Identification
NameCarbocisteine
Accession NumberDB04339  (EXPT00835, DB02476)
TypeSmall Molecule
GroupsApproved
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
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ActithiolAlmirall
LisomucilSanofi-Aventis
MuciclarPfizer
MucodyneSanofi-Aventis
MucolexGeneral Pharma
RhinathiolSanofi-Aventis
TransbronchinMeda
Brand mixturesNot Available
Categories
UNII740J2QX53R
CAS number638-23-3
WeightAverage: 179.194
Monoisotopic: 179.025228471
Chemical FormulaC5H9NO4S
InChI KeyGBFLZEXEOZUWRN-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.

Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Glutathione S-transferase PProteinunknownNot AvailableHumanP09211 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot 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.Withdrawn
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
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.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
GliquidoneThe risk or severity of adverse effects can be increased when Gliquidone is combined with Carbocisteine.Approved
GlisoxepideThe risk or severity of adverse effects can be increased when Glisoxepide is combined with Carbocisteine.Approved
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, Vet Approved
KetoconazoleThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Carbocisteine.Approved, Investigational
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
TolazamideThe risk or severity of adverse effects can be increased when Tolazamide is combined with Carbocisteine.Approved
TolbutamideThe risk or severity of adverse effects can be increased when Tolbutamide is combined with Carbocisteine.Approved
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesR05CB03 — Carbocisteine
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentCoughing / Upper Respiratory Tract Infections1
Not AvailableCompletedTreatmentObstructive Sleep Apnoea (OSA)1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-4900000000-be70a21dba38823e65e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-4938b5336a3e3dd8ef9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-2e03758abd92fb012326View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-14a74cb7928bcc5929f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0005-9000000000-c17875b6b7ae40cc59f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0006-9000000000-c4d5bc66488a8c749f2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-a9d785fbb33e2697f96aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-1900000000-2819ca720ebc627de3cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ir9-9400000000-4b365357562747ccc151View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0229-9000000000-dd36050965c88158d31bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03k9-9000000000-dc423269c034eeee7369View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01p9-9800000000-667bc6a74e6ab57aec38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01p9-4900000000-643ad96ca5ded235eff4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-2900000000-3125c68407eed34d9654View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9500000000-ae4a2feb1a0541a5f6f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00du-9100000000-611fe19d8bc07f2ccc36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01tc-4900000000-ea145a8cbe7b28667330View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-3da087ea0d68c7cacd26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-9000000000-c648cd0af81d99915af5View in MoNA
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentL-cysteine-S-conjugates
Alternative ParentsL-alpha-amino acids / Dicarboxylic acids and derivatives / Amino acids / Sulfenyl compounds / Dialkylthioethers / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
SubstituentsL-cysteine-s-conjugate / Alpha-amino acid / L-alpha-amino acid / Dicarboxylic acid or derivatives / Amino acid / Carboxylic acid / Thioether / Sulfenyl compound / Dialkylthioether / Amine
Molecular FrameworkAliphatic acyclic compounds
External Descriptorsnon-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 June 23, 2017 10:18