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Indapamide

HCID 3702
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
26807-65-8
Standard SMILES
CC1Cc2ccccc2N1NC(=O)c1ccc(Cl)c(S(N)(=O)=O)c1
InChIKey
NDDAHWYSQHTHNT-UHFFFAOYSA-N
Molecular formula
C16H16ClN3O3S
Average molar mass
365.8 g/mol
Monoisotopic mass
365.0600902

Overview

Indapamide is a sulfonamide formed by condensation of the carboxylic group of 4-chloro-3-sulfamoylbenzoic acid with the amino group of 2-methyl-2,3-dihydro-1H-indol-1-amine. It has a role as a diuretic and an antihypertensive agent. It is a member of indoles, a sulfonamide and an organochlorine compound. It is functionally related to a benzamide.

Names & identifiers

Preferred name
Indapamide
IUPAC
4-chloro-N-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide
English name
Indapamide
Molecular formula
C16H16ClN3O3S
Molecular weight
365.83

Names & synonyms

indapamide26807-65-8IndamolVeroxilLozolFludexIndaflexIpamixNoranatTandixBajatenNatrilix
Show more names
INDAPAMIDndapamideIdapamideIndapamide CRSN-(4-CHLORO-3-SULFAMOYLBENZAMIDO)-2-METHYLINDOLINE4-chloro-N-[(2S)-2-Methyl-2,3-dihydro-1H-indol-1-yl]-3-sulfaMoylbenzaMides1520
TertensifArifonDamideIndapamidaMetindamideNatrixflupamidindamide

Database identifiers

CAS
26807-65-8
PubChem CID
3702
DTXSID
DTXSID7044633
ChEMBL
CHEMBL406
ChEBI
CHEBI:5893
UNII
F089I0511L
EC Number
248-012-7
Nikkaji
J10.425F

Properties

Computed structural properties

XLogP
2.9
Topological polar surface area
101 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
3
Heavy atoms
24
Formal charge
0
Complexity
580

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals

Pharmaceuticals -> Diuretics

LogP · 2 items

2.2

1.83

Solubility · 2 items

3.42e-02 g/L

>54.9 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 5 items

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Thiazide Diuretics

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Antihypertensive medicines

Melting Point · 2 items

160-162

161 °C

Physical DescriptionSolid
Dissociation Constants8.8
Collision Cross Section · 4 items

195.9 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID7044633]

184.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.5% (1 of 68) of reports.

Warning

H361 (86.8%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 68 reports by companies from 14 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationIndapamide: Non hazardous
Hazard Classes and CategoriesRepr. 2 (86.8%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Indapamide

Ambiguous-DILI-concern

5

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
2
rtecs
CV2451200
hs_code
2935904000
Toxicity
LD50 in rats, mice, guinea pigs (mg/kg): 393-421, 410-564, 347-416 i.p.; 394-440, 577-635, 272-358 i.v.; >3000 all species orally (Kyncl)
Signal word
Warning

Chemistry & industry

Pharmacology

ATC Code · 3 items

C03BA11

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding · 1 item

Approximately 76-79% of indapamide is protein bound. Indapamide binds primarily to alpha 1-acid glycoprotein and less significantly to serum albumin and lipoproteins. In the blood, indapamide is extensively and preferentially bound to erythrocytes.

Pharmacodynamics · 1 item

Classified as a sulfonamide diuretic, indapamide is an effective antihypertensive agent and by extension, has shown efficacy in the prevention of target organ damage. Administration of indapamide produces water and electrolyte loss, with higher doses associated with increased diuresis. Severe and clinically significant electrolyte disturbances may occur with indapamide use - for example, hypokalemia resulting from renal potassium loss may lead to QTc prolongation. Further electrolyte imbalances may occur due to renal excretion of sodium, chloride, and magnesium. Other indapamide induced changes include increases in plasma renin and aldosterone, and reduced calcium excretion in the urine. In many studies investigating the effects of indapamide in both non-diabetic and diabetic hypertensive patients, glucose tolerance was not significantly altered. However, additional studies are necessary to assess the long term metabolic impacts of indapamide, since thiazide related impaired glucose tolerance can take several years to develop in non-diabetic patients.

Mechanism of Action · 1 item

Indapamide acts on the nephron, specifically at the proximal segment of the distal convoluted tubule where it inhibits the Na+/Cl- cotransporter, leading to reduced sodium reabsorption. As a result, sodium and water are retained in the lumen of the nephron for urinary excretion. The effects that follow include reduced plasma volume, reduced venous return, lower cardiac output, and ultimately decreased blood pressure. Interestingly, it is likely that thiazide-like diuretics such as indapamide have additional blood pressure lowering mechanisms that are unrelated to diuresis. This is exemplified by the observation that the antihypertensive effects of thiazides are sustained 4-6 weeks after initiation of therapy, despite recovering plasma and extracellular fluid volumes. Some studies have suggested that indapamide may decrease responsiveness to pressor agents while others have suggested it can decrease peripheral resistance. Although it is clear that diuresis contributes to the antihypertensive effects of indapamide, further studies are needed to investigate the medication’s ability to decrease peripheral vascular resistance and relax vascular smooth muscle.

Related reactions

6 records
New reaction record
HRID 1195235 reaction equation
HRID 1195235As productuspto-grants-1992_05
HRID 1203584 reaction equation
HRID 1203584As productTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
HRID 1589420 reaction equation
HRID 1589420As productuspto-grants-1986_02
HRID 1589421 reaction equation
HRID 1589421As productuspto-grants-1986_02
HRID 1589422 reaction equation
HRID 1589422As productuspto-grants-1986_02
HRID 2372912 reaction equation
HRID 2372912As productuspto-grants-1992_03

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

191.35 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

185.6 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Physicochemical properties

Melting point
160 · 160-162°C
Boiling point
110.4 °C · 110.4°C (rough estimate)
alpha
-0.8 · -0.8~+0.8°(D/20℃) (c=5, C2H5OH)
Density
1.2895 · 1.2895 (rough estimate)
refractive index
1.61 · 1.6100 (estimate)
storage temp.
-20 °C · -20°C Freezer
solubility
Practically insoluble in water, soluble in ethanol (96 per cent).
pka
pKa (25°) 8.8 ± 0.2
form
Solid
color
White to Off-White
Water Solubility
Soluble in ethanol. Insoluble in water
Merck
14 · 14,4935
BCS Class
1 · 1
InChIKey
NDDAHWYSQHTHNT-UHFFFAOYSA-N
CAS DataBase Reference
26807 · 26807-65-8(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
89 I0511L · F089I0511L
ATC code
3 BA11 · C03BA11
EPA Substance Registry System
3 · Benzamide, 3-(aminosulfonyl)-4-chloro-N-(2,3-dihydro-2-methyl-1H-indol-1-yl)- (26807-65-8)
Protein binding
79 % · 79%
Excreted unchanged in urine
5 · 5-7%
Volume of distribution
0.3 · 0.3-1.3(L/kg)
Biological half-life
14 · 14-24 / Unchanged
Symbol(GHS)
8 · GHS08
Signal word
Warning
Hazard statements
361 d-H362 · H361d-H362
Precautionary statements
202 · P202-P260-P263-P264-P270-P308+P313
WGK Germany
2 · 2
RTECS
2451200 · CV2451200
HS Code
2935904000 · 2935904000
Toxicity
50 in · LD50 in rats, mice, guinea pigs (mg/kg): 393-421, 410-564, 347-416 i.p.; 394-440, 577-635, 272-358 i.v.; >3000 all species orally (Kyncl)
Symbol(GHS)
GHS08
Hazard statements
H361d-H362
Precautionary statements
P202-P260-P263-P264-P270-P308+P313
Biological Half-LifeIndapamide is characterized by biphasic elimination. In healthy subjects, indapamide's elimination half-life can range from 13.9 to 18 hours. The long half-life is conducive to once-daily dosing.
Metabolism/Metabolites · 1 item

As a result of extensive metabolism in the liver, the majority of indapamide excreted is metabolized, with only 7% remaining unchanged. In humans, as many as 19 distinct indapamide metabolites may be produced, although not all have been identified. There are several metabolic routes through which indapamide may be metabolized, and CYP3A4 is the main enzyme involved in the corresponding hydroxylation, carboxylation, and dehydrogenation reactions. Indapamide can undergo dehydrogenation to form M5, then oxidation to form M4, then further hydroxylation at the indole moiety to form M2. These reactions are facilitated by CYP3A4. Another route of metabolism occurs when indapamide is first hydroxylated to M1 by CYP3A4. M1 then undergoes dehydrogenation to form M3 and is further oxidized to form M2. Hydroxylation of indapamide’s indole moiety is thought to form the major metabolite (M1), which is less pharmacologically active compared to its parent compound according to animal studies. Indapamide may also undergo epoxidation via CYP3A4 to form a reactive epoxide intermediate. The unstable epoxide intermediate may then undergo dihydroxylation via microsomal epoxide hydrolase to form M6, or glutathione conjugation to form M7.

FDA Pharmacological Classification · 6 items

F089I0511L

INDAPAMIDE

Physiologic Effects [PE] - Increased Diuresis

Established Pharmacologic Class [EPC] - Thiazide-like Diuretic

Indapamide is a Thiazide-like Diuretic. The physiologic effect of indapamide is by means of Increased Diuresis.

INDAPAMIDE

MeSH Pharmacological Classification · 3 items

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

Agents that promote the excretion of urine through their effects on kidney function.

Agents that inhibit SODIUM CHLORIDE SYMPORTERS. They act as DIURETICS. Excess use is associated with HYPOKALEMIA.

Absorption, Distribution and Excretion · 4 items

The bioavailability of indapamide is virtually complete after an oral dose and is unaffected by food or antacids. Indapamide is highly lipid-soluble due to its indoline moiety - a characteristic that likely explains why indapamide’s renal clearance makes up less than 10% of its total systemic clearance. The Tmax occurs approximately 2.3 hours after oral administration. The Cmax and AUC0-24 values are 263 ng/mL and 2.95 ug/hr/mL, respectively.

An estimated 60-70% of indapamide is eliminated in the urine, while 16-23% is eliminated in the feces.

Some sources report an apparent volume of distribution of 25 L for indapamide, while others report a value of approximately 60 L.

Indapamide's renal and hepatic clearance values are reported to be 1.71 mL/min and 20-23.4 mL/min, respectively.

Cellular LocationsMembrane
Metabolite PathwaysIndapamide Action Pathway

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >50
Use ClassificationPharmaceuticals
Applications · 3 items

UsesFor the treatment of mild to moderate essential hypertension.

DescriptionIndapamide is a derivative of benzolsulfonamide and its mechanism of action is analogous to that of thiazides. It is intended for lowering arterial blood pressure and as an adjuvant drug for treating edema caused by cardiac insufficiency. Indapamide can be detected in urine. This product is intended for research and forensic applications.

UsesUsed as an antihypertensive. Diuretic.

Upstream & downstream products

Upstream raw materials

1-Amino-2-methylindoline hydrochloride4-Chloro-5-sulphamoylbenzoic acidINDAPAMIDE RELATED COMPOUND A (50 MG) (4-CHLORO-N-(2-METHYL-INDOL-1-YL)-3-SULFAMOYLBEN-ZAMIDE) (AS)2-Methylindolin-1-amine4-Chloro-3-sulfamoylbenzoyl chloride2-Methylindoline

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
苏州朗恩生物科技有限公司13921996628 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
上海波以尔化工有限公司[email protected]
北京亿思研科技开发中心010-56645598 13366904824 · [email protected]
济南德瑞丰环保化工有限公司0531-83554928 13854196079 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
武汉威顺达科技发展有限公司86-027-88774375 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
唐山默内德贸易有限公司0315-8309571 15633399667 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
Hebei Qige Biological Technology Co. Ltd+86 +8618733132031
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
安徽科迪达化工有限公司0554-2106669 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
湖南华腾制药有限公司400-8592883 15367835770 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
润泽制药(苏州)有限公司+86-512-62831367 13140980067 · [email protected]
江苏倍达医药科技有限公司0512-63009836 18994340901 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Ring Specialty Chemicals Inc.+1 416 493 6870 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
上海润栖医药科技有限公司021-38751876 15000076078 · [email protected]
济南元泰化工有限公司0531-69959492 18366108822 · [email protected]

Additional notes

DefinitionChEBI: A sulfonamide formed by condensation of the carboxylic group of 4-chloro-3-sulfamoylbenzoic acid with the amino group of 2-methyl-2,3-dihydro-1H-indol-1-amine.