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Chemistry

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Also known as: 81409-90-7, Dostinex, Cabaser, Cabergolinum [latin], Cabergolina [spanish], Cabergolinum
Molecular Formula
C26H37N5O2
Molecular Weight
451.6  g/mol
InChI Key
KORNTPPJEAJQIU-KJXAQDMKSA-N
FDA UNII
LL60K9J05T

Cabergoline
An ergoline derivative and dopamine D2-agonist that inhibits PROLACTIN secretion. It is used in the management of HYPERPROLACTINEMIA, and to suppress lactation following childbirth for medical reasons. Cabergoline is also used in the management of PARKINSON DISEASE.
Cabergoline is an Ergot Derivative.
1 2D Structure

Cabergoline

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6aR,9R,10aR)-N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
2.1.2 InChI
InChI=1S/C26H37N5O2/c1-5-11-30-17-19(25(32)31(26(33)27-6-2)13-8-12-29(3)4)14-21-20-9-7-10-22-24(20)18(16-28-22)15-23(21)30/h5,7,9-10,16,19,21,23,28H,1,6,8,11-15,17H2,2-4H3,(H,27,33)/t19-,21-,23-/m1/s1
2.1.3 InChI Key
KORNTPPJEAJQIU-KJXAQDMKSA-N
2.1.4 Canonical SMILES
CCNC(=O)N(CCCN(C)C)C(=O)C1CC2C(CC3=CNC4=CC=CC2=C34)N(C1)CC=C
2.1.5 Isomeric SMILES
CCNC(=O)N(CCCN(C)C)C(=O)[C@@H]1C[C@H]2[C@@H](CC3=CNC4=CC=CC2=C34)N(C1)CC=C
2.2 Other Identifiers
2.2.1 UNII
LL60K9J05T
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-((6-allylergolin-8beta-yl)carbonyl)-1-(3-(dimethylamino)propyl)-3-ethylurea

2. 1-ethyl-2-(3'-dimethylaminopropyl)-3-(6'-allylergoline-8'-beta-carbonyl)urea Diphosphate

3. Cabaser

4. Cabaseril

5. Cabergoline Diphosphate

6. Dostinex

7. Fce 21336

8. Fce-21336

9. Galastop

2.3.2 Depositor-Supplied Synonyms

1. 81409-90-7

2. Dostinex

3. Cabaser

4. Cabergolinum [latin]

5. Cabergolina [spanish]

6. Cabergolinum

7. Cabergolina

8. Fce-21336

9. Fce 21336

10. Velactis

11. 1-((6-allylergolin-8beta-yl)carbonyl)-1-(3-(dimethylamino)propyl)-3-ethylurea

12. Cabaseril

13. Chebi:3286

14. Ll60k9j05t

15. Dsstox_cid_2719

16. 1-[(6-allylergoline-8beta-yl)carbonyl]-1-[3-(dimethylamino)propyl]-3-ethylurea

17. 1-ethyl-3-(3'-dimethylamionpropyl)-2-(6'-allylergoline-8'beta-carbonyl)urea

18. (8r)-6-allyl-n-[3-(dimethylamino)propyl]-n-(ethylcarbamoyl)ergoline-8-carboxamide

19. Dsstox_rid_76698

20. Dsstox_gsid_22719

21. (6ar,9r,10ar)-7-allyl-n-(3-(dimethylamino)propyl)-n-(ethylcarbamoyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

22. (8beta)-n-[3-(dimethylamino)propyl]-n-[(ethylamino)carbonyl]-6-(2-propenyl)-ergoline-8-carboxamide

23. Sogilen

24. Dostinex (tn)

25. 1-[3-(dimethylamino)propyl]-3-ethyl-1-{[(2r,4r,7r)-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]carbonyl}urea

26. Cabaser (tn)

27. Cas-81409-90-7

28. Sr-05000001493

29. Brn 6020775

30. Unii-ll60k9j05t

31. Caberlin

32. Ncgc00167821-01

33. Cabergoline [usan:usp:inn:ban]

34. Cg-101

35. Mfcd00867887

36. Cabergoline [mi]

37. Cabergoline [inn]

38. Cabergoline [jan]

39. Cabergoline [usan]

40. Gtpl37

41. Cabergoline [vandf]

42. Cabergoline [mart.]

43. Schembl42292

44. Cabergoline [usp-rs]

45. Cabergoline [who-dd]

46. (8beta)-n-[3-(dimethylamino)propyl]-n-(ethylcarbamoyl)-6-(prop-2-en-1-yl)ergoline-8-carboxamide

47. Bidd:gt0775

48. Cabergoline (jan/usp/inn)

49. Chembl1201087

50. Dtxsid6022719

51. Cabergoline, >=98% (hplc)

52. Cabergoline [orange Book]

53. Cabergoline [ep Monograph]

54. Hms2090a09

55. Hms3886h05

56. Cabergoline [usp Monograph]

57. Zinc3800008

58. Tox21_112589

59. Bdbm50426497

60. S5842

61. Akos015961587

62. Tox21_112589_1

63. Db00248

64. Fce-21336fce-21336

65. Cabergoline [ema Epar Veterinary]

66. Ncgc00344544-01

67. (8beta)-n-[3-(dimethylamino)propyl]-n-[(ethylamino)carbonyl]-6-prop-2-en-1-ylergoline-8-carboxamide

68. Ac-26126

69. Ergoline-8-carboxamide, N-(3-(dimethylamino)propyl)-n-((ethylamino)carbonyl)-6-(2-propenyl)-, (8-beta)-

70. Ergoline-8beta-carboxamide, N-(3-(dimethylamino)propyl)-n-((ethylamino)carbonyl)-6-(2-propenyl)-

71. Hy-15296

72. C08187

73. D00987

74. F17353

75. Ab01275484-01

76. 409c907

77. Q423308

78. Sr-05000001493-1

79. Sr-05000001493-2

80. Brd-k86882815-001-01-6

81. Cabergoline, European Pharmacopoeia (ep) Reference Standard

82. Cabergoline, United States Pharmacopeia (usp) Reference Standard

83. Ethyl4-methyl-2-pyridin-3-yl-1,3-thiazole-5-carboxylate

84. 1-((6-allylergolin-8.beta.-yl)carbonyl)-1-(3-(dimethylamino)propyl)-3-ethylurea

85. 6-allyl-n-[3-(dimethylamino)propyl]-n-[(ethylamino)carbonyl]-ergoline-8beta-carboxamide

86. N-[3-(dimethylamino)propyl]-n-(ethylcarbamoyl)-6-allyl-ergoline-8beta-carboxamide

87. (6ar,9r,10ar)-n-[3-(dimethylamino)propyl]-n-(ethylcarbamoyl)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide

88. (9r,10ar)-7-allyl-n-(3-(dimethylamino)propyl)-n-(ethylcarbamoyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

89. Ergoline-8.beta.-carboxamide, N-(3-(dimethylamino)propyl)-n-((ethylamino)carbonyl)-6-(2-propenyl)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 451.6 g/mol
Molecular Formula C26H37N5O2
XLogP33.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count8
Exact Mass451.29472544 g/mol
Monoisotopic Mass451.29472544 g/mol
Topological Polar Surface Area71.7 Ų
Heavy Atom Count33
Formal Charge0
Complexity713
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameCabergoline
PubMed HealthCabergoline (By mouth)
Drug ClassesAntiparkinsonian, Prolactin Secretion Inhibitor
Drug LabelCabergoline tablets contain cabergoline, a dopamine receptor agonist. The chemical name for cabergoline is 1-[(6-Allylergolin-8-yl)carbonyl]-1-[3-(dimethylamino)propyl]-3-ethylurea. Its molecular formula is C26H37N5O2, and its molecular weight is 4...
Active IngredientCabergoline
Dosage FormTablet
RouteOral
Strength0.5mg
Market StatusPrescription
CompanyMylan Pharms; Ivax Sub Teva Pharms; Actavis Labs Fl; Apotex; Par Pharm; Impax Labs

2 of 2  
Drug NameCabergoline
PubMed HealthCabergoline (By mouth)
Drug ClassesAntiparkinsonian, Prolactin Secretion Inhibitor
Drug LabelCabergoline tablets contain cabergoline, a dopamine receptor agonist. The chemical name for cabergoline is 1-[(6-Allylergolin-8-yl)carbonyl]-1-[3-(dimethylamino)propyl]-3-ethylurea. Its molecular formula is C26H37N5O2, and its molecular weight is 4...
Active IngredientCabergoline
Dosage FormTablet
RouteOral
Strength0.5mg
Market StatusPrescription
CompanyMylan Pharms; Ivax Sub Teva Pharms; Actavis Labs Fl; Apotex; Par Pharm; Impax Labs

4.2 Drug Indication

For the treatment of hyperprolactinemic disorders, either idiopathic or due to prolactinoma (prolactin-secreting adenomas). May also be used to manage symptoms of Parkinsonian Syndrome as monotherapy during initial symptomatic management or as an adjunct to levodopa therapy during advanced stages of disease.


For use in the herd management programme of dairy cows as an aid in the abrupt drying-off by reducing milk production to:

- reduce milk leakage at drying off;

- reduce the risk of new intramammary infections during the dry period;

- reduce discomfort.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cabergoline stimulates centrally-located dopaminergic receptors resulting in a number of pharmacologic effects. Five dopamine receptor types from two dopaminergic subfamilies have been identified. The dopaminergic D1 receptor subfamily consists of D1 and D5 subreceptors, which are associated with dyskinesias. The dopaminergic D2 receptor subfamily consists of D2, D3 and D4 subreceptors, which are associated with improvement of symptoms of movement disorders. Thus, agonist activity specific for D2 subfamily receptors, primarily D2 and D3 receptor subtypes, are the primary targets of dopaminergic antiparkinsonian agents. It is thought that postsynaptic D2 stimulation is primarily responsible for the antiparkinsonian effect of dopamine agonists, while presynaptic D2 stimulation confers neuroprotective effects. This semisynthetic ergot derivative exhibits potent agonist activity on dopamine D2- and D3-receptors. It also exhibits: agonist activity (in order of decreasing binding affinities) on 5-hydroxytryptamine (5-HT)2B, 5-HT2A, 5-HT1D, dopamine D4, 5-HT1A, dopamine D1, 5-HT1B and 5-HT2C receptors and antagonist activity on α2B, α2A, and α2C receptors. Parkinsonian Syndrome manifests when approximately 80% of dopaminergic activity in the nigrostriatal pathway of the brain is lost. As this striatum is involved in modulating the intensity of coordinated muscle activity (e.g. movement, balance, walking), loss of activity may result in dystonia (acute muscle contraction), Parkinsonism (including symptoms of bradykinesia, tremor, rigidity, and flattened affect), akathesia (inner restlessness), tardive dyskinesia (involuntary muscle movements usually associated with long-term loss of dopaminergic activity), and neuroleptic malignant syndrome, which manifests when complete blockage of nigrostriatal dopamine occurs. High dopaminergic activity in the mesolimbic pathway of the brain causes hallucinations and delusions; these side effects of dopamine agonists are manifestations seen in patients with schizophrenia who have overractivity in this area of the brain. The hallucinogenic side effects of dopamine agonists may also be due to 5-HT2A agonism. The tuberoinfundibular pathway of the brain originates in the hypothalamus and terminates in the pituitary gland. In this pathway, dopamine inhibits lactotrophs in anterior pituitary from secreting prolactin. Increased dopaminergic activity in the tuberoinfundibular pathway inhibits prolactin secretion.


5.2 MeSH Pharmacological Classification

Antiparkinson Agents

Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)


Dopamine Agonists

Drugs that bind to and activate dopamine receptors. (See all compounds classified as Dopamine Agonists.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CABERGOLINE
5.3.2 FDA UNII
LL60K9J05T
5.3.3 Pharmacological Classes
Ergot Derivative [EPC]; Ergolines [CS]
5.4 ATC Code

QG02CB03


G02CB03

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


G - Genito urinary system and sex hormones

G02 - Other gynecologicals

G02C - Other gynecologicals

G02CB - Prolactine inhibitors

G02CB03 - Cabergoline


N - Nervous system

N04 - Anti-parkinson drugs

N04B - Dopaminergic agents

N04BC - Dopamine agonists

N04BC06 - Cabergoline


5.5 Absorption, Distribution and Excretion

Absorption

First-pass effect is seen, however the absolute bioavailability is unknown.


Route of Elimination

After oral dosing of radioactive cabergoline to five healthy volunteers, approximately 22% and 60% of the dose was excreted within 20 days in the urine and feces, respectively. Less than 4% of the dose was excreted unchanged in the urine.


Clearance

renal cl=0,008 L/min

nonrenal cl=3.2 L/min


5.6 Metabolism/Metabolites

Hepatic. Cabergoline is extensively metabolized, predominately via hydrolysis of the acylurea bond of the urea moiety. Cytochrome P-450 mediated metabolism appears to be minimal. The main metabolite identified in urine is 6-allyl-8b-carboxy-ergoline (4-6% of dose). Three other metabolites were identified urine (less than 3% of dose).


5.7 Biological Half-Life

The elimination half-life is estimated from urinary data of 12 healthy subjects to range between 63 to 69 hours.


5.8 Mechanism of Action

The dopamine D2 receptor is a 7-transmembrane G-protein coupled receptor associated with Gi proteins. In lactotrophs, stimulation of dopamine D2 causes inhibition of adenylyl cyclase, which decreases intracellular cAMP concentrations and blocks IP3-dependent release of Ca2+ from intracellular stores. Decreases in intracellular calcium levels may also be brought about via inhibition of calcium influx through voltage-gated calcium channels, rather than via inhibition of adenylyl cyclase. Additionally, receptor activation blocks phosphorylation of p42/p44 MAPK and decreases MAPK/ERK kinase phosphorylation. Inhibition of MAPK appears to be mediated by c-Raf and B-Raf-dependent inhibition of MAPK/ERK kinase. Dopamine-stimulated growth hormone release from the pituitary gland is mediated by a decrease in intracellular calcium influx through voltage-gated calcium channels rather than via adenylyl cyclase inhibition. Stimulation of dopamine D2 receptors in the nigrostriatal pathway leads to improvements in coordinated muscle activity in those with movement disorders. Cabergoline is a long-acting dopamine receptor agonist with a high affinity for D2 receptors. Receptor-binding studies indicate that cabergoline has low affinity for dopamine D1, α1,- and α2- adrenergic, and 5-HT1- and 5-HT2-serotonin receptors.


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D6 D8, SY.NO. 234\/2,234\/3,","city":"TURKAPALLY(V),SHAMEERPET, HYDERABAD","supplier":"USP","supplierCountry":"ITALY","foreign_port":"WASHINGTON, DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.00175","unit":"KGS","unitRateFc":"20344000","totalValueFC":"36625.7","currency":"USD","unitRateINR":"1744518120","date":"22-May-2024","totalValueINR":"3052906.71","totalValueInUsd":"36625.7","indian_port":"Hyderabad Air","hs_no":"29396900","bill_no":"3604587","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON, DULLES I","supplierAddress":"7135 ENGLISH MUFFIN WAY FREDERICK,MD 21704 USA Frederick, , United States United States","customerAddress":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1719858600,"product":"CABERGOLINE(702350)","address":"FLAT NO 305, TARA TOWERS, SALEEM NAGAR, MALAKPET, HEYDERABAD","city":"HYDERABAD","supplier":"TEVA API","supplierCountry":"NETHERLANDS","foreign_port":"PRAGUE - RUZYNE","customer":"RITSA PHARMA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.21","actualQuantity":"0.21","unit":"KGS","unitRateFc":"350000","totalValueFC":"74123.3","currency":"USD","unitRateINR":"29505000","date":"02-Jul-2024","totalValueINR":"6196050","totalValueInUsd":"74123.3","indian_port":"Hyderabad Air","hs_no":"29182990","bill_no":"4290760","productDescription":"API","marketType":"REGULATED MARKET","country":"NETHERLANDS","selfForZScoreResived":"Pharma Grade","supplierPort":"PRAGUE - RUZYNE","supplierAddress":"Piet Hein Building, Piet Heinkade107,1019 GM AmsterdamThe Netherlands NL","customerAddress":"FLAT NO 305, TARA TOWERS, SALEEM NAGAR, MALAKPET, HEYDERABAD"}]
04-Mar-2021
30-Sep-2024
KGS
overview
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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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