CHLORPROPAMIDE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H13ClN2O3S
Molecular Weight	276.74
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1

InChI

InChIKey=RKWGIWYCVPQPMF-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C10H13ClN2O3S
Molecular Weight	276.74
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/011641s066lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68002747

Chlorpropamide (DIABINESE®), is a sulfonylurea hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. It appears to lower the blood glucose acutely by stimulating the release of insulin from the pancreas, an effect dependent upon functioning beta cells in the pancreatic islets. The mechanism by which chlorpropamide (DIABINESE®) lowers blood glucose during long-term administration has not been clearly established. Extra-pancreatic effects may play a part in the mechanism of action of oral sulfonylurea hypoglycemic drugs. While chlorpropamide is a sulfonamide derivative, it is devoid of antibacterial activity. Chlorpropamide (DIABINESE®) may also prove effective in controlling certain patients who have experienced primary or secondary failure to other sulfonylurea agent.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sulfonylurea receptor 1, Kir6.2 13 Target ID: CHEMBL2096972 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22209866	Inhibitor 8504		3.04 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/011641s066lbl.pdf	Primary		Approved 8583	DIABINESE Approved Use Chlorpropamide tablets are indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Launch Date 1958

C_max

Value	Dose	Co-administered	Analyte	Population
28.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5053812/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORPROPAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
545 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5053812/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORPROPAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
33.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5053812/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CHLORPROPAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
PEPT1 27 PEPT2 13 BSEP 550 CYP51 2 MRP4 290 MRP2 499 MRP3 246 CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060 NTCP 39 OATP1B1 1079 OATP1B3 961 P-gp 1741	CYP2C19 1119 CYP1A2 1197 CYP2A6 626 CYP2C8 810 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ5OCJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ5OCJ9fQ%3D%3D	no [IC50 >10 uM]
BSEP 554	inhibitor 4027 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50344965, https://pubmed.ncbi.nlm.nih.gov/21965623/	no [IC50 >1000 uM]
MRP2 625	inhibitor 4027 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50344965, https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50344965, https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50344965, https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP51 2	inhibitor 4027 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50344965	no [IC50 >200 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ5OCJ9fQ%3D%3D	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ5OCJ9fQ%3D%3D	yes [Inhibition 10 uM]
NTCP 40	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1Mjg3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ5OCJ9fQ%3D%3D	yes [Inhibition 100 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
P-gp 1932	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ5OCJ9fQ%3D%3D	yes
PEPT1 29	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00672, https://pubmed.ncbi.nlm.nih.gov/10748266/	yes
PEPT2 17	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00672, https://pubmed.ncbi.nlm.nih.gov/10748266/	yes

Drug as victim

Target	Modality	Activity
CYP2C9 1193	substrate 4014 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000094202, https://pubmed.ncbi.nlm.nih.gov/15842554/	major [Km 249.6 uM]
CYP2C19 1119	substrate 4014 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000094202, https://pubmed.ncbi.nlm.nih.gov/15842554/	major [Km 584.9 uM]
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15842554/	minor
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15842554/	minor
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15842554/	minor
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15842554/	minor
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15842554/	minor
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15842554/	minor

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMNDk4In19

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3650	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3650
ChemicalBook	CB8677954	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8677954
eMolecules	535781	https://www.emolecules.com/cgi-bin/more?vid=535781
MolPort	MolPort-001-779-601	https://www.molport.com/shop/molecule-link/MolPort-001-779-601
Selleck Chemicals	chlorpropamide	http://www.selleckchem.com/products/chlorpropamide.html
ZINC	ZINC000001530599	http://zinc15.docking.org/substances/ZINC000001530599

PubMed

Title	Date	PubMed
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.	2014-01	24085192
Pharmacogenomic analysis of ATP-sensitive potassium channels coexpressing the common type 2 diabetes risk variants E23K and S1369A.	2012-03	22209866
Epac2: a sulfonylurea receptor?	2012-02	22260657
Ameliorative effects of Cnidoscolus aconitifolius on alloxan toxicity in Wistar rats.	2010-09	21327141
Maitake mushroom extracts ameliorate progressive hypertension and other chronic metabolic perturbations in aging female rats.	2010-06-07	20567593
Comprehensive in silico prediction and analysis of chlamydial outer membrane proteins reflects evolution and life style of the Chlamydiae.	2009-12-29	20040079
A conformational polymorphic transition in the high-temperature epsilon-form of chlorpropamide on cooling: a new epsilon'-form.	2009-12	19923705
Metformin use and prostate cancer in Caucasian men: results from a population-based case-control study.	2009-11	19653109
Quantitative 35Cl nuclear quadrupole resonance in tablets of the antidiabetic medicine Diabinese.	2009-07-01	19492808
Chlorpropamide treatment restores the reduced carrageenan-induced paw edema and pleural exudate volume in diabetic rats.	2008-09	18777112
Studying the human brain anatomical network via diffusion-weighted MRI and Graph Theory.	2008-04-15	18272400
Inhibition by natural dietary substances of gastrointestinal absorption of starch and sucrose in rats 2. Subchronic studies.	2007-08-10	17713601
Inhibition by natural dietary substances of gastrointestinal absorption of starch and sucrose in rats and pigs: 1. Acute studies.	2007-08-06	17713600
A new gamma-polymorph of chlorpropamide: 4-chloro-N-(propylaminocarbonyl)benzenesulfonamide.	2007-06	17551203
Effect of pressure up to 5.5GPa on dry powder samples of chlorpropamide form-A.	2006-12-11	16920295
Correlating structure and function in ATP-sensitive K+ channels.	1998-07	9683320
Chlorpropamide-induced ADH release, hyponatremia and central pontine myelinolysis in diabetes mellitus.	1995-12	8928190
Reconstitution of IKATP: an inward rectifier subunit plus the sulfonylurea receptor.	1995-11-17	7502040
Hypertension secondary to chlorpropamide with amelioration by changing to insulin.	1993-04	8507452
Chlorpropamide induced syndrome of inappropriate secretion of antidiuretic hormone.	1991-08	1814884
Chlorpropamide or chlorpromazine?	1991-01-15	2043180
Prolonged cholestasis and disappearance of interlobular bile ducts following chlorpropamide and erythromycin ethylsuccinate. Case of drug interaction?	1988-12	3265170
The mechanisms of sulfonylurea-induced immune hemolysis: case report and review of the literature.	1986-11	3766527
A case of chronic liver disease due to tolazamide.	1985-07	4007403
Chlorpropamide-induced cholestatic jaundice and pseudomembranous colitis.	1985-05	2859803
Incidence of severe sideeffects during therapy with sulfonylureas and biguanides.	1985	3865878
Chlorpropamide-induced hemolytic anemia.	1984-12	6510223
Acute hemolytic anemia associated with a chlorpropamide-induced apparent auto-anti-Jka.	1984-05-01	6427987
The effect of chlorpropamide hyponatremia on mental status in a nursing home population.	1983-05	6842150
Nephrotic syndrome and immune complex glomerulonephritis associated with chlorpropamide therapy.	1983-02	6218754
Chlorpropamide-induced hypoglycemia. A dramatic presentation of celiac disease.	1982-02-12	7057563
Chlorpropamide-induced optic neuropathy.	1982-02	7059267
Chlorpropamide-induced Syndrome of Inappropriate Antidiuretic Hormone Secretion.	1981-07	7240625
Chlorpropamide-induced haemolytic anaemia.	1981-01	7279824
Tolazamide-induced cholestasis.	1980-08	7403921
Megaloblastic anaemia due to vitamin B12 malabsorption associated with long-term metformin treatment.	1980-05-17	7388472
Hypoglycemic coma, jaundice, and pure RBC aplasia following chlorpropamide therapy.	1980-05	7396601
Chlorpropamide-induced pure RBC aplasia.	1980-05	7396598
Chlorpropamide induced syndrome of inappropriate antidiuretic hormone secretion.	1980-04	7218172
Reduction of the severity of nephropathy in aging Fischer 344 rats treated with analogs of arylsulfonyluria.	1979-07	473209
Chlorpropamide-alcohol flushing: a definition of its relation to non-insulin-dependent diabetes.	1978-12-02	728708
Chlorpropamide-alcohol flushing: a dominantly inherited trait associated with diabetes.	1978-12-02	728707
Encephalopathy induced by oral hypoglycemic drugs.	1977-08	879949
[Case of hypoglycemic coma in a female patient with diabetes insipidus treated with chlorpropamide].	1974-01-01	4848193
Chlorpropamide and angina pectoris.	1973-03	4694904
Inappropriate secretion of antidiuretic hormone induced by chlorpropamide.	1972-03	5029389
Severe hypoglycaemic shock caused by chlorpropamide. (Case report).	1971-01	5560028
Chlorpropamide-induced immune hemolytic anemia.	1970-10-22	5458054
Pure red blood cell aplasia associated with chlorpropamide therapy. Patient summary and review of the literature.	1969-04	5781455
Haemolysis and agranulocytosis complicating treatment with methyldopa.	1967-10-14	6047854

Patents

Sample Use Guides

In Vivo Use Guide

The mild to moderately severe, middle-aged, stable type 2 diabetes patient should be started on 250 mg daily. In elderly patients, debilitated or malnourished patients, and patients with impaired renal or hepatic function, the initial and maintenance dosing should be conservative to avoid hypoglycemic reactions. Older patients should be started on smaller amounts of DIABINESE®, in the range of 100 to 125 mg daily.

Route of Administration: Oral

In Vitro Use Guide

The ATP-sensitive potassium channels containing the K23/A1369 risk haplotype were significantly less sensitive to inhibition by chlorpropamide (IC50 values for risk haplotype K23/A1369 vs. nonrisk haplotype E23/S1369 = 4.19 vs. 3.04 uM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:18 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:18 GMT 2025`
Record UNII	WTM2C3IL2X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIABINESE

Preferred Name

English

CHLORPROPAMIDE

Official Name

English

CHLORPROPAMIDE [EP IMPURITY]

Common Name

English

CHLORPROPAMIDE [USP-RS]

Common Name

English

CHLORPROPAMIDE [MI]

Common Name

English

GLUCAMIDE

Brand Name

English

CHLORPROPAMIDE [HSDB]

Common Name

English

chlorpropamide [INN]

Common Name

English

CHLORPROPAMIDE [ORANGE BOOK]

Common Name

English

NSC-44634

Code

English

CHLORPROPAMIDE [MART.]

Common Name

English

BENZENESULFONAMIDE, 4-CHLORO-N-((PROPYLAMINO)CARBONYL)-

Systematic Name

English

Chlorpropamide [WHO-DD]

Common Name

English

CHLORPROPAMIDE [JAN]

Common Name

English

1-((P-CHLOROPHENYL)SULFONYL)-3-PROPYLUREA

Common Name

English

CHLORPROPAMIDE [VANDF]

Common Name

English

NSC-626720

Code

English

CHLORPROPAMIDE [USP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA10BB02