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METHYL 3-[4-(2-HYDROXY-3-PROPAN-2-YLAMINO-PROPOXY)PHENYL]PROPANOATE HYDROCHLORIDE

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15 API Suppliers, 10 USDMF, 4 EU WC, 4 NDC API, 10 Listed Suppliers, $ API Reference Price

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42 FDF Dossiers, 25 FDA Orange Book, 9 Europe, 2 Canada, 1 South Africa, 5 Listed Dossiers

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2 Canada
1 South Africa
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DRUG PRODUCT COMPOSITIONS

INJECTABLE;INJECTION - 10MG/ML, INJECTABLE;INJECTION - 1GM/100ML, INJECTABLE;INJECTION - 2GM/100ML

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INJECTABLE;INJECTION - 2GM/100ML

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7 Health Canada Patents

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Zhejiang Esmolol Hydrochloride

Synopsis

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3EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 81161-17-3, Esmolol hcl, Brevibloc, Esmolol (hydrochloride), Asl-8052, Esmolol hydrochloride [usan]

Molecular Formula

C₁₆H₂₆ClNO₄

Molecular Weight

331.8 g/mol

InChI Key

GEKNCWBANDDJJL-UHFFFAOYSA-N

FDA UNII

V05260LC8D

Esmolol Hydrochloride is the hydrochloride salt form of esmolol, a short and rapid-acting beta adrenergic antagonist belonging to the class II anti-arrhythmic drugs and devoid of intrinsic sympathomimetic activity. Esmolol hydrochloride competitively blocks beta-1 adrenergic receptors in cardiac muscle and reduces the contractility and cardiac rate of heart muscle, thereby decreasing cardiac output and myocardial oxygen demands. This agent also decreases sympathetic output centrally and blocks renin secretion. At higher doses, esmolol hydrochloride also blocks beta-2 receptors located in bronchial and vascular smooth muscle, thereby leading to smooth muscle relaxation.

1 2D Structure

Esmolol Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl 3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]propanoate;hydrochloride

2.1.2 InChI

InChI=1S/C16H25NO4.ClH/c1-12(2)17-10-14(18)11-21-15-7-4-13(5-8-15)6-9-16(19)20-3;/h4-5,7-8,12,14,17-18H,6,9-11H2,1-3H3;1H

2.1.3 InChI Key

GEKNCWBANDDJJL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)NCC(COC1=CC=C(C=C1)CCC(=O)OC)O.Cl

2.2 Other Identifiers

2.2.1 UNII

V05260LC8D

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Asl 8052

2. Asl-8052

3. Brevibloc

4. Esmolol

2.3.2 Depositor-Supplied Synonyms

1. 81161-17-3

2. Esmolol Hcl

3. Brevibloc

4. Esmolol (hydrochloride)

5. Asl-8052

6. Esmolol Hydrochloride [usan]

7. Methyl 3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]propanoate;hydrochloride

8. Asl8052

9. V05260lc8d

10. Dsstox_cid_28929

11. Dsstox_rid_83195

12. Dsstox_gsid_49003

13. Benzenepropanoic Acid, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, Methyl Ester, Hydrochloride

14. Asl 8052

15. (+-)-methyl P-(2-hydroxy-3-(isopropylamino)propoxy)hydrocinnamate Hydrochloride

16. 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)benzenepropanoic Acid Methyl Ester Hcl

17. Chebi:4857

18. Cas-81161-17-3

19. Hsdb 6530

20. Ncgc00185766-01

21. Brevibloc In Plastic Container

22. Unii-v05260lc8d

23. Sr-01000763706

24. Methyl 3-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)propanoate Hydrochloride

25. Methyl 3-{4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl}propanoate Hydrochloride

26. Brevibloc (tn)

27. Clol

28. Brevibloc Double Strength In Plastic Container

29. Schembl41086

30. Esmolol Hydrochloride- Bio-x

31. Mls001401393

32. Chembl1201115

33. Dtxsid7049003

34. Esmolol Hydrochloride (jan/usp)

35. Esmolol Hydrochloride [mi]

36. Esmolol Hydrochloride [jan]

37. Bcp28434

38. Hy-b1392

39. Esmolol Hydrochloride [hsdb]

40. Tox21_113496

41. Esmolol Hydrochloride [vandf]

42. Mfcd00941432

43. S4100

44. Esmolol Hydrochloride [mart.]

45. Akos015895316

46. Esmolol Hydrochloride [usp-rs]

47. Esmolol Hydrochloride [who-dd]

48. Tox21_113496_1

49. Ab07716

50. Ac-6972

51. Ccg-100972

52. Ccg-220890

53. Cs-4908

54. Ks-1353

55. Nc00222

56. Ncgc00185766-04

57. Be164425

58. Benzenepropanoic Acid, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, Methyl Ester, Hydrochloride, (+-)-

59. Smr000469141

60. Esmolol Hydrochloride [orange Book]

61. Esmolol Hydrochloride [usp Monograph]

62. Ft-0601541

63. Ft-0667970

64. Ft-0667971

65. Sw197602-3

66. D00644

67. Esmolol Hydrochloride, >=98% (hplc), Solid

68. F20655

69. 1-(3-methylphenyl)piperazinedihydrochloridehydrate

70. 598e034

71. 81161-17-3, 81147-92-4(free Base)

72. J-003862

73. Q-201070

74. Sr-01000763706-4

75. Q27106523

76. Esmolol Hcl; Brevibloc; Asl-8052; Asl 8052; Asl 805

77. Esmolol Hydrochloride, United States Pharmacopeia (usp) Reference Standard

78. (+/-)-methyl P-(2-hydroxy-3-(isopropylamino)propoxy)hydrocinnamate Hydrochloride

79. (+/-)-methyl P-[2-hydroxy-3-(isopropylamino) Propoxy]hydrocinnamate Hydrochloride

80. Methyl 3-{4-[2-hydroxy-3-(isopropylamino)propoxy]-phenyl}propanoate Hydrochloride

81. Benzenepropanoic Acid, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, Methyl Ester, Hydrochloride (1:1)

82. Benzenepropanoic Acid, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, Methyl Ester, Hydrochloride, (+/-)-

83. Methyl 3-{4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl}propanoate Hydrochloride (esmolol Hcl)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₆ClNO₄
Molecular Weight	331.8 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	10
Exact Mass	331.1550360 g/mol
Monoisotopic Mass	331.1550360 g/mol
Topological Polar Surface Area	67.8 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	288
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 8
Drug Name	Brevibloc
PubMed Health	Esmolol (Injection)
Drug Classes	Antiarrhythmic, Group II, Cardiovascular Agent
Drug Label	BREVIBLOC (Esmolol Hydrochloride) is a beta adrenergic receptor blocker with a very short duration of action (elimination half-life is approximately 9 minutes). Esmolol hydrochloride is:()-Methyl p-[2-hydroxy-3-(isopropylamino) propoxy] hydrocinnam...
Active Ingredient	Esmolol hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	10mg/ml
Market Status	Prescription
Company	Baxter Hlthcare

2 of 8
Drug Name	Brevibloc double strength in plastic container
Active Ingredient	Esmolol hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	2gm/100ml
Market Status	Prescription
Company	Baxter Hlthcare

3 of 8
Drug Name	Brevibloc in plastic container
Drug Label	Esmolol hydrochloride is a beta1-selective (cardioselective) adrenergic receptor blocking agent with a very short duration of action (elimination half-life is approximately 9 minutes). Esmolol hydrochloride is:()-Methyl p-[2-hydroxy-3-(isopropylami...
Active Ingredient	Esmolol hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	1gm/100ml
Market Status	Prescription
Company	Baxter Hlthcare

4 of 8
Drug Name	Esmolol hydrochloride
Active Ingredient	Esmolol hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	2000mg/100ml (20mg/ml); 2500mg/250ml (10mg/ml); 10mg/ml
Market Status	Tentative Approval; Prescription
Company	Fresenius Kabi Usa; Hq Speciality Pharma; Mylan Institutional; Eurohlth Intl

5 of 8
Drug Name	Brevibloc
PubMed Health	Esmolol (Injection)
Drug Classes	Antiarrhythmic, Group II, Cardiovascular Agent
Drug Label	BREVIBLOC (Esmolol Hydrochloride) is a beta adrenergic receptor blocker with a very short duration of action (elimination half-life is approximately 9 minutes). Esmolol hydrochloride is:()-Methyl p-[2-hydroxy-3-(isopropylamino) propoxy] hydrocinnam...
Active Ingredient	Esmolol hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	10mg/ml
Market Status	Prescription
Company	Baxter Hlthcare

6 of 8
Drug Name	Brevibloc double strength in plastic container
Active Ingredient	Esmolol hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	2gm/100ml
Market Status	Prescription
Company	Baxter Hlthcare

7 of 8
Drug Name	Brevibloc in plastic container
Drug Label	Esmolol hydrochloride is a beta1-selective (cardioselective) adrenergic receptor blocking agent with a very short duration of action (elimination half-life is approximately 9 minutes). Esmolol hydrochloride is:()-Methyl p-[2-hydroxy-3-(isopropylami...
Active Ingredient	Esmolol hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	1gm/100ml
Market Status	Prescription
Company	Baxter Hlthcare

8 of 8
Drug Name	Esmolol hydrochloride
Active Ingredient	Esmolol hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	2000mg/100ml (20mg/ml); 2500mg/250ml (10mg/ml); 10mg/ml
Market Status	Tentative Approval; Prescription
Company	Fresenius Kabi Usa; Hq Speciality Pharma; Mylan Institutional; Eurohlth Intl

4.2 Therapeutic Uses

Adrenergic Beta-Antagonists

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Esmolol is used IV principally to provide rapid, temporary control of ventricular rate in patients with supraventricular tachyarrhythmias (SVT) (eg, atrial flutter and/or fibrillation, sinus tachycardia).

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1748

Esmolol may be preferred to longer-acting B-adrenergic blocking agents for the short-term control of ventricular rate in patients with SVT because of the drug's rapid onset and short duration of effects, ... .

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1748

Esmolol is indicated for rapid and short-term control of ventricular rate in patients with atrial fibrillation or atrial flutter in perioperative, postoperative, or other emergency situations. It is also indicated in noncompensatory sinus tachycardia judged by the physician to need intervention. (Esmolol is used for control of heart rate in patients with myocardial ischemia. /NOT included in US product labeling/) It is not recommended for use in chronic situations where transfer to another agent is anticipated. /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1231

For more Therapeutic Uses (Complete) data for ESMOLOL HYDROCHLORIDE (6 total), please visit the HSDB record page.

4.3 Drug Warning

Because of the risk of esmolol induced hypotension, blood pressure should be monitored closely during therapy with this drug, especially in patients with low pretreatment blood pressure (eg, systolic blood pressure less than 105 mm Hg). Hypotension can occur at any dose level with esmolol but usually is dose related, and doses exceeding 200 ug/kg per minute recommended by the manufacturer for the management of supraventricular tachyarrhythmias. Reversal of hypotension usually occurs within 30 minutes of discontinuing the drug or reducing the rate of IV infusion.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1751

... Esmolol is contraindicated in patients with second- or third-degree atrioventricular blocks, sinus bradycardia, cardiogenic shock, or overt cardiac failure.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1751

Esmolol may mask signs and symptoms of hypoglycemia (eg, tachycardia, palpitation, blood pressure changes, tremor, feelings of anxiety, but not sweating or dizziness) and may potentiate insulin-induced hypoglycemia; therefore, the drug should be used with caution in patients with diabetes mellitus or hypoglycemia.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1751

Because of de-esterified metabolite (ASL 8123) of esmolol is eliminated mainly by the kidneys, ... the drug should be used with caution in patients with renal impairment, especially severe impairment.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1751

For more Drug Warnings (Complete) data for ESMOLOL HYDROCHLORIDE (16 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Adrenergic beta-1 Receptor Antagonists

Drugs that bind to and block the activation of ADRENERGIC BETA-1 RECEPTORS. (See all compounds classified as Adrenergic beta-1 Receptor Antagonists.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

beta-Adrenergic Blocker [EPC]; Adrenergic beta-Antagonists [MoA]

5.3 Absorption, Distribution and Excretion

It is not known whether esmolol and/or ASL 8123 cross the placenta in humans, but the drug has been shown to cross the placenta in animals. In animals, fetal artery esmolol concentrations were about 10% of maternal concentrations at the completion of infusion. It also is not known whether esmolol and/or ASL 8123 are distributed into milk.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1753

Following IV administration, esmolol is rapidly and widely distributed. The apparent volumes of distribution of esmolol and its de-esterifed metabolite (ASL 8123) in healthy adults are approximately 3.4 and 0.41 l/kg, respectively, following iv administration. In healthy adults, the volumes of distribution of esmolol in the central compartment and at steady state are approximately 0.87 and 1.2 l/kg, respectively, following IV administration. The apparent volume of distribution appears to be decreased in patients undergoing coronary artery bypass surgery and increased in patients with renal impairment undergoing peritoneal dialysis and in patients with liver cirrhosis.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1753

Following IV administration in rats, esmolol is ditributed into liver and kidneys, but only minimally into CSF, spleen, or testes.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1753

In vitro, esmolol is approximately 55% bound to plasma proteins, mainly albumin and alpha-1-acid glycoprotein. Protein binding of esmolol to alpha-1-acid glycoprotein does not appear to be concentration dependent at esmolol concentrations of 3-110 ug/ml. In vitro, ASL 8123 is approximately 10% bound to plasma proteins.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1753

For more Absorption, Distribution and Excretion (Complete) data for ESMOLOL HYDROCHLORIDE (10 total), please visit the HSDB record page.

5.4 Metabolism/Metabolites

Esmolol is rapidly and extensively metabolized via esterases (probably arylesterase), principally in the cytosol of erythrocytes. Metabolism of the drug also may occur in highly perfused tissues that contain esterases (eg, liver, kidneys). Hydrolysis of the methyl ester moiety results in formation of the de-esterified (free acid) metabolite, 4-(2-hydroxy-3-((1-methylethyl)amino) propoxy)benzenepropanoic acid (ASL 8123), and methanol. Esmolol does not appear to be susceptible to hydrolysis via serum cholinesterase (pseudocholinesterase), acetylcholinesterase, or carbonic anhydrase. It is estimated that about 83% of an esmolol dose is metabolized to ASL 8123. ASL 8123 has a low affinity for beta-adrenergic receptors, exhibiting only minimal (about 1,000- to 1,500-fold less potent than esmolol) beta-blocking activity in animals and no appreciable blockade in humans. Unlike esmolol, ASL 8123 is eliminated principally by the kidneys, and the elimination half-life of the metabolite may be increased up to tenfold in patients with renal impairment; however, such accumulation is not thought to be clinically important since ASL 8123 has only minimal beta-blocking activity. The amount of methanol formed during hydrolysis of the drug does not appear to be clinically important. Following IV infusion of esmolol hydrochloride doses of 300 ug/kg per minute for up to l6 hours of 150 ug/kg per minute for 24 hours, blood methanol concentrations ranged from 2.8-5.9 or 2.9-13.2 ug/ml, respectively, being less than 2% of those usually associated with methanol toxicity.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1753

5.5 Biological Half-Life

Following IV infusion in adults, the half life of esmolol averages about 2 minutes in the initial distribution phase and about 9 minutes (range: 5-23 minutes) in the terminal elimination phase, although considerable interindividual variation in blood elimination half life exists.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1753

Free acid metabolite: approx 3.7 hr (increased up to tenfold in renal failure)

5.6 Mechanism of Action

Esmolol selectively inhibits response to adrenergic stimuli by competitively blocking cardiac B1-adrenergic receptors, while having little effect on the B2-adrenergic receptors of bronchial and vascular smooth muscle. At high doses (e.g., greater than 300 ug/kg per minute), this selectivity of esmolol for B1-adrenergic receptors usually diminishes, and the drug will competitively inhibit B1-and B2-adrenergic receptors.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1752

By inhibiting myocardial beta1-adrenergic receptors, esmolol produces negative chronotropic and inotropic activity. Through its myocardial B1-adrenergic blocking action, esmolol decreases resting and exercise-induced heart rate, reflex orthostatic tachycardia, myocardial contractility, rate of left ventricular pressure rise (dp/dt), right ventricular contractility, and cardiac index.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1752

The decrease in myocardial contractility, arterial pressure, and heart rate produced by esmolol can lead to a reduction in myocardial oxygen consumption, which may account for the effectiveness of the drug in myocardial ischemia.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1753

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API Reference Price

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