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Chemistry

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Also known as: 72956-09-3, Coreg, Dilatrend, Eucardic, Kredex, Carvedilolum [latin]
Molecular Formula
C24H26N2O4
Molecular Weight
406.5  g/mol
InChI Key
OGHNVEJMJSYVRP-UHFFFAOYSA-N
FDA UNII
0K47UL67F2

Carvedilol
A carbazole and propanol derivative that acts as a non-cardioselective beta blocker and vasodilator. It has blocking activity for ALPHA 1 ADRENERGIC RECEPTORS and, at higher doses, may function as a blocker of CALCIUM CHANNELS; it also has antioxidant properties. Carvedilol is used in the treatment of HYPERTENSION; ANGINA PECTORIS; and HEART FAILURE. It can also reduce the risk of death following MYOCARDIAL INFARCTION.
Carvedilol is an alpha-Adrenergic Blocker and beta-Adrenergic Blocker. The mechanism of action of carvedilol is as an Adrenergic alpha-Antagonist and Adrenergic beta1-Antagonist and Adrenergic beta2-Antagonist.
1 2D Structure

Carvedilol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol
2.1.2 InChI
InChI=1S/C24H26N2O4/c1-28-21-10-4-5-11-22(21)29-14-13-25-15-17(27)16-30-23-12-6-9-20-24(23)18-7-2-3-8-19(18)26-20/h2-12,17,25-27H,13-16H2,1H3
2.1.3 InChI Key
OGHNVEJMJSYVRP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC1=CC=CC=C1OCCNCC(COC2=CC=CC3=C2C4=CC=CC=C4N3)O
2.2 Other Identifiers
2.2.1 UNII
0K47UL67F2
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 14c-labeled Carvedilol

2. Bm 14190

3. Bm-14190

4. Bm14190

5. Carvedilol Hydrochloride

6. Carvedilol, (+)

7. Carvedilol, (+)-isomer

8. Carvedilol, (+-)-isomer

9. Carvedilol, (-)

10. Carvedilol, (-)-isomer

11. Carvedilol, (r)-isomer

12. Carvedilol, (s)-isomer

13. Carvedilol, 14c Labeled

14. Carvedilol, 14c-labeled

15. Coreg

16. Coropres

17. Dilatrend

18. Eucardic

19. Kredex

20. Querto

2.3.2 Depositor-Supplied Synonyms

1. 72956-09-3

2. Coreg

3. Dilatrend

4. Eucardic

5. Kredex

6. Carvedilolum [latin]

7. Carvedilolum

8. Querto

9. Bm 14190

10. 1-(9h-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol

11. Bm-14190

12. Dimitone

13. Artist

14. Skf 105517

15. 1-(9h-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol

16. 1-((9h-carbazol-4-yl)oxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)propan-2-ol

17. Coronis

18. Korvasan

19. Talliton

20. Dq 2466

21. Dq-2466

22. C07ag02

23. (+-)-1-(carbazol-4-yloxy)-3-((2-(o-methoxyphenoxy)ethyl)amino)-2-propanol

24. Chembl723

25. Nsc-758694

26. Sk&f-105517

27. Bm 14.190

28. Bm-14-190

29. Bm-14.190

30. Chebi:3441

31. 0k47ul67f2

32. [3-(9h-carbazol-4-yloxy)-2-hydroxypropyl][2-(2-methoxyphenoxy)ethyl]amine

33. 1-(9h-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol

34. Skf-105517

35. (r)-bm 14190

36. (s)-bm 14190

37. Coropress

38. Dibloc

39. R-(+)-carvedilol

40. S-(-)-carvedilol

41. 1-(9h-carbazol-4-yloxy)-3-[(2-{[2-(methyloxy)phenyl]oxy}ethyl)amino]propan-2-ol

42. Smr000449280

43. Artist (tn)

44. Coreg (tn)

45. Hsdb 7044

46. Sr-01000759289

47. Unii-0k47ul67f2

48. Mfcd00869663

49. 1-(9h-carbazol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol

50. Carvedilol D5

51. Eg-p042

52. Mfcd00864692

53. Carvedilol - Bio-x

54. Bm14190

55. Carvedilol [usan:usp:inn:ban:jan]

56. Spectrum_001665

57. Carvedilol [mi]

58. Carvedilol [inn]

59. Carvedilol [jan]

60. Spectrum2_001673

61. Spectrum3_001182

62. Spectrum4_000636

63. Spectrum5_001436

64. Carvedilol [hsdb]

65. Carvedilol [usan]

66. Carvedilol [vandf]

67. Carvedilol [mart.]

68. Carvedilol [usp-rs]

69. Carvedilol [who-dd]

70. Schembl22293

71. Gtpl551

72. Kbiogr_001252

73. Kbioss_002145

74. Mls000758299

75. Mls000759508

76. Mls001424092

77. Mls006011886

78. Spbio_001885

79. Carvedilol (jp17/usp/inn)

80. Carvedilol [orange Book]

81. Dtxsid8022747

82. Schembl10082334

83. Schembl13287211

84. Bdbm25759

85. Kbio2_002145

86. Kbio2_004713

87. Kbio2_007281

88. Kbio3_002323

89. Carvedilol [ep Monograph]

90. (r)-1-[(4-carbazolyl)oxy]-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol

91. Carvedilol [usp Monograph]

92. Hms2051n03

93. Hms2089b09

94. Hms2093e12

95. Hms3261e15

96. Hms3269n11

97. Hms3393n03

98. Hms3413b14

99. Hms3655o14

100. Hms3677b14

101. Hms3715d15

102. Hms3750i15

103. Hms3884e12

104. Pharmakon1600-01504257

105. Carvedilol 1.0 Mg/ml In Methanol

106. ((c)i)-carvedilol-d4(ethyl-d4)

107. Amy40801

108. Bcp23386

109. Ex-a5746

110. Hy-b0006

111. Tox21_500347

112. Bbl029064

113. Mfcd00869664

114. Nsc758694

115. S1831

116. Stk621453

117. Akos005554967

118. Carvedilol, >=98% (hplc), Solid

119. Ac-1641

120. Bcp9000493

121. Ccg-100917

122. Ccg-207952

123. Cs-1194

124. Db01136

125. Ks-1037

126. Lp00347

127. Nc00167

128. Nsc 758694

129. Sb17441

130. Sdccgsbi-0206771.p002

131. 2-propanol, 1-(9h-carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-, (+-)-

132. Ncgc00167832-01

133. Ncgc00167832-02

134. Ncgc00167832-03

135. Ncgc00167832-04

136. Ncgc00167832-19

137. Ncgc00261032-01

138. Bc164291

139. Sy129821

140. Sy283162

141. Bcp0726000253

142. Sbi-0206771.p001

143. Db-055704

144. Db-057556

145. Db-057557

146. Ft-0603055

147. Ft-0603057

148. Ft-0652640

149. Ft-0664397

150. Sw197547-3

151. C06875

152. D00255

153. F19969

154. Ab00639903-07

155. Ab00639903-09

156. Ab00639903_10

157. Ab00639903_11

158. Ab00639903_12

159. 956c093

160. L001243

161. Q412534

162. Q-200801

163. Sr-01000759289-5

164. Sr-01000759289-6

165. Sr-01000759289-9

166. Brd-a10977446-001-04-8

167. Brd-a10977446-001-05-5

168. Brd-a10977446-045-01-1

169. Z2786051695

170. Carvedilol, European Pharmacopoeia (ep) Reference Standard

171. Ethyl 2-(9-(pyridin-4-ylmethyl)-9h-fluoren-9-yl)acetate

172. Carvedilol, United States Pharmacopeia (usp) Reference Standard

173. 1-(9h-carbazol-4-yloxy)-3-[2-(2-methoxy-phenoxy)-ethylamino]-propan-2-ol

174. Carvedilol, Pharmaceutical Secondary Standard; Certified Reference Material

175. (+/-)-1-carbazol-4-yloxy)-3-((2-(o-methoxyphenoxy)ethyl)amino)-2-propanol

176. 1-(carbazol-4-yloxy)-3-((2-(o-methoxy-phenoxy)ethyl)amino)-2-propanol

177. Carvedilol For System Suitability, European Pharmacopoeia (ep) Reference Standard

178. 107741-96-8

179. 2-propanol, 1-(9h-carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-, (+/-)-

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 406.5 g/mol
Molecular Formula C24H26N2O4
XLogP34.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count10
Exact Mass406.18925731 g/mol
Monoisotopic Mass406.18925731 g/mol
Topological Polar Surface Area75.7 Ų
Heavy Atom Count30
Formal Charge0
Complexity508
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameCarvedilol
PubMed HealthCarvedilol (By mouth)
Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
Drug LabelCarvedilol is a nonselective -adrenergic blocking agent with 1-blocking activity. It is ()-1-(Carbazol-4-yloxy)-3-[[2-(o-methoxyphenoxy)ethyl]amino]-2-propanol. Carvedilol is a racemic mixture with the following structure:Carvedilol tablets, US...
Active IngredientCarvedilol
Dosage FormTablet
RouteOral
Strength6.25mg; 25mg; 3.125mg; 12.5mg
Market StatusPrescription
CompanyRanbaxy; Glenmark Generics; Teva; Apotex; Aurobindo Pharma; Sun Pharm Inds; Beximco Usa; Pliva Hrvatska Doo; Taro; Lupin; Zydus Pharms Usa; Dr Reddys Labs; Sandoz; Cipla; Mylan; Hikma

2 of 6  
Drug NameCoreg
PubMed HealthCarvedilol (By mouth)
Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
Drug LabelCarvedilol is a nonselective -adrenergic blocking agent with 1-blocking activity. It is ()-1-(Carbazol-4-yloxy)-3-[[2-(o-methoxyphenoxy)ethyl]amino]-2-propanol. Carvedilol is a racemic mixture with the following structure:COREG is a white, oval...
Active IngredientCarvedilol
Dosage FormTablet
RouteOral
Strength6.25mg; 25mg; 3.125mg; 12.5mg
Market StatusPrescription
CompanySmithkline Beecham

3 of 6  
Drug NameCoreg cr
PubMed HealthCarvedilol (By mouth)
Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
Active IngredientCarvedilol phosphate
Dosage FormCapsule, extended release
RouteOral
Strength10mg; 80mg; 40mg; 20mg
Market StatusPrescription
CompanySb Pharmco

4 of 6  
Drug NameCarvedilol
PubMed HealthCarvedilol (By mouth)
Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
Drug LabelCarvedilol is a nonselective -adrenergic blocking agent with 1-blocking activity. It is ()-1-(Carbazol-4-yloxy)-3-[[2-(o-methoxyphenoxy)ethyl]amino]-2-propanol. Carvedilol is a racemic mixture with the following structure:Carvedilol tablets, US...
Active IngredientCarvedilol
Dosage FormTablet
RouteOral
Strength6.25mg; 25mg; 3.125mg; 12.5mg
Market StatusPrescription
CompanyRanbaxy; Glenmark Generics; Teva; Apotex; Aurobindo Pharma; Sun Pharm Inds; Beximco Usa; Pliva Hrvatska Doo; Taro; Lupin; Zydus Pharms Usa; Dr Reddys Labs; Sandoz; Cipla; Mylan; Hikma

5 of 6  
Drug NameCoreg
PubMed HealthCarvedilol (By mouth)
Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
Drug LabelCarvedilol is a nonselective -adrenergic blocking agent with 1-blocking activity. It is ()-1-(Carbazol-4-yloxy)-3-[[2-(o-methoxyphenoxy)ethyl]amino]-2-propanol. Carvedilol is a racemic mixture with the following structure:COREG is a white, oval...
Active IngredientCarvedilol
Dosage FormTablet
RouteOral
Strength6.25mg; 25mg; 3.125mg; 12.5mg
Market StatusPrescription
CompanySmithkline Beecham

6 of 6  
Drug NameCoreg cr
PubMed HealthCarvedilol (By mouth)
Drug ClassesAntianginal, Antihypertensive, Cardiovascular Agent
Active IngredientCarvedilol phosphate
Dosage FormCapsule, extended release
RouteOral
Strength10mg; 80mg; 40mg; 20mg
Market StatusPrescription
CompanySb Pharmco

4.2 Therapeutic Uses

Adrenergic alpha-1 Receptor Antagonists; Adrenergic beta-Antagonists; Antihypertensive Agents; Vasodilator Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


Carvedilol is indicated for the treatment of mild-to-severe chronic heart failure of ischemic or cardiomyopathic origin, usually in addition to diuretics, ACE inhibitors, and digitalis, to increase survival and, also, to reduce the risk of hospitalization. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


Carvedilol is indicated to reduce cardiovascular mortality in clinically stable patients who have survived the acute phase of a myocardial infarction and have a left ventricular ejection fraction of greater than 40 percent (with or without symptomatic heart failure). /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


Carvedilol is indicated for the management of essential hypertension. It can be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


For more Therapeutic Uses (Complete) data for CARVEDILOL (10 total), please visit the HSDB record page.


4.3 Drug Warning

Carvedilol is contraindicated in the following conditions: Bronchial asthma or related bronchospastic conditions. Deaths from status asthmaticus have been reported following single doses of carvedilol; second- or third-degree AV block; sick sinus syndrome; severe bradycardia (unless a permanent pacemaker is in place); Patients with cardiogenic shock or who have decompensated heart failure requiring the use of intravenous inotropic therapy. Such patients should first be weaned from intravenous therapy before initiating carvedilol; patients with severe hepatic impairment; patients with a history of a serious hypersensitivity reaction (eg, Stevens-Johnson syndrome, anaphylactic reaction, angioedema) to any component of this medication or other medications containing carvedilol.

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


Patients with coronary artery disease, who are being treated with carvedilol, should be advised against abrupt discontinuation of therapy. Severe exacerbation of angina and the occurrence of myocardial infarction and ventricular arrhythmias have been reported in angina patients following the abrupt discontinuation of therapy with beta-blockers. The last 2 complications may occur with or without preceding exacerbation of the angina pectoris. As with other beta-blockers, when discontinuation of carvedilol is planned, the patients should be carefully observed and advised to limit physical activity to a minimum. Carvedilol should be discontinued over 1 to 2 weeks whenever possible. If the angina worsens or acute coronary insufficiency develops, it is recommended that carvedilol be promptly reinstituted, at least temporarily. Because coronary artery disease is common and may be unrecognized, it may be prudent not to discontinue therapy with carvedilol abruptly even in patients treated only for hypertension or heart failure.

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


Worsening heart failure or fluid retention may occur during up-titration of carvedilol. If such symptoms occur, diuretics should be increased and the carvedilol dose should not be advanced until clinical stability resumes. Occasionally it is necessary to lower the carvedilol dose or temporarily discontinue it. Such episodes do not preclude subsequent successful titration of, or a favorable response to, carvedilol. In a placebo-controlled trial of patients with severe heart failure, worsening heart failure during the first 3 months was reported to a similar degree with carvedilol and with placebo. When treatment was maintained beyond 3 months, worsening heart failure was reported less frequently in patients treated with carvedilol than with placebo. Worsening heart failure observed during long-term therapy is more likely to be related to the patients' underlying disease than to treatment with carvedilol.

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


Rarely, use of carvedilol in patients with heart failure has resulted in deterioration of renal function. Patients at risk appear to be those with low blood pressure (systolic blood pressure greater than 100 mm Hg), ischemic heart disease and diffuse vascular disease, and/or underlying renal insufficiency. Renal function has returned to baseline when carvedilol was stopped. In patients with these risk factors it is recommended that renal function be monitored during up-titration of carvedilol and the drug discontinued or dosage reduced if worsening of renal function occurs.

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


For more Drug Warnings (Complete) data for CARVEDILOL (24 total), please visit the HSDB record page.


4.4 Drug Indication

Carvedilol is indicated to treat mild to severe heart failure, left ventricular dysfunction after myocardial infarction with ventricular ejection fraction 40%, or hypertension.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Carvedilol reduces tachycardia through beta adrenergic antagonism and lowers blood pressure through alpha-1 adrenergic antagonism. It has a long duration of action as it is generally taken once daily and has a broad therapeutic index as patients generally take 10-80mg daily. Patients taking carvedilol should not abruptly stop taking this medication as this may exacerbate coronary artery disease.


5.2 MeSH Pharmacological Classification

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)


Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)


Adrenergic alpha-1 Receptor Antagonists

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


Adrenergic beta-Antagonists

Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety. (See all compounds classified as Adrenergic beta-Antagonists.)


Antihypertensive Agents

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. (See all compounds classified as Antihypertensive Agents.)


Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CARVEDILOL
5.3.2 FDA UNII
0K47UL67F2
5.3.3 Pharmacological Classes
Adrenergic beta1-Antagonists [MoA]; Adrenergic beta2-Antagonists [MoA]; alpha-Adrenergic Blocker [EPC]; beta-Adrenergic Blocker [EPC]; Adrenergic alpha-Antagonists [MoA]
5.4 ATC Code

C07AG02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


C - Cardiovascular system

C07 - Beta blocking agents

C07A - Beta blocking agents

C07AG - Alpha and beta blocking agents

C07AG02 - Carvedilol


5.5 Absorption, Distribution and Excretion

Absorption

Carvedilol has a bioavailability of 25-35%. Carvedilol has a Tmax of 1 to 2 hours. Taking carvedilol with a meal increases Tmax without increasing AUC. Carvedilol doses of 50mg lead to a Cmax of 122-262g/L and an AUC of 717-1600g/L\*h. Carvedilol doses of 25mg lead to a Cmax of 24-151g/L and an AUC of 272-947g/L\*h. Carvedilol doses of 12.5mg lead to a Cmax of 58-69g/L and an AUC of 208-225g/L\*h.


Route of Elimination

16% of carvedilol is excreted in the urine with <2% excreted as unmetabolized drug. Carvedilol is primarily excreted in the bile and feces.


Volume of Distribution

Carvedilol has a volume of distribution of 1.5-2L/kg or 115L.


Clearance

The plasma clearance of carvedilol has been reported as 0.52L/kg or 500-700mL/min.


Carvedilol is rapidly and extensively absorbed following oral administration, with absolute bioavailability of approximately 25 percent to 35 percent due to a significant degree of first-pass metabolism.

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011 https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


Food decreases the rate of the drug's absorption (ie, increases time to peak plasma concentration), but not the extent (ie, no effect on bioavailability) of absorption. Administration with food may decrease the risk of orthostatic hypotension.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 1888


Following oral administration of radiolabelled carvedilol to healthy volunteers, carvedilol accounted for only about 7 percent of the total radioactivity in plasma as measured by area under the curve (AUC). Less than 2 percent of the dose was excreted unchanged in the urine. ... The metabolites of carvedilol are excreted primarily via the bile into the feces.

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011 https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


Carvedilol is more than 98 percent bound to plasma proteins, primarily with albumin. The plasma-protein binding is independent of concentration over the therapeutic range.

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011 https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


For more Absorption, Distribution and Excretion (Complete) data for CARVEDILOL (13 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Carvedilol can be hydroxlated at the 1 position by CYP2D6, CYP1A2, or CYP1A1 to form 1-hydroxypheylcarvedilol; at the 4 position by CYP2D6, CYP2E1, CYP2C9, or CYP3A4 to form 4'-hydroxyphenylcarvedilol; at the 5 position by CYP2D6, CYP2C9, or CYP3A4 to form 5'-hydroxyphenylcarvedilol; and at the 8 position by CYP1A2, CYP3A4, and CYP1A1 to form 8-hydroxycarbazolylcarvedilol. Carvedilol can also be demethylated by CYP2C9, CYP2D6, CYP1A2, or CYP2E1 to form O-desmethylcarvedilol. Carvedilol and its metabolites may undergo further sulfate conjugation or glucuronidation before elimination. Carvedilol can be O-glucuronidated by UGT1A1, UGT2B4, and UGT2B7 to form carvedilol glucuronide.


Carvedilol is metabolized primarily by aromatic ring oxidation and glucuronidation. The oxidative metabolites are further metabolized by conjugation via glucuronidation and sulfation.

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011 https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


Carvedilol is extensively metabolized; phenol ring demethylation and hydroxylation produce 3 metabolites with beta-adrenergic blocking activity and (weak) vasodilating activity. Plasma concentrations of active metabolites are about 10% those of carvedilol. The 4'-hydroxyphenyl metabolite is 13 times more potent than carvedilol in beta-adrenergic blocking activity.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 1888


Compared to carvedilol, the 3 active metabolites exhibit weak vasodilating activity. Plasma concentrations of the active metabolites are about one-tenth of those observed for carvedilol and have pharmacokinetics similar to the parent.

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011 https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


Carvedilol undergoes stereoselective first-pass metabolism with plasma levels of R(+)-carvedilol approximately 2 to 3 times higher than S(-)-carvedilol following oral administration in healthy subjects.

US Natl Inst Health; DailyMed. Current Medication Information for CARVEDILOL (carvedilol) tablet (May 2011). Available from, as of September 19, 2011 https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=0b802a9c-332f-4ea8-bb34-75c677264654


For more Metabolism/Metabolites (Complete) data for CARVEDILOL (7 total), please visit the HSDB record page.


Carvedilol has known human metabolites that include (2S,3S,4S,5R)-6-[1-(9H-Carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

The half life of carvedilol is between 7-10 hours, though significantly shorter half lives have also been reported.


The half-life of carvedilol is 7-10 hours; 5-9 hours for R(+)-carvedilol, and 7-11 hours for S(-)-carvedilol.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 1888


The pharmacokinetics and absolute bioavailability of carvedilol have been studied in 20 male healthy volunteers in a randomised 4-period, cross-over trial. Carvedilol 12.5 mg was given i.v., 50 mg was administered p.o. as a suspension and 25 and 50 mg were given in a capsule formulation. For the 50 mg capsule Cmax was 66 micrograms.l-1, tmax 1.2 h, t1/2 6.4 h. The t1/2 after i.v. administration was 2.4 h, CL 589 ml/min and VZ 132 l. The absolute bioavailability was 24% (50 mg capsule). The kinetics after the 25 and 50 mg capsules were consistent with dose linearity.

PMID:3428345 von Mollendorff E, et al; Eur J Clin Pharmacol 33(5): 511-513 (1987)


5.8 Mechanism of Action

Carvedilol inhibits exercise induce tachycardia through its inhibition of beta adrenoceptors. Carvedilol's action on alpha-1 adrenergic receptors relaxes smooth muscle in vasculature, leading to reduced peripheral vascular resistance and an overall reduction in blood pressure. At higher doses, calcium channel blocking and antioxidant activity can also be seen. The antioxidant activity of carvedilol prevents oxidation of low density lipoprotein and its uptake into coronary circulation.


Carvedilol is a nonselective beta-adrenergic blocking agent with selective alpha1-adrenergic blocking activity. The principal physiologic action of carvedilol is to competitively block adrenergic stimulation of beta-receptors within the myocardium (beta1-receptors) and within bronchial and vascular smooth muscle (beta2-receptors), and to a lesser extent alpha1-receptors within vascular smooth muscle. The beta1-antagonist activity of carvedilol is similar to that of propranolol and greater than that of labetalol, and the duration of carvedilol's effect is longer than those of labetalol and propranolol.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 1888


Studies in animals indicate that the drug may exert an antioxidant effect on the myocardium and an antiproliferative effect on intimal tissue. The commercially available drug is a racemic mixture of the 2 enantiomers, (R)[+] and (S)[-], and both enantiomers have equal alpha1-adrenergic blocking activity; however, only the S(-)-enantiomer of carvedilol has beta-adrenergic blocking activity. Carvedilol does not exhibit intrinsic sympathomimetic (beta1-agonist) activity and possesses only weak membrane-stabilizing (local anesthetic) activity.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 1888


Vasodilation resulting in reduced total peripheral resistance mediated through carvedilol's alpha1-adrenergic blockade and reduced sympathetic tone appear to play a major role in the drug's hypotensive effect. Carvedilol causes reductions in cardiac output, exercise-induced tachycardia, isoproterenol-induced tachycardia, and reflex orthostatic tachycardia. Clinically important beta-adrenergic blocking activity of carvedilol usually is evident within 1 hour of oral administration, and the drug's hypotensive effect is similar to that of metoprolol. Carvedilol's alpha1-adrenergic blocking effects, which contribute to the drug's hypotensive effects, generally are evident within 30 minutes of oral administration and include reductions in phenylephrine-induced pressor effects, vasodilation, and decreased peripheral vascular resistance. The dose-dependent hypotensive effect of carvedilol results in blood pressure (systolic and diastolic) reductions of 5-46% with little, if any, reflex tachycardia. This hypotensive effect occurs approximately 30 minutes after oral administration and has a maximum effect 1.5-7 hours after oral administration.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 1888


The precise mechanism of the beneficial effects of carvedilol in the treatment of congestive heart failure has not been fully elucidated. beta1-Adrenergic blockade and vasodilation generally are associated with reflex tachycardia and peripheral vasoconstriction in therapeutic agents in which one of these pharmacologic effects predominates, but the combined effects of carvedilol appear to attenuate these two major untoward responses by balancing the potential adverse effects associated with adrenergic blockade and vasodilation. The drug's vasodilatory action appears to enable the patient to tolerate the negative inotropic effect of carvedilol during the initiation and titration of therapy in the treatment of compensated heart failure.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 1888


For more Mechanism of Action (Complete) data for CARVEDILOL (18 total), please visit the HSDB record page.


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D6 D8, SY.NO. 234\/2,234\/3,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724869800,"product":"CARVEDILOL RELATED COMPOUND D (QTY: 2 X 15MG, VALUE USD: 903\/EACH) (FOC)","address":"P.NO. 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07-Jan-2021
31-Aug-2024
KGS
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - TABLET;ORAL - 12.5MG

USFDA APPLICATION NUMBER - 20297

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DOSAGE - TABLET;ORAL - 25MG

USFDA APPLICATION NUMBER - 20297

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DOSAGE - TABLET;ORAL - 3.125MG

USFDA APPLICATION NUMBER - 20297

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DOSAGE - TABLET;ORAL - 6.25MG

USFDA APPLICATION NUMBER - 20297

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