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

Stem definition	Drug id	CAS RN
mucolytics	66	616-91-1

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
1.60	g	Inhal.solution
0.50	g	O

ADMET properties:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	61.28 µM/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:

Date	Agency	Company	Orphan
Sept. 14, 1963	FDA	APOTHECON

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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)

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Bioact source
Superoxide dismutase [Mn], mitochondrial	Enzyme	P04179	SODM_HUMAN	WOMBAT-PK
Vascular endothelial growth factor A	Secreted	P15692	VEGFA_HUMAN	WOMBAT-PK
Cytochrome c	Unclassified	P99999	CYC_HUMAN	WOMBAT-PK

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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