Tolazamide

Tolazamide
Clinical data


AHFS/Drugs.com	Monograph
MedlinePlus	a682482
License data	US FDA: Tolazamide
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	A10BB05 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	?
Metabolism	metabolized in the liver to active metabolites
Biological half-life	7 hours
Excretion	Renal (85%) and fecal (7%)
Identifiers
IUPAC name N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide
CAS Number	1156-19-0
PubChem (CID)	5503
IUPHAR/BPS	6847
DrugBank	DB00839^Y
ChemSpider	5302^Y
UNII	9LT1BRO48Q^Y
KEGG	D00379^Y
ChEBI	CHEBI:9613
ChEMBL	CHEMBL817^Y
ECHA InfoCard	100.013.262
Chemical and physical data
Formula	C₁₄H₂₁N₃O₃S
Molar mass	311.401 g/mol
3D model (Jmol)	Interactive image
SMILES O=S(=O)(c1ccc(cc1)C)NC(=O)NN2CCCCCC2
InChI InChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18)^Y Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N^Y
(verify)

Tolazamide is an oral blood glucose lowering drug used for people with Type 2 diabetes. It is part of the sulfonylurea family (ATC A10BB).

Synthesis

para-Toluenesulfonamide is converted to its carbamate with ethyl chloroformate in the presence of a base. Heating that intermediate with azepane leads to the displacement of the ethoxy group and the formation of tolazemide:^[1]

Tolazemide synthesis:^[2] U.S. Patent 3,063,903 GB 887886 DE 1196200

References

↑ Wright, J. B.; Willette, R. E. (1962). J. Med. Chem. 5 (4): 815–822. doi:10.1021/jm01239a016. Missing or empty |title= (help)
↑ Wright, J. B.; Willette, R. E. (1962). "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of medicinal and pharmaceutical chemistry. 91: 815–22. PMID 14056414.

External links

NIH/Medline

Oral anti-diabetic drugs, insulins and insulin analogs, and other drugs used in diabetes (A10)

Insulin

Sensitizers

Biguanides	Buformin^‡ Metformin^# Phenformin^‡

TZDs/"glitazones" (PPAR)	Ciglitazone^§ Darglitazone^§ Englitazone^§ Lobeglitazone Netoglitazone^§ Pioglitazone Rivoglitazone^† Rosiglitazone Troglitazone^‡

Dual PPAR agonists	Aleglitazar^† Muraglitazar^§ Saroglitazar Tesaglitazar^§

Secretagogues

K⁺_ATP

Sulfonylureas	1st generation: Acetohexamide Carbutamide Chlorpropamide Glycyclamide Metahexamide Tolazamide Tolbutamide 2nd generation: Glibenclamide (glyburide)^# Glibornuride Glicaramide Gliclazide Glimepiride Glipizide Gliquidone Glisoxepide Glyclopyramide

Meglitinides/"glinides"	Mitiglinide Nateglinide Repaglinide

GLP-1 agonists

DPP-4 inhibitors/"gliptins"

Free fatty acid receptor 1 (GPR40)

Fasiglifam^†

Analogs/other insulins

fast-acting (Insulin aspart
Insulin glulisine
Insulin lispro)
short-acting (Regular insulin)
long-acting (Insulin detemir
Insulin glargine
NPH insulin)
ultra-long-acting (Insulin degludec)
inhalable (Exubera^‡
Afrezza)

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§

Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose

Amylin analog	Pramlintide

Sodium glucose transporter (SGLT2) inhibitors/"gliflozins"	Canagliflozin Dapagliflozin Empagliflozin Ipragliflozin Remogliflozin^§ Sergliflozin^§ Tofogliflozin^†

Other	Benfluorex^‡ Bromocriptine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Ion channel modulators

Calcium (Ca²⁺)

Blockers	L-type-selective: Dihydropyridines: Amlodipine Aranidipine Azelnidipine Barnidipine Clevidipine Cronidipine Darodipine Dexniguldipine Elgodipine Elnadipine Felodipine Flordipine Furnidipine Iganidipine Isradipine Lacidipine Lemildipine Lercanidipine Levamlodipine Levniguldipine Manidipine Mepirodipine Mesudipine Nicardipine Nifedipine Niguldipine Niludipine Nilvadipine Nimodipine Nisoldipine Nitrendipine Olradipine Oxodipine Palonidipine Pranidipine Ryodipine (riodipine) Sagandipine Sornidipine Teludipine Tiamdipine Trombodipine Vatanidipine; Diltiazem derivatives: Clentiazem Diltiazem Iprotiazem Nictiazem Siratiazem; Phenylalkylamines: Anipamil Dagapamil Devapamil Dexverapamil Emopamil Etripamil Falipamil Gallopamil Levemopamil Nexopamil Norverapamil Ronipamil Tiapamil Verapamil; Others: AH-1058 Brinazarone Budiodarone Celivarone Cyproheptadine Dronedarone Fantofarone SR-33805 N-type-selective: ω-Conotoxins ω-Conotoxin GVIA Caroverine Huwentoxin XVI Leconotide (ω-conotoxin CVID) PD-173212 Ralfinamide Safinamide Z160 Ziconotide (ω-conotoxin MVIIA) P-type-selective: ω-Agatoxin IVA ω-Agatoxin IVB R-type-selective: SNX-482 T-type-selective: ABT-639 ML-218 Niflumic acid NNC 55-0396 ProTx I Z944 Zonisamide Non-selective: ω-Agatoxin TK ω-Conotoxin MVIIC Benidipine Bepridil Cilnidipine Cinnarizine Dotarizine Efonidipine Flunarizine Lamotrigine Levetiracetam Lomerizine Loperamide Mibefradil NP078585 Ruthenium red TROX-1 α₂δ subunit-selective (gabapentinoids): 4-Methylpregabalin Arbaclofen Arbaclofen placarbil Atagabalin Baclofen Gabapentin Gabapentin enacarbil Imagabalin Mirogabalin PD-200,347 PD-217,014 PD-299,685 Phenibut Pregabalin Others/unsorted: Bencyclane Berbamine Bevantolol Canadine Carboxyamidotriazole Cycleanine Dauricine Dimeditiapramine Diproteverine Enpiperate Eperisone Elpetrigine Ethadione Ethosuximide Fasudil Fendiline Fostedil JTV-519 Lidoflazine Magnesium Manoalide Mesuximide Monatepil Naftopidil Ochratoxin A Osthol Otilonium bromide Paramethadione Phensuximide Pinaverium Prenylamine Rhynchophylline Sesamodil Silperisone Sipatrigine Terodiline Tetrahydropalmatine Tetrandrine Tolperisone Trimethadione Valperinol

Openers	L-type-selective: Bay K8644

Potassium (K⁺)

Blockers	3,4-Diaminopyridine (amifampridine) 4-Aminopyridine (fampridine/dalfampridine) Adekalant Almokalant Amiodarone Azimilide Bretylium Bunaftine Charybdotoxin Clamikalant Conotoxins Dalazatide Dendrotoxin Dofetilide Dronedarone E-4031 Hanatoxin HgeTx1 HsTx1 Ibutilide Inakalant Kaliotoxin Linopirdine Lolitrem B Maurotoxin Nifekalant Notoxin Paxilline Pinokalant ShK-186 Sotalol Tedisamil Terikalant Tetraethylammonium Vernakalant GIRK blockers: Barium Caramiphen Cloperastine Clozapine Dextromethorphan Ethosuximide Ifenprodil Tertiapin Tipepidine hERG blockers: Ajmaline Amiodarone AmmTX3 Astemizole Azaspiracid AZD1305 Azimilide Bedaquiline BeKm-1 BmTx3 BRL-32872 Chlorpromazine Cisapride Clarithromycin Darifenacin Dextropropoxyphene Diallyl trisulfide Domperidone E-4031 Ergtoxins Erythromycin Gigactonine Haloperidol Ketoconazole Norpropoxyphene Orphenadrine Pimozide PNU-282,987 Promethazine Ranolazine Roxithromycin Sertindole Solifenacin Tamulotoxin Terodiline Terfenadine Thioridazine Tolterodine Vanoxerine Vernakalant K_ATP blockers: Acetohexamide Carbutamide Chlorpropamide Glibenclamide (glyburide) Glibornuride Glicaramide Gliclazide Glimepiride Glipizide Gliquidone Glisoxepide Glyclopyramide Glycyclamide Metahexamide Mitiglinide Nateglinide Repaglinide Tolazamide Tolbutamide

Openers	K_ATP openers: Aprikalim Bimakalim Cromakalim Emakalim Levcromakalim Mazokalim Rilmakalim Sarakalim Others: Diazoxide Flupirtine Minoxidil ML-297 Naminidil Nicorandil Pinacidil Retigabine Rottlerin

Sodium (Na⁺)

Blockers	VGSC blockers: Antianginals: Ranolazine; Antiarrhythmics (class I): Ajmaline Aprindine Disopyramide Dronedarone Encainide Flecainide Lidocaine Lorajmine Lorcainide Mexiletine Moricizine Pilsicainide Prajmaline Procainamide Propafenone Quinidine Sparteine Tocainide; Anticonvulsants: Acetylpheneturide Carbamazepine Cenobamate Chlorphenacemide Elpetrigine Eslicarbazepine acetate Ethotoin Fosphenytoin Lacosamide Licarbazepine Mephenytoin Oxcarbazepine Oxitriptyline Phenacemide Pheneturide Phenytoin Rufinamide Sipatrigine Topiramate Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium Valproic acid Valpromide Zonisamide; Diuretics: Amiloride Benzamil Triamterene; Local anesthetics: pFBT Amylocaine Articaine Benzocaine Bupivacaine (Levobupivacaine, Ropivacaine) Butacaine Butamben Chloroprocaine Cinchocaine Cocaine Cyclomethycaine Dimethocaine Diphenhydramine Etidocaine Hexylcaine Iontocaine Lidocaine Mepivacaine Meprylcaine Metabutoxycaine Orthocaine Piperocaine Prilocaine Procaine Propoxycaine Proxymetacaine Risocaine Tetracaine Trimecaine; Analgesics: AZD-3161 DSP-2230 Funapide GDC-0276 NKTR-171 PF-04531083 PF-05089771 Ralfinamide Raxatrigine RG7893 (GDC-0287); Toxins: Conotoxins Neosaxitoxin Saxitoxin Tetrodotoxin; Others: Buprenorphine Evenamide Menthol Safinamide Tricyclic antidepressants

Openers	VGSC openers: Atracotoxins (Robustoxin, Versutoxin) Ciguatoxins ENaC openers: Solnatide

Chloride (Cl⁻)

Blockers	Bumetanide DIDS Flufenamic acid Furosemide Glibenclamide Lonidamine Meclofenamic acid Mefenamic acid Mepacrine Niflumic acid Piretanide Talniflumate Tolfenamic acid Trifluoperazine

Openers	CFTR openers: 1,7-Phenanthroline 1,10-Phenanthroline 4,7-Phenanthroline 7,8-Benzoquinoline Phenanthridine

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