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N-Carbamylglutamate

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11 Europe
1 Canada
2 South Africa
1 Listed Dossiers

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1 Minakem, 2 SPI Pharma, 1 DKSH, 2 Faran Shimi Pharmaceutical, 1 Chynops Pharma, 8 Gangwal Healthcare, 1 ACG Worldwide, 1 Alcedo Pharmachem, 6 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 5 BASF, 10 Corel Pharma Chem, 3 DFE Pharma, 6 Gangwal Chemicals, 5 Ideal Cures Pvt Ltd, 1 Ingredion Pharma Solutions, 15 Kerry, 3 Kima Chemical, 6 Lonza Capsugel, 3 Microlex e.U, 1 NEWEDGE Overseas, 1 Novo Excipients, 2 Pharmatrans-Sanaq, 2 Pluviaendo, 3 Prachin Chemical, 1 Qianhao Chemical (Hebei) Co., Ltd, 1 Qualicaps, 8 Roquette, 6 Seppic, 3 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 9 Sigachi Industries, 2 The Dow Chemical Company, 2 Vasa Pharmachem

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Synopsis

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Chemistry

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Also known as: 1188-38-1, N-carbamyl-l-glutamic acid, (s)-2-ureidopentanedioic acid, Carbaglu, N-carbamylglutamate, N-carbamoyl-l-glutamic acid

Molecular Formula

C₆H₁₀N₂O₅

Molecular Weight

190.15 g/mol

InChI Key

LCQLHJZYVOQKHU-VKHMYHEASA-N

FDA UNII

5L0HB4V1EW

Carglumic Acid is an orally active, synthetic structural analogue of N-acetylglutamate (NAG) and carbamoyl phosphate synthetase 1 (CPS 1) activator, with ammonia lowering activity. NAG, which is formed by the hepatic enzyme N-acetylglutamate synthase (NAGS), is an essential allosteric activator of the enzyme carbamoyl phosphate synthetase 1 (CPS 1). CPS 1 plays an essential role in the urea cycle and converts ammonia into urea. Upon oral administration, carglumic acid can replace NAG in NAGS deficient patients and activates CPS 1, which prevents hyperammonaemia.

Carglumic acid is a Carbamoyl Phosphate Synthetase 1 Activator. The mechanism of action of carglumic acid is as a Carbamoyl Phosphate Synthetase 1 Activator.

1 2D Structure

Carglumic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-(carbamoylamino)pentanedioic acid

2.1.2 InChI

InChI=1S/C6H10N2O5/c7-6(13)8-3(5(11)12)1-2-4(9)10/h3H,1-2H2,(H,9,10)(H,11,12)(H3,7,8,13)/t3-/m0/s1

2.1.3 InChI Key

LCQLHJZYVOQKHU-VKHMYHEASA-N

2.1.4 Canonical SMILES

C(CC(=O)O)C(C(=O)O)NC(=O)N

2.1.5 Isomeric SMILES

C(CC(=O)O)[C@@H](C(=O)O)NC(=O)N

2.2 Other Identifiers

2.2.1 UNII

5L0HB4V1EW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Carbamylglutamate

2. N-carbamoyl-l-glutamate

3. N-carbamoylglutamate

4. N-carbamylglutamate

2.3.2 Depositor-Supplied Synonyms

1. 1188-38-1

2. N-carbamyl-l-glutamic Acid

3. (s)-2-ureidopentanedioic Acid

4. Carbaglu

5. N-carbamylglutamate

6. N-carbamoyl-l-glutamic Acid

7. Ureidoglutaric Acid

8. Carbamylglutamic Acid

9. Carbamino-l-glutamic Acid

10. (2s)-2-(carbamoylamino)pentanedioic Acid

11. L-n-carbamoylglutamic Acid

12. N-carbamyl-l-glutamate

13. N-carbamyl-glutamic Acid

14. L-glutamic Acid, N-(aminocarbonyl)-

15. Oe-312

16. 5l0hb4v1ew

17. N-carbamoyl-l-glutamate

18. Chebi:71028

19. N-carbamoylglutamate

20. Oe 312

21. Nsc-760124

22. Oe 312 (laboratory Code Designation)

23. Dsstox_cid_26706

24. Dsstox_rid_81839

25. Dsstox_gsid_46706

26. Carglumic Acid [inn]

27. Carbamylglutamate

28. Carbaglu (tn)

29. Cas-1188-38-1

30. N-(aminocarbonyl)-l-glutamic Acid(carglumic Acid)

31. Unii-5l0hb4v1ew

32. Carglumic Acid [usan:inn]

33. Carglumic-acid

34. Acido Carglumico

35. Acide Carglumique

36. Acidum Carglumicum

37. Glutamic Acid, N-carbamoyl-, L-

38. Ncgc00167549-01

39. Carglumic Acid [mi]

40. Carglumic Acid [jan]

41. Carglumic Acid [usan]

42. Schembl373546

43. Carglumic Acid [vandf]

44. Gtpl7458

45. Carbamyl-l-glutamic Acid

46. Carglumic Acid [mart.]

47. Carglumic Acid [usp-rs]

48. Carglumic Acid [who-dd]

49. Chembl1201780

50. Dtxsid7046706

51. Carglumic Acid (jan/usan/inn)

52. Carglumic Acid [ema Epar]

53. Oe312

54. Bcp16753

55. Hy-b0711

56. Zinc1530283

57. Tox21_112544

58. Carglumic Acid [orange Book]

59. Mfcd00047874

60. S5301

61. Akos010384789

62. N-carbamyl-l-glutamic Acid Crystalline

63. Tox21_112544_1

64. Cs-8208

65. Db06775

66. Nsc 760124

67. Ncgc00274073-01

68. Ds-17934

69. C-1805

70. C05829

71. D07130

72. A804117

73. Q822884

74. J-507608

75. Z1551429737

76. Carglumic Acid, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₆H₁₀N₂O₅
Molecular Weight	190.15 g/mol
XLogP3	-2.4
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	190.05897142 g/mol
Monoisotopic Mass	190.05897142 g/mol
Topological Polar Surface Area	130 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	227
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Carbaglu
PubMed Health	Carglumic acid (By mouth)
Drug Classes	Hyperammonemia Agent
Active Ingredient	Carglumic acid
Dosage Form	Tablet
Route	Oral
Strength	200mg
Market Status	Prescription
Company	Orphan Europe

2 of 2
Drug Name	Carbaglu
PubMed Health	Carglumic acid (By mouth)
Drug Classes	Hyperammonemia Agent
Active Ingredient	Carglumic acid
Dosage Form	Tablet
Route	Oral
Strength	200mg
Market Status	Prescription
Company	Orphan Europe

4.2 Drug Indication

For the treatment of acute and chronic hyperammonaemia in patients with N-acetylglutamate synthase (NAGS) deficiency. This enzyme is an important component of the urea cycle to prevent build up of neurotoxic ammonium in the blood.

FDA Label

Carbaglu is indicated in treatment of:

- hyperammonaemia due to N-acetylglutamate-synthase primary deficiency;

- hyperammonaemia due to isovaleric acidaemia;

- hyperammonaemia due to methymalonic acidaemia;

- hyperammonaemia due to propionic acidaemia.

5 Pharmacology and Biochemistry

5.1 Pharmacology

The median Tmax of Carbaglu was 3 hours (range: 2-4). The daily dose of carglumic acid ranges from 100 to 250 mg/kg and this does are normally adjusted to maintain normal plasma levels of ammonia.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

CARGLUMIC ACID

5.2.2 FDA UNII

5L0HB4V1EW

5.2.3 Pharmacological Classes

Carbamoyl Phosphate Synthetase 1 Activators [MoA]; Carbamoyl Phosphate Synthetase 1 Activator [EPC]

5.3 ATC Code

A16AA05

A - Alimentary tract and metabolism

A16 - Other alimentary tract and metabolism products

A16A - Other alimentary tract and metabolism products

A16AA - Amino acids and derivatives

A16AA05 - Carglumic acid

5.4 Absorption, Distribution and Excretion

Absorption

30% bioavailability; Cmax, mean, 100 mg/kg dose = 2.6 g/mL (range of 1.9 - 4.8) Carglumic acid is not subject to to intracellular degradation.

Route of Elimination

Following administration of a single radiolabeled oral dose of 100 mg/kg of body weight, 9% of the dose was excreted unchanged in the urine and up to 60% of the dose was excreted unchanged in the feces.

Volume of Distribution

The apparent volume of distribution was 2657 L (range: 1616-5797).

Clearance

The apparent total clearance was 5.7 L/min (range 3.0-9.7), the renal clearance was 290 mL/min (range 204-445), and the 24-hour urinary excretion was 4.5 % of the dose (range 3.5-7.5).

5.5 Metabolism/Metabolites

A proportion of carglumic acid may be metabolized by the intestinal bacterial flora. The likely end product of carglumic acid metabolism is carbon dioxide, eliminated through the lungs.

5.6 Biological Half-Life

Median values for the terminal half-life was 5.6 hours (range 4.3-9.5).

5.7 Mechanism of Action

Carglumic acid is a synthetic structural analogue of N-acetylglutamate (NAG), which is an essential allosteric activator of the liver enzyme carbamoyl phosphate synthetase 1 (CPS1). CPS1 is found in the mitochondria and is the first enzyme of the urea cycle, which converts ammonia into urea. Carglumic acid acts as a replacement for NAG in NAGS deficiency patients by activating CPS1 but it does not help to regulate the urea cycle.

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API Reference Price

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D6 D8, SY.NO. 234\/2,234\/3,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1717612200,"product":"CARGLUMIC ACID(QTY:1 X 0.45 G, VALUE: USD 31.50) (FOC)","address":"P.NO. 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D6 D8, SY.NO. 234\/2,234\/3,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1717612200,"product":"CARGLUMIC ACID(QTY:4 X 0.2 G, VALUE: USD 21.22\/EACH) (FOC)","address":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,","city":"TURKAPALLY(V),SHAMEERPET, HYDERABAD","supplier":"UNITED STATES PHRAMACOPEIAL CONVENTION","supplierCountry":"UNITED STATES","foreign_port":"WASHINGTON, DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.0008","unit":"KGS","unitRateFc":"106100","totalValueFC":"89","currency":"USD","unitRateINR":"9291325","date":"06-Jun-2024","totalValueINR":"7433.06","totalValueInUsd":"89","indian_port":"Hyderabad Air","hs_no":"29241900","bill_no":"3860385","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON, DULLES I","supplierAddress":"7135 ENGLISH MUFFIN WAY FREDERICK,MD US 21704SDNF United States","customerAddress":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1717612200,"product":"CARGLUMIC ACID(QTY:4 X 0.75 G, VALUE: USD 43.83\/EACH) (FOC)","address":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,","city":"TURKAPALLY(V),SHAMEERPET, HYDERABAD","supplier":"UNITED STATES PHRAMACOPEIAL CONVENTION","supplierCountry":"UNITED STATES","foreign_port":"WASHINGTON, DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.003","unit":"KGS","unitRateFc":"58440","totalValueFC":"183.9","currency":"USD","unitRateINR":"5117676.7","date":"06-Jun-2024","totalValueINR":"15353.03","totalValueInUsd":"183.9","indian_port":"Hyderabad Air","hs_no":"29241900","bill_no":"3860385","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON, DULLES I","supplierAddress":"7135 ENGLISH MUFFIN WAY FREDERICK,MD US 21704SDNF United States","customerAddress":"P.NO. D6 D8, SY.NO. 234\/2,234\/3,"}]

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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N-Carbamylglutamate

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

4 API Suppliers

4 USDMF

1 JDMF

1 EU WC

6 NDC API

1 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

2 Drugs in Development

FINISHED DOSAGE FORMULATIONS

18 FDF Dossiers

3 FDA Orange Book

11 Europe

1 Canada

2 South Africa

1 Listed Dossiers

RELATED EXCIPIENT COMPANIES

1 Minakem

2 SPI Pharma

1 DKSH

2 Faran Shimi Pharmaceutical

1 Chynops Pharma

8 Gangwal Healthcare

1 ACG Worldwide

1 Alcedo Pharmachem

6 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

5 BASF

10 Corel Pharma Chem

3 DFE Pharma

6 Gangwal Chemicals

5 Ideal Cures Pvt Ltd

1 Ingredion Pharma Solutions

15 Kerry

3 Kima Chemical

6 Lonza Capsugel

3 Microlex e.U

1 NEWEDGE Overseas

1 Novo Excipients

2 Pharmatrans-Sanaq

2 Pluviaendo

3 Prachin Chemical

1 Qianhao Chemical (Hebei) Co., Ltd

1 Qualicaps

8 Roquette

6 Seppic

3 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

9 Sigachi Industries

2 The Dow Chemical Company

2 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

42 Coating Systems & Additives

21 Controlled & Modified Release

19 Fillers, Diluents & Binders

18 Disintegrants & Superdisintegrants

17 Direct Compression

12 Granulation

12 Thickeners and Stabilizers

11 Lubricants & Glidants

8 Co-Processed Excipients

6 Taste Masking

5 Film Formers & Plasticizers

5 Empty Capsules

5 Chewable & Orodispersible Aids

4 Vegetarian Capsules

4 API Stability Enhancers

3 Rheology Modifiers

3 Emulsifying Agents

2 Coloring Agents

1 Surfactant & Foaming Agents

1 Solubilizers

1 Topical

DIGITAL CONTENT

2 DATA COMPILATION #PharmaFlow