Carbocisteine

Identification

Name
Carbocisteine
Accession Number
DB04339  (EXPT00835, DB02476)
Type
Small Molecule
Groups
Approved, Investigational
Description

Carbocisteine is a mucolytic that reduces the viscosity of sputum and so can be used to help relieve the symptoms of chronic obstructive pulmonary disorder (COPD) and bronchiectasis by allowing the sufferer to bring up sputum more easily. Carbocisteine should not be used with antitussives (cough suppressants) or medicines that dry up bronchial secretions. Carbocisteine is produced by alkylation of cysteine with chloroacetic acid.

Structure
Thumb
Synonyms
  • (L)-2-Amino-3-(carboxymethylthio)propionic acid
  • (R)-S-(carboxymethyl)cysteine
  • 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
International/Other Brands
Actithiol (Almirall) / Lisomucil (Sanofi-Aventis) / Muciclar (Pfizer) / Mucodyne (Sanofi-Aventis) / Mucolex (General Pharma) / Rhinathiol (Sanofi-Aventis) / Transbronchin (Meda)
Categories
UNII
740J2QX53R
CAS number
638-23-3
Weight
Average: 179.194
Monoisotopic: 179.025228471
Chemical Formula
C5H9NO4S
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

Pharmacology

Indication

Used to help relieve the symptoms of chronic obstructive pulmonary disorder (COPD) and bronchiectasis.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutathione S-transferase PNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetohexamideThe risk or severity of adverse effects can be increased when Acetohexamide is combined with Carbocisteine.Approved, Investigational, Withdrawn
CarbutamideThe risk or severity of adverse effects can be increased when Carbutamide is combined with Carbocisteine.Experimental
CefotetanThe risk or severity of adverse effects can be increased when Cefotetan is combined with Carbocisteine.Approved
ChloramphenicolThe risk or severity of adverse effects can be increased when Chloramphenicol is combined with Carbocisteine.Approved, Vet Approved
ChlorpropamideThe risk or severity of adverse effects can be increased when Chlorpropamide is combined with Carbocisteine.Approved, Investigational
DisulfiramThe risk or severity of adverse effects can be increased when Disulfiram is combined with Carbocisteine.Approved
GlibornurideThe risk or severity of adverse effects can be increased when Glibornuride is combined with Carbocisteine.Investigational, Withdrawn
GliclazideThe risk or severity of adverse effects can be increased when Gliclazide is combined with Carbocisteine.Approved
GlimepirideThe risk or severity of adverse effects can be increased when Glimepiride is combined with Carbocisteine.Approved
GlipizideThe risk or severity of adverse effects can be increased when Glipizide is combined with Carbocisteine.Approved, Investigational
GliquidoneThe risk or severity of adverse effects can be increased when Gliquidone is combined with Carbocisteine.Approved, Investigational
GlisoxepideThe risk or severity of adverse effects can be increased when Glisoxepide is combined with Carbocisteine.Investigational
GlyburideThe risk or severity of adverse effects can be increased when Glyburide is combined with Carbocisteine.Approved
GriseofulvinThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Carbocisteine.Approved, Investigational, Vet Approved
KetoconazoleThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Carbocisteine.Approved, Investigational
MetahexamideThe risk or severity of adverse effects can be increased when Metahexamide is combined with Carbocisteine.Experimental
MetronidazoleThe risk or severity of adverse effects can be increased when Metronidazole is combined with Carbocisteine.Approved
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Carbocisteine.Approved, Investigational
TolazamideThe risk or severity of adverse effects can be increased when Tolazamide is combined with Carbocisteine.Approved, Investigational
TolbutamideThe risk or severity of adverse effects can be increased when Tolbutamide is combined with Carbocisteine.Approved, Investigational
Food Interactions
Not Available

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
Not Available
External Links
KEGG Drug
D00175
KEGG Compound
C03727
PubChem Compound
193653
PubChem Substance
46507988
ChemSpider
168055
BindingDB
50213735
ChEBI
16163
ChEMBL
CHEMBL396416
HET
CCS
Wikipedia
Carbocisteine
ATC Codes
R05CB03 — Carbocisteine
PDB Entries
1dss / 1err / 1gti / 1l2i / 1stf / 2bj4 / 2jfa / 2jx4 / 3dmt / 3pqz
show 10 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentCoughing / Upper Respiratory Tract Infections1
Not AvailableCompletedTreatmentObstructive Sleep Apnoea (OSA)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-2900000000-3125c68407eed34d9654
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-9500000000-ae4a2feb1a0541a5f6f0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00du-9100000000-611fe19d8bc07f2ccc36
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01tc-4900000000-ea145a8cbe7b28667330
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9300000000-3da087ea0d68c7cacd26
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-007c-9000000000-c648cd0af81d99915af5
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

Taxonomy

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
L-cysteine-s-conjugate / Alpha-amino acid / L-alpha-amino acid / Dicarboxylic acid or derivatives / Amino acid / Carboxylic acid / Thioether / Sulfenyl compound / Dialkylthioether / Amine
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-cysteine thioether (CHEBI:16163)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
S-nitrosoglutathione binding
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on July 02, 2018 18:15