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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
S-carboxymethylcysteine
External Identifiers 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
SaltsNot Available
Categories
UNII740J2QX53R
CAS number638-23-3
WeightAverage: 179.194
Monoisotopic: 179.025228471
Chemical FormulaC5H9NO4S
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as s-alkyl-l-cysteines. These are cysteine derivatives that carry an alkyl chain attached to the sulfanyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentS-alkyl-L-cysteines
Alternative Parents
Substituents
  • S-alkyl-l-cysteine
  • Dicarboxylic acid or derivatives
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationUsed to help relieve the symptoms of chronic obstructive pulmonary disorder (COPD) and bronchiectasis.
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
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
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
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
CefotetanThe risk or severity of adverse effects can be increased when Cefotetan 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.
GlimepirideThe risk or severity of adverse effects can be increased when Glimepiride is combined with Carbocisteine.
GlipizideThe risk or severity of adverse effects can be increased when Glipizide is combined with Carbocisteine.
GlyburideThe risk or severity of adverse effects can be increased when Glyburide is combined with Carbocisteine.
GriseofulvinThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Carbocisteine.
KetoconazoleThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Carbocisteine.
MetronidazoleThe risk or severity of adverse effects can be increased when Metronidazole is combined with Carbocisteine.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Carbocisteine.
TolazamideThe risk or severity of adverse effects can be increased when Tolazamide is combined with Carbocisteine.
TolbutamideThe risk or severity of adverse effects can be increased when Tolbutamide is combined with Carbocisteine.
Food InteractionsNot Available

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
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:24