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 98.62 14.05 27 11537 1174 53336328
Infection susceptibility increased 82.63 14.05 28 11536 2509 53334993
Inhibitory drug interaction 77.45 14.05 26 11538 2264 53335238
Impaired quality of life 68.17 14.05 29 11535 4842 53332660
Glucose tolerance impaired 62.50 14.05 28 11536 5292 53332210
Chronic obstructive pulmonary disease 53.39 14.05 66 11498 61007 53276495
Bone density decreased 50.77 14.05 31 11533 11033 53326469
Stevens-Johnson syndrome 48.05 14.05 41 11523 24541 53312961
Acute hepatic failure 48.04 14.05 35 11529 16685 53320817
Rheumatoid arthritis 45.41 14.05 7 11557 314524 53022978
Purpura 43.73 14.05 28 11536 10825 53326677
Toxicity to various agents 42.58 14.05 124 11440 219474 53118028
Poor quality sleep 42.52 14.05 33 11531 17290 53320212
Toxic epidermal necrolysis 41.44 14.05 37 11527 23513 53313989
Tongue oedema 39.37 14.05 19 11545 4248 53333254
Metabolic acidosis 39.10 14.05 47 11517 42195 53295307
Hepatic encephalopathy 38.83 14.05 26 11538 10833 53326669
Overdose 37.15 14.05 76 11488 107660 53229842
Hyperlipidaemia 37.02 14.05 32 11532 19483 53318019
Oral herpes 34.76 14.05 32 11532 21147 53316355
Impaired work ability 32.76 14.05 26 11538 14064 53323438
Anaphylactoid reaction 32.58 14.05 16 11548 3715 53333787
Hepatotoxicity 32.55 14.05 35 11529 27845 53309657
Thrombocytopenia 31.46 14.05 83 11481 138644 53198858
Drug-induced liver injury 31.19 14.05 35 11529 29198 53308304
Hypercapnia 30.81 14.05 17 11547 5010 53332492
Product dose omission issue 30.72 14.05 3 11561 191617 53145885
Immune-mediated pancreatitis 30.34 14.05 6 11558 59 53337443
Joint swelling 30.06 14.05 7 11557 234631 53102871
Rash maculo-papular 27.36 14.05 33 11531 29716 53307786
Congenital central hypoventilation syndrome 27.32 14.05 5 11559 31 53337471
Pneumonia 26.75 14.05 165 11399 407004 52930498
Drug interaction 26.68 14.05 106 11458 219223 53118279
Brain oedema 25.24 14.05 22 11542 13536 53323966
Erysipelas 24.95 14.05 17 11547 7284 53330218
Herpes simplex hepatitis 24.87 14.05 7 11557 337 53337165
Respiratory failure 23.66 14.05 61 11503 100451 53237051
Skin disorder 23.46 14.05 28 11536 24930 53312572
Coma 22.98 14.05 45 11519 61738 53275764
Postresuscitation encephalopathy 22.76 14.05 4 11560 19 53337483
Model for end stage liver disease score increased 22.27 14.05 4 11560 22 53337480
Post procedural haematoma 21.77 14.05 9 11555 1399 53336103
Coagulopathy 21.72 14.05 24 11540 19674 53317828
Tongue exfoliation 21.58 14.05 5 11559 109 53337393
Hepatic failure 21.12 14.05 32 11532 35774 53301728
Sputum increased 20.72 14.05 10 11554 2236 53335266
Brain herniation 19.61 14.05 11 11553 3345 53334157
Pain 19.59 14.05 64 11500 588334 52749168
Face oedema 19.51 14.05 23 11541 20217 53317285
Oliguria 19.26 14.05 16 11548 9222 53328280
Arthralgia 19.03 14.05 42 11522 439741 52897761
Hepatitis fulminant 18.84 14.05 11 11553 3608 53333894
Respiratory tract oedema 18.61 14.05 6 11558 460 53337042
Arthropathy 18.55 14.05 4 11560 141449 53196053
Chronic hepatitis C 18.43 14.05 5 11559 210 53337292
Cataract 18.27 14.05 36 11528 49584 53287918
Respiratory distress 18.23 14.05 29 11535 33798 53303704
Brain death 17.96 14.05 10 11554 2998 53334504
General physical health deterioration 17.83 14.05 71 11493 146871 53190631
Jaundice 17.75 14.05 27 11537 30286 53307216
Systemic lupus erythematosus 17.60 14.05 3 11561 125411 53212091
Contraindicated product administered 17.45 14.05 4 11560 135625 53201877
Urogenital haemorrhage 17.35 14.05 5 11559 262 53337240
Adrenocorticotropic hormone deficiency 17.23 14.05 5 11559 269 53337233
Autoimmune hepatitis 16.50 14.05 14 11550 8304 53329198
Anaphylactic shock 16.50 14.05 22 11542 21871 53315631
Lip pain 16.46 14.05 8 11556 1816 53335686
Delirium 16.41 14.05 31 11533 41398 53296104
Activated partial thromboplastin time prolonged 16.35 14.05 13 11551 7046 53330456
Macroangiopathy 16.17 14.05 4 11560 116 53337386
Decerebrate posture 16.14 14.05 4 11560 117 53337385
Treatment failure 16.10 14.05 4 11560 128399 53209103
Dose calculation error 16.01 14.05 4 11560 121 53337381
Junctional ectopic tachycardia 15.76 14.05 4 11560 129 53337373
Acute respiratory distress syndrome 15.41 14.05 22 11542 23310 53314192
Medication error 15.39 14.05 28 11536 36337 53301165
Flank pain 15.34 14.05 17 11547 13979 53323523
Injection site pain 15.29 14.05 3 11561 113388 53224114
Musculoskeletal stiffness 15.16 14.05 4 11560 123364 53214138
Intentional overdose 15.00 14.05 40 11524 67165 53270337
Acute kidney injury 14.85 14.05 100 11464 253768 53083734
Swelling 14.59 14.05 12 11552 191093 53146409
Pyrexia 14.45 14.05 142 11422 403051 52934451
Soft tissue swelling 14.39 14.05 6 11558 953 53336549
Multiple organ dysfunction syndrome 14.36 14.05 35 11529 55642 53281860

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 72.69 12.91 60 11713 20533 32481220
Dyspnoea 57.74 12.91 271 11502 361774 32139979
Pneumonia 57.44 12.91 267 11506 354985 32146768
Congenital hiatus hernia 50.02 12.91 13 11760 271 32501482
General physical health deterioration 45.59 12.91 117 11656 115142 32386611
Stevens-Johnson syndrome 45.16 12.91 44 11729 18665 32483088
Chronic obstructive pulmonary disease 38.79 12.91 66 11707 48687 32453066
Breath sounds abnormal 33.31 12.91 23 11750 6022 32495731
Respiratory failure 28.09 12.91 94 11679 107088 32394665
Productive cough 25.57 12.91 45 11728 34071 32467682
Cell death 25.33 12.91 14 11759 2472 32499281
Product dose omission issue 24.28 12.91 4 11769 102571 32399182
Systemic infection 24.20 12.91 13 11760 2170 32499583
Cyanosis 23.91 12.91 26 11747 12527 32489226
Klebsiella infection 23.48 12.91 21 11752 7991 32493762
Bilirubin conjugated abnormal 23.09 12.91 6 11767 125 32501628
Completed suicide 21.04 12.91 4 11769 92513 32409240
Middle ear inflammation 20.77 12.91 3 11770 0 32501753
Bronchiectasis 19.85 12.91 18 11755 6974 32494779
Wrong dose 19.28 12.91 7 11766 457 32501296
Cough 19.16 12.91 100 11673 138717 32363036
Malignant melanoma in situ 18.69 12.91 9 11764 1194 32500559
Oral herpes 18.54 12.91 15 11758 4982 32496771
Medication error 17.24 12.91 30 11743 22505 32479248
Death 17.06 12.91 76 11697 382441 32119312
Acute respiratory failure 16.69 12.91 34 11739 28694 32473059
Deafness bilateral 16.39 12.91 8 11765 1094 32500659
Bronchospasm 16.33 12.91 20 11753 10935 32490818
Product prescribing error 16.07 12.91 27 11746 19690 32482063
Nikolsky's sign 15.50 12.91 5 11768 228 32501525
Multiple organ dysfunction syndrome 15.47 12.91 58 11715 69796 32431957
Drug abuse 15.28 12.91 5 11768 80238 32421515
Kidney rupture 15.09 12.91 5 11768 248 32501505
Acidosis 14.89 12.91 19 11754 10827 32490926
Graft loss 14.74 12.91 7 11766 901 32500852
Pyrexia 14.46 12.91 178 11595 319790 32181963
Skin odour abnormal 14.31 12.91 7 11766 961 32500792
Acute hepatic failure 13.69 12.91 20 11753 12949 32488804
Septic shock 13.43 12.91 55 11718 68934 32432819
Full blood count abnormal 13.37 12.91 10 11763 2963 32498790
Intestinal prolapse 13.36 12.91 4 11769 142 32501611
Skin haemorrhage 13.35 12.91 11 11762 3748 32498005
Anaphylactoid reaction 13.23 12.91 9 11764 2299 32499454
Empyema 13.20 12.91 10 11763 3021 32498732

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
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 EPC N0000175776 Mucolytic
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
CHEBI has role CHEBI:173084 ferroptosis inhibitors
CHEBI has role CHEBI:176497 anti-aging drugs

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
6GM/30ML (200MG/ML) ACETADOTE CUMBERLAND PHARMS N021539 Jan. 23, 2004 RX INJECTABLE INTRAVENOUS 8399445 Aug. 24, 2025 METHOD OF TREATING ACETAMINOPHEN OVERDOSE WITH ACETYLCYSTEINE SOLUTIONS
6GM/30ML (200MG/ML) ACETADOTE CUMBERLAND PHARMS N021539 Jan. 23, 2004 RX INJECTABLE INTRAVENOUS 8653061 Aug. 24, 2025 METHOD OF TREATING ACETAMINOPHEN OVERDOSE WITH ACETYLCYSTEINE SOLUTIONS
6GM/30ML (200MG/ML) ACETADOTE CUMBERLAND PHARMS N021539 Jan. 23, 2004 RX INJECTABLE INTRAVENOUS 9327028 July 21, 2031 COMPOSITION AND METHOD FOR PROVIDING A REDUCTION IN SIDE EFFECTS FOR HUMAN PATIENTS IN NEED OF ACETYLCYSTEINE THERAPY
6GM/30ML (200MG/ML) ACETADOTE CUMBERLAND PHARMS N021539 Jan. 23, 2004 RX INJECTABLE INTRAVENOUS 8722738 April 6, 2032 METHOD OF TREATING ACETAMINOPHEN OVERDOSE WITH ACETYLCYSTEINE SOLUTIONS
2.5GM CETYLEV ARBOR PHARMS LLC N207916 Jan. 29, 2016 DISCN TABLET, EFFERVESCENT ORAL 8747894 May 8, 2032 METHOD OF TREATING ACETAMINOPHEN OVERDOSE WITH ACETYLCYSTEINE SOLUTIONS
2.5GM CETYLEV ARBOR PHARMS LLC N207916 Jan. 29, 2016 DISCN TABLET, EFFERVESCENT ORAL 9561204 May 8, 2032 METHOD OF TREATING ACETAMINOPHEN OVERDOSE WITH ACETYLCYSTEINE SOLUTIONS
500MG CETYLEV ARBOR PHARMS LLC N207916 Jan. 29, 2016 DISCN TABLET, EFFERVESCENT ORAL 8747894 May 8, 2032 METHOD OF TREATING ACETAMINOPHEN OVERDOSE WITH ACETYLCYSTEINE SOLUTIONS
500MG CETYLEV ARBOR PHARMS LLC N207916 Jan. 29, 2016 DISCN TABLET, EFFERVESCENT ORAL 9561204 May 8, 2032 METHOD OF TREATING ACETAMINOPHEN OVERDOSE WITH ACETYLCYSTEINE SOLUTIONS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Cytochrome c Enzyme WOMBAT-PK
Vascular endothelial growth factor A Secreted WOMBAT-PK
Superoxide dismutase [Mn], mitochondrial Enzyme WOMBAT-PK
Glutathione synthetase Enzyme MODULATOR DRUGBANK
Cystine/glutamate transporter Transporter MODULATOR SCIENTIFIC LITERATURE

External reference:

IDSource
4018810 VUID
N0000147113 NUI
D00221 KEGG_DRUG
197 RXNORM
C0001047 UMLSCUI
CHEBI:28939 CHEBI
1ZT PDB_CHEM_ID
SC2 PDB_CHEM_ID
CHEMBL600 ChEMBL_ID
DB06151 DRUGBANK_ID
D000111 MESH_DESCRIPTOR_UI
12035 PUBCHEM_CID
1535 INN_ID
10945 IUPHAR_LIGAND_ID
WYQ7N0BPYC UNII
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 25021-812 INJECTION, SOLUTION 200 mg INTRAVENOUS ANDA 22 sections
Acetylcysteine HUMAN PRESCRIPTION DRUG LABEL 1 51754-0104 INJECTION 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