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account log in personal tools donate create account log in contents move to sidebar hide top 1 mechanism of action 2 pharmacokinetics 3 cautions and contraindications toggle cautions and contraindications subsection 3 1 other side effects 4 chemical properties toggle chemical properties subsection 4 1 solubility 5 see also 6 references toggle the table of contents chlorpropamide 16 languages العربية تۆرکجه cymraeg deutsch español فارسی bahasa indonesia italiano ଓଡ଼ିଆ português română srpskohrvatski српскохрватски српски srpski kiswahili తెలుగు türkçe edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical compound not to be confused with chlorpromazine pharmaceutical compound chlorpropamide clinical data trade names diabinese ahfs drugs com monograph medlineplus a682479 license data us fda chlorpropamide pregnancy category au c routes of administration oral atc code a10bb02 who legal status legal status au s4 prescription only ca only uk pom prescription only us only pharmacokinetic data bioavailability 90 protein binding 90 metabolism 1 elimination half life 36 hours excretion renal glomerular filtration reabsorption tubular secretion identifiers iupac name 4 chloro n propylcarbamoyl benzenesulfonamide cas number 94 20 2 y pubchem cid 2727 iuphar bps 6801 drugbank db00672 y chemspider 2626 y unii wtm2c3il2x kegg d00271 y chebi chebi 3650 y chembl chembl498 y comptox dashboard epa dtxsid9020322 echa infocard 100 002 104 chemical and physical data formula c 10 h 13 cl n 2 o 3 s molar mass 276 74 g mol 1 3d model jsmol interactive image melting point 126 to 130 c 259 to 266 f smiles o s o c1ccc cl cc1 nc o nccc inchi inchi 1s c10h13cln2o3s c1 2 7 12 10 14 13 17 15 16 9 5 3 8 11 4 6 9 h3 6h 2 7h2 1h3 h2 12 13 14 y key rkwgiwycvpqpmf uhfffaoysa n y verify chlorpropamide is a diabetes medication belonging to the sulfonylurea class of organic compounds it is used to treat diabetes mellitus type 2 it is a long acting first generation sulfonylurea mechanism of action edit like other sulfonylureas chlorpropamide acts to increase the secretion of insulin so it is only effective in patients who have some pancreatic beta cell function it can cause relatively long episodes of hypoglycemia this is one reason why shorter acting sulfonylureas such as gliclazide or tolbutamide are used instead the risk of hypoglycemia makes this drug a poor choice for the elderly and patients with mild to moderate hepatic and renal impairment chlorpropamide is also used in partial central diabetes insipidus 1 pharmacokinetics edit maximal plasma concentrations are reached 3 to 5 hours after quick and nearly complete 90 resorption from the gut plasma half life is 36 hours the drug is effective for about 24 hours longer than other sulfonylureas a stable plasma level is only reached after three days of continuous application 90 of the drug are bound to plasma proteins at least two albumin binding sites exist more than 99 of chlorpropamide are excreted unchanged via the kidneys it is first filtrated in the glomeruli then reabsorbed and finally secreted into the tubular lumen 1 cautions and contraindications edit further information sulfonylurea side effects and cautions chlorpropamide and other sulfonylureas encourage weight gain so they are generally not favored for use in very obese patients metformin glucophage is considered a better drug for these patients sulfonylureas should be used with caution or generally avoided in patients with hepatic and renal impairment patients with porphyria patients who are breastfeeding patients with ketoacidosis and elderly patients 1 2 other side effects edit the most common side effects are skin related such as rashes photoallergy and in rare cases stevens johnson syndrome 1 less common side effects of chlorpropamide include gastrointestinal symptoms such as nausea vomiting and diarrhea 2 it may cause facial flushing after the ingestion of alcohol 3 in very high doses it can increase secretion of antidiuretic hormone adh which can lead to hyponatremia 1 it also markedly raises the serum level of alkaline phosphatase citation needed chemical properties edit chlorpropamide is a white crystalline powder with no characteristic taste or smell it exhibits polymorphism its acid dissociation constant p k a is 5 0 at 20 c 1 solubility edit solvent solubility 1 water ph 6 1 450 water ph 7 3 insoluble acetone 1 5 dichloromethane 1 9 ethanol 1 12 diethyl ether 1 200 see also edit tolbutamide tolazamide glyburide glipizide references edit 1 2 3 4 5 6 7 dinnendahl v fricke u eds 2010 arzneistoff profile in german vol 4 23 ed eschborn germany govi pharmazeutischer verlag isbn 978 3 7741 9846 3 1 2 chlorpropamide drugs com archived from the original on 2021 03 04 retrieved 2018 01 23 fitzgerald mg gaddie r malins jm o sullivan dg 1962 alcohol sensitivity in diabetics receiving chlorpropromide diabetes 11 40 3 pmid 13893349 v t e oral diabetes medication insulins and insulin analogues and other drugs used in diabetes a10 insulins and insulin analogues fast acting insulin aspart insulin glulisine insulin lispro short acting regular insulin long acting insulin detemir insulin glargine lixisenatide nph insulin lente insulin ultralente insulin ultra long acting insulin degludec insulin aspart liraglutide insulin efsitora insulin icodec semaglutide inhalable exubera afrezza oral insulin tregopil who em withdrawn from market clinical trials phase iii never to phase iii non insulins insulin sensitizers biguanides buformin metformin phenformin tzds glitazones and ppar agonists ciglitazone darglitazone englitazone lobeglitazone netoglitazone pioglitazone rivoglitazone rosiglitazone troglitazone dual ppar agonists aleglitazar muraglitazar saroglitazar tesaglitazar amylin analogues and dacras cagrilintide pramlintide 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 receptor agonists albiglutide danuglipron dulaglutide exenatide liraglutide lixisenatide orforglipron semaglutide taspoglutide glp1 poly agonist peptides mazdutide glp 1 gcgr retatrutide glp 1 gip gcgr tirzepatide glp 1 gip dpp 4 inhibitors gliptins alogliptin anagliptin evogliptin garvagliptin gemigliptin gosogliptin linagliptin melogliptin omarigliptin retagliptin saxagliptin sitagliptin teneligliptin trelagliptin vildagliptin other aldose reductase inhibitors epalrestat fidarestat ranirestat tolrestat zenarestat alpha glucosidase inhibitors acarbose miglitol voglibose sglt2 inhibitors gliflozins bexagliflozin canagliflozin dapagliflozin empagliflozin ertugliflozin ipragliflozin luseogliflozin remogliflozin sergliflozin sotagliflozin tofogliflozin velagliflozin other benfluorex bromocriptine imeglimin combinations alogliptin metformin canagliflozin metformin cagrilintide semaglutide dapagliflozin metformin dapagliflozin saxagliptin dapagliflozin saxagliptin metformin empagliflozin linagliptin empagliflozin metformin gemigliptin rosuvastatin glibenclamide glyburide metformin glimepiride rosiglitazone linagliptin metformin metformin acarbose metformin ertugliflozin metformin evogliptin metformin gemigliptin metformin repaglinide metformin sulfonylureas metformin teneligliptin phenformin sulfonylureas pioglitazone alogliptin pioglitazone glimepiride pioglitazone metformin pioglitazone sitagliptin rosiglitazone metformin saxagliptin metformin sitagliptin dapagliflozin sitagliptin ertugliflozin sitagliptin metformin sitagliptin simvastatin vildagliptin metformin who em withdrawn from market clinical trials phase iii never to phase iii v t e ion channel modulators calcium vdccs tooltip voltage dependent calcium channels blockers l type selective dihydropyridines amlodipine telmisartan and indapamide 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 tetrahydropalmatine 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 α 2 δ 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 ethanol alcohol ethosuximide fasudil fendiline fostedil imepitoin jtv 519 lidoflazine magnesium manoalide mesuximide monatepil naftopidil ochratoxin a osthol otilonium bromide paramethadione phensuximide pinaverium bromide prenylamine rhynchophylline sesamodil silperisone sipatrigine terodiline tetrandrine tolperisone trimethadione valperinol activators l type selective bay k8644 potassium vgkcs tooltip voltage gated potassium channels 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 quinidine shk 186 sotalol tedisamil terikalant tetraethylammonium vernakalant herg kcnh2 k v 11 1 specific 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 quinidine ranolazine roxithromycin sertindole solifenacin tamulotoxin terodiline terfenadine thioridazine tolterodine vanoxerine vernakalant kcnq k v 7 specific linopirdine spooky toxin sstx xe 991 activators kcnq k v 7 specific azetukalner encukalner cb03 154 flupirtine opakalim pynegabine retigabine ezogabine irks tooltip inwardly rectifying potassium channel blockers k atp tooltip atp sensitive potassium channel specific acetohexamide carbutamide chlorpropamide glibenclamide glyburide glibornuride glicaramide gliclazide glimepiride glipizide gliquidone glisoxepide glyclopyramide glycyclamide metahexamide mitiglinide nateglinide repaglinide tolazamide tolbutamide girk tooltip g protein coupled inwardly rectifying potassium channel specific barium caramiphen cloperastine clozapine dextromethorphan ethosuximide ifenprodil tertiapin tipepidine activators k atp tooltip atp sensitive potassium channel specific aprikalim bimakalim cromakalim diazoxide emakalim levcromakalim mazokalim minoxidil minoxidil sulfate naminidil nicorandil pinacidil rilmakalim sarakalim girk tooltip g protein coupled inwardly rectifying potassium channel specific ml 297 vu0456810 k ca tooltip calcium activated potassium channel blockers bk ca specific ethanol alcohol gal 021 activators bk ca specific chlorzoxazone estradiol flindokalner flufenamic acid isopimaric acid meclofenamic acid niflumic acid nimesulide riluzole rottlerin mallotoxin tamoxifen tolfenamic acid vsn16r k2ps tooltip tandem pore domain potassium channel blockers 12 o tetradecanoylphorbol 13 acetate arachidonic acid fluoxetine norfluoxetine activators riluzole sodium vgscs tooltip voltage gated sodium channels 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 lamotrigine lacosamide licarbazepine mephenytoin oxcarbazepine oxitriptyline phenacemide pheneturide phenytoin relutrigine rufinamide sipatrigine topiramate sodium valproate valnoctamide valproate pivoxil valproate semisodium valproic acid valpromide zonisamide local anesthetics p fbt 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 suzetrigine toxins conotoxins neosaxitoxin saxitoxin tetrodotoxin zetekitoxin ab others buprenorphine evenamide menthol mint safinamide tricyclic antidepressants activators aconitine atracotoxins ω atracotoxin robustoxin versutoxin batrachotoxin ciguatoxins grayanotoxins poneratoxin enac tooltip epithelial sodium channel blockers amiloride benzamil triamterene activators solnatide asics tooltip acid sensing ion channel blockers a 317567 amiloride aspirin ibuprofen pctx1 chloride caccs tooltip calcium activated chloride channel blockers crofelemer dids ethacrynic acid flufenamic acid fluoxetine furosemide glibenclamide mefloquine mibefradil niflumic acid activators carbachol cftr tooltip cystic fibrosis transmembrane conductance regulator blockers glibenclamide lonidamine piretanide activa...
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