Details of the Drug

General Information of Drug (ID: DM02AWV)

Drug Name

Tolbutamide

Synonyms

Aglicid; Arcosal; Arkozal; Artosin; Artozin; Beglucin; Butamid; Butamide; Butamidum; Diaben; Diabesan; Diabetamid; Diabetol; Diabuton; Diasulfon; Diaval; Dirastan; Dolipol; Drabet; Glyconon; Ipoglicone; Mobenol; Orabet; Oralin; Oramide; Orezan; Orinase; Orinaz; Oterben; Pramidex; Rastinon; Restinon; Tarasina; Tolbet;Tolbusal; Tolbutamid; Tolbutamida; Tolbutamidum; Tolbutone; Toluina; Tolumid; Toluran; Toluvan; Tolylsulfonylbutylurea; Willbutamide; Apotex Brand of Tolbutamide; Aventis Brand of Tolbutamide; BerlinChemie Brand of Tolbutamide; Butamide Brand of Tolbutamide; Hoechst Brand of Tolbutamide; Pfizer Brand of Tolbutamide; TOLBUTAMIDE USP; Tolbutamide Aventis Brand; Tolbutamide Butamide Brand; Tolbutamide Hoechst Brand; Tolbutamide Pfizer Brand; Valdecasas Brand of Tolbutamide; Yamanouchi Brand of Tolbutamide; D 860; HLS 831; T 0891; U 2043; Apo-Tolbutamide; Berlin-Chemie Brand of Tolbutamide; Novo-Butamide; Orinase (TN); Sk-tolbutamide; Tol-Tab; Tolbutamida [INN-Spanish]; Tolbutamidum [INN-Latin]; Tolbutamide [INN:BAN:JAN]; R.A.N. Brand of Tolbutamide; Tolbutamid R.A.N.; Tolbutamide (JP15/USP/INN); N-4-Methylbenzolsulfonyl-N-butylurea; N-4-(Methylbenzolsulfonyl)-n-butylurea; N-Butyl-N'-p-toluenesulfonylurea; N-n-Butyl-N'-tosylurea; N-(4-Methylbenzenesulfonyl)-N'-butylurea; N-(4-Methylphenylsulfonyl)-N'-butylurea; N-(p-Tolylsulfonyl)-N'-butylcarbamide; N-Butyl-N'-(4-methylphenylsulfonyl)urea; N-Butyl-N'-(p-tolylsulfonyl)urea; N-Butyl-N'-toluene-p-sulfonylurea; N-(p-tolylsulfonyl)-N'-n-butylurea; 1-Butyl-3-(4-methylphenylsulfonyl)urea; 1-Butyl-3-(p-methylphenylsulfonyl)urea; 1-Butyl-3-(p-tolylsulfonyl)urea; 1-Butyl-3-(para-tolylsulfonyl) urea; 1-Butyl-3-tosylurea; 1-butyl-3-(4-methylphenyl)sulfonylurea; 1-p-Toluenesulfonyl-3-butylurea; 3-(p-Tolyl-4-sulfonyl)-1-butylurea; 3-(p-tolylsulfonyl)-1-butylurea; 3-[p-Tolyl-4-sulfonyl]-1-butylurea

Indication

Disease Entry	ICD 11	Status	REF
Advanced cancer	2A00-2F9Z	Approved	[1]
Non-insulin dependent diabetes	5A11	Approved	[2]
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Therapeutic Class

Hypoglycemic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

270.35

Logarithm of the Partition Coefficient (xlogp)

2.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Bioavailability: 85% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 0.21 mL/min/kg [5]
Elimination: 0% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 7 hours [5]
Metabolism: The drug is metabolized via the liver []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 123.17236 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.05% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.12 L/kg [5]
Water Solubility: The ability of drug to dissolve in water is measured as 0.109 mg/mL [3]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Bone marrow failure	Not Available	ABCC8	OTCWQ54I	[7]
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Chemical Identifiers

Formula: C12H18N2O3S
IUPAC Name: 1-butyl-3-(4-methylphenyl)sulfonylurea
Canonical SMILES: 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)
InChIKey: JLRGJRBPOGGCBT-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5505
ChEBI ID: CHEBI:27999
CAS Number: 64-77-7
DrugBank ID: DB01124
TTD ID: D06OIV
VARIDT ID: DR00104
INTEDE ID: DR1612
ACDINA ID: D00685

Combinatorial Drugs (CBD)

Click to Jump to the Detailed CBD Information of This Drug

Repurposed Drugs (RPD)

Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
ATP-binding cassette transporter C8 (ABCC8)	TTP835K	ABCC8_HUMAN	Blocker	[8]
ATP-binding cassette transporter C9 (ABCC9)	TTEF5MJ	ABCC9_HUMAN	Blocker	[8]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Sulfonylurea receptor 1 (ABCC8)	DTI58LU	ABCC8_HUMAN	Substrate	[9]
Sulfonylurea receptor 2 (ABCC9)	DT3JCE6	ABCC9_HUMAN	Substrate	[9]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[10]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[11]
Cytochrome P450 2C8 (CYP2C8)	DES5XRU	CP2C8_HUMAN	Substrate	[12]
Cytochrome P450 2C18 (CYP2C18)	DEZMWRE	CP2CI_HUMAN	Substrate	[13]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Albumin (ALB)	OTVMM513	ALBU_HUMAN	Protein Interaction/Cellular Processes	[14]
ATP-binding cassette sub-family C member 8 (ABCC8)	OTCWQ54I	ABCC8_HUMAN	Drug Response	[7]
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[15]
ATP-sensitive inward rectifier potassium channel 11 (KCNJ11)	OTPUUELV	KCJ11_HUMAN	Gene/Protein Processing	[16]
Cytochrome P450 2C19 (CYP2C19)	OTFMJYYE	CP2CJ_HUMAN	Biotransformations	[17]
Cytochrome P450 2C8 (CYP2C8)	OTHCWT42	CP2C8_HUMAN	Biotransformations	[18]
Insulin (INS)	OTZ85PDU	INS_HUMAN	Protein Interaction/Cellular Processes	[19]
Programmed cell death protein 4 (PDCD4)	OTZ6NXUX	PDCD4_HUMAN	Gene/Protein Processing	[20]
Transmembrane protease serine 2 (TMPRSS2)	OTN44YQ5	TMPS2_HUMAN	Gene/Protein Processing	[21]
Tumor necrosis factor alpha-induced protein 3 (TNFAIP3)	OTVLI4DD	TNAP3_HUMAN	Gene/Protein Processing	[20]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Advanced cancer

ICD Disease Classification

2A00-2F9Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
ATP-binding cassette transporter C9 (ABCC9)	DTT	ABCC9	6.51E-01	0.02	0.06
ATP-binding cassette transporter C9 (ABCC9)	DTT	ABCC9	8.46E-01	0.02	0.22
Sulfonylurea receptor 1 (ABCC8)	DTP	SUR1	2.48E-02	1.04E-01	3.79E-01
Sulfonylurea receptor 1 (ABCC8)	DTP	SUR1	6.55E-02	1.00E-01	4.41E-01
Sulfonylurea receptor 2 (ABCC9)	DTP	SUR2	6.51E-01	2.26E-02	6.23E-02
Sulfonylurea receptor 2 (ABCC9)	DTP	SUR2	8.46E-01	2.42E-02	2.17E-01
Cytochrome P450 2C18 (CYP2C18)	DME	CYP2C18	8.28E-05	1.33E-01	1.20E+00
Cytochrome P450 2C18 (CYP2C18)	DME	CYP2C18	1.51E-03	-1.83E-01	-2.01E-01
Cytochrome P450 2C8 (CYP2C8)	DME	CYP2C8	2.41E-01	3.17E-02	2.29E-01
Cytochrome P450 2C8 (CYP2C8)	DME	CYP2C8	5.67E-01	5.11E-02	1.35E-01
Mephenytoin 4-hydroxylase (CYP2C19)	DME	CYP2C19	4.79E-03	1.32E-01	7.85E-01
Mephenytoin 4-hydroxylase (CYP2C19)	DME	CYP2C19	1.82E-01	-1.71E-02	-9.86E-02
Cytochrome P450 2C9 (CYP2C9)	DME	CYP2C9	7.33E-02	5.59E-02	2.99E-01
Cytochrome P450 2C9 (CYP2C9)	DME	CYP2C9	5.65E-03	-7.28E-02	-1.24E-01

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Tolbutamide (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Sodium bicarbonate	DMMU6BJ	Moderate	Decreased absorption of Tolbutamide due to altered gastric pH caused by Sodium bicarbonate.	Acidosis [5C73]	[22]
Tromethamine	DMOBLGK	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Tolbutamide caused by Tromethamine mediated altered urine pH.	Acidosis [5C73]	[23]
Arn-509	DMT81LZ	Moderate	Increased metabolism of Tolbutamide caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[24]
Oxymetholone	DMFXUT8	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Oxymetholone.	Aplastic anaemia [3A70]	[25]
Clarithromycin	DM4M1SG	Moderate	Increased plasma concentration of Tolbutamide and Clarithromycin due to competitive binding of plasma proteins.	Bacterial infection [1A00-1C4Z]	[26]
Alpelisib	DMEXMYK	Moderate	Increased metabolism of Tolbutamide caused by Alpelisib mediated induction of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[27]
Fenofibric acid	DMGO2MC	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Fenofibric acid.	Cardiovascular disease [BA00-BE2Z]	[28]
Anisindione	DM2C48U	Moderate	Increased plasma concentration of Tolbutamide and Anisindione due to competitive binding of plasma proteins.	Coagulation defect [3B10]	[29]
Osilodrostat	DMIJC9X	Moderate	Decreased metabolism of Tolbutamide caused by Osilodrostat mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[30]
Ivacaftor	DMZC1HS	Moderate	Decreased metabolism of Tolbutamide caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[31]
MK-8228	DMOB58Q	Moderate	Increased metabolism of Tolbutamide caused by MK-8228 mediated induction of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[32]
Vortioxetine	DM6F1PU	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Vortioxetine.	Depression [6A70-6A7Z]	[28]
Isocarboxazid	DMAF1NB	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Isocarboxazid.	Depression [6A70-6A7Z]	[28]
Escitalopram	DMFK9HG	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Escitalopram.	Depression [6A70-6A7Z]	[28]
SODIUM CITRATE	DMHPD2Y	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Tolbutamide caused by SODIUM CITRATE mediated altered urine pH.	Discovery agent [N.A.]	[23]
Brivaracetam	DMSEPK8	Minor	Decreased metabolism of Tolbutamide caused by Brivaracetam mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[24]
Sulfinpyrazone	DMEV954	Moderate	Decreased metabolism of Tolbutamide caused by Sulfinpyrazone.	Gout [FA25]	[33]
Rifapentine	DMCHV4I	Moderate	Increased metabolism of Tolbutamide caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[34]
Etravirine	DMGV8QU	Moderate	Decreased metabolism of Tolbutamide caused by Etravirine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[35]
Captopril	DM458UM	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Captopril.	Hypertension [BA00-BA04]	[28]
Sodium acetate anhydrous	DMH21E0	Minor	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Tolbutamide caused by Sodium acetate anhydrous mediated altered urine pH.	Hypo-osmolality/hyponatraemia [5C72]	[23]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Tolbutamide caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[36]
Hydroxychloroquine	DMSIVND	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Hydroxychloroquine.	Malaria [1F40-1F45]	[28]
Sulphadoxine	DMZI2UF	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Sulphadoxine.	Malaria [1F40-1F45]	[25]
Vemurafenib	DM62UG5	Moderate	Decreased metabolism of Tolbutamide caused by Vemurafenib mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[36]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Tolbutamide caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[36]
Mecasermin	DM1O3BY	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Mecasermin.	Multiple structural anomalies syndrome [LD2F]	[28]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Tolbutamide caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[24]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Tolbutamide caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[37]
Rasagiline	DM3WKQ4	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Rasagiline.	Parkinsonism [8A00]	[28]
Choline salicylate	DM8P137	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Choline salicylate.	Postoperative inflammation [1A00-CA43]	[25]
Lonafarnib	DMGM2Z6	Moderate	Decreased metabolism of Tolbutamide caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[38]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Tolbutamide caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[39]
Salsalate	DM13P4C	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Salsalate.	Rheumatoid arthritis [FA20]	[28]
Ifosfamide	DMCT3I8	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Ifosfamide.	Solid tumour/cancer [2A00-2F9Z]	[28]
Methyltestosterone	DMWLFGO	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Methyltestosterone.	Solid tumour/cancer [2A00-2F9Z]	[28]
Lusutrombopag	DMH6IKO	Moderate	Decreased clearance of Tolbutamide due to the transporter inhibition by Lusutrombopag.	Thrombocytopenia [3B64]	[37]
Pramlintide	DM0EZ9Q	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Pramlintide.	Type-1/2 diabete [5A10-5A11]	[28]
Olsalazine	DMZW9HA	Moderate	Increased risk of hypoglycemia by the combination of Tolbutamide and Olsalazine.	Ulcerative colitis [DD71]	[28]
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⏷ Show the Full List of 39 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Tolbutamide 500 mg tablet	500 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Tolbutamide FDA Label
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