Carbocisteine

Identification

Name
Carbocisteine
Accession Number
DB04339
Description

Carbocisteine is a mucolytic that reduces the viscosity of sputum to relieve the symptoms of chronic obstructive pulmonary disorder (COPD) and bronchiectasis through easier expulsion of mucus. Carbocisteine should not be used with antitussives (cough suppressants) or medicines that dry up bronchial secretions as they are functional antagonists. Carbocisteine is produced by alkylation of cysteine with chloroacetic acid.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
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

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Indication

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

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutathione S-transferase PNot AvailableHumans
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
Adverse Effects
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
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.
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.
GliquidoneThe risk or severity of adverse effects can be increased when Gliquidone 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.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
Not Available

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more
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
FLUIFORTSyrup450 mg/5mlOralบริษัท เอ็ม แอนด์ เอ็ช แมนูแฟคเจอริ่ง จำกัด2006-03-01Not applicableThailand flag
MURHINOLTablet375 mgOralบริษัท บางกอกแล็ป แอนด์ คอสเมติค จำกัด จำกัด2003-11-05Not applicableThailand flag
คาร์บอคเตอร์Tablet, coatedOralบริษัท ฟาร์มาสันต์ แล็บบอราตอรี่ส์ จำกัด1996-01-30Not applicableThailand flag
คาร์โบซิส ชนิดเม็ดTablet375 mgOralบริษัท ที. แมน ฟาร์มา จำกัด2007-07-25Not applicableThailand flag
คาร์โบซิสเทอีน-นิด้า ไซรัปSyrup250 mg/5mLOralบริษัท นิด้า ฟาร์มา อินคอร์ปอเรชั่น จำกัด จำกัด2010-08-312020-09-23Thailand flag
คาร์โบซิสเทอีน-นิด้า ไซรัปสำหรับเด็กSyrup100 mg/5mLOralบริษัท นิด้า ฟาร์มา อินคอร์ปอเรชั่น จำกัด จำกัด2010-08-312020-09-23Thailand flag
คาร์โบตินSyrup250 mg/5mLOralบริษัท ยูเมด้า จำกัด2003-04-25Not applicableThailand flag
คาร์โบเพคท์Tablet375 mgOralบริษัท วี.เอส.ฟาร์ม่า (1971) จำกัด จำกัด2001-10-12Not applicableThailand flag
คาร์โบเพคท์ ไซรัปSyrup100 mg/5mLOralบริษัท วี.เอส.ฟาร์ม่า (1971) จำกัด จำกัด2002-05-30Not applicableThailand flag
คาร์โบเฟล็กซ์ ชนิดน้ำเชื่อมSyrup250 mg/5mlOralบริษัท เบสซี่ แอรอน จำกัด2020-04-20Not applicableThailand 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)

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. NPRA Product Information: Mucoprom (carbocisteine/promethazine hydrochloride) oral syrup [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 11 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentCoughing / Upper Respiratory Tract Infection1
4RecruitingTreatmentAcute Tracheobronchitis / Acute Upper Respiratory Infection1
3Active Not RecruitingTreatmentAdenocarcinoma Of Esophagus / Adenocarcinomas of the Gastroesophageal Junction / Stage IB Esophageal Cancer AJCC v7 / Stage IIA Esophageal Cancer AJCC v7 / Stage IIB Esophageal Cancer AJCC v7 / Stage IIIA Esophageal Cancer AJCC v7 / Stage IIIB Esophageal Cancer AJCC v71
3Active Not RecruitingTreatmentAdenocarcinoma of Lung Stage IV / Recurrent Large Cell Lung Carcinoma / Recurrent Lung Adenocarcinoma / Recurrent Squamous Cell Lung Carcinoma / Stage IV Large Cell Lung Carcinoma / Stage IV Squamous Cell Lung Carcinoma1
3Active Not RecruitingTreatmentAdenocarcinoma, Mucinous / Carcinoma, Undifferentiated / Clear Cell Adenocarcinoma / Fallopian Tube Clear Cell Adenocarcinoma / Fallopian Tube Endometrioid Adenocarcinoma / Fallopian Tube Mucinous Adenocarcinoma / Fallopian Tube Serous Adenocarcinoma / Fallopian Tube Transitional Cell Carcinoma / Fallopian Tube Undifferentiated Carcinoma / Ovarian Brenner Tumor / Ovarian Clear Cell Adenocarcinofibroma / Ovarian Clear Cell Adenocarcinoma / Ovarian Endometrioid Adenocarcinoma / Ovarian Seromucinous Carcinoma / Ovarian Serous Adenocarcinoma / Ovarian Transitional Cell Carcinoma / Ovarian Undifferentiated Carcinoma / Primary Peritoneal Clear Cell Adenocarcinoma / Primary Peritoneal Endometrioid Adenocarcinoma / Primary Peritoneal Serous Adenocarcinoma / Primary Peritoneal Transitional Cell Carcinoma / Primary Peritoneal Undifferentiated Carcinoma / Recurrent Fallopian Tube Carcinoma / Recurrent Ovarian Carcinoma / Recurrent Primary Peritoneal Carcinoma1
3Active Not RecruitingTreatmentAnaplastic Ependymoma / Brain Ependymoma / Cellular Ependymoma / Clear Cell Ependymoma / Ependymomas / Papillary Ependymoma1
3Active Not RecruitingTreatmentAnaplastic Medulloblastoma / Medulloblastomas1
3Active Not RecruitingTreatmentBMI >30 kg/m2 / Endometrial Clear Cell Adenocarcinoma / Endometrial Serous Adenocarcinoma / Fatigue / Neurotoxicity Syndrome / Stage I Uterine Corpus Cancer AJCC v7 / Stage II Uterine Corpus Cancer AJCC v71
3Active Not RecruitingTreatmentBorderline Ovarian Mucinous Tumor / Ovarian Mucinous Cystadenocarcinoma / Recurrent Fallopian Tube Carcinoma / Recurrent Ovarian Carcinoma / Stage IA Fallopian Tube Cancer AJCC v6 and v7 / Stage IA Ovarian Cancer AJCC v6 and v7 / Stage IB Fallopian Tube Cancer AJCC v6 and v7 / Stage IB Ovarian Cancer AJCC v6 and v7 / Stage IC Fallopian Tube Cancer AJCC v6 and v7 / Stage IC Ovarian Cancer AJCC v6 and v7 / Stage IIA Fallopian Tube Cancer AJCC v6 and v7 / Stage IIA Ovarian Cancer AJCC V6 and v7 / Stage IIB Fallopian Tube Cancer AJCC v6 and v7 / Stage IIB Ovarian Cancer AJCC v6 and v7 / Stage IIC Fallopian Tube Cancer AJCC v6 and v7 / Stage IIC Ovarian Cancer AJCC v6 and v7 / Stage IIIA Fallopian Tube Cancer AJCC v7 / Stage IIIA Ovarian Cancer AJCC v6 and v7 / Stage IIIB Fallopian Tube Cancer AJCC v7 / Stage IIIB Ovarian Cancer AJCC v6 and v7 / Stage IIIC Fallopian Tube Cancer AJCC v7 / Stage IIIC Ovarian Cancer AJCC v6 and v7 / Stage IV Fallopian Tube Cancer AJCC v6 and v7 / Stage IV Ovarian Cancer AJCC v6 and v71
3Active Not RecruitingTreatmentChildhood Atypical Teratoid/Rhabdoid Tumor1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SyrupOral7.5 g
SyrupOral5 g
Granule1.5 G
SolutionOral50 mg
Powder, for solutionOral300 MG
Granule, for solutionOral2.7 G
SyrupOral2.7 G/10ML
SyrupOral90 MG/ML
SolutionOral20 MG/ML
SolutionOral50 MG/ML
SyrupOral100 mg/5mL
SyrupOral125 MG/5ML
SuspensionOral5 g
SolutionOral10 g
Powder, for solutionOral1.35 G
Powder, for solutionOral2.7 G
SyrupOral450 mg/5ml
SyrupOral9 %
SyrupOral9 g/100mL
SyrupOral2 g
Granule100 MG
Granule375 MG
SolutionOral2 G/100ML
SolutionOral5 G/100ML
SuspensionOral1.67 g/100mL
GelOral7.5 %
Granule, for suspensionOral1.5 G
Granule, for suspensionOral2.25 g
SyrupOral750 MG/15ML
TabletOral1.5 G
SuspensionOral50 mg
CapsuleOral300 MG
Granule, for solutionOral300 mg
Granule, for suspensionOral300 MG
SyrupOral20 MG/ML
SyrupOral7.5 %
Granule, for solutionOral1.5 G
SyrupOral150 ML
SyrupOral2 g/100ml
SyrupOral50 mg/ml
PowderOral5 G
TabletOral250 mg
TabletOral375 mg
SyrupOral250 mg/5ml
CapsuleOral250 mg
CapsuleOral375 mg
SyrupOral100 mg
SyrupOral100 ml
SyrupOral0.5 mg/ml
TabletOral100 MG
TabletOral750 MG
SyrupOral
SyrupOral2 %
SyrupOral5 %
SyrupOral2.5 mg/5ml
PowderOral1500 MG
SyrupOral100 MG/ML
SyrupOral3 g
Tablet, coatedOral
SolutionOral250 mg/5ml
SuspensionOral200 mg/5ml
SuspensionOral500 mg/5ml
CapsuleOral500 mg
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

Targets

Kind
Protein
Organism
Humans
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 13:24 / Updated on February 21, 2021 18:51