acetylcysteine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
mucolytics 66 616-91-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • N-Acetylcysteine
  • acetylcysteine
  • acetadote
  • acetilcysteina
  • L-Acetylcysteine
The N-acetyl derivative of CYSTEINE. It is used as a mucolytic agent to reduce the viscosity of mucous secretions. It has also been shown to have antiviral effects in patients with HIV due to inhibition of viral stimulation by reactive oxygen intermediates. N-Acetylcystene (NAC) as a precursor to the antioxidant glutathione modulates glutamatergic, neurotrophic, and inflammatory pathways. The potential applications of NAC to facilitate recovery after traumatic brain injury, cerebral ischemia, and in treatment of cerebrovascular vasospasm after subarachnoid hemorrhage.
  • Molecular weight: 163.19
  • Formula: C5H9NO3S
  • CLOGP: -0.62
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 66.40
  • ALOGS: -1.51
  • ROTB: 3

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.60 g Inhal.solution
0.50 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 61.28 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 5 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.55 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.17 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 5.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 14, 1963 FDA APOTHECON

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Body tinea 68.44 13.77 19 9606 916 46675521
Impaired quality of life 55.56 13.77 22 9603 3220 46673217
Infection susceptibility increased 52.62 13.77 19 9606 2160 46674277
Inhibitory drug interaction 50.45 13.77 18 9607 1977 46674460
Stevens-Johnson syndrome 49.65 13.77 40 9585 23257 46653180
Chronic obstructive pulmonary disease 49.16 13.77 60 9565 57573 46618864
Toxic epidermal necrolysis 44.84 13.77 37 9588 22241 46654196
Glucose tolerance impaired 41.01 13.77 20 9605 4811 46671626
Acute hepatic failure 35.08 13.77 27 9598 14694 46661743
Bone density decreased 32.67 13.77 22 9603 9730 46666707
Hepatic encephalopathy 31.86 13.77 22 9603 10135 46666302
Anaphylactoid reaction 31.28 13.77 15 9610 3476 46672961
Immune-mediated pancreatitis 31.22 13.77 6 9619 53 46676384
Pneumonia 30.87 13.77 156 9469 376164 46300273
Rheumatoid arthritis 28.92 13.77 7 9618 240208 46436229
Overdose 28.37 13.77 64 9561 101915 46574522
Poor quality sleep 27.94 13.77 24 9601 15229 46661208
Purpura 27.60 13.77 20 9605 9938 46666499
Erysipelas 26.52 13.77 17 9608 6921 46669516
Tongue oedema 26.46 13.77 14 9611 3992 46672445
Thrombocytopenia 26.26 13.77 71 9554 126510 46549927
Rash maculo-papular 25.36 13.77 30 9595 27844 46648593
Drug interaction 24.03 13.77 94 9531 203000 46473437
Postresuscitation encephalopathy 22.96 13.77 4 9621 19 46676418
Tongue exfoliation 22.95 13.77 5 9620 86 46676351
Post procedural haematoma 22.56 13.77 9 9616 1342 46675095
Model for end stage liver disease score increased 22.47 13.77 4 9621 22 46676415
Product dose omission issue 22.15 13.77 4 9621 168516 46507921
Hyperlipidaemia 22.12 13.77 23 9602 18516 46657921
Hypercapnia 21.92 13.77 13 9612 4613 46671824
Respiratory failure 21.51 13.77 55 9570 94761 46581676
Impaired work ability 21.37 13.77 19 9606 12617 46663820
Dose calculation error 20.28 13.77 4 9621 41 46676396
Face oedema 19.75 13.77 22 9603 19131 46657306
Chronic hepatitis C 19.56 13.77 5 9620 175 46676262
Respiratory distress 19.15 13.77 28 9597 31888 46644549
Autoimmune hepatitis 17.89 13.77 14 9611 7800 46668637
Oral herpes 17.85 13.77 21 9604 19369 46657068
Drug-induced liver injury 17.82 13.77 24 9601 25344 46651093
Macroangiopathy 17.34 13.77 4 9621 90 46676347
Delirium 17.25 13.77 29 9596 37199 46639238
Anaphylactic shock 17.09 13.77 21 9604 20253 46656184
Lip pain 17.03 13.77 8 9617 1770 46674667
Medication error 16.95 13.77 26 9599 30885 46645552
Dyspnoea 16.34 13.77 170 9455 515378 46161059
Joint swelling 16.17 13.77 7 9618 166066 46510371
Bronchospasm 16.13 13.77 18 9607 15689 46660748
Brain oedema 15.83 13.77 16 9609 12462 46663975
Poisoning deliberate 15.60 13.77 13 9612 7913 46668524
Coagulopathy 15.34 13.77 19 9606 18480 46657957
Herpes simplex sepsis 15.10 13.77 3 9622 32 46676405
Soft tissue swelling 15.06 13.77 6 9619 892 46675545
Activated partial thromboplastin time prolonged 15.04 13.77 12 9613 6877 46669560
General physical health deterioration 14.83 13.77 55 9570 115714 46560723
Normochromic normocytic anaemia 14.77 13.77 10 9615 4462 46671975
Dysphoria 14.53 13.77 10 9615 4579 46671858
Depersonalisation/derealisation disorder 14.38 13.77 6 9619 1004 46675433
Adrenocorticotropic hormone deficiency 14.24 13.77 4 9621 201 46676236
Hepatic failure 14.13 13.77 25 9600 33391 46643046
Toxicity to various agents 14.06 13.77 83 9542 211683 46464754
Skin disorder 14.04 13.77 20 9605 22243 46654194
Infective pulmonary exacerbation of cystic fibrosis 13.97 13.77 14 9611 10793 46665644
Metabolic acidosis 13.87 13.77 27 9598 38753 46637684

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxic epidermal necrolysis 82.83 12.35 60 10234 17880 29924304
Pneumonia 62.55 12.35 253 10041 334053 29608131
Stevens-Johnson syndrome 49.53 12.35 44 10250 17512 29924672
Dyspnoea 47.68 12.35 233 10061 333062 29609122
General physical health deterioration 38.24 12.35 97 10197 99847 29842337
Respiratory failure 27.97 12.35 87 10207 100555 29841629
Cell death 26.98 12.35 14 10280 2297 29939887
Chronic obstructive pulmonary disease 25.69 12.35 52 10242 46074 29896110
Klebsiella infection 25.07 12.35 20 10274 6867 29935317
Cyanosis 24.31 12.35 25 10269 11910 29930274
Bilirubin conjugated abnormal 23.40 12.35 6 10288 125 29942059
Completed suicide 21.66 12.35 4 10290 99488 29842696
Middle ear inflammation 20.93 12.35 3 10291 0 29942184
Pyrexia 17.55 12.35 166 10128 294323 29647861
Wrong dose 17.51 12.35 6 10288 348 29941836
Product dose omission issue 17.32 12.35 5 10289 91626 29850558
Deafness bilateral 16.92 12.35 8 10286 1074 29941110
Cough 16.52 12.35 86 10208 125556 29816628
Bronchospasm 16.42 12.35 19 10275 10319 29931865
Multiple organ dysfunction syndrome 15.90 12.35 53 10241 63434 29878750
Medication error 15.89 12.35 27 10267 20945 29921239
Nikolsky's sign 15.82 12.35 5 10289 225 29941959
Kidney rupture 15.53 12.35 5 10289 239 29941945
Graft loss 15.37 12.35 7 10287 863 29941321
Skin haemorrhage 14.72 12.35 11 10283 3429 29938755
Product prescribing error 14.65 12.35 23 10271 16710 29925474
Drug abuse 14.58 12.35 5 10289 82067 29860117
Anaphylactoid reaction 14.10 12.35 9 10285 2177 29940007
Intestinal prolapse 13.59 12.35 4 10290 141 29942043
Death 13.59 12.35 70 10224 357213 29584971
Palatal oedema 12.99 12.35 6 10288 764 29941420
Mucosal erosion 12.83 12.35 6 10288 787 29941397
Pulmonary fibrosis 12.76 12.35 21 10273 15869 29926315
Myoclonic epilepsy 12.59 12.35 6 10288 820 29941364
Productive cough 12.40 12.35 30 10264 29923 29912261

Pharmacologic Action:

SourceCodeDescription
ATC R05CB01 RESPIRATORY SYSTEM
COUGH AND COLD PREPARATIONS
EXPECTORANTS, EXCL. COMBINATIONS WITH COUGH SUPPRESSANTS
Mucolytics
ATC S01XA08 SENSORY ORGANS
OPHTHALMOLOGICALS
OTHER OPHTHALMOLOGICALS
Other ophthalmologicals
ATC V03AB23 VARIOUS
ALL OTHER THERAPEUTIC PRODUCTS
ALL OTHER THERAPEUTIC PRODUCTS
Antidotes
FDA PE N0000008867 Decreased Respiratory Secretion Viscosity
FDA EPC N0000175429 Antidote
FDA MoA N0000175547 Reduction Activity
FDA EPC N0000175776 Mucolytic
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000975 Antioxidants
MeSH PA D000998 Antiviral Agents
MeSH PA D005100 Expectorants
MeSH PA D016166 Free Radical Scavengers
MeSH PA D019141 Respiratory System Agents
FDA PE N0000175960 Increased Glutathione Concentration
FDA EPC N0000175961 Antidote for Acetaminophen Overdose
CHEBI has role CHEBI:22586 antioxidants
CHEBI has role CHEBI:35441 anti-infective drugs
CHEBI has role CHEBI:36044 anti-virus drug
CHEBI has role CHEBI:48578 free-radical scavenger
CHEBI has role CHEBI:73336 vulneraries
CHEBI has role CHEBI:74529 tylenol poisoning antidotes
CHEBI has role CHEBI:77034 mucolytics
CHEBI has role CHEBI:77746 h. sapiens metabolites

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Bronchiectasis indication 12295008 DOID:9563
Amyloidosis indication 17602002 DOID:9120
Bronchitis indication 32398004 DOID:6132
General anesthesia indication 50697003
Poisoning by acetaminophen indication 70273001
Cystic fibrosis of the lung indication 86555001
Atelectasis due to Mucous Obstruction indication
Thick Bronchial Secretions indication
Contrast Media-Induced Nephrotoxicity Prevention indication
Meconium ileus off-label use 206523001
Bronchial Studies off-label use
Bronchospasm contraindication 4386001
Peptic ulcer contraindication 13200003 DOID:750
Esophageal varices contraindication 28670008
Low blood pressure contraindication 45007003
Decreased respiratory function contraindication 80954004
Acute exacerbation of asthma contraindication 708038006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.22 acidic
pKa2 9.96 acidic
pKa3 12.92 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Superoxide dismutase [Mn], mitochondrial Enzyme WOMBAT-PK
Vascular endothelial growth factor A Secreted WOMBAT-PK
Cytochrome c Unclassified WOMBAT-PK

External reference:

IDSource
WYQ7N0BPYC UNII
4018810 VUID
N0000147113 NUI
D00221 KEGG_DRUG
C1330030 UMLSCUI
CHEBI:28939 CHEBI
1ZT PDB_CHEM_ID
SC2 PDB_CHEM_ID
CHEMBL600 ChEMBL_ID
12035 PUBCHEM_CID
DB06151 DRUGBANK_ID
D000111 MESH_DESCRIPTOR_UI
1535 INN_ID
10945 IUPHAR_LIGAND_ID
197 RXNORM
4127 MMSL
48605 MMSL
893 MMSL
d00762 MMSL
000720 NDDF
003524 NDDF
387440002 SNOMEDCT_US
77731008 SNOMEDCT_US
4018810 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 0409-3307 SOLUTION 100 mg ORAL ANDA 17 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 0409-3308 SOLUTION 200 mg ORAL ANDA 17 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 0517-7504 INHALANT 100 mg RESPIRATORY (INHALATION) ANDA 18 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 0517-7510 INHALANT 100 mg RESPIRATORY (INHALATION) ANDA 18 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 0517-7604 INHALANT 200 mg RESPIRATORY (INHALATION) ANDA 18 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 0517-7610 INHALANT 200 mg RESPIRATORY (INHALATION) ANDA 18 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 0517-7630 INHALANT 200 mg RESPIRATORY (INHALATION) ANDA 18 sections
acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 0574-0805 INJECTION 200 mg INTRAVENOUS NDA 22 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 17478-660 INJECTION 200 mg INTRAVENOUS ANDA 22 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 25021-812 INJECTION, SOLUTION 200 mg INTRAVENOUS ANDA 22 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 54868-5670 SOLUTION 200 mg ORAL ANDA 18 sections
Acetylcysteine Human Prescription Drug Label 1 55150-259 INJECTION, SOLUTION 6 g INTRAVENOUS ANDA 22 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 55154-5730 INHALANT 100 mg RESPIRATORY (INHALATION) ANDA 18 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 55154-5731 INHALANT 200 mg RESPIRATORY (INHALATION) ANDA 18 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 63323-690 SOLUTION 200 mg ORAL ANDA 17 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 63323-690 SOLUTION 200 mg ORAL ANDA 17 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 63323-691 SOLUTION 100 mg ORAL ANDA 17 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 63323-692 SOLUTION 200 mg ORAL ANDA 17 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 63323-693 SOLUTION 100 mg ORAL ANDA 17 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 63323-694 SOLUTION 200 mg ORAL ANDA 17 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 63323-694 SOLUTION 200 mg ORAL ANDA 17 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 63323-695 SOLUTION 100 mg ORAL ANDA 17 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 63323-963 INJECTION, SOLUTION 200 mg INTRAVENOUS ANDA 24 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 63323-963 INJECTION, SOLUTION 200 mg INTRAVENOUS ANDA 24 sections
ACETADOTE HUMAN PRESCRIPTION DRUG LABEL 1 66220-207 INJECTION, SOLUTION 200 mg INTRAVENOUS NDA 22 sections
ACETYLCYSTEINE HUMAN PRESCRIPTION DRUG LABEL 1 70710-1015 INJECTION, SOLUTION 200 mg INTRAVENOUS ANDA 20 sections
ACETYLCYSTEINE HUMAN PRESCRIPTION DRUG LABEL 1 70771-1412 INJECTION, SOLUTION 200 mg INTRAVENOUS ANDA 1 sections