohexylamino)carbonyl]amino}sulfonyl)phenethyl]-5-chloro-2-methoxybenzamide NC00566 NCGC00015467-01
    NCGC00015467-02 NCGC00015467-03 NCGC00015467-04
    NCGC00015467-05 NCGC00015467-06 NCGC00015467-07
    NCGC00015467-08 NCGC00015467-09 NCGC00015467-10
    NCGC00015467-11 NCGC00015467-12 NCGC00015467-13
    NCGC00015467-14 NCGC00015467-15 NCGC00015467-16
    NCGC00015467-17 NCGC00015467-18 NCGC00015467-20
    NCGC00015467-36 NCGC00016689-01 NCGC00023447-02
    NCGC00023447-04 NCGC00023447-05 NCGC00023447-06
    NCGC00023447-07 NCGC00023447-08 NCGC00023447-09
    NCGC00023447-10 NCGC00023447-11 NCGC00023447-12
    NCGC00254662-01 NCGC00261184-01 NINDS_000481
    NSC-759618 NSC759618 Nadib
    Neogluconin Norglicem 5 Normoglucon
    Novo-Glyburide Opera_ID_801 Oprea1_764617
    Orabetic Pharmakon1600-02300229 Pira
    Praeciglucon Prestwick0_000316 Prestwick1_000316
    Prestwick2_000316 Prestwick3_000316 Prestwick_569
    Probes1_000431 Probes2_000378 Prodiabet
    Q420626 RP-1127 RT-000122
    Renabetic S1716 SAM002564212
    SB17414 SBB057426 SBI-0050483.P003
    SC-17437 SCHEMBL22009 SMR000058229
    SPBio_001831 SPBio_002531 SPECTRUM2300229
    SR-01000000196 SR-01000000196-2 SR-01000000196-4
    SR-01000000196-5 SR-01000000196-6 SR-01000000196-8
    ST024780 STK362992 SW195828-5
    SX6K58TVWC SYN3026 Semi-Euglucon
    Semi-Gliben-Puren N Semi-daonil Spectrum2_001816
    Spectrum3_001327 Spectrum4_001199 Spectrum5_001631
    Spectrum_000250 Sugril Suraben
    Tiabet Tocris-0911 Tox21_110158
    Tox21_110158_1 Tox21_300758 Tox21_500499
    U 26452 U-26,452 U-26452
    UNII-SX6K58TVWC UPCMLD-DP006 UPCMLD-DP006:001
    UR 606 Urea, 1-((p-(2-(chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexyl- Urea, 1-(p-(2-(5-chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexyl-
    W-108874 W-5054 Yuglucon
    Z277540138 ZINC537805 ZNNLBTZKUZBEKO-UHFFFAOYSA-N
    glyburide glyburide (glibenclamide)

    DrugBank Name Glyburide
    DrugBank DB01016
    CAS Number 10238-21-8, 1219803-02-7, 159997-94-1
    PubChem Compound 3488
    KEGG Compound ID C07022
    KEGG Drug D00336
    PubChem.Substance 46509154
    ChEBI 5441
    PharmGKB PA449782
    ChemSpider 3368
    BindingDB 50012957.0
    TTD DAP000037
    Wikipedia Glibenclamide