CARGLUMIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H10N2O5
Molecular Weight	190.154
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LCQLHJZYVOQKHU-VKHMYHEASA-N

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

HIDE SMILES / InChI

Molecular Formula	C6H10N2O5
Molecular Weight	190.154
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022562lbl.pdf | http://www.recordati.com/resources/Pubblicazione/___e5f362471c2c448d873585839d6dd521_/carbaglu-authorized-in-canada.pdf

Carglumic acid is a Carbamoyl Phosphate Synthetase 1 (CPS 1) allosteric modulator. 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. Carglumic acid under the trade name Carbaglu indicated as adjunctive therapy for the treatment of acute hyperammonemia due to the deficiency of the hepatic enzyme N-acetylglutamate synthase (NAGS). In addition, as maintenance therapy for the treatment of chronic hyperammonemia due to the deficiency of the hepatic enzyme N-acetylglutamate synthase (NAGS). This rare genetic disorder results in elevated blood levels of ammonia, which can eventually cross the blood–brain barrier and cause neurologic problems, cerebral edema, coma, and death.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Carbamoyl-phosphate synthase [ammonia], mitochondrial 2 Target ID: CHEMBL2362990 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21403788	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute hyperammonemia 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022562lbl.pdf	Primary		Approved 8429	CARBAGLU Approved Use Carbaglu (carglumic acid) is a Carbamoyl Phosphate Synthetase 1 (CPS 1) activator indicated as: • Adjunctive therapy for the treatment of acute hyperammonemia due to the deficiency of the hepatic enzyme N-acetylglutamate synthase (NAGS). (1.1) • Maintenance therapy for the treatment of chronic hyperammonemia due to the deficiency of the hepatic enzyme N-acetylglutamate synthase (NAGS). (1.2) Launch Date 2010
Chronic hyperammonemia 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022562lbl.pdf	Palliative		Approved 8429	CARBAGLU Approved Use Carbaglu (carglumic acid) is a Carbamoyl Phosphate Synthetase 1 (CPS 1) activator indicated as: • Adjunctive therapy for the treatment of acute hyperammonemia due to the deficiency of the hepatic enzyme N-acetylglutamate synthase (NAGS). (1.1) • Maintenance therapy for the treatment of chronic hyperammonemia due to the deficiency of the hepatic enzyme N-acetylglutamate synthase (NAGS). (1.2) Launch Date 2010

C_max

Value	Dose	Co-administered	Analyte	Population
2892 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25677217/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		CARGLUMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.6 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/30780843/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		CARGLUMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
23.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25677217/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		CARGLUMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25677217/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		CARGLUMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.6 h REVIEW https://pubmed.ncbi.nlm.nih.gov/30780843/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		CARGLUMIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
96.3 mg/kg 2 times / day multiple, oral Recommended Dose: 96.3 mg/kg, 2 times / day Route: oral Route: multiple Dose: 96.3 mg/kg, 2 times / day Sources: https://ojrd.biomedcentral.com/articles/10.1186/s13023-016-0406-2	unhealthy, 5 day n = 21 Health Status: unhealthy Condition: methylmalonic aciduria Age Group: 5 day Sex: M+F Population Size: 21 Sources: https://ojrd.biomedcentral.com/articles/10.1186/s13023-016-0406-2	Sources: https://ojrd.biomedcentral.com/articles/10.1186/s13023-016-0406-2

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2A6 707 CYP2C8 911 CYP2C19 1478 CYP2E1 882 CYP3A4/5 278	CYP1A 22 CYP2B 10 CYP1A2 1054	CYP1A 56 CYP2B6 547 CYP3A4/5 124

Drug as perpetrator

Target	Modality	Activity
CYP1A 121	inducer 1573 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=38 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 11-12, 38	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=12 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 12, 39-42	no
CYP2A6 739	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=12 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 12, 39-42	no
CYP2B6 1001	inducer 1573 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=38 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 11-12, 38	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=12 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 12, 39-42	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=12 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 12, 39-42	no
CYP2C8 965	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=12 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 12, 39-42	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=12 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 12, 39-42	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=12 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 12, 39-42	no
CYP2E1 970	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=12 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 12, 39-42	no
CYP3A4/5 335	inducer 1573 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=38 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 11-12, 38	no
CYP3A4/5 335	inhibitor 3277 Sources: https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_A100_2.pdf#page=23, https://www.pmda.go.jp/drugs/2016/P20161021006/710794000_22800AMX00708_I100_1.pdf#page=12 Page: (PMDA_A100_2 in Japanese) 23, (PMDA_I100_1 in Japanese) 12, 39-42	no

Drug as victim

Target	Modality	Activity
CYP1A 22	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022562s000pharmr.pdf#page=30 Page: 30, 35	no
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022562s000pharmr.pdf#page=30 Page: 30.0	no
CYP2B 10	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022562s000pharmr.pdf#page=30 Page: 30.0	no
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022562s000pharmr.pdf#page=30 Page: 30.0	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:71028	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:71028
ChemicalBook	CB6183743	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6183743
MolPort	MolPort-012-207-739	https://www.molport.com/shop/molecule-link/MolPort-012-207-739
ZINC	ZINC000001530283	http://zinc15.docking.org/substances/ZINC000001530283
eMolecules	8294431	https://www.emolecules.com/cgi-bin/more?vid=8294431

PubMed

Title	Date	PubMed
[Orphan drugs and metabolic disorders].	2001 Aug 1-15	11588713
Mixture of N-carbamoyl-L-glutamate plus L-arginine can protect rats with liver cirrhosis from acute ammonia intoxication.	2001 Dec	11738098
Hyperinsulinism and hyperammonemia syndrome: report of twelve unrelated patients.	2001 Sep	11518822
N-acetylglutamate synthase deficiency and the treatment of hyperammonemic encephalopathy.	2002 Dec	12447942
N-carbamylglutamate enhances ammonia detoxification in a patient with decompensated methylmalonic aciduria.	2003 Aug	12948747
Hyperammonaemia as a cause of psychosis in an adolescent.	2003 Nov	12942317
Mammalian N-acetylglutamate synthase.	2004 Apr	15050968
Carglumic acid: new preparation. An advance in rare urea cycle disorders.	2004 Feb	15055204
Restoration of ureagenesis in N-acetylglutamate synthase deficiency by N-carbamylglutamate.	2004 Oct	15480384
Neonatal hyperammonemia: the N-carbamoyl-L-glutamic acid test.	2005 Aug	16126063
Mutations and polymorphisms in the human N-acetylglutamate synthase (NAGS) gene.	2007 Aug	17421020
Carglumic acid: a second look. Confirmed progress in a rare urea cycle disorder.	2008 Apr	18516804
Carglumic acid: an additional therapy in the treatment of organic acidurias with hyperammonemia?	2008 Jan 30	18234091
Uncovering metabolic pathways relevant to phenotypic traits of microbial genomes.	2009	19284550
[N-carbamyl glutamate treatment in hyperammoniemia decompensated propionic acidaemia].	2009 Dec	19850540
Effects of a single dose of N-carbamylglutamate on the rate of ureagenesis.	2009 Dec	19660971
The first use of N-carbamylglutamate in a patient with decompensated maple syrup urine disease.	2009 Sep	19688253
Outpatient treatment of propionic acidemia-associated hyperammonemia with N-carbamoyl-L-glutamate in an infant.	2010 Apr	20435240
Gateways to clinical trials.	2010 Dec	21225012
Favourable long-term outcome after immediate treatment of neonatal hyperammonemia due to N-acetylglutamate synthase deficiency.	2010 Feb	19533169
Biochemical efficacy of N-carbamylglutamate in neonatal severe hyperammonaemia due to propionic acidaemia.	2010 Jan	19680687
N-carbamylglutamate augments ureagenesis and reduces ammonia and glutamine in propionic acidemia.	2010 Jul	20566609
Role of carglumic acid in the treatment of acute hyperammonemia due to N-acetylglutamate synthase deficiency.	2011	21941437

Patents

Sample Use Guides

In Vivo Use Guide

Adult Dosage: The recommended initial dose for acute hyperammonemia is 100 mg/kg/day to 250 mg/kg/day. Concomitant administration of other ammonia lowering therapies is recommended. Dosing should be titrated based on individual patient plasma ammonia levels and clinical symptoms. The recommended maintenance dose should be titrated to target normal plasma ammonia level for age. Based on limited data in 22 patients receiving maintenance treatment with Carbaglu in a retrospective case series, maintenance doses were usually less than 100 mg/kg/day. The total daily dose should be divided into 2 to 4 doses and rounded to the nearest 100 mg. (i.e. half a Carbaglu Tablet) Pediatric Dosage: The recommended initial dose for acute hyperammonemia is 100 mg/kg/day to 250 mg/kg/day. Concomitant administration of other ammonia lowering therapies is recommended. Dosing should be titrated based on individual patient plasma ammonia levels and clinical symptoms. The recommended maintenance dose should be titrated to target normal plasma ammonia level for age. Based on limited data in 22 patients receiving maintenance treatment with Carbaglu in a retrospective case series, maintenance doses were usually less than 100 mg/kg/day. The total daily dose should be divided into 2 to 4 doses.

Route of Administration: Oral

In Vitro Use Guide

Carglumic acid-treated (1, 5, 10 mM) and untreated cancer cells were stained with propidium iodide to determine DNA contents in the human pancreatic adenocarcinoma cell lines, AsPC1 and human triple-negative breast cancer cell lines MDA-MB-231. The results showed that carglumic acid did not induce complete cell cycle arrest. Instead, we observed more sub-G1 cells among carglumic acid-treated AsPC1 and MDA-MB-231 cells than among untreated cells, indicating that cell death occurred in response to carglumic acid. Sub-G1 cells accounted for 1.6% and 26.3% of untreated and treated AsPC1 cells, respectively , and for 1.8% and 12.8% of untreated and treated MDA-MB-231 cells, respectively. In order to further determine whether cancer cells under go cell death through apoptosis after carglumic acid treatment, we measured caspase activity in AsPC1 cells treated with carglumic acid. The results showed that caspase-3 activity increased in a dose-dependent manner. Together, these data suggest that carglumic acid inhibits cancer cell proliferation by inducing apoptosis.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:34:51 GMT 2023` Edited by `admin` on `Fri Dec 15 16:34:51 GMT 2023`
Record UNII	5L0HB4V1EW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARGLUMIC ACID

Official Name

English

CARBAMYL-L-GLUTAMIC ACID

Systematic Name

English

N-CARBAMYL-L-GLUTAMIC ACID

Common Name

English

L-GLUTAMIC ACID, N-(AMINOCARBONYL)-

Common Name

English

CARGLUMIC ACID [JAN]

Common Name

English

CARGLUMIC ACID [EMA EPAR]

Common Name

English

CARGLUMIC ACID [USP-RS]

Common Name

English

CARGLUMIC ACID [ORANGE BOOK]

Common Name

English

CARGLUMIC ACID [MART.]

Common Name

English

Carglumic acid [WHO-DD]

Common Name

English

OE-312

Code

English

NSC-760124

Code

English

OE 312

Code

English

CARGLUMIC ACID [MI]

Common Name

English

carglumic acid [INN]

Common Name

English

N-CARBAMYLGLUTAMATE

Systematic Name

English

CARGLUMIC ACID [VANDF]

Common Name

English

CARGLUMIC ACID [USAN]

Common Name

English

CARBAGLU

Brand Name

English

N-CARBAMOYL-L-GLUTAMIC ACID

Systematic Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

CARBAGLU (AUTHORIZED: AMINO ACID METABOLISM, INBORN ERRORS)

Created by admin on Fri Dec 15 16:34:51 GMT 2023 , Edited by admin on Fri Dec 15 16:34:51 GMT 2023

FDA ORPHAN DRUG

109997

Created by admin on Fri Dec 15 16:34:51 GMT 2023 , Edited by admin on Fri Dec 15 16:34:51 GMT 2023

WHO-VATC

QA16AA05

Created by admin on Fri Dec 15 16:34:52 GMT 2023 , Edited by admin on Fri Dec 15 16:34:52 GMT 2023

EU-Orphan Drug

EU/3/00/007

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NDF-RT

N0000184144

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WHO-ATC

A16AA05

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NCI_THESAURUS

C78275

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FDA ORPHAN DRUG

352111

Created by admin on Fri Dec 15 16:34:51 GMT 2023 , Edited by admin on Fri Dec 15 16:34:51 GMT 2023

Code System Code Type Description

EPA CompTox

DTXSID7046706

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PRIMARY

MERCK INDEX

m3108

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Merck Index

SMS_ID

100000089544

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RS_ITEM_NUM

1096586

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CAS

1188-38-1

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EVMPD

SUB20051

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WIKIPEDIA

CARGLUMIC ACID

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DAILYMED

5L0HB4V1EW

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PRIMARY

IUPHAR

7458

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PRIMARY

NSC

760124

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DRUG CENTRAL

3068

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FDA UNII

5L0HB4V1EW

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NCI_THESAURUS

C76884

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USAN

XX-21

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INN

8008

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RXCUI

401713

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RxNorm

PUBCHEM

121396

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PRIMARY

ChEMBL

CHEMBL1201780

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PRIMARY

NDF-RT

N0000184143

Created by admin on Fri Dec 15 16:34:51 GMT 2023 , Edited by admin on Fri Dec 15 16:34:51 GMT 2023

PRIMARY

Carbamoyl Phosphate Synthetase 1 Activators [MoA]

CHEBI

71028

Created by admin on Fri Dec 15 16:34:51 GMT 2023 , Edited by admin on Fri Dec 15 16:34:51 GMT 2023

PRIMARY

DRUG BANK

DB06775

Created by admin on Fri Dec 15 16:34:51 GMT 2023 , Edited by admin on Fri Dec 15 16:34:51 GMT 2023

PRIMARY

EVMPD

SUB13236MIG

Created by admin on Fri Dec 15 16:34:51 GMT 2023 , Edited by admin on Fri Dec 15 16:34:51 GMT 2023

ALTERNATIVE

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					O7EX2BZ64S

CARBAMOYL PHOSPHATE SYNTHETASE 1

TARGET -> ACTIVATOR


					5L0HB4V1EW

CARGLUMIC ACID

EXCRETED UNCHANGED

Comments:

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

Qualification:

FECAL

Amount:


					5L0HB4V1EW

CARGLUMIC ACID

EXCRETED UNCHANGED

Comments:

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.

Qualification:

URINE

Amount:

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(4S)-2,5-Dioxo-4-imidazolidinepropanoic acid

IMPURITY -> PARENT

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CARGLUMIC ACID

ACTIVE MOIETY

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC

Tmax	PHARMACOKINETIC

Volume of Distribution	PHARMACOKINETIC

Details

SMILES

InChI

DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022562lbl.pdf | http://www.recordati.com/resources/Pubblicazione/___e5f362471c2c448d873585839d6dd521_/carbaglu-authorized-in-canada.pdf

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Doses

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022562lbl.pdf | http://www.recordati.com/resources/Pubblicazione/___e5f362471c2c448d873585839d6dd521_/carbaglu-authorized-in-canada.pdf

C_max

T_1/2

Drug as perpetrator