Tolbutamide

Details

• Internal ID: fc36df61-ba18-4e15-b0f0-05d5fae8cc8d
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzenesulfonamides
• IUPAC Name: 1-butyl-3-(4-methylphenyl)sulfonylurea
• SMILES (Canonical): CCCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)C
• SMILES (Isomeric): CCCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)C
• InChI: InChI=1S/C12H18N2O3S/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)
• InChI Key: JLRGJRBPOGGCBT-UHFFFAOYSA-N
• Popularity: 10,895 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₈N₂O₃S
• Molecular Weight: 270.35 g/mol
• Exact Mass: 270.10381361 g/mol
• Topological Polar Surface Area (TPSA): 83.60 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.78
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 64-77-7
• Orinase
• Arkozal
• Willbutamide
• Butamide
• Diabetamid
• Ipoglicone
• Glyconon
• Rastinon
• Tolbutamid
• Aglicid
• Artosin
• Diaben
• Tolumid
• 1-Butyl-3-tosylurea
• Diasulfon
• Artozin
• Butamid
• Diabetol
• Diabuton
• Dirastan
• Dolipol
• Mobenol
• Oterben
• Pramidex
• Tolbusal
• Toluina
• Toluvan
• Tolylsulfonylbutylurea
• 1-Butyl-3-(p-tolylsulfonyl)urea
• Drabet
• Orabet
• Oralin
• Orezan
• Orinaz
• Tolbutamidum
• Sk-tolbutamide
• N-(Butylcarbamoyl)-4-methylbenzenesulfonamide
• N-n-Butyl-N'-tosylurea
• Tolbutamida
• 1-p-Toluenesulfonyl-3-butylurea
• 1-Butyl-3-(p-methylphenylsulfonyl)urea
• Arcosal
• Beglucin
• Butamidum
• Diabesan
• N-Butyl-N'-(p-tolylsulfonyl)urea
• Tarasina
• Tolbutone
• Tolbet
• N-Butyl-N'-p-toluenesulfonylurea
• 3-(p-Tolyl-4-sulfonyl)-1-butylurea
• N-(4-Methylphenylsulfonyl)-N'-butylurea
• N-Butyl-N'-(4-methylphenylsulfonyl)urea
• HLS 831
• N-(4-Methylbenzenesulfonyl)-N'-butylurea
• N-(Sulfonyl-p-methylbenzene)-N'-N-butylurea
• Orinase (TN)
• Tolumide
• N-(p-Tolylsulfonyl)-N'-butylcarbamide
• NCI-C01763
• N-4-Methylbenzolsulfonyl-N-butylurea
• Urea, 1-butyl-3-(p-tolylsulfonyl)-
• D 860
• Tolbutamidum [INN-Latin]
• 1-butyl-3-(4-methylphenyl)sulfonylurea
• 1-Butyl-3-(4-methylphenylsulfonyl)urea
• Benzenesulfonamide, N-[(butylamino)carbonyl]-4-methyl-
• Tolbutamida [INN-Spanish]
• N-Butyl-N'-toluene-p-sulfonylurea
• CCRIS 592
• N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide
• N-4-(Methylbenzolsulfonyl)-n-butylurea
• HSDB 3393
• N-(p-Methylbenzenesulfonyl)-N'-butylurea
• UNII-982XCM1FOI
• EINECS 200-594-3
• 982XCM1FOI
• MFCD00027169
• NSC 23813
• NSC-23813
• U 2043
• BRN 1984428
• 3-butyl-1-(4-methylbenzenesulfonyl)urea
• DTXSID8021359
• CHEBI:27999
• N-(Sulfonyl-p-methylbenzene)-N'-butylurea
• 3-butyl-1-[(4-methylbenzene)sulfonyl]urea
• Benzenesulfonamide, N-((butylamino)carbonyl)-4-methyl-
• NSC-87833
• 1-BUTYL-3-(4-METHYLBENZENESULFONYL)UREA
• CHEMBL782
• N-((Butylamino)carbonyl)-4-methylbenzenesulfonamide
• MLS000028399
• DTXCID801359
• Tolbutamide [USP:INN:BAN:JAN]
• 4-11-00-00396 (Beilstein Handbook Reference)
• CAS-64-77-7
• toluran
• NCGC00015999-10
• SMR000058363
• Tolbutamide form I^L^
• Tolbutamidum (INN-Latin)
• Tolbutamida (INN-Spanish)
• TOLBUTAMIDE (MART.)
• TOLBUTAMIDE [MART.]
• TOLBUTAMIDE (USP-RS)
• TOLBUTAMIDE [USP-RS]
• TOLBUTAMIDE (EP MONOGRAPH)
• Tolbutamide (USP:INN:BAN:JAN)
• TOLBUTAMIDE [EP MONOGRAPH]
• TOLBUTAMIDE (USP MONOGRAPH)
• TOLBUTAMIDE [USP MONOGRAPH]
• SR-01000003059
• tolbutamide IL
• tolbutamide III
• Prestwick_471
• Spectrum_000447
• Tolbutamide form I^H^
• Opera_ID_112
• TOLBUTAMIDE [MI]
• Prestwick0_000190
• Prestwick1_000190
• Prestwick2_000190
• Prestwick3_000190
• Spectrum2_001210
• Spectrum3_000599
• Spectrum4_000358
• Spectrum5_001272
• Lopac-T-0891
• TOLBUTAMIDE [INN]
• TOLBUTAMIDE [JAN]
• N-n-Butyl-N''-tosylurea
• TOLBUTAMIDE [HSDB]
• WLN: 4MVMSWR D1
• T 0891
• TOLBUTAMIDE [VANDF]
• NCIOpen2_009592
• BIDD:PXR0179
• CBiol_001920
• Lopac0_001154
• SCHEMBL15918
• BSPBio_000119
• BSPBio_001507
• BSPBio_002078
• KBioGR_000227
• KBioGR_000795
• KBioGR_002275
• KBioSS_000227
• KBioSS_000927
• KBioSS_002276
• TOLBUTAMIDE [WHO-DD]
• TOLBUTAMIDE [WHO-IP]
• MLS001148399
• MLS002152944
• DivK1c_000341
• SPECTRUM1500581
• SPBio_001000
• SPBio_002040
• BPBio1_000131
• GTPL6848
• Tolbutamide (JP17/USP/INN)
• Tolbutamide, analytical standard
• HMS501B03
• KBio1_000341
• KBio2_000227
• KBio2_000927
• KBio2_002275
• KBio2_002795
• KBio2_003495
• KBio2_004843
• KBio2_005363
• KBio2_006063
• KBio2_007411
• KBio3_000453
• KBio3_000454
• KBio3_001578
• KBio3_002755
• A10BB03
• TOLBUTAMIDE [ORANGE BOOK]
• V04CA01
• cMAP_000008
• NINDS_000341
• Bio1_000206
• Bio1_000695
• Bio1_001184
• Bio2_000227
• Bio2_000707
• HMS1361L09
• HMS1568F21
• HMS1791L09
• HMS1989L09
• HMS2089C17
• HMS2092M21
• HMS2095F21
• HMS2232H16
• HMS3259A08
• HMS3263H09
• HMS3402L09
• HMS3651N03
• HMS3712F21
• Pharmakon1600-01500581
• BCP09192
• HY-B0401
• NSC23813
• TOLBUTAMIDUM [WHO-IP LATIN]
• N-Butyl-N''-(p-tolylsulfonyl)urea
• Tox21_110279
• Tox21_201612
• Tox21_302795
• Tox21_501154
• BDBM50027886
• CCG-39141
• NSC757354
• NSC813220
• s2443
• 1-Butyl-3-(para-tolylsulfonyl)-urea
• AKOS015894999
• Tox21_110279_1
• DB01124
• LP01154
• NC00543
• NSC-757354
• NSC-813220
• SDCCGSBI-0051121.P004
• Tolbutamide 1.0 mg/ml in Acetonitrile
• IDI1_000341
• IDI1_033977
• N-(n-Butyl)-N'-p-toluene-sulfonylurea
• NCGC00015999-01
• NCGC00015999-02
• NCGC00015999-03
• NCGC00015999-04
• NCGC00015999-05
• NCGC00015999-06
• NCGC00015999-07
• NCGC00015999-08
• NCGC00015999-09
• NCGC00015999-11
• NCGC00015999-12
• NCGC00015999-13
• NCGC00015999-14
• NCGC00015999-15
• NCGC00015999-16
• NCGC00015999-17
• NCGC00015999-19
• NCGC00015999-20
• NCGC00015999-29
• NCGC00022721-03
• NCGC00022721-04
• NCGC00022721-05
• NCGC00022721-06
• NCGC00022721-07
• NCGC00022721-08
• NCGC00022721-09
• NCGC00022721-10
• NCGC00256548-01
• NCGC00259161-01
• NCGC00261839-01
• AC-12490
• AS-14136
• SY014891
• N-(4-Methylphenylsulfonyl)-N''-butylurea
• N-Butyl-N''-(4-methylphenylsulfonyl)urea
• SBI-0051121.P003
• AB00052110
• EU-0101154
• FT-0603265
• N-(P-TOLYLSULFONYL)N'-BUTYLCARBAMIDE
• SW196681-3
• T3690
• BIM-0051121.0001
• C07148
• D00380
• D87667
• EN300-124678
• U-2043
• AB00052110-16
• AB00052110_17
• AB00052110_18
• N'-4-METHYLBENZENESULFONYL-N''-BUTYLUREA
• Tolbutamide, VETRANAL(TM), analytical standard
• A834879
• Q414275
• SR-01000003059-2
• SR-01000003059-4
• SR-01000003059-7
• W-104820
• BRD-K85119730-001-06-5
• BRD-K85119730-001-17-2
• N'-butyl-N-(p-tolylsulfonyl)carbamimidate;Tolbutamide
• Z44591715
• Tolbutamide, European Pharmacopoeia (EP) Reference Standard
• 1-(([(Butylamino)carbonyl]amino)sulfonyl)-4-methylbenzene #
• Tolbutamide, United States Pharmacopeia (USP) Reference Standard

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9858	98.58%
Caco-2	+	0.7455	74.55%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5241	52.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8448	84.48%
P-glycoprotein inhibitior	-	0.9566	95.66%
P-glycoprotein substrate	-	0.7296	72.96%
CYP3A4 substrate	-	0.7748	77.48%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.7587	75.87%
CYP3A4 inhibition	-	0.9613	96.13%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9504	95.04%
CYP1A2 inhibition	-	0.9443	94.43%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.8810	88.10%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6100	61.00%
Carcinogenicity (trinary)	Non-required	0.7012	70.12%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9540	95.40%
Skin irritation	+	0.6544	65.44%
Skin corrosion	-	0.9268	92.68%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4493	44.93%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8554	85.54%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7140	71.40%
Acute Oral Toxicity (c)	III	0.7713	77.13%
Estrogen receptor binding	-	0.8740	87.40%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	-	0.5371	53.71%
Glucocorticoid receptor binding	-	0.8786	87.86%
Aromatase binding	-	0.6051	60.51%
PPAR gamma	-	0.7376	73.76%
Honey bee toxicity	-	0.9942	99.42%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9654	96.54%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	223.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.40%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.34%	95.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	93.07%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	92.96%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	92.86%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.08%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.66%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.45%	94.33%
CHEMBL255	P29275	Adenosine A2b receptor	84.98%	98.59%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.79%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.58%	99.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	80.38%	92.08%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5505
• LOTUS: LTS0119487
• wikiData: Q414275