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Chlorpropamide - Wikipedia

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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	C₁₀H₁₃ClN₂O₃S
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 an antidiabetic drug, 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

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

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

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

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

Chlorpropamide is a white crystalline powder with no characteristic taste or smell. It exhibits polymorphism. Its acid dissociation constant pK_a is 5.0 at 20 °C.^[1]

Solubility

Solvent	Solubility^[1]
Water, pH 6	1:450
Water, pH 7.3	insoluble
Acetone	1:5
Dichlormethane	1:9
Ethanol	1:12
Diethylether	1:200

References

^ ^a ^b ^c ^d ^e ^f ^g 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.
^ ^a ^b "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.

Oral diabetes medication, insulins and insulin analogs, and other drugs used in diabetes (A10)

Insulins / insulin analogs

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 icodec^† (+semaglutide)
inhalable	Exubera^‡ Afrezza

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^‡Withdrawn from market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

Non-insulins

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^§
Amylin analogs 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

GLP1 poly-agonist peptides	Mazdutide (GLP-1/GCGR) Retatrutide^§ (GLP-1/GIP/GCGR) Tirzepatide (GLP-1/GIP)

DPP-4 inhibitors/"gliptins"

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§
Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose
SGLT2 inhibitors/"gliflozins"	Canagliflozin Dapagliflozin Empagliflozin^# Ertugliflozin Ipragliflozin Luseogliflozin Remogliflozin^§ Sergliflozin^§ Sotagliflozin Tofogliflozin^† Velagliflozin
Other	Benfluorex^‡ Bromocriptine Imeglimin

Combinations

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^‡Withdrawn from market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

Ion channel modulators

Calcium

VDCCs

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
Tetrahydropalmatine

R-type-selective: SNX-482

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

Activators

L-type-selective: Bay K8644

Potassium

VGKCs

Blockers

hERG (KCNH2, K_v11.1)-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

Activators

KCNQ (K_v7)-specific: Flupirtine
Retigabine

IRKs

Blockers

K_ATPTooltip 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

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific: Barium
Caramiphen
Cloperastine
Clozapine
Dextromethorphan
Ethosuximide
Ifenprodil
Tertiapin
Tipepidine

Activators

K_ATPTooltip ATP-sensitive potassium channel-specific: Aprikalim
Bimakalim
Cromakalim
Diazoxide
Emakalim
Levcromakalim
Mazokalim
Minoxidil
Minoxidil sulfate
Naminidil
Nicorandil
Pinacidil
Rilmakalim
Sarakalim

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific: ML-297 (VU0456810)

K_Ca

Blockers	BK_Ca-specific: Ethanol (alcohol) GAL-021
Activators	BK_Ca-specific: Flufenamic acid Meclofenamic acid Niflumic acid Nimesulide Rottlerin (mallotoxin) Tolfenamic acid

K2Ps

Blockers	12-O-Tetradecanoylphorbol-13-acetate Arachidonic acid Fluoxetine Norfluoxetine
Activators	Riluzole

Sodium

VGSCs

Blockers

Antianginals: Ranolazine

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

Activators

Aconitine
Atracotoxins (ω-Atracotoxin, Robustoxin, Versutoxin)
Batrachotoxin
Ciguatoxins
Grayanotoxins
Poneratoxin

ENaC

Blockers	Amiloride Benzamil Triamterene
Activators	Solnatide

ASICs

Blockers	A-317567 Amiloride Aspirin Ibuprofen PcTX1

Chloride

CaCCs

Blockers	Crofelemer DIDS Ethacrynic acid Flufenamic acid Fluoxetine Furosemide Glibenclamide Mefloquine Mibefradil Niflumic acid
Activators	Carbachol

CFTR

Blockers	Glibenclamide Lonidamine Piretanide
Activators	1,7-Phenanthroline 1,10-Phenanthroline 4,7-Phenanthroline 7,8-Benzoquinoline Ivacaftor Phenanthridine

Unsorted

Blockers	Bumetanide Flufenamic acid Meclofenamic acid Mefenamic acid Mepacrine Niflumic acid Talniflumate Tolfenamic acid Trifluoperazine

Others

TRPsTooltip Transient receptor potential channels	See here instead.
LGICsTooltip Ligand gated ion channels	See here instead.

See also: Receptor/signaling modulators • Transient receptor potential channel modulators

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