TOLBUTAMIDE SODIUM

First approved in 1957

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H17N2O3S.Na
Molecular Weight	292.33
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CCCCNC(=O)[N-]S(=O)(=O)C1=CC=C(C)C=C1

InChI

InChIKey=QKHDBRQBSNZFAK-UHFFFAOYSA-M

InChI=1S/C12H18N2O3S.Na/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11;/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C12H18N2O3S
Molecular Weight	270.348
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB01124
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/tolbutamide.html

Tolbutamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It is structurally similar to acetohexamide, chlorpropamide and tolazamide and belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas lower blood glucose in patients with NIDDM by directly stimulating the acute release of insulin from functioning beta cells of pancreatic islet tissue by an unknown process that involves a sulfonylurea receptor (receptor 1) on the beta cell. Sulfonylureas inhibit the ATP-potassium channels on the beta cell membrane and potassium efflux, which results in depolarization and calcium influx, calcium-calmodulin binding, kinase activation, and release of insulin-containing granules by exocytosis, an effect similar to that of glucose.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
K-ATP channels, Rattus norvegicus 2 Target ID: K-ATP channels, Rattus norvegicus Sources: https://www.ncbi.nlm.nih.gov/pubmed/11523905	Inhibitor 8504		0.8 µM [IC50]
Sulfonylurea receptor 1, Kir6.2 13 Target ID: CHEMBL2096972 Sources: http://www.drugbank.ca/drugs/DB01124	Inhibitor 8504		1.15 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: https://www.drugs.com/dosage/tolbutamide.html	Primary		Approved 8583	Tolbutamide Approved Use Tolbutamide tablets are indicated as an adjunct to diet to lower the blood glucose in patients with non-insulin-dependent diabetes mellitus (type II) whose hyperglycemia cannot be controlled by diet alone. Launch Date 1989

C_max

Value	Dose	Co-administered	Analyte	Population
51.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9021442/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		TOLBUTAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
998.42 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9021442/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		TOLBUTAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
418 min EXPERIMENT https://link.springer.com/article/10.1007%2FBF00614021	20 mg/kg bw single, intravenous dose: 20 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		TOLBUTAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
5% EXPERIMENT https://link.springer.com/article/10.1007%2FBF00614021	20 mg/kg bw single, intravenous dose: 20 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		TOLBUTAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT2B10 31 UGT1A6 136 UGT2B7 197 UGT1A1 246 UGT1A4 98 OATP1B1 1079	CYP2C19 1119 OAT2 125 P-gp 2052

Drug as perpetrator

Target	Modality	Activity
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23248200/ Page: 8.0	not significant [IC50 >100 uM]
UGT1A6 171	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20939765/ Page: 7.0	weak [IC50 281 uM]
UGT1A1 303	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20939765/ Page: 7.0	weak [IC50 >300 uM]
UGT1A4 100	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20939765/ Page: 7.0	weak [IC50 >300 uM]
UGT2B10 33	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20939765/ Page: 7.0	weak [IC50 >300 uM]
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20939765/ Page: 7.0	weak [IC50 >300 uM]

Drug as victim

Target	Modality	Activity
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9811164/	no
CYP2C19 1119	substrate 4014 Sources: https://dmd.aspetjournals.org/content/28/3/354.long	yes
CYP2C9 1193	substrate 4014 Sources: https://dmd.aspetjournals.org/content/28/3/354.long	yes
OAT2 125	substrate 4014 Sources: https://jpet.aspetjournals.org/content/jpet/early/2018/01/11/jpet.117.245951.full.pdf?with-ds=yes#page=3 Page: 3.0	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY564984	https://www.001chemical.com/chem/64-77-7
3B Scientific (Wuhan) Corp	3B2-0418	http://www.3bsc.com/index/pro_info.php?id=19774
AA Blocks	AA00E9FG	http://www.aablocks.com/goods/Goods/detail?id=AA00E9FG
Aaron Chemicals	AR00EA78	http://www.aaronchem.com/64-77-7
abcr GmbH	AB132954	http://www.abcr.com/shop/en/AB132954
AbMole Bioscience	M3077	http://www.abmole.com/products/tolbutamide.html
Acadechem	ACDS-029217	http://www.acadechemical.com/product/103916
Achemo Scientific Limited	AC-14868	http://www.achemo.com/product_view.asp?ID=4758
AHH Chemical co.,ltd	API-1399	http://www.ahhchemical.com/product/API-1399.html
AK Scientific, Inc. (AKSCI)	J10018	http://www.aksci.com/item_detail.php?cat=J10018
AK Scientific, Inc. (AKSCI)	K045	http://www.aksci.com/item_detail.php?cat=K045
Alfa Aesar	B21698	https://www.alfa.com/en/catalog/B21698/
Alfa Chemistry	AP64777-A	https://reagents.alfa-chemistry.com/product/tolbutamide-cas-64-77-7-14588.html
Alfa Chemistry	AP64777-B	https://reagents.alfa-chemistry.com/product/tolbutamide-cas-64-77-7-14589.html
Allbio Pharm Co., Ltd	AD02724	http://www.allbiopharm.com/product/n/AD02724
Alsachim	2985	http://www.alsachim.com/product-C4057-glo.bal-view.html
ApexBio Technology	B2194	http://www.apexbt.com/tolbutamide-28680.html
Ark Pharm	AK115688	http://www.arkpharminc.com/products/64-77-7.html
Aurum Pharmatech LLC	NE30724	http://www.Aurumpharmatech.com/Product/ProductDetails/NE30724
Avantor Inc	101096-316	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-316
BenchChem	B545540	https://www.benchchem.com/product/b545540
BioChemPartner	BCP09192	http://www.biochempartner.com/64-77-7-BCP09192
BioCrick	BCC5001	http://www.biocrick.com/Tolbutamide-BCC5001.html
BioSynth	W-104820	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-104820.html
BLD Pharm	BD154332	http://www.bldpharm.com/products/64-77-7.html
Capot Chemical	18102	http://www.capotchem.com/en/18102.htm
Capot Chemical	PubChem18102	http://www.capotchem.com/en/18102.htm
Chem Scene	CS-2500	http://www.chemscene.com/64-77-7.html
ChemMol	30102245	http://www.chemmol.com/chemmol/30102245.html
ChemMol	49410146	http://www.chemmol.com/chemmol/49410146.html
Chemspace	CSSB00000696203	https://chem-space.com/CSSB00000696203
Clearsynth	CS-T-44523	https://www.clearsynth.com/en/CST44523.html
CSNpharm	CSN12105	https://www.csnpharm.com/products/tolbutamide.html
DC Chemicals	DC9023	http://www.dcchemicals.com/product_show-Tolbutamide.html
Debye Scientific	DB-054728	http://www.debyesci.com/cas_64-77-7.html
Enamine	Z44591715	https://www.enaminestore.com/catalog/Z44591715
Finetech	FT-0603265	http://www.finetechnology-ind.com/prod/detail/pub/64-77-7.html
Glentham Life Sciences	GP0797	http://www.glentham.com/products/product/GP0797/
Hairui	HR124945	http://www.hairuichem.com/en/product/64-77-7.html
Lab Network	LN00235930	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00235930
LGC Standards	DRE-C17589900	https://www.lgcstandards.com/US/en/p/DRE-C17589900
LGC Standards	LGCAMP1089.00-11	https://www.lgcstandards.com/US/en/p/LGCAMP1089.00-11
LGC Standards	LGCFOR1089.00	https://www.lgcstandards.com/US/en/p/LGCFOR1089.00
LGC Standards	MM1089.00	https://www.lgcstandards.com/US/en/p/MM1089.00
mcule	MCULE-9720356859	https://mcule.com/MCULE-9720356859/
MedChem Express	HY-B0401	https://www.medchemexpress.com/Tolbutamide.html
Molcore	MC564984	https://www.molcore.com/product/64-77-7
MuseChem	I004440	https://www.musechem.com/product/I004440.html
Oakwood	47218	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=41080&ExtHyperLink=1
Selleck Chemicals	S2443	http://www.selleckchem.com/products/tolbutamide.html
Sigma-Aldrich	1670003_USP	https://www.sigmaaldrich.com/catalog/product/usp/1670003?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	46968_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/46968?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	T0891_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/t0891?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	T1700000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/t1700000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S013560	http://www.sinfoobiotech.com/product/1016958
Smolecule	S545540	http://www.smolecule.com/products/s545540
THE BioTek	bt-285914	https://www.thebiotek.com/product/inhibitors/bt-285914
VladaChem	VL144721	https://www.vladachem.com/product.php?products=64-77-7
VladaChem	VL271328-100G	https://www.vladachem.com/product.php?products=64-77-7

PubMed

Title	Date	PubMed
Minipig cytochrome P450 3A, 2A and 2C enzymes have similar properties to human analogs.	2001	11737866
Effects of nicorandil administration on survival rate and arrhythmias during reperfusion in anesthetized rabbits.	2001	11598418
Phorbol ester impairs electrical excitation of rat pancreatic beta-cells through PKC-independent activation of KATP channels.	2001	11560763
Drug interactions with irbesartan.	2001	11523726
Interaction of sulfonylurea-conjugated polymer with insulinoma cell line of MIN6 and its effect on insulin secretion.	2001 Apr	11426400
Effect of leptin on insulin, glugacon and somatostatin secretion in the perfused rat pancreas.	2001 Apr	11383923
Changes in the dissolution of tolbutamide by a traditional Chinese medicine, Sho-saiko-to (Xiao Chaihu Tang).	2001 Apr	11305604
Uncoupling protein 2: a possible link between fatty acid excess and impaired glucose-induced insulin secretion?	2001 Apr	11289045
ION-pair liquid chromatography technique for the estimation of metformin in its multicomponent dosage forms.	2001 Apr	11274860
Sulfonylurea receptors inhibit the epithelial sodium channel (ENaC) by reducing surface expression.	2001 Aug	11512032
An ATP-sensitive K(+) conductance in dissociated neurones from adult rat intracardiac ganglia.	2001 Aug 1	11483702
Desensitization of insulin secretory response to imidazolines, tolbutamide, and quinine. II. Electrophysiological and fluorimetric studies.	2001 Dec 15	11755123
Hyperinsulinism of infancy: the regulated release of insulin by KATP channel-independent pathways.	2001 Feb	11272144
Effects of sho-saiko-to (xiao chai hu tang), a Chinese traditional medicine, on the gastric function and absorption of tolbutamide in rats.	2001 Feb	11218729
Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors.	2001 Jan	11225565
Is diclofenac a valuable CYP2C9 probe in humans?	2001 Jan-Feb	11294368
Longitudinal changes in body fat in African American and Caucasian children: influence of fasting insulin and insulin sensitivity.	2001 Jul	11443186
In vivo effect of clarithromycin on multiple cytochrome P450s.	2001 Jul	11408369
Swelling-induced changes in cytosolic [Ca2++] in insulin-secreting cells: a role in regulatory volume decrease?	2001 Jul 5	11476951
Free radical-mediated tolbutamide desensitization of K+ATP channels in rat pancreatic beta-cells.	2001 Jun	11523905
Tolbutamide stimulation of pancreatic beta-cells involves both cell recruitment and increase in the individual Ca(2+) response.	2001 Jun	11399675
Establishment of the transformants expressing human cytochrome P450 subtypes in HepG2, and their applications on drug metabolism and toxicology.	2001 Jun	11377097
Hypoglycemic effect of Hibiscus rosa sinensis L. leaf extract in glucose and streptozotocin induced hyperglycemic rats.	2001 Mar	11495291
Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline.	2001 Mar	11465391
Characterization of glass solutions of poorly water-soluble drugs produced by melt extrusion with hydrophilic amorphous polymers.	2001 Mar	11291745
Role of common sequence variants in insulin secretion in familial type 2 diabetic kindreds: the sulfonylurea receptor, glucokinase, and hepatocyte nuclear factor 1alpha genes.	2001 Mar	11289470
Protein kinase C-dependent and -independent inhibition of Ca(2+) influx by phorbol ester in rat pancreatic beta-cells.	2001 Mar	11282458
Measurements of cytoplasmic Ca2+ in islet cell clusters show that glucose rapidly recruits beta-cells and gradually increases the individual cell response.	2001 Mar	11246873
Interaction of stilbene disulphonates with cloned K(ATP) channels.	2001 Mar	11226127
Specific desensitization of sulfonylurea- but not imidazoline-induced insulin release after prolonged tolbutamide exposure.	2001 Mar 1	11239495
Complexation with tolbutamide modifies the physicochemical and tableting properties of hydroxypropyl-beta-cyclodextrin.	2001 Mar 14	11250099
Involvement of calmodulin in glucagon-like peptide 1(7-36) amide-induced inhibition of the ATP-sensitive K+ channel in mouse pancreatic beta-cells.	2001 May	11429650
In vitro evaluation of valproic acid as an inhibitor of human cytochrome P450 isoforms: preferential inhibition of cytochrome P450 2C9 (CYP2C9).	2001 Nov	11736863
Monoclonal antibodies specific and inhibitory to human cytochromes P450 2C8, 2C9, and 2C19.	2001 Nov	11602516
Quantification of beta-cell function during IVGTT in Type II and non-diabetic subjects: assessment of insulin secretion by mathematical methods.	2001 Oct	11692185
Clinical relevance of genetic polymorphisms in the human CYP2C subfamily.	2001 Oct	11678778
The effects of St John's wort (Hypericum perforatum) on human cytochrome P450 activity.	2001 Oct	11673747
Molecular modelling and 1H-NMR: ultimate tools for the investigation of tolbutamide: beta-cyclodextrin and tolbutamide: hydroxypropyl-beta-cyclodextrin complexes.	2001 Oct	11605649
Fasting glucose insulin ratio: a useful measure of insulin resistance in girls with premature adrenarche.	2001 Oct	11600513
Insulin activates ATP-sensitive K(+) channels in pancreatic beta-cells through a phosphatidylinositol 3-kinase-dependent pathway.	2001 Oct	11574397
Diabetogenic effect of cyclosporin A is mediated by interference with mitochondrial function of pancreatic B-cells.	2001 Oct	11562451
Effects of tolbutamide and N-benzoyl-D-phenylalanine (NBDP) on the regulation of [Ca2+]i oscillations in mouse pancreatic islets.	2001 Oct 1	11543727
Effect of Cirsium pascuarense on blood glucose levels of normoglycaemic and alloxan-diabetic mice.	2001 Sep	11536391
Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells.	2001 Sep	11504818
Mechanism-based inactivation of CYP2C11 by diclofenac.	2001 Sep	11502726
ATP-independent anoxic activation of ATP-sensitive K+ channels in dorsal vagal neurons of juvenile mice in situ.	2002	11801367
Novel properties of peptides derived from the sequence coded by exon 26A of human elastin.	2002 Feb	11809415
Triterpenes from Agarista mexicana as potential antidiabetic agents.	2002 Feb	11807966
S2' substrate specificity and the role of His110 and His111 in the exopeptidase activity of human cathepsin B.	2002 Feb 1	11802791
A key role for beta-cell cytosolic phospholipase A(2) in the maintenance of insulin stores but not in the initiation of insulin secretion.	2002 Jan	11756328

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Diabetes Type 2 Initial dose: 1 to 2 g orally once a day or in divided doses through the day -Adjust dose based on blood glucose response Maintenance dose: 0.25 to 3 g orally once a day or in divided doses through the day Maximum dose: 3 g per day

Route of Administration: Oral

In Vitro Use Guide

Insulin effects were eliminated in the presence of a ATP-dependent K+ (K(ATP)) channel antagonist tolbutamide (200 uM) in brain stem slices

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:54:08 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:08 GMT 2025`
Record UNII	E830VC49W5
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TOLBUTAMIDE SODIUM

Common Name

English

TOLBUTAMIDE SODIUM SALT

Preferred Name

English

TOLBUTAMIDE SODIUM SALT [MI]

Common Name

English

TOLBUTAMIDE SODIUM [ORANGE BOOK]

Common Name

English

TOLBUTAMIDE SODIUM [VANDF]

Common Name

English

1-BUTYL-3-(P-TOLYLSULFONYL)UREA, MONOSODIUM SALT

Common Name

English

BENZENESULFONAMIDE, N-((BUTYLAMINO)CARBONYL)-4-METHYL-, MONOSODIUM SALT

Common Name

English

Tolbutamide sodium [WHO-DD]

Common Name

English

SODIUM TOLBUTAMIDE

Common Name

English

ORINASE DIAGNOSTIC

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97936