Carbocisteine

Identification

Summary

Carbocisteine is a expectorant mucolytic used in the relief of respiratory of COPD and other conditions associated with increased mucus viscosity.

Generic Name
Carbocisteine
DrugBank Accession Number
DB04339
Background

Dyspnea and cough are common symptoms of chronic obstructive pulmonary disease (COPD)11 and other respiratory conditions characterized by increased mucus production. Individuals with COPD have a greater risk of pulmonary infection due to the growth and accumulation of viruses and bacteria in thick bronchial mucus. Carbocisteine is a mucolytic drug that alleviates respiratory symptoms and infections by reducing the viscosity of mucus, allowing it to be expelled.16

Several licenses for this drug were withdrawn following serious and fatal paradoxical effects after carbocisteine therapy in children; respiratory dress, dyspnea, and cough aggravation were reported by physicians in France and Italy.3 Carbocisteine is currently not FDA or Health Canada approved, but is approved for use in Asia, Europe, and South America.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 179.194
Monoisotopic: 179.025228471
Chemical Formula
C5H9NO4S
Synonyms
  • (L)-2-Amino-3-(carboxymethylthio)propionic acid
  • (R)-S-(carboxymethyl)cysteine
  • carbocisteína
  • Carbocisteine
  • L-3-((carboxymethyl)thio)alanine
  • L-carbocysteine
  • S-(carboxymethyl)-(R)-cysteine
  • S-carboxymethyl-L-cysteine
  • S-carboxymethylcysteine
External IDs
  • AHR-3053
  • LJ 206
  • LJ-206
  • NSC-14156
  • R05CB03

Pharmacology

Indication

Carbocisteine is indicated over the counter and in prescription formulas to clear airway secretions in conditions associated with increased mucus.19,20,21

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofCoughing••• •••••••••••••••••••• • •••••
Treatment ofRespiratory illness•••••••••••••••••••• •••• •••••••• ••• ••••••••• •••••••• ••• ••••••••••• ••••••• ••• ••••••••• •••••• ••••••• ••••••• •••• ••••••
Treatment ofRespiratory illness••• •••••••••• •••• ••••••
Symptomatic treatment ofExcess mucus or phlegm••• •••••••••••••••••••• • •••••
Symptomatic treatment ofExcess mucus or phlegm••• •••••••••••••••••••• • •••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Due to its mucolytic effects, carbocisteine significantly reduces sputum viscosity, cough, dyspnea and fatigue.1,2 Additionally, it prevents pulmonary infections by decreasing accumulated mucus in the respiratory tract; this is especially beneficial in preventing exacerbations of COPD caused by bacteria and viruses.2 It has in-vitro anti-inflammatory activity with some demonstrated action against free radicals.2

Mechanism of action

The hypersecretion of mucus characterizes serious respiratory conditions including asthma, cystic fibrosis (CF), and chronic obstructive pulmonary disease (COPD).8 It blocks bacterial adherence to cells, preventing pulmonary infections.2 Glycoproteins (fucomucins, sialomucins and sulfomucins) regulate the viscoelastic properties of bronchial mucus. Increased fucomucins can be found in the mucus of patients with COPD. Carbocisteine serves to restore equilibrium between sialomucins and fucomucins, likely by intracellular stimulation of sialyl transferase enzyme, thus reducing mucus viscosity.2

A study found that L-carbocisteine can inhibit damage to cells by hydrogen peroxide (H2O2) by activating protein kinase B (Akt) phosphorylation, suggesting that carbocisteine may have antioxidant effects and prevent apoptosis of lung cells.5 There is some evidence that carbocisteine suppresses NF-κB and ERK1/2 MAPK signalling pathways, reducing TNF-alpha induced inflammation in the lungs, as well as other inflammatory pathways.8,9 An in-vitro study found that L-carbocisteine reduces intracellular adhesion molecule 1 (ICAM-1), inhibiting rhinovirus 14 infection, thereby reducing airway inflammation.10

TargetActionsOrganism
UPI-PLC X domain-containing protein 3
inhibitor
Humans
ULactosylceramide alpha-2,3-sialyltransferase
inducer
Humans
Absorption

Carbocisteine is rapidly absorbed in the gastrointestinal tract when taken orally with peak serum concentrations achieved within 1 to 1.7 hours.2

Volume of distribution

Carbocisteine penetrates well into the lung and bronchial secretions.2

Protein binding

Plasma protein binding information for carbocisteine is not readily available in the literature.

Metabolism

Metabolic pathways for carbocisteine include acetylation, decarboxylation, and sulfoxidation, leading to the formation of pharmacologically inactive carbocisteine derivatives. Significant variability exists in metabolism due to genetic polymorphism in sulfoxidation capacity. Two cytosolic enzymes are responsible for the metabolism of carbocisteine: cysteine dioxygenase and phenylalanine 4-hydroxylase.7 Reduced metabolism can cause increased exposure to carbocisteine, explaining variable clinical response between patients who may polymorphisms affecting the enzymes responsible for carbocisteine metabolism.2 It is generally accepted that sulfodixation is the main metabolic pathway of carbocisteine, however, one group of researchers found a novel urinary metabolite, S-(carboxymethylthio)-L-cysteine (CMTC). No cysteinyl sulfoxide metabolites were found in the urine of patients taking carbocisteine in this study.4

Route of elimination

About 30% to 60% of an orally administered dose is detected unchanged in the urine.2

Half-life

The plasma half-life of carbicostine is 1.33 hours.2

Clearance

Clearance information for carbocisteine is not readily available in the literature.

Adverse Effects
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Toxicity

The oral LD50 of carbocisteine in rats is >15000 mg/kg.15 An overdose with carbocisteine is likely to result in gastrointestinal discomfort with nausea and vomiting.14

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetohexamideThe risk or severity of adverse effects can be increased when Acetohexamide is combined with Carbocisteine.
ChloramphenicolThe risk or severity of adverse effects can be increased when Chloramphenicol is combined with Carbocisteine.
ChlorpropamideThe risk or severity of adverse effects can be increased when Chlorpropamide is combined with Carbocisteine.
DisulfiramThe risk or severity of adverse effects can be increased when Disulfiram is combined with Carbocisteine.
GliclazideThe risk or severity of adverse effects can be increased when Gliclazide is combined with Carbocisteine.
Food Interactions
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Carbocisteine lysine1D1Y95PXXA49673-81-6SAGXGPWVLUSDSQ-RVZXSAGBSA-N
International/Other Brands
Actithiol (Almirall) / Lisomucil (Sanofi-Aventis) / Muciclar (Pfizer) / Mucodyne (Sanofi-Aventis) / Mucolex (General Pharma) / Rhinathiol (Sanofi-Aventis) / Transbronchin (Meda)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CARBOSOL SYRUP 125MG/5MLSyrup125 MG/5MLOralPRIME PHARMACEUTICAL SDN. BHD.2020-09-08Not applicableMalaysia flag
CARBOSOL TABLET 375MGTablet375 MGOralPRIME PHARMACEUTICAL SDN. BHD.2020-09-08Not applicableMalaysia flag
FLUIFORTSyrup450 mg/5mlOralบริษัท เอ็ม แอนด์ เอ็ช แมนูแฟคเจอริ่ง จำกัด2006-03-01Not applicableThailand flag
FluiFort -2.7g SachetGranule, for solution2.7 gOralEURODRUG LABORATORIES (M) SDN. BHD.2020-09-08Not applicableMalaysia flag
FLUIFORT® Syrup 9g/100mlSyrup9 g/100mLOralEURODRUG LABORATORIES (M) SDN. BHD.2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AXIM TOSTHERAPY FORTE®Carbocisteine (3 g) + Guaifenesin (2 g)SyrupOralLaboratorios Incobra S.A.2021-09-02Not applicableColombia flag
CP Cough SyrupCarbocisteine (100 mg) + Promethazine hydrochloride (2.5 mg)SyrupOralHovid Berhad2020-09-08Not applicableMalaysia flag
Mucoease Plus SyrupCarbocisteine (100 mg) + Promethazine hydrochloride (2.5 mg)SyrupOralPHARMANIAGA MANUFACTURING BERHAD2020-09-08Not applicableMalaysia flag
MUCOPROM SYRUPCarbocisteine (100 mg/5ml) + Promethazine hydrochloride (2.5 mg/5ml)SyrupOralXEPA-SOUL PATTINSON (MALAYSIA) SDN. BHD.2020-09-08Not applicableMalaysia flag
Promethiol SyrupCarbocisteine (20 mg/ml) + Promethazine hydrochloride (0.5 mg/ml)SyrupOralY.S.P. INDUSTRIES (M) SDN. BHD.2020-09-08Not applicableMalaysia flag

Categories

ATC Codes
R05CB03 — Carbocisteine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-cysteine-S-conjugates
Alternative Parents
L-alpha-amino acids / Dicarboxylic acids and derivatives / Amino acids / Sulfenyl compounds / Dialkylthioethers / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
show 1 more
Substituents
Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Carbonyl group / Carboxylic acid / Dialkylthioether / Dicarboxylic acid or derivatives / Hydrocarbon derivative / L-alpha-amino acid
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-cysteine thioether (CHEBI:16163)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
740J2QX53R
CAS number
638-23-3
InChI Key
GBFLZEXEOZUWRN-VKHMYHEASA-N
InChI
InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
IUPAC Name
(2R)-2-amino-3-[(carboxymethyl)sulfanyl]propanoic acid
SMILES
N[C@@H](CSCC(O)=O)C(O)=O

References

Synthesis Reference

Maierhofer, A. and Wagner, H.: US. Patent 4,129,593; December 12,1978: assigned to Deutsche Gold- und Silber-Scheideanstalt vormals Roessler (Germany).

General References
  1. Alibasic E, Skopljak A, Cengic A, Krstovic G, Trifunovic N, Catic T, Kapo B, Mehic M, Hadzimuratovic A: Efficacy of carbocisteine in the treatment of chronic obstructive pulmonary disease and impact on the quality of life. Med Glas (Zenica). 2017 Aug 1;14(2):182-188. doi: 10.17392/906-17. [Article]
  2. Hooper C, Calvert J: The role for S-carboxymethylcysteine (carbocisteine) in the management of chronic obstructive pulmonary disease. Int J Chron Obstruct Pulmon Dis. 2008;3(4):659-69. [Article]
  3. Mallet P, Mourdi N, Dubus JC, Bavoux F, Boyer-Gervoise MJ, Jean-Pastor MJ, Chalumeau M: Respiratory paradoxical adverse drug reactions associated with acetylcysteine and carbocysteine systemic use in paediatric patients: a national survey. PLoS One. 2011;6(7):e22792. doi: 10.1371/journal.pone.0022792. Epub 2011 Jul 27. [Article]
  4. Gregory WL, James OF, Turner I, Meese CO, Idle JR: Re-evaluation of the metabolism of carbocisteine in a British white population. Pharmacogenetics. 1993 Oct;3(5):270-4. doi: 10.1097/00008571-199310000-00007. [Article]
  5. Yoshida M, Nakayama K, Yasuda H, Kubo H, Kuwano K, Arai H, Yamaya M: Carbocisteine inhibits oxidant-induced apoptosis in cultured human airway epithelial cells. Respirology. 2009 Sep;14(7):1027-34. doi: 10.1111/j.1440-1843.2009.01594.x. Epub 2009 Aug 2. [Article]
  6. Hofmann U, Eichelbaum M, Seefried S, Meese CO: Identification of thiodiglycolic acid, thiodiglycolic acid sulfoxide, and (3-carboxymethylthio)lactic acid as major human biotransformation products of S-carboxymethyl-L-cysteine. Drug Metab Dispos. 1991 Jan-Feb;19(1):222-6. [Article]
  7. Prasanta Raghab Mohapatra, Deepak Aggarwal: Carbocisteine for acute exacerbations of COPD . 2008 Nov 8;372(9650):1630-1631. [Article]
  8. Balsamo R, Lanata L, Egan CG: Mucoactive drugs. Eur Respir Rev. 2010 Jun;19(116):127-33. doi: 10.1183/09059180.00003510. [Article]
  9. Wang W, Guan WJ, Huang RQ, Xie YQ, Zheng JP, Zhu SX, Chen M, Zhong NS: Carbocisteine attenuates TNF-alpha-induced inflammation in human alveolar epithelial cells in vitro through suppressing NF-kappaB and ERK1/2 MAPK signaling pathways. Acta Pharmacol Sin. 2016 May;37(5):629-36. doi: 10.1038/aps.2015.150. Epub 2016 Mar 21. [Article]
  10. Yamaya M, Nomura K, Arakawa K, Nishimura H, Lusamba Kalonji N, Kubo H, Nagatomi R, Kawase T: Increased rhinovirus replication in nasal mucosa cells in allergic subjects is associated with increased ICAM-1 levels and endosomal acidification and is inhibited by L-carbocisteine. Immun Inflamm Dis. 2016 Apr 15;4(2):166-181. doi: 10.1002/iid3.102. eCollection 2016 Jun. [Article]
  11. Devine JF: Chronic obstructive pulmonary disease: an overview. Am Health Drug Benefits. 2008 Sep;1(7):34-42. [Article]
  12. Medici TC, Radielovic P: Effects of drugs on mucus glycoproteins and water in bronchial secretion. J Int Med Res. 1979;7(5):434-42. doi: 10.1177/030006057900700518. [Article]
  13. NPRA Product Information: Mucoprom (carbocisteine/promethazine hydrochloride) oral syrup [Link]
  14. Medicines UK: Carbocisteine 250 mg/ 5 ml syrup [Link]
  15. Toronto Research Chemical MSDS: Carbocisteine [Link]
  16. NIH StatPearls: Mucolytic Medications [Link]
  17. NHS UK: Carbocisteine [Link]
  18. NIH Stat Pearls: Chronic Obstructive Pulmonary Disease (COPD) [Link]
  19. FDA Thailand: LOVISCOL INFANT (Carbocisteine) oral drops [Link]
  20. INVIMA information: PEDIALAB® 50 mg/ 1 mL (carbocisteine) oral solution [Link]
  21. FDA Thailand: CARBOCTER (carbocisteine) oral tablet [Link]
KEGG Drug
D00175
KEGG Compound
C03727
PubChem Compound
193653
PubChem Substance
46507988
ChemSpider
168055
BindingDB
50213735
RxNav
2023
ChEBI
16163
ChEMBL
CHEMBL396416
ZINC
ZINC000001529732
PDBe Ligand
CCS
Wikipedia
Carbocisteine
PDB Entries
1dss / 1err / 1gti / 1l2i / 1stf / 2bj4 / 2jfa / 2jx4 / 3dmt / 3pqz
show 20 more

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
4CompletedTreatmentCough / Upper Respiratory Tract Infection1somestatusstop reasonjust information to hide
4Unknown StatusTreatmentAcute Tracheobronchitis / Acute Upper Respiratory Infections1somestatusstop reasonjust information to hide
3RecruitingTreatmentBronchiectasis1somestatusstop reasonjust information to hide
1CompletedTreatmentBronchitis1somestatusstop reasonjust information to hide
Not AvailableCompletedTreatmentObstructive Sleep Apnea (OSA)1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SyrupOral5.0000 g
SyrupOral7.5 g
SyrupOral5 g
SyrupOral100 mg
SolutionOral5 g
SolutionOral50 mg
Powder, for solutionOral
Granule, for solutionOral2.7 G
SyrupOral2.7 G/10ML
SyrupOral90 MG/ML
SolutionOral
SyrupOral
SyrupOral125 MG/5ML
Granule, for solutionOral
SolutionOral5.0000 g
SuspensionOral5 g
SolutionOral10 g
Powder, for solutionOral1.35 G
Powder, for solutionOral2.7 G
SyrupOral450 mg/5ml
SyrupOral9 %
SyrupOral9 g/100mL
Granule
SuspensionOral
GelOral7.5 %
Granule, for suspensionOral1.5 G
Granule, for suspensionOral2.25 g
SyrupOral50 mg/ml
SyrupOral750 MG/15ML
TabletOral1.5 G
SuspensionOral50 mg
CapsuleOral300 MG
Granule, for solutionOral300 mg
Granule, for suspensionOral300 MG
SyrupOral2 %
SyrupOral20 MG/ML
SyrupOral5 %
SyrupOral7.5 %
SyrupOral3 g
Granule, for solutionOral1.5 G
SyrupOral150 ML
Granule, for suspensionOral
PowderOral
TabletOral250 mg
CapsuleOral250 mg
CapsuleOral375 mg
SyrupOral100 ml
SyrupOral2 g
TabletOral
CapsuleOral
SyrupOral
SyrupOral2 g/100ml
SyrupOral5 g/100ml
SuspensionOral250 mg/5ml
Tablet, coatedOral375 mg
SyrupOral250 mg/5ml
TabletOral375 mg
SolutionOral250 mg/5ml
SyrupOral100 mg/5ml
SuspensionOral200 mg/5ml
SuspensionOral500 mg/5ml
CapsuleOral500 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)185-187https://www.trc-canada.com/prod-img/MSDS/C178760MSDS.pdf
boiling point (°C)417.3 ± 45.0http://www.chemspider.com/Chemical-Structure.168055.html
water solubility1.6g/Lhttps://patents.google.com/patent/CN104511025B/en
logP-4.24https://chem.nlm.nih.gov/chemidplus/rn/638-23-3
pKa1.84https://hmdb.ca/metabolites/HMDB0029415
Predicted Properties
PropertyValueSource
Water Solubility21.6 mg/mLALOGPS
logP-3.2ALOGPS
logP-3.3Chemaxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.84Chemaxon
pKa (Strongest Basic)9.14Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area100.62 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity39.11 m3·mol-1Chemaxon
Polarizability16.69 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7756
Blood Brain Barrier-0.5616
Caco-2 permeable-0.7891
P-glycoprotein substrateNon-substrate0.6275
P-glycoprotein inhibitor INon-inhibitor0.9756
P-glycoprotein inhibitor IINon-inhibitor0.997
Renal organic cation transporterNon-inhibitor0.9394
CYP450 2C9 substrateNon-substrate0.8676
CYP450 2D6 substrateNon-substrate0.8484
CYP450 3A4 substrateNon-substrate0.7652
CYP450 1A2 substrateNon-inhibitor0.9091
CYP450 2C9 inhibitorNon-inhibitor0.9542
CYP450 2D6 inhibitorNon-inhibitor0.9441
CYP450 2C19 inhibitorNon-inhibitor0.9462
CYP450 3A4 inhibitorNon-inhibitor0.9426
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9973
Ames testNon AMES toxic0.8896
CarcinogenicityNon-carcinogens0.8995
BiodegradationReady biodegradable0.5294
Rat acute toxicity1.5786 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9802
hERG inhibition (predictor II)Non-inhibitor0.9721
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9530000000-8e6125018eb1d194853b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-4900000000-be70a21dba38823e65e0
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-4938b5336a3e3dd8ef9d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-2e03758abd92fb012326
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-14a74cb7928bcc5929f0
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0005-9000000000-c17875b6b7ae40cc59f7
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0006-9000000000-c4d5bc66488a8c749f2c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0900000000-a9d785fbb33e2697f96a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-1900000000-2819ca720ebc627de3cd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ir9-9400000000-4b365357562747ccc151
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0229-9000000000-dd36050965c88158d31b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03k9-9000000000-dc423269c034eeee7369
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01p9-9800000000-667bc6a74e6ab57aec38
MS/MS Spectrum - , positiveLC-MS/MSsplash10-01p9-4900000000-643ad96ca5ded235eff4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-4900000000-e6eb77e334645f3ed1a0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-2f642e34cedaf17631be
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-3498fd7dc7118f7be1db
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0076-9100000000-ad5a1b23cbfd0679890f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-aacf52fb363575af8502
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-9000000000-c8bf11217c9e1296ae9f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-133.7237661
predicted
DarkChem Lite v0.1.0
[M-H]-133.7429661
predicted
DarkChem Lite v0.1.0
[M-H]-127.95926
predicted
DeepCCS 1.0 (2019)
[M+H]+137.8054335
predicted
DarkChem Standard v0.1.0
[M+H]+133.1212661
predicted
DarkChem Lite v0.1.0
[M+H]+131.77814
predicted
DeepCCS 1.0 (2019)
[M+Na]+132.6549661
predicted
DarkChem Lite v0.1.0
[M+Na]+132.6729661
predicted
DarkChem Lite v0.1.0
[M+Na]+141.1714
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Not Available
Specific Function
Phosphoric diester hydrolase activity
Gene Name
PLCXD3
Uniprot ID
Q63HM9
Uniprot Name
PI-PLC X domain-containing protein 3
Molecular Weight
36312.46 Da
References
  1. Ishibashi Y, Imai S, Inouye Y, Okano T, Taniguchi A: Effects of carbocisteine on sialyl-Lewis x expression in an airway carcinoma cell line stimulated with tumor necrosis factor-alpha. Eur J Pharmacol. 2006 Jan 20;530(3):223-8. doi: 10.1016/j.ejphar.2005.11.017. Epub 2006 Jan 4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Sialyltransferase activity
Specific Function
Catalyzes the formation of ganglioside GM3 (alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1, 4-beta-D-glucosylceramide).
Gene Name
ST3GAL5
Uniprot ID
Q9UNP4
Uniprot Name
Lactosylceramide alpha-2,3-sialyltransferase
Molecular Weight
47989.385 Da
References
  1. Balsamo R, Lanata L, Egan CG: Mucoactive drugs. Eur Respir Rev. 2010 Jun;19(116):127-33. doi: 10.1183/09059180.00003510. [Article]
  2. Hooper C, Calvert J: The role for S-carboxymethylcysteine (carbocisteine) in the management of chronic obstructive pulmonary disease. Int J Chron Obstruct Pulmon Dis. 2008;3(4):659-69. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Contradictory information exists in the literature regarding the involvement of this enzyme in the metabolism of carbocisteine.
General Function
Ferrous iron binding
Specific Function
Initiates several important metabolic pathways related to pyruvate and several sulfurate compounds including sulfate, hypotaurine and taurine. Critical regulator of cellular cysteine concentrations...
Gene Name
CDO1
Uniprot ID
Q16878
Uniprot Name
Cysteine dioxygenase type 1
Molecular Weight
22971.745 Da
References
  1. Prasanta Raghab Mohapatra, Deepak Aggarwal: Carbocisteine for acute exacerbations of COPD . 2008 Nov 8;372(9650):1630-1631. [Article]
  2. Steventon GB, Mitchell SC, Angulo S, Barbas C: An investigation into possible xenobiotic-endobiotic inter-relationships involving the amino acid analogue drug, S-carboxymethyl-L-cysteine and plasma amino acids in humans. Amino Acids. 2012 May;42(5):1967-73. doi: 10.1007/s00726-011-0926-y. Epub 2011 May 11. [Article]
  3. Steventon GB, Khan S, Mitchell SC: Comparison of the sulfur-oxygenation of cysteine and S-carboxymethyl-l-cysteine in human hepatic cytosol and the role of cysteine dioxygenase. J Pharm Pharmacol. 2018 Aug;70(8):1069-1077. doi: 10.1111/jphp.12944. Epub 2018 Jun 8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Phenylalanine 4-monooxygenase activity
Specific Function
Not Available
Gene Name
PAH
Uniprot ID
P00439
Uniprot Name
Phenylalanine-4-hydroxylase
Molecular Weight
51861.565 Da
References
  1. Prasanta Raghab Mohapatra, Deepak Aggarwal: Carbocisteine for acute exacerbations of COPD . 2008 Nov 8;372(9650):1630-1631. [Article]
  2. Boonyapiwat B, Forbes B, Steventon GB: Phenylalanine hydroxylase: possible involvement in the S-oxidation of S-carboxymethyl-l-cysteine. Anal Biochem. 2004 Dec 1;335(1):91-7. doi: 10.1016/j.ab.2004.08.003. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Sialyltransferase activity
Specific Function
Catalyzes the formation of ganglioside GM3 (alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1, 4-beta-D-glucosylceramide).
Gene Name
ST3GAL5
Uniprot ID
Q9UNP4
Uniprot Name
Lactosylceramide alpha-2,3-sialyltransferase
Molecular Weight
47989.385 Da
References
  1. Hooper C, Calvert J: The role for S-carboxymethylcysteine (carbocisteine) in the management of chronic obstructive pulmonary disease. Int J Chron Obstruct Pulmon Dis. 2008;3(4):659-69. [Article]
  2. Balsamo R, Lanata L, Egan CG: Mucoactive drugs. Eur Respir Rev. 2010 Jun;19(116):127-33. doi: 10.1183/09059180.00003510. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 11, 2021 10:25