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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Tolbutamide is a potassium channel blocker, sulfonylurea oral hypoglycemic drug.
Synonyms: D 860; HLS 831; Tolbutamide, Artosin, Diabetol, Orinase
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 64-77-7 |
Formula : | C12H18N2O3S |
M.W : | 270.35 |
SMILES Code : | O=S(C1=CC=C(C)C=C1)(NC(NCCCC)=O)=O |
Synonyms : |
D 860; HLS 831; Tolbutamide, Artosin, Diabetol, Orinase
|
MDL No. : | MFCD00027169 |
InChI Key : | JLRGJRBPOGGCBT-UHFFFAOYSA-N |
Pubchem ID : | 5505 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With SoLo-D241G unspecific peroxygenase; dihydrogen peroxide; ascorbic acid; In aq. phosphate buffer; acetonitrile; at 30℃; for 1h;pH 7.0;Enzymatic reaction;Catalytic behavior; | General procedure: Reaction mixtures (1mL) contained purified peroxygenases (PaDa-I, JaWa, SoLo and SoLo-D241G mutants, 0.1muM), substrate (1mM, dissolved in 10% acetonitrile), potassium phosphate buffer (100mM, pH 7.0), ascorbic acid (4mM) and a single dosage of H2O2 (1mM). All reactions were stirred at 30C for one hour until reaction stopped. |
With glucose-6-phosphate dehydrogenase; DL-dithiothreitol; human cytochrome P450 2C9; NADP; 1,2-dilauroyl-sn-glicero-3-phosphatidylcholine; NADPH-P450 reductase; In aq. phosphate buffer; at 37℃; for 0.0333333h;pH 7.4;Enzymatic reaction; | General procedure: Assays were done as described previously (4) with minorchanges. Typical incubations included 0.2 M P450 4A11, 0.4M NADPH-P450 reductase, 0.4 M b5, 150 M L--dilauroylsn-glycero-3-phosphocholine (DLPC; Sigma-Aldrich), 100 mMpotassium phosphate buffer (pH 7.4), and the indicated concentrationof lauric acid ([1-14C]lauric acid, usually added as anaqueous 10 mM solution of sodium laurate) in a final volume of0.25 ml. b5 was included because it stimulates the catalyticactivity (4). Following temperature equilibration to 37 C for 5min, reactions were initiated by the addition of an NADPHregeneratingsystem consisting of 0.5 mM NADP, 10 mM glucose6-phosphate, and 1 IU ml1 yeast glucose 6-phosphate dehydrogenase (66). Reactions generally proceeded at 37 C for2 min and were terminated with 1.0 ml of ethyl acetate containing0.1% CH3CO2H (v/v), and, following mixing with a vortexdevice, the mixtures were centrifuged (103 g for 10 min). A0.8-ml aliquot of the ethyl acetate layer (upper phase) was transferredto a clean tube, and the solvent was removed under anN2stream.The dried extracts were dissolved in 200l of a 1:1 mixture ofH2O/CH3CN containing 0.1% CH3CO2H (v/v) and 10 Mbutylated hydroxytoluene, and aliquots were analyzed on areversed-phase (octadecylsilane, C18) HPLC column (5 m,2.1 100 mm (Waters, Milford, MA)) coupled with a radioactivitydetector (-RAM, IN/US Systems, Tampa, FL). Reactionproducts and substrate were eluted at a flow rate of 0.6 mlmin1 using an increasing linear gradient ofCH3CN(including0.1% (v/v) HCO2H) from 35 to 95% (v/v) over 30 min.Assays with P450s other than P450 4A11 were performed asdescribed previously, with the modification of either preincubationwith DTT (1 mM) for 10 min or not (the DTT remainedin the reactions): P450 2C8-paclitaxel as substrate (67), P4502C9-<strong>[64-77-7]tolbutamid</strong>e as substrate (68), P450 2D6-bufuralol assubstrate (69), P450 3A4-nifedipine as substrate (70), P45019A1-testosterone as substrate (71), P450 21A2-progesteroneas substrate (72), P450 2A6-coumarin as substrate (73), andP450s 1B1-, 1A1-, and 1A2-7-ethoxyresorufin as substrate(74). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
and the further antidiabetic compound is selected from the group consisting of ... glibenclamide, acetohexamide, chloropropamide, glibornuride, tolbutamide, tolazamide, glipizide, carbutamide, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | In water; N,N-dimethyl-formamide; | b. Hydroxyethyl n-butyl carbamate (6.84 g.) and p-toluenesulfonamide (4.10 g. as sodium salt) in DMF (175 ml.) were heated at 110 for 3 hours. The product was filtered, the solvent evaporated in vacuo, and the residue taken up in water (100 ml.). A small insoluble residue of unreacted sulfonamide (500 mg., 7.3%) remained. The pH of the solution was adjusted to 8 with 10% aqueous acetic acid and the resulting precipitate was filtered off. The filtrate was acidified with 10% aqueous acetic acid to yield crude 1-(p-toluenesulfonyl)-3-n-butyl-urea (1.8 g., 18%). One recrystallization gave a sample m.p. 126-128 (i-r identical with authentic sample). |